The LeanScale Podcast · Episode 117

You Can't Get Promoted Until You Replace Yourself

Cole Gillespie on writing the recipe for a sales rep, turning "responsive" into a three-hour SLA, the four things every person should expect off the elevator, and why the leader who has to be asked for the raise already lost

Cole Gillespie · Chief Revenue Officer, Branch · Branch Hosted by Anthony Enrico
Published Updated 01:13:28 64 min read 12849 words
Sales Leadership Sales Enablement Sales Compensation GTM Strategy
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Executive Summary

The one-paragraph brief, extended

Why this conversation matters — and who should spend the hour.

Cole Gillespie, Chief Revenue Officer at Branch, the workforce payments platform, got the sales leadership job on one condition: he could not leave the rep job until he had replaced himself. He was young, eager, and convinced that being charming and charismatic was what made him effective — so the exercise started from the wrong question: how could one replace their personality? Forced to write down what he actually did each day, he found something else. How many phone calls, when he made them, how he followed up, how he stayed organised. Four appointments a day, four days a week. He calls the result a recipe, and it proved more useful as an onboarding document for future reps than as his own exit ticket.

The interesting half was qualitative. Everyone agrees a rep should be fast to follow up, but as Cole puts it, if fast to you is two weeks and fast to me is two hours, we're in trouble. So he converted adjectives into service levels — customer calls returned in three hours, channel partner calls same day — and told partners the standard up front. That, he says, is how he replaced himself: he could set a standard and behave his way into it. It also defused criticism: instead of getting defensive he could state the standard and ask what actually happened.

The other half was the career obituary: when you leave this job, what will your manager, your peers and your customers say about you? Cole built it from a pattern — travelling a market with a rep, hearing partners praise them, then coming back after that rep left and hearing the opposite: never followed up, never understood my deals, never kept me updated. He bet they never knew. He is just as blunt about hiring: he has been wrong about who would make it roughly 20 to 30 percent of the time, and an interview is a salesperson selling themselves.

Scaled up, this becomes a contract. Cole tells anyone on a revenue team he leads that off the elevator they should expect four things: to know what good and bad performance look like and be aligned with their manager on it, to be compensated fairly, to be treated with respect, and to have the tools to do the job. If one is missing, that is the leader's problem. On pay, the trap is the junior hire who became a superstar and still sits at the bottom of the band; he would rather give a 50 percent increase nobody asked for than wait for a competitor's offer and match it. Anthony Enrico lands it: if they have to ask, it's already too late. On resourcing, he would rather spend more than he forecast than hold someone to a target while withholding the people, money and time — while watching for the leader whose every new problem resolves to a new hire.

The last third turns personal. Cole runs a text thread with his two kids called Dad Wisdom, and the lesson he most wants in it is the one he learned late: once your basic needs are met, every promotion stops being an obvious step and becomes a trade between satisfaction, impact, who you work with, industry, title and compensation. He plotted through promotion after promotion before noticing he had chosen a career without deciding to. So when someone says they want to be a CRO, he asks why — promotion for the sake of promotion is not always good, and he respects the top performer who looks at management and says no.

Key Takeaways

15 things worth stealing

The load-bearing ideas, each with the business implication and who should care.

01

Replacing yourself is a writing exercise, not a hiring exercise

Cole's boss made the promotion conditional on replacing himself. His first instinct was that the job was impossible, because he believed charm and charisma were what made him effective — how could one replace their personality? Writing down the tactical detail (call volume, timing, follow-up, organisation, the funnel) produced a recipe instead.

Why it matters: The document outlived its original purpose. It became the onboarding artifact for future reps, and Cole still asks the same question today: what is our recipe, and what framework are we putting a new rep into?

Sales LeadersRevenue ExecutivesFounders
02

Capitulation is the moment a rep stops copying and starts owning

Cole would put a new rep into a market and insist they follow the playbook. Some would obediently work the steps like they were baking a cake — valuable, but without intent or motivation behind the actions it is not that useful. Then, three or six months in, the rep says: I get it, I'll do what you told me, but I'm going to be myself while I do it.

Why it matters: That turn is the goal, not a sign of drift. Product and process knowledge is the foundation; the rep's own personality is what makes the foundation work.

Sales LeadersRevenue Executives
03

Hiring for personality is the trap — and salespeople are the hardest people to vet

Cole has been surprised roughly 20 to 30 percent of the time by someone he doubted who made it on determination, curiosity and repetition. He has also seen plenty of great personalities close no deals. He resents the idea that salespeople come in one flavour of human, and cites a colleague nothing like him who was a fantastic seller.

Why it matters: Technical founders hiring their first go-to-market leaders are at the sharpest end of this: an interview is a salesperson selling themselves. Hire for the characteristics that predict performance, not for how someone behaves in a room.

FoundersSales LeadersRevenue Executives
04

The career obituary: write the ending, then work backwards

Cole ran this exercise with his team — when you leave your job, what will your manager, your peers and your customers say about you? It came from watching partners praise a rep to their face and then, once that rep was gone, say they never followed up, never understood the deals and never kept anyone updated.

Why it matters: His conclusion was that the people who left almost certainly never knew. Deciding the reputation you want in advance turns it into something you can build on purpose rather than discover on the way out.

Sales LeadersRevenue Executives
05

Convert vague adjectives into SLAs, because "fast" is a relative term

Everybody agrees a rep should be responsive and fast to follow up — nobody argues with that. But if fast to you is two weeks and fast to me is two hours, both sides think they are right and the relationship breaks anyway. Cole's answer was to write specific numbers: customer phone calls returned in three hours, channel partner calls same day.

Why it matters: He told partners the standard up front, so when someone asked whether Cole was responsive, the answer was a number rather than an impression. In his words, he could set a standard and then behave his way into it.

Sales LeadersRevenue ExecutivesFounders
06

A published standard turns defensiveness into curiosity

When someone told Cole he was not good at following up or including them, his instinct was to get defensive. Having the standard written down changed the conversation: he could say this is a thing I try hard to be good at, here is how I try to do it, and it sounds like I did not do it well — can you tell me what happened?

Why it matters: Even when the other person has no specific example and it just feels that way, both sides leave knowing what was intended and what the agreement is. The specificity removes the ambiguity of using the same words while speaking different languages.

Sales LeadersRevenue Executives
07

Four things everyone should expect off the elevator

Cole tells anyone on a revenue team he leads that the table stakes are: understanding what good and bad performance look like and being aligned with their manager on it, being compensated fairly (he is careful to say fairly, not the best), being treated with respect, and having the tools necessary to execute the job.

Why it matters: If any of the four is missing, the person needs to raise their hand — because it is the leader's problem to solve, not theirs. The contract is deliberately short enough to be remembered and audited.

Sales LeadersRevenue ExecutivesFounders
08

Ambiguity about performance is a tax on the work itself

Cole spent years early on managing the feelings of people interpreting their manager's tone in Slack messages and emails to work out whether they were doing a good job. He wants that percentage of someone's life back and pointed at the job. Anthony's version: if someone has to come and ask, the leader has not made it clear enough.

Why it matters: If you walk into a performance review hoping your manager thinks the way you do, you are already off to a bad start. Alignment on the definition lets both sides look at the same performance and reach the same verdict.

Sales LeadersRevenue ExecutivesFounders
09

OKRs above, activity expectations below

As CRO managing VPs, Cole sets strategic priorities, aligns them to the founder's vision, has each department set its own vision in line with that, and allocates people, time and money to those objectives — four to six things reviewed with his leaders every two weeks, calling the quarter's shot on the metrics that lead to success. He deliberately avoids being prescriptive about tactical activity at that level.

Why it matters: At the rep level he inverts it and gets far more specific about activity expectations. Misallocating resources is his own tell that he has not prioritised properly.

Sales LeadersRevenue ExecutivesRevOps Leaders
10

Effort is the rep's to bring; quality is a joint problem

Cole draws a hard line: he will create an environment where someone can flourish, but pulling effort out of a person is not his job — the rep owes him that. If he has hired correctly he usually has to turn people down rather than up. Quality is different: any deficiency in the funnel points to a coaching opportunity, not a problem sent from God.

Why it matters: His operating check is that he should be the second most informed person in a rep's territory. If he is the first, the rep is not doing the job — and both of them have a problem.

Sales LeadersRevenue Executives
11

Raise the star's pay before they ask — the match arrives too late

The scenario Cole names is the junior hire who became a superstar and is still near the bottom of the band because of the experience they had when they joined. He would rather hand over a 50 percent base increase nobody asked for than let a competitor bid and then match. Anthony's framing: if they have to ask, it's already too late.

Why it matters: Both argue the cause is usually negligence rather than malice — the information never reaches someone with the agency to fix it, or there is no review process flagging it. Anthony's team uses Rippling to surface tenure-versus-band drift automatically.

FoundersRevenue ExecutivesSales Leaders
12

The unasked raise is a trust deposit you spend later

Anthony describes receiving exactly this call — more options and a salary increase, unprompted — and wanting to run through a brick wall for the company, because it signalled that the company sees everything and will treat you fairly without you flagging it. Cole's point is that the deposit gets drawn down when you have to change a territory or a quota.

Why it matters: The trust built by fixing pay before it was raised is what gets a person to sit through the conversation they do not like and see it through.

FoundersRevenue ExecutivesSales Leaders
13

Resourcing is the fourth promise, and the one leaders skip

Cole's worst-feeling scenario is the one where everything else is right — aligned on performance, paid fairly, treated respectfully — but you are simply not given the people, money or time to do the job well. He would rather spend more than he thought he had to and eat the forecast miss as the consequence of being wrong.

Why it matters: His counterweight is the leader whose every new problem resolves to a new hire: that is someone solving for the easiest path rather than for efficiency. His better signal is the person who takes on everything and never complains — that is the one he calls to ask whether they actually have what they need.

Revenue ExecutivesSales LeadersFounders
14

Be careful which balls you pick up

Cole's advice to maturing leaders: people are going to roll balls to your feet, and once you pick one up, you own it. In an effort to be helpful you end up responsible for what somebody else could have done. A leader's job is to prioritise their department and allocate resources; where priorities outweigh resources, that is a managerial conversation.

Why it matters: Hero ball can look like under-resourcing when it is actually over-prioritisation. Anthony's complement is forcing high-output people to stop taking things on, and to take PTO, before they burn out.

Sales LeadersRevenue ExecutivesRevOps Leaders
15

Respect means civility, not the absence of friction

Cole does not mind friction and views direct communication as a sign of trust. He thinks it is completely fair to review someone's performance objectively and independently of who they are as a person — you can have bad performance and still be a good person, and good people have bad ideas. What he excludes is incivility: humiliating or demeaning someone is out of bounds.

Why it matters: He is sceptical of the blanket "no assholes policy" because defining the asshole is the hard part, and it can read as a ban on interesting personalities. What he actually objects to is ambiguity — he would rather a leader say plainly what is tolerated here, including that people curse, than leave the line unstated.

Sales LeadersRevenue ExecutivesFounders
Frameworks Discussed

10 named models

Every framework Jimmy names, defined and time-stamped.

Replace Yourself on Paper

03:19

Writing down the tactical detail of how you personally do the job — call volume, timing, follow-up, organisation, the funnel and its conversion rates — until what looked like personality turns out to be a repeatable recipe someone else can run.

Cole was given the sales leadership job on the condition that he replace himself first. Because he believed charm and charisma drove his results, the exercise began as an impossible one. What came out was a document more valuable for onboarding future reps than for getting him promoted, and it is still the question he asks when new reps join: what is our recipe, and what framework are we putting them into?

Capitulation

05:48

The point, usually three to six months in, where a rep stops obediently executing the playbook and says: I get it, I know how to do this, and I'm going to bring myself to the job.

Cole named the pattern after watching new reps follow the steps like a cake recipe. Following the steps has value, but without intent and motivation behind the actions it is not that useful. Capitulation is the signal that the foundation has been absorbed and the rep's own personality can now do the work.

The Career Obituary

15:16

An exercise in which a rep writes what their manager, peers and customers will say about them when they leave the job — and then works backwards to the behaviours that would earn it.

The idea came from Cole travelling markets with reps, hearing partners praise them to their face, and then hearing the opposite after those reps had gone: never followed up, never understood my deals, never kept me updated. He assumed the departed reps never knew. Anthony compares it to asking what people will say at your funeral so you can decide how to live today, with less existential dread attached.

Reputation SLAs

18:13

Translating the qualitative reputation you want — responsive, honest, knowledgeable — into stated numeric service levels, then publishing them to the people who will judge you by them.

Cole's version: customer phone calls returned in three hours, channel partner calls same day, announced to partners up front so the standard is mutual. It answers the problem that fast to one person is two weeks and fast to another is two hours. It also converts vague criticism into a specific conversation about what actually happened.

The Four Things Off the Elevator

21:23

The table-stakes contract Cole gives anyone on a revenue team he leads: know what good and bad performance look like and be aligned with your manager on it; be compensated fairly; be treated with respect; have the tools necessary to execute the job.

If any of the four is missing, the person is expected to raise their hand, because it is the leader's problem to fix. Cole uses it as a zoom-out check when managing managers: is it actually true that everyone here has these four, to the standard we claim?

OKRs Above, Activity Below

25:09

Running strategy by objectives at the leadership level — four to six priorities aligned to the founder's vision, reviewed with leaders every two weeks — while getting far more prescriptive about activity expectations at the individual rep level.

As CRO, Cole sets the strategic priorities, has each department align its own vision to them, and allocates people, time and money accordingly; misallocated resources are his own tell that he prioritised wrongly. He avoids tactical prescription at the VP level so leaders have agency inside the framework, and inverts that for reps, where activity is explicit and funnel deficiencies drive coaching.

Pay Before They Ask

35:36

Proactively catching a high performer's base and OTE up to what the role is now worth, rather than waiting for them to lobby or for a competitor's offer you would then match.

Cole's scenario is the junior hire who became a star while still sitting near the bottom of the band because of the experience they had when they joined — fair at the time, stale now. He would rather hand over a 50 percent increase nobody asked for, because if you were going to match the competitor anyway, the employee is entitled to ask why they had to ask. Anthony adds the arithmetic: the extra salary is not close to the cost of recruiting, ramping and an empty seat.

Be Careful Which Balls You Pick Up

47:19

Cole's rule for maturing leaders: people will roll problems to your feet, and the moment you pick one up you own it — so choose deliberately rather than reflexively.

Helping by absorbing other people's work turns their problems into yours and makes you responsible for what someone else could have done. A leader is expected to prioritise their department and allocate resources; when priorities outweigh resources, that is a management conversation, not a reason to play hero ball. Sometimes what looks like under-resourcing is over-prioritisation.

From Survival to Choice

1:01:18

The moment a career stops being a ladder of obvious next steps and becomes a set of trades — once basic needs are met, every promotion is a compromise between satisfaction, impact, title and compensation rather than a straightforward step up.

Cole describes progressing from inside to outside sales to management because each step was logical, fun and better paid — and then realising he had chosen a career without deliberately choosing it. Ten or fifteen years in, the switching cost is real. It is the lesson he most wants his kids to have, so they never mistake a race for survival for a decision.

The Cocktail

1:04:06

The five ingredients Cole weighs in any job — compensation, title, industry, leading people, and impact — tested by asking whether more money, a better title and a different industry would make you happy if you led nobody and felt no impact.

For Cole the answer is no: he loves leading and developing people regardless of industry, and would be genuinely unsatisfied without an impact he himself judges to be positive. Who he does it with now matters enormously. He uses the same question on people leaving for a bigger salary and title, because the elements they are trading away are the ones they usually miss later.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“People are going to roll balls to your feet. Just be careful which ones you pick up.”
Cole Gillespie 00:00
“And the challenge was, listen, you can't leave this job until you replace yourself.”
Cole Gillespie 02:33
“Once I started doing it I got really excited about almost like writing a recipe to be a sales rep.”
Cole Gillespie 03:38
“Capitulation, which is inevitably three or six months in the rep would say: I got it, I know how to do this, but I'm just gonna be myself and I'm gonna do what you told me to do and I'm gonna bring myself to the job. And you're like, good, now we're getting somewhere.”
Cole Gillespie 05:48
“I really, really believe that you can teach the craft of selling something to people to roughly anybody.”
Cole Gillespie 06:09
“It's a great lesson for hiring, because when you're hiring for people, if you're hiring for a personality, you can fall into that trap.”
Cole Gillespie 08:32
“Sales is trying to convince somebody to buy something that you genuinely think is going to be good for them.”
Cole Gillespie 10:38
“The idea was, when you leave your job, what will your manager say about you? What will your peers, what will your customers say about you?”
Cole Gillespie 15:30
“If fast to you is two weeks and fast to me is two hours, then we're in trouble.”
Cole Gillespie 17:53
“I return customer phone calls in three hours, I return channel partner phone calls same day. And so I started building little SLAs into what I did. This is like how I replaced myself.”
Cole Gillespie 18:13
“When they get off the elevator they should expect at least four things. One, they should expect to understand what good or bad performance looks like, and they should have alignment with their manager.”
Cole Gillespie 21:23
“I know when people come to me asking, it's like, oh, if you have to ask then I haven't made this clear enough.”
Anthony Enrico 22:59
“Any deficiency that we see in the funnel tells us something about a coaching opportunity, an opportunity to improve.”
Cole Gillespie 28:18
“What is a little bit more in their salary versus the cost of needing to go fully replace this person? It's not even close.”
Anthony Enrico 33:03
“I want to set the example to my team of: no, we pay fairly, we're not looking for a deal, and so they don't need to raise their hand.”
Cole Gillespie 35:47
“Yeah, if they have to ask it's already too late.”
Anthony Enrico 36:07
“I would rather spend more money than I thought I had to spend to stay true to the thing of, it's just fair to give somebody the resources they need to do the job.”
Cole Gillespie 42:47
“I'm not unkind. I would never humiliate you, I would never demean who you are as a human, as a brother, as a son, as a mother — that's completely out of bounds. But we can talk about your performance objectively. That's completely fair.”
Cole Gillespie 51:11
“After my basic needs were met, everything was kind of a choice I was making between job satisfaction and impact, and title and compensation. Those were the compromises.”
Cole Gillespie 1:01:18
“That's like promotion for the sake of promotion, and that's not always good.”
Cole Gillespie 1:11:32
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Sales Leaders

  • Before promoting your best rep, make them write down what they actually do all day — call volume, timing, follow-up, organisation, funnel conversion — and keep the document as your onboarding recipe.
  • Expect and welcome capitulation: the rep who says 'I get it, but I'm going to be myself' has absorbed the playbook, not abandoned it.
  • Run the career obituary exercise: have each rep write what their manager, peers and customers will say when they leave, then work backwards to the behaviours.
  • Turn every vague adjective in your standard — responsive, thorough, communicative — into a stated number, and tell customers and partners what it is.
  • Be explicit about what good and bad performance look like, so nobody spends their week interpreting your Slack tone; if someone has to ask, you did not make it clear enough.
  • Get specific about activity expectations at the rep level and treat funnel deficiencies as coaching opportunities rather than verdicts.
  • Aim to be the second most informed person in each rep's territory — if you are the first, the rep is not doing the job.

Revenue Executives

  • Give every person on the revenue team the same four-part contract: a shared definition of performance, fair pay, respect, and the resources to execute — and make raising a missing one their right, not their risk.
  • At the leadership level, set four to six priorities aligned to the founder's vision, review them with your leaders every two weeks, and allocate people, time and money against them rather than prescribing tactics.
  • Treat misallocated resources as evidence that you prioritised wrongly, not that your leaders underperformed.
  • Watch for the leader whose every new problem is solved by an incremental hire — and separately, call the person who never complains to ask whether they actually have what they need.
  • Say out loud what is tolerated here, including where the line on language and friction sits; the ambiguity does more damage than the standard.
  • Ask the person who says they want to be a CRO why they want it, and respect the top performer who decides management is not for them.

Founders

  • Assume a sales interview is a salesperson selling themselves; hire for the characteristics that predict performance rather than how someone carries a room.
  • Stay open to being wrong about who will make it — Cole has been surprised roughly 20 to 30 percent of the time.
  • Audit your comp bands for the early hire who is now a star but still sits at the bottom of the range, and fix it before a competitor bids.
  • Put a review process or system in place that flags tenure-versus-band drift automatically, so the fix does not depend on a manager noticing.
  • Spend more than you forecast when a team is genuinely under-resourced, and treat the overrun as the consequence of having forecast wrong.
  • Remember that a good product to sell is itself a retention tool — selling something you believe helps the buyer is what makes the job fun.
Operations Takeaways

By function

The same conversation, filtered for RevOps, pipeline/marketing ops, and customer ops.

Revenue Operations

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Metrics Mentioned

The numbers, with context

3 hours
Callback SLA

Cole's stated standard for returning customer phone calls; channel partner calls were same day. Published to partners so 'responsive' had a number attached.

Age 27
Running the sales team

Cole was leading the entire sales team by 27, after opening a Texas territory from zero selling commercial loans to dentists.

4 appointments a day, 4 days a week
Rep appointment cadence in the original playbook

One of the activity-level items in the recipe Cole wrote, with Mondays or Fridays reserved to catch up.

20–30% of the time
Times Cole was wrong about who would make it

How often someone he doubted succeeded through determination, curiosity and repetition — his argument against hiring for personality.

3–6 months
Capitulation window

How long it typically took a new rep to stop executing the playbook obediently and start owning it in their own voice.

4
Things everyone should expect off the elevator

Clear performance expectations with manager alignment, fair compensation, respectful treatment, and the tools to do the job.

4–6, reviewed every 2 weeks
Leadership priorities tracked

Cole's OKR cadence as CRO: the handful of things that matter most, with a leadership meeting every two weeks against the quarter's called shot.

Up to 50% base increase
Catch-up raise for a stale top performer

The size of unprompted increase Cole would give rather than wait for a competitor to offer 50 percent more and then match it.

Under $10M to $120M in revenue
Beam Benefits growth under Cole as CRO

From the episode's guest background, alongside a decade-plus leading small business sales and BD at Bank of America and running BD at LendingClub through its IPO.

10–15 years
Career switching cost sets in

Cole's marker for when you stop having a job and start having a career, after which changing direction carries a meaningful cost.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

BranchFintech / Workforce Payments

Cole's employer, where he is Chief Revenue Officer. Introduced in the cold open as the workforce payments platform.

00:06Company →
LeanScaleGTM Operations

Anthony's company, used as his worked example twice: early hires who took a bet on the company at low starting pay and get caught up quickly once they perform, and the team he built around people he chose — including his childhood best friend, his wife and his youngest sister.

32:28 · 1:08:03Company →
RipplingHR / Workforce Software

The HR system Anthony's team uses to flag compensation drift — it surfaces that someone has been in a role a while and is paid below comparable people, prompting a raise before the employee has to ask.

33:40Company →

People

Cole Gillespieguest

CRO at Branch, the workforce payments platform; previously CRO at Beam Benefits and a decade-plus leading small business sales and BD at Bank of America and LendingClub.

Chief Revenue Officer, BranchProfile →
Anthony Enricohost

Co-founder of LeanScale and host of The LeanScale Podcast.

Co-FounderProfile →

Tools & software

SalesforceCRM

Cole dates his original rep playbook by noting it predated Salesforce — he could not download funnel metrics or conversion rates, so he compiled them by hand.

Website ↗
ClaudeAI Assistant

Anthony's running joke about the Dad Wisdom text thread: give it a couple of years, plug it into Claude, and Cole's kids will not miss a beat. He returns to it in the wrap.

Website ↗
Methodologies referenced Writing the rep recipeReputation SLAsThe career obituary exerciseTwo-week leadership metric reviewProactive band catch-upThe resourcing check-in call
Related LeanScale Services

Where this shows up in the work

Sales Enablement Build

Stand up a zero-based, sales-academy enablement motion sized to your span of control and sales complexity.

Cole's recipe is a sales enablement artifact built the hard way — the tactical detail of a top rep's day turned into an onboarding framework, with activity expectations, reputation SLAs and funnel-based coaching attached.

Frequently Asked Questions

Straight answers

Generated from the conversation, marked up for search and AI extraction.

What does it mean to replace yourself before getting promoted?

Cole Gillespie, now CRO at Branch, was told early in his career that he could not leave his rep job until he had replaced himself. He assumed it was impossible, because he believed being charming, outgoing and charismatic was what made him effective — and you cannot hand someone your personality. Writing down what he actually did every day produced something different: how many phone calls he made and when, how he followed up, how he stayed organised, four appointments a day four days a week, and the funnel maths behind it. The result was a recipe another person could run. It turned out to be more valuable as an onboarding document for future reps than as his own exit ticket, and he still asks the same question when new reps join: what is our recipe, and what framework are we putting them into?

What is capitulation in sales management?

Capitulation is the term Cole Gillespie used for the moment a new rep stops executing a playbook obediently and starts owning it. He would place a rep in a market and insist they follow the steps. Some would work through the tasks the way you would follow a cake recipe — useful, but without intent and motivation behind the actions it does not produce much. Then, usually three to six months in, the rep would come back and say: I get it, I know how to do this, I'll do what you told me to do, but I'm going to bring myself to the job. That is the point Cole was waiting for. Product and process knowledge is the foundation of a good salesperson, but the rep's own personality is what makes the foundation work.

What is a career obituary and how do you use it with a sales team?

The career obituary is an exercise Cole Gillespie ran with his reps: write what your manager, your peers and your customers will say about you when you leave this job, then work backwards to the behaviours that would earn it. He built it from a pattern he kept observing. Travelling a market with a rep, the channel partners would say glowing things to their faces. After that rep left, the same partners would say the opposite — this person never followed up, never understood my deals, never kept me updated. His conclusion was that the reps who left almost certainly never knew. Deciding the reputation you want in advance makes it something you can manufacture deliberately rather than discover on the way out.

How do you turn a vague expectation like 'be responsive' into something measurable?

Attach a number and publish it. Cole Gillespie's point is that nobody argues with 'be fast to follow up' — but if fast to you is two weeks and fast to me is two hours, both people think they are right and the relationship still breaks. So he wrote specific service levels into his own working standard: customer phone calls returned within three hours, channel partner calls returned the same day. He then told customers and partners the standard up front, so when someone asked whether Cole was responsive, the answer was a number rather than an impression. The same specificity defuses vague criticism. Rather than getting defensive, he could state the standard he works to and ask what actually happened.

What should every person on a revenue team expect from their leader?

Cole Gillespie gives anyone on a revenue team he leads a four-part contract they should expect the moment they get off the elevator. One, they should understand what good and bad performance look like, and be aligned with their manager on it. Two, they should be compensated fairly — he is careful to say fairly, not the best. Three, they should be treated with respect. Four, they should have the tools necessary to execute their job. If any of the four is missing, they are expected to raise their hand, because it is the leader's problem to fix rather than the employee's to absorb. He also uses the list as a zoom-out audit when managing managers: is it actually true, to the standard we claim, that everyone here has all four?

Should you raise a top performer's pay before they ask for it?

Cole Gillespie and Anthony Enrico both say yes. The scenario is the person hired at a junior level and at the bottom of the comp band who turned into a superstar — fair when they joined, stale now. Cole would rather hand over an increase of up to 50 percent that nobody asked for than wait for a competitor to bid and then match, because the employee is entitled to ask why they had to ask. Anthony's arithmetic is that a little more salary is nowhere near the cost of recruiting, ramping and an empty seat, and that you also forfeit what that person would have become over the next six to twenty-four months. Both think the usual cause is negligence rather than malice: the information never reaches someone with the agency to fix it, or no review process flags it.

How do you tell an under-resourced leader from one who is empire building?

Cole Gillespie admits it is tricky, and offers two signals. The warning sign is the leader in whose organisation every new problem or request resolves to a new hire — that is someone solving for the easiest path rather than for efficiency and effectiveness, without the cost structure in mind. The counter-signal is the leader who takes on everything, never complains, and starts scrambling. That is the person Cole calls proactively to ask whether they genuinely have what they need. His related advice for maturing leaders is that people will roll balls to your feet, and the moment you pick one up you own it. Sometimes what presents as under-resourcing is actually over-prioritisation, and that is a management conversation worth having.

When does a career stop being survival and start being a choice?

Cole Gillespie's answer is: the moment your basic needs are met, whatever those mean to you. He describes a career of obvious next steps — inside sales to outside sales to management — each one logical, better paid and more recognised. Once the house, the car, the food and some discretionary income were covered, every further promotion stopped being a step and became a trade between job satisfaction, impact, who you work with, industry, title and compensation. He did not appreciate that at the time and plotted through promotions until he looked up and realised he had chosen a career without deciding to. Ten or fifteen years in, the switching cost is real. It is the lesson he most wants his kids to carry, and why he asks aspiring CROs why they want the job.

Timeline

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Click any chapter to open it in the transcript.

00:00Cold open + intro 01:14"You can't leave this job until you replace yourself" 03:12Writing the recipe for a sales rep 04:27How much of sales is process versus personality 05:44Capitulation: when a rep stops copying and starts owning 08:08The trap of hiring for personality 14:33The career obituary 18:00Turning "responsive" into a three-hour SLA 21:15The four things you should expect off the elevator 25:01OKRs at the VP level, activity at the rep level 29:36Paying fairly when your best rep joined at the bottom of the band 36:39The raise nobody asked for 42:10Resourcing the job — the fourth thing, and the one leaders skip 49:30Respect, friction, and the "no assholes policy" problem 58:01Dad Wisdom 1:00:09When a career stops being survival and becomes a choice 1:04:00The cocktail: comp, title, industry, people, impact 1:11:05"Why do you want to be a CRO?" 1:12:19Wrap
Full Transcript

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Broken into chapters, searchable, verbatim from the audio. Speakers inferred (not diarized).

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00:00Cold open + intro

0:00 "My thing I will have to say is just be careful. People are going to roll balls to your feet. Just be careful which ones you pick up."

0:06 Cole Gillespie is the Chief Revenue Officer at Branch and he is one of the

0:11 few revenue leaders who will tell you flatly that sales is a teachable craft,

0:15 then get a little heated defending it. He started out selling commercial loans to

0:20 dentists, which he is the first to admit he knew nothing about, got shipped to

0:25 Texas to open up a new territory from Xero and was running the entire sales team by

0:30 the age of 27. "Sales is, it's trying to convince somebody to buy something that

0:39 you genuinely think is going to be good for them. They called it a career

0:43 obituary. But if you, if fast to you is two weeks and fast to me is two hours

0:51 then we're, we're in trouble." Yeah if they have to ask it's already too late.

0:56 In this episode Cole walks through the entire arc and the lessons he would hand

1:01 to anyone starting a career today, including his own kids.

01:14"You can't leave this job until you replace yourself"

1:14 Cole, early on your boss told you he would promote you to run the sales team

1:19 but only after you replaced yourself, what happened when you actually sat down

1:25 and tried to write down what you did? Yeah it was, it was one of the harder

1:33 things I think I had to do. Important context, I was a fairly young person

1:39 right, professionally, kind of earlier in my career, and I had a great boss. The guy

1:45 I worked for at the time was one of the founders and still one of the most

1:52 influential people in my career. So oftentimes I'm still liable to quote him

1:58 to some of the people that were close to me or around me. I'll pull up

2:03 John's name. But I was, and I know I say I was running the sales team, that's true.

2:09 They reported to me I still feel like John was the leader of the sales team

2:14 and was the man. But I was doing like fairly well as a rep managing a market

2:22 and traveling around and carrying a quota and doing all those things. And he

2:28 wanted me to step up and lead the sales group and have those people report to me.

2:33 And the challenge was, listen you can't leave this job until you replace

2:39 yourself. That was the challenge to me. Of course Anthony I was like very eager

2:44 to be promoted. You know what I mean? Like the second he told me I was

2:48 promoted I was like let's go tomorrow, tomorrow couldn't come fast enough. So it

2:54 was an interesting challenge for me though because I think at the time I

2:57 thought, although I tried to be methodical about the process of sales, I

3:03 bet you it's true that I thought, you know, that being charming or outgoing or

3:09 charismatic was really important to the sales process. And so like how could one

03:12Writing the recipe for a sales rep

3:13 do that? How could one replace their personality? So it forced me to dig into

3:19 the actual tactical like what is it that I do every day? How many phone calls do I

3:23 make? When do I make them? How do I follow up? How do I stay organized? Really the

3:31 funnel and the science behind going through the process. And it was

3:33 interesting to map it all out. And once I started doing it I got really excited

3:38 about almost like writing a recipe to be a sales rep. It was such an important

3:45 document. Like I found it incredibly useful even to onboard future reps

3:49 because I would say I actually have a game plan. If you follow this game plan

3:53 there's some comfort in knowing that, you know, it inject your own personality into

3:59 it and you might find success was like incredibly, incredibly helpful. And so in

4:04 a lot of ways it was helpful for me to put on paper the things that I was doing

4:09 tactically that maybe made me effective. But it was also an incredibly useful

4:14 tool to onboard future sales reps and something I still think about. Like when

4:18 we're when we're onboarding new reps I think about what is our recipe and what

4:22 is the framework that we're gonna put a rep into. Yeah so it was valuable. If you

04:27How much of sales is process versus personality

4:27 had to put a weight to it because it does feel like there is some component

4:32 of personality, likability, natural, EQ that you may have versus the process.

4:39 What percentage would you say sales is on the process side? If you follow the

4:45 playbook you can be successful versus some skills you need on the personality

4:50 side. Yeah so I think what's important I used to call this, Anthony, I used to

4:58 call this capitulation. So we would we would put a new rep into a market and I

5:04 would say and at the time I was probably fairly strict about it. I was like follow

5:09 this playbook it's going to work. Hopefully I do a better job of being less

5:15 kind of you know rigid about it. But you would see people you would see people

5:22 kind of like obediently go through the tasks. Does this make sense? Like follow

5:27 it as if they were baking a cake and and although there's value in that you

5:34 really want you really want there to be meaning behind the action like just

5:38 following the steps is valuable but if there isn't kind of intent and

5:42 motivation behind the actions it's it's not that useful. And so I would call it

05:44Capitulation: when a rep stops copying and starts owning

5:48 capitulation which is inevitably three or six months in the rep would say I got

5:52 it. I know how to do this but I'm just gonna be myself and I'm gonna do what

5:56 you told me to do and I'm gonna bring myself to the to the job and you're like

5:59 good now we're getting somewhere. So I said that in the answer to your question

6:04 which is like I think product and process knowledge is it I think it's the

6:09 foundation of a good salesperson and I really really believe that you can teach

6:13 the craft of selling something to people to roughly anybody which I love this is

6:20 a thing I love about selling. But it is hard to deny that people who are

6:26 naturally extroverted people who are naturally sort of high in EQ and maybe

6:32 people who are genuinely curious about other people and good listeners are

6:37 going to make good salespeople. So that is true. I think where I hedge is I don't

6:44 like it all the notion that you have to be necessarily one personality type to

6:50 fit those criteria. Does that make sense? So when I say it doesn't make sense yeah

6:55 yeah so so I sort of resent the idea that salespeople of any kind are sort of

7:04 like one flavor of human in in and to give you an example I've I've worked I

7:10 remember early on in my career working with somebody who I really really like

7:14 liked then and still like today and he was so opposite of my personality right

7:21 and I found him incredibly charming I thought he was incredibly likable I

7:26 thought he was a fascinating person with fascinating interests and he was a great

7:31 salesperson he really was he was fantastic but we share roughly nothing

7:37 in common right and I just think that's a good example of like how these things

7:43 can work out. Was there anyone throughout and maybe this is the person but was

7:48 there anyone throughout your career who you feel most people would have written

7:53 off as not able to cut it in sales that really surprised you by being diligent

7:58 going through the playbook learning the craft and then applying it? Yeah he's he's

8:05 somebody that comes to mind but I but I will tell you like I've been surprised

08:08The trap of hiring for personality

8:13 20-30 percent of the time where I meet somebody who I think is this person

8:19 gonna make it in through determination curiosity repetition you know what I

8:26 mean that that it ends up working and I end up being completely wrong it's it's

8:32 a great lesson for hiring because when you're hiring for people if you're

8:36 hiring for a personality you can fall into that trap. I've seen a lot of

8:41 really good personalities that don't close any deals too so I've seen that

8:44 side of the equation as well. This is what I think is so I'll talk to like

8:49 founders a lot and in particular technical founders engineering product

8:54 types and they're looking to hire their first like go-to-market theater or they've

8:58 hired their first couple you know salespeople and I'll say it's hard right

9:05 because salespeople tend to be really charming and really good at sales and an

9:09 interview is kind of them selling themselves it's it's really got a hard

9:13 to vet salespeople if you haven't like lived in that ecosystem and hired a bunch

9:18 of salespeople before so I think like exactly to your point I'm completely

9:24 open-minded to being surprised so I try to stay really disciplined around hiring

9:28 the characteristics of people that I think will make good salespeople and less

9:34 on the this person you know looks a certain way acts a certain way behaves a

9:39 certain way in a room and therefore here she will be really good at sales and I

9:45 think like going into sales I sort of thought I sort of had like an allergic

9:51 reaction to the idea that I was a salesperson early on you know um do you

9:57 ever meet people who go home for Thanksgiving and they say I'm in business

10:01 development they don't say they're in sales you know when asked right like a

10:06 little bit embarrassed by the trade yeah yeah yeah I don't like that but I

10:14 think that's that was maybe me earlier because I thought like sales was about

10:19 manipulating people you know like salespeople had moved

10:24 Anthony you know they were taught techniques on how to manipulate people

10:29 and I didn't like that at all I thought that was like not something I wanted to

10:34 be associated with and then what I think I learned and got really excited about

10:38 later was the idea that sales is it's trying to convince somebody to buy

10:46 something that you genuinely think is going to be good for them right right

10:51 right and that's a lot of fun you know that's I give you can I give you an

10:58 example I share with people yeah I say I think one of the best jobs in the world

11:05 would be if there is a cure to cancer to be the sales rep of the cure to cancer I

11:12 know sometimes that rubs people the wrong way but how exciting would it be

11:16 to like pull the list of everybody who has like let's go the people have the

11:20 most severe they have like they're in terrible prognosis yeah and you have the

11:26 cure for them and you can get them connected and make it happen I mean what

11:30 an amazing job that would be I think you're right but I never admittedly

11:37 never thought of that people have a bad reaction to that they think like

11:41 commercializing the cure to cancer is gross I think it's taking it yeah it's

11:45 taking it that way but I just mean connecting people with problems to a

11:47 product that can solve it yeah I don't get into the pricing mechanics of it I

11:54 kind of leave the metaphor just at the connection piece I'm sure it could be

11:58 taken that far but but I think the point is when you're when you're representing a

12:03 really good product that's solving a real problem sales is fun when you're

12:09 not when you're trying to push a product that isn't really adding a lot of value

12:12 it's a night yeah totally agree totally and this is this is like I think that's

12:19 really good advice for people who are thinking and I'm sure that's obvious

12:22 right people are thinking about am I happy in this job do I want a different

12:27 job in the obvious thing that comes to things that come to mind are like how is

12:32 my title what's my compensation structure right those are kind of how am

12:37 I going to be able to hit quota there's obviously important things but how

12:44 passionate you are about selling the product how how passionate you are about

12:49 genuinely trying to convince somebody to do something you think is going to be

12:52 good for them is an exciting that's an exciting product to try to sell and I

13:00 love spirited debate and I love having those types of conversations with

13:07 people and so if I feel like the product is going to be valuable for you I have a

13:15 fairly insatiable amount of energy to try to convince you to do it and if I

13:20 didn't I think I'd be really bummed that I wouldn't want to do it anymore you

13:24 know to me like I would be I would be a legitimately bad salesperson that's I'm

13:29 sure that's true yeah at your core if you're not believing in what you're

13:34 selling it's very very hard to do and I have been in some companies where I'm

13:37 like the product is okay but it's not getting me super excited and making me

13:45 want to jump out of bed every morning yeah and that's a tough spot to be I'm

13:50 curious if we could go back to your playbook and when you first started to

13:56 codify the things that you were doing what's in there what what's something

14:00 that you follow to this day you've taken that playbook and shared with sales

14:05 people what are those core things that every salesperson should be following

14:09 yeah so there were now keep in mind this was like I'm gonna date myself but this

14:15 was like pre Salesforce you know I mean so was it like you were just gonna be

14:20 like download my funnel metrics and here's what my conversion rights look

14:23 like and all of that right so I had to do some of that stuff by hand I know

14:27 that sounds crazy so what what I think is interesting is there were there were

14:33The career obituary

14:33 the obvious things that you had to do there were like I make this number of

14:37 phone calls every day I have this number of prospects that I reach out to right I

14:41 go on four appointments a day four days a week I use my Mondays to catch up or

14:47 Fridays to catch up on X Y and Z there's that was really valuable because that

14:51 was activity level stuff that was going to be helpful right but the interesting

14:57 thing and the thing that I think was was a little bit more eye-opening for me

15:02 was there were a lot of like qualitative metrics in there that were really

15:07 helpful to define so I'll give you an example so I would write I remember I

15:12 did this exercise with the team and I called it it's a little bit a little bit

15:16 more bit but hang in there with me which is like I called it a career

15:19 obituary I've brought up the cancer example so I called it career obituary

15:30 and the idea was like when you leave your job what are what will your manager

15:35 say about you what will your peers what will your customers say about you in the

15:39 in the sense that I had the opportunity where I would work with I would travel

15:44 into a market right and I'd go on appointments with a rep and he or she

15:48 would take me around to all of the you know it was very channel driven so he or

15:54 she would take me around to like a lot of the channel partners that they were

15:58 working with who would say glowing things oh I'd love so-and-so and they're

16:02 great I really enjoy working with him or her and then I would leave and then you

16:07 hear a bunch of stuff right guys are they would leave mm-hmm I would come back

16:12 and say so-and-so left we're gonna bring a new rep in they say oh well good

16:15 because this person never followed up they never understood my deals they never

16:19 kept me updated I rarely you get it right I thought that's fascinating

16:24 because I bet the people who left don't know that it totally makes sense yeah

16:30 no I just think any like proactive reflection to kind of put yourself in

16:36 that endpoint and then bring you down to the current point you know sometimes not

16:40 not to get too like philosophical but people do that about their lives like

16:43 hey what is what are people gonna say about you at your funeral type of thing

16:46 so how do I live today like that I think this probably won't create as much

16:52 existential dread for people but keeping them locked into their career knowing

16:55 hey did I do everything that I should have done or I'd want my legacy at this

17:02 company to be I think it's very smart so along those lines you asked me the

17:07 question about the like the formula I would develop like okay well I want my I

17:13 want my channel partners to think I'm responsive to think I you know I'm

17:19 honest in my communication to think that I'm knowledgeable about the product the

17:23 process and the competitors knowledgeable about how to help them in

17:26 their business right wasn't a lot of things it was like a handful of things

17:28 and then I thought what a great gift this is because I can actually

17:32 manufacture that reputation if I do those things right great but here's the

17:39 catch was like inevitably somebody would say well be fast to follow up with me

17:46 right if that makes sense who would argue with that nobody but if you if fast

17:53 to you is two weeks and fast to me is two hours then we're we're in trouble

18:00Turning "responsive" into a three-hour SLA

18:00 because I think I'm fast and you revise first you think you're fast and I don't

18:05 think you're fast at all right because my my priorities are my idea of fast is

18:09 different so there were these like subjective qualitative things that I

18:13 started to dial in which is like I return customer phone calls in three

18:17 hours I return vendor you know channel partner phone calls same day and so I

18:22 started building like little SLAs into what I did this is like how I replaced

18:27 myself yeah and and then it was helpful to clarify that in communication with

18:33 customers and channel partners which is listen if you reach out to me and you

18:37 don't get me expect to hear back in three hours that's it that that's what

18:41 you should expect okay got it and then when somebody would ask how was cool is

18:45 he responsive they'll say yeah he gets back to me in three hours that's the

18:48 expectation I have any other good enough and I thought that was like early on in

18:54 my career I thought this is this is really helpful for me because I don't

18:58 have to like I can I can manufacture sort of the reputation maybe might be too

19:07 much of a loaded word right but how partners feel about me and customers

19:11 feel about me because I can set a standard and then just behave my way

19:15 into it and and I will say it was helpful where sometimes people feel like

19:22 you're not doing something that you that you feel like you're doing I mean that

19:25 stuff happens all the time but it was right right and so it was helpful to have

19:30 this like agreement with people who worked for me and with me in a similar

19:35 way where they say I don't think you're like you know I don't think you're

19:40 really good at following up with me or you know including me in these things

19:44 are doing XYZ and instead of getting defensive which I would be prone to do

19:50 you know I would say stuff like oh really shoot because I tried that's a

19:58 thing I try really hard to be good at and the way I try to do it is this way

20:01 but it sounds like I didn't do that all that well can you tell me what happened

20:06 well I don't really have an example for you just it feels that way okay well

20:11 understand this is what I'm trying to do and that's the approach I try to take so

20:14 and so now I took something I might overreact to or get defensive into and to

20:19 just curiosity well and I think the specificity of everything to like rather

20:29 than just throwing out words assuming we're all on the same page and it's

20:33 like you're using the same words but speaking a different language yeah so

20:37 having that specificity in the detail behind it to say hey yeah this is a okay

20:42 this is the agreement we had these are the standards that we understand and

20:45 there's not ambiguity baked in it's very clear of what you what you need to do I

20:50 imagine and I know we talked about this a little bit on our prep session for

20:54 this imagine when you're building teams and you're scaling the reputation

20:59 standard that you have with your team that part of the contract is super

21:03 important yes yeah I I can be pretty specific about this like I'll tell roughly

21:15The four things you should expect off the elevator

21:15 anybody who who works in the revenue or get a team I'm leading that when they

21:23 get off the elevator they should expect at least four things okay one they should

21:27 expect to understand what good or bad performance looks like and they should

21:33 have alignment with their manager okay they should be compensated fairly for

21:38 that I didn't say the best okay I didn't say it's fairly they should be treated

21:44 with respect and they should have the tools necessary to execute on their job

21:49 that's standard everybody gets that and if they don't they need to raise their

21:54 hand right because that's our problem it's something we need to give to them

21:57 and so that's that's the table stakes and the reason why that's important to

22:02 me is like on the on the first one I spent a lot of time early on in my

22:08 career managing the feelings of people who worked in the organization on

22:15 whether they were doing well or not they the feeling that they weren't doing well

22:19 or the inadequacy that they weren't getting enough positive feedback or the

22:24 feeling of misalignment of like I'm almost interpreting my manager's

22:29 response to slack messages or text messages or emails or phone calls and it

22:34 doesn't sound like he or she is like that happy with me I wonder if I'm doing

22:38 a bad job right does any of this sound familiar to you I've I've been in that

22:42 situation on both sides I've been in the situation where I'm wondering am I doing

22:46 what I'm supposed to be doing because I think I am but tones weird you're not

22:51 very specific we're not responsive and then I know I've been in a leadership

22:56 position where I haven't set the standard of what good looks like well

22:59 enough and I know when people come to me asking it's like oh if you have to ask

23:05 then I haven't made this clear enough yeah it's your responsibility right right

23:10 yeah yeah yeah and in I'm particularly I'm particularly trying to solve getting

23:17 getting rid of that percentage of your life that you spend worrying about it and

23:22 getting it focused on the job and so it's interesting to learn how much like

23:29 mental stress and anxiety people can spend trying to interpret whether they're

23:35 doing a good job or not or reaching for the things that they might be thinking

23:39 looks like good performance and one I think it's just a bummer of a way to do

23:43 your job like if you're going into a performance review and you think I hope

23:48 my manager thinks the way I do you're off to a bad start like that's a I would

23:55 feel bad as a manager that that person feels that way and so I want to eliminate

23:59 that I just want I just want everybody to say I think I know what good

24:03 performance looks like in my boss and I are aligned on what that is now I can

24:06 objectively look at my performance and we both can't and say whether it's good

24:10 or bad and I think there's a lot of value in that I think it gives people a

24:15 lot of comfort on what they need to work towards and I think it takes a lot of

24:18 noise and extracurricular activity that can be focused on the job out of the

24:22 equation and then I the rest of the stuff I think is fairly straightforward

24:28 I think it might be straightforward but I'd actually like to dive in a little

24:33 bit more detail because I think somebody especially kind of moving into a sales

24:38 management role for the first time this is so classic you take happen to you

24:43 it's gonna happen to salespeople till the end of time you take a great rep take

24:49 them out of the field now they start managing and it's a whole new skill set

24:52 it's a whole new thing so when you're setting the expectation of what good

24:57 looks like maybe some examples how specific do you get I know we talked

25:01OKRs at the VP level, activity at the rep level

25:01 about SLAs on things but is there anything else in there that might be

25:04 surprising to a sales manager of how specific you are to directly communicate

25:09 what good looks like so I traditionally work on like an okay our system that's

25:18 probably not revolutionary right so I think when managing like I'm in my role

25:23 today as CRO I'm gonna be managing VPs so it's my job to set the strategic

25:29 priorities of the revenue organization align them as closely as I can to the

25:32 founders vision in the company and then make sure every individual department

25:36 understands how they can set their strategic vision for their department in

25:41 line with mine and then I allocate resources to those leaders in order to

25:45 hit the objectives that I most highly prize okay so to the degree that I

25:49 miss allocate resources then I'm likely not prioritized appropriately and that

25:55 would be people time or money right there's normally the resources that I'm

26:00 dealing with so at that level I try to keep it succinct enough that what are

26:06 the four to six things that we care the most about how are we doing on those and

26:11 then are we regularly checking in on those I do I do a meeting with my

26:14 leaders every two weeks and we try to call our shot for the quarter in terms

26:19 of metrics that are going to lead to success how are those going what did we

26:23 think was going to happen if it's doing better why if it's doing worse are we

26:27 cutting bait do we understand what we've learned and then we we kind of move on

26:31 so that's the way I do it today and I try as hard as I can not to be more

26:37 prescriptive on the tactical activity level stuff that has to be done because

26:41 I want to give people the agency to operate inside of a framework that I'm

26:45 setting the strategy for make sense makes sense now but on a rep level I will

26:53 get far more specific about here's the activity expectation than I expect okay

26:59 now activity you're responsible for okay so nothing words you can give me effort I

27:06 can't really get effort from you like it's not my job to pull effort from you

27:10 of course I need to give you an environment where you can flourish and

27:13 you feel motivated and all of the things I said before are still true but you

27:17 need to bring the effort to the job that really is your responsibility not mine

27:21 and if I've hired correctly I usually have to turn people down not up in that

27:26 in that world right usually people are shot out of a cannon yes I also phrase

27:32 it the same way I want someone you know pushing me not me needing to push them

27:37 too yeah so when I feel like oh wow I better keep up with somebody that I've

27:41 run on the team yeah that's a good that's a good sign yeah my challenge is

27:45 usually I need if I'm managing a rep I need to be the second moment most

27:49 informed person in their territory second mm-hmm if I'm one we've got a

27:54 problem because now I'm more I I am now more knowledgeable about your market your

28:02 territory your competition your funnel your customers than you are that's not

28:06 great that's not great so you owe you owe me the effort you OS the effort and

28:13 then when it comes to quality it's a collaborative effort where I'm these any

28:18 deficiency that we see in the funnel tells us something about a coaching

28:23 opportunity an opportunity to improve so you're really good at driving but you

28:27 know pipeline and people are very interested in the pipeline but we're not

28:31 seeing the conversion rate that others are seeing or that we would expect that

28:35 you expect for yourself that's fine I bet you somebody has a solution out

28:39 there together we can work on a solution to how to improve it it's not a problem

28:43 sent from God this is you know something we can work on together and so who's

28:47 really great at it what are they doing what can we incorporate into that now

28:50 as a manager I can help you do that and I should help you do that but that's you

28:57 know I think that's where I get into the recipe type stuff is I'm getting I'm

29:00 mixing the activity level with the quality makes it makes a ton of sense

29:06 and then and then moving into the second one compensating fairly easy to say I

29:12 think most people want to do that I don't think anybody's leading a team

29:15 saying I'd like to underpay the team and then just hope they do well I do think

29:21 sometimes though especially now this this might be one of the first times I'm

29:25 experiencing this and in my career is with inflation and and things changing

29:31 like what does good compensation look like where do you go to make sure that

29:36Paying fairly when your best rep joined at the bottom of the band

29:37 you are compensating the roles fairly yeah so our people department does a

29:42 good job of using you know like named database of roles that give you

29:48 compensation bands that we try to stay you know have a benchmark for and stay

29:52 in there so it acts as like our source of truth for our we objectively inside

29:57 of a pay band for our region and for the role relative to comparable companies

30:04 but I expanding on your point do we're were you leading people during the

30:12 pandemic and sort of the you were okay I started first real people leading was

30:21 probably 2015 or so where it's like a sizable team and and working on that and

30:28 then pandemic hit and things started to really expand especially in the tech

30:34 industry and then ever since it's just like what what does good compensation

30:41 look like sometimes it looks really good here and even certain regions you know

30:47 we'll get candidates that are really excited about a certain thing and then

30:50 others where we're like three times off and like how is there that much

30:54 disparity in pay expectations out in the market right now well I break yes I

31:00 agree and I bring it up because there was a moment somewhere like in or coming

31:05 out of the pandemic where there was a shortage of talent people are just like

31:08 paying like crazy for talent everybody's everybody's comp was just going up

31:13 dramatically and it was a real challenge to try to understand am I paying fairly

31:18 am I paying appropriately in and I'll give you I'll give you another example

31:24 you tell me whether you've experienced this or not you hire somebody in a sales

31:29 role who is a little bit more junior so they're on the lower end of the comp

31:34 spectrum comp range and they're an incredible out performer they end up

31:39 being a complete superstar that you think is you know going to continue to

31:44 do great things for your organization for a really long time but if you're

31:48 being honest their base salary in their OTE is lower because of their you know

31:55 experience when they joined and that that's fair because you took a chance on

31:58 them and they took a chance on you so that's that's fair but if you look at

32:02 their performance today you think crap a competitor would pay probably way more

32:06 for this person today because it's been a few years and they're just a star and

32:10 then you're left with the challenge of like am I getting a deal is that what

32:14 I'm trying to do am I compensating this person fairly or am I legitimately just

32:18 hoping they don't get an offer from one of my competitors because then I'm

32:22 gonna pay them up yeah right right have you been in that scenario before 100%

32:28 and especially here at at lean scale we have people the very beginning there's

32:33 only so much we could pay at the beginning so like a ton of people took a

32:38 real bet on me took a bit on the company and then I am so quick to for high

32:45 performers so quick to catch them up to where we think that role should be with

32:52 the right experience because also if you lose that person the amount you're gonna

32:58 spend on recruiting and time and not and having that seat vacant it's like what

33:03 is what is a little bit more in their salary versus the cost of needing to go

33:07 fully replace this person it's not even close yeah yeah the the I think it's

33:14 great you do that by the way I do you think do you think that's unique I don't

33:22 think people are intentionally not upping people's pay but I don't think

33:29 they're paying attention to it I think what happens is they have their eyes on

33:33 other things and then a couple years go by and they haven't really addressed it

33:37 or they maybe don't have a really great review process where it's getting flagged

33:40 we have it flagged we use we use rippling and it'll literally say like

33:44 this person's been here a while and compared to other people in the role you

33:48 might want to up their stuff they're like okay yeah so I think some people it's

33:52 more just negligence and then and then that person leaves and not even not to

33:58 make it like too exaggerated but you're not just missing their performance at

34:01 that time if they were a top performer you're missing what they're going to be

34:05 in the next six months 12 months 24 months - so you're missing out on that

34:09 potential and totally agree and they won I agree with your assessment I don't

34:15 think I hopefully people aren't doing it in a

34:19 malicious way I think legitimately either that that information isn't

34:22 bubbling up above their manager level right maybe the manager doesn't know

34:26 they have agency to actually increase a salary pretty dramatically to catch

34:29 somebody up so I think there are a lot of reasons for it but I do think it

34:34 happens and and what I would add is that person or those people tend to be the

34:41 great culture people in your organization and they tend to be a great

34:46 kind of like examples of a growth in an organization looks like and so you know

34:51 you love to have those people who started started you know as an SDR or

34:57 whatever had got an 80-year-old and was a little bit junior but then crushed

35:00 quota continue to go on and on and the stories are you know rocket fuel for the

35:06 other other folks that in the organization that see that person as like

35:12 of the people that they look up to and so to lose them is is heartbreaking so I

35:15 think setting that example as you're going through and exactly what you talked

35:19 about you're at a startup you're hiring people at disparate compensation bands

35:23 you're probably getting trying to get a lot of people on the boat we just want

35:26 to be a part of the team and so yeah salaries are a little bit mixed up and

35:30 you look back and it's been a few years and you think I might have to like

35:36 maybe give this person a 50% increase in their base salary and that person's not

35:42 asking for it but I kind of I'm kind of at a decision I'm doing it because

35:47 that's the thing I want to set the example to my team of no we we pay

35:51 fairly we're not looking for a deal and so they don't need to raise their hand

35:54 that's something that we do for folks so that you know a competitor doesn't say

36:00 well I'm willing to give you 50% more and we say oh well we'll match it's like

36:04 well if you were gonna match why didn't you just do it like why do I have to ask

36:07 for it yeah if they have to ask it's already too late and and I've been on

36:13 the receiving end of this too by the way I've had some fantastic leaders

36:16 throughout my career and I've wasn't even on my radar I was happy with my comp

36:22 I was really enjoying the job enjoying the cult everything we're doing and

36:26 excited about it and I would just get a call like hey we added more options and

36:31 increase your salary to this just want you to know like we're really excited

36:34 about what you're doing and to me I'm like oh my gosh we're gonna go run

36:39The raise nobody asked for

36:39 through a brick wall for this company like that would get me fired up so much

36:43 because it's not just communicating that it's communicating a level of trust in

36:49 every other aspect of your role and every other aspect of the organization

36:54 too because it's saying hey you see everything and you notice and you're

37:03 gonna treat me fairly no matter what it is and you're not gonna wait for me to

37:07 raise it as a red flag so it says a lot when you do that totally great in you

37:14 said an important word there which is trust in like there there will be times

37:18 where you have to deliver tough messages to people around changes that you're

37:22 making to territories or changes that you're making to quota or whatever you're

37:26 gonna eventually gonna be in a spot where you have to say this isn't gonna

37:31 feel really good but I'm gonna have to do it and and the the trust that you've

37:39 hopefully built by doing things like that will will hopefully carry you in the

37:43 conversation for somebody to say you've always done you've you've done the right

37:47 thing productively for me in the past and so although I don't like this I'm

37:50 willing to we have built trust enough that I'm willing to see it through and

37:56 that's I think that's like super important in keeping the culture right

38:02 now let me let me ask you this though have you had the opposite have you had

38:07 people where you were you were under earning and nobody said anything and you

38:12 found out I don't know if I ever found out but there's been a few times I

38:18 assumed and maybe the company wasn't in a position to pay at a certain rate or

38:25 not but it all it did was kept my eyes and ears open for any other potential

38:32 opportunity so if because it feels like hey I'm kind of getting used here and

38:39 if they would kind of keep my pay here and there were times where I would ask

38:43 like hey this feels low I'm doing some benchmark research I'm not asking to be

38:47 greedy it's just like this feels pretty low and yeah it just made me think okay

38:55 well then it also puts you in a situation where like I can't really meet

39:02 certain needs too so like I have to go somewhere else or find something else so

39:08 just puts you in that position right away yeah I admire people who can do that

39:14 well I'm not good at it I'm not good at lobbying for money on behalf of myself

39:22 I'll tell like any most people who come to me I'll usually say who asked for a

39:26 raise is good for you for advocating for yourself you know step one good for you

39:32 and I don't do that well so I'll like I don't know how to do it I don't know the

39:37 right words to use I don't feel right doing it like it's not a thing that just

39:42 comes naturally to me and I don't understand I'm comfortable in you know

39:47 other ways that might be conceived perceived as you know like not

39:51 confrontational but sort of like where friction might be involved so when I see

39:56 people do it well I think that's cool I don't know how to do that well I think

40:02 if you have if you have to do it then ideally you just don't have to there's

40:08 only been a couple times where I felt like I had to really speak up and say

40:11 something and if that's the case and there's probably already other stuff

40:15 going on unless you just have a completely wrong perspective but every

40:19 other time I have felt even if it was lower but maybe I had high trust I felt

40:25 hey I know they're doing the best they can and there's probably some

40:28 opportunities for growth later so I I trust they're not trying to get a deal

40:32 on my expertise or experience whatever it is they're just that's everything that

40:38 they can offer at this point in time but I also trust that it will grow in the

40:41 future I think that's okay but if you feel like hey am I getting screwed here

40:46 are they just doing this because they feel like they can yeah then it's just

40:50 more systemic than that yeah that's right and you make a good point which is

40:55 there there are times where companies just simply they don't have the

40:58 resources for it and you understand that that's different that's different from I

41:01 know you have the resources you're just not doing it it's important just right

41:05 right okay I'm taking a chance on earlier company but I also know coming in

41:09 here means as the company grows there's gonna be so many more opportunities so I

41:13 think that's that's okay but these are all the things where something as simple

41:17 as compensate your team fairly can be so much deeper and mean so much more than

41:24 just making sure their W2 looks good so I think you staying true to that and

41:30 making it important helps keep those teams keep them longer keep them

41:36 performing well and have that psychological safety to yeah keep doing a

41:40 good job I I hope so and I think the resources to do the job is one of those

41:46 things that might look obvious that's also important because there are times

41:51 where people need sometimes it's a manager who needs personnel you're

41:57 asking them for a performance and an expectation simply not resourcing them

42:01 with the people they need to do the job really well and that doesn't feel good

42:05 right I know what my performance is supposed to be you and I are aligned on

42:09 it I am being compensated fairly you're always respectful nice me but I don't

42:10Resourcing the job — the fourth thing, and the one leaders skip

42:13 you're simply not giving me the people or the money or the time to do the job

42:18 well and that doesn't feel fair so it doesn't feel like I'm being set up to to

42:22 be successful and I think just as a framework it's important to almost just

42:29 zoom out from some of these decision in particular when you're managing managers

42:32 and say well if this is kind of our if this is table stakes for people who work

42:36 here is it true that they have the resources to do their job is that true

42:41 to the standard that we expect and if the answer is no but well just tell me

42:47 though tell me the butt part right because I would rather spend more money

42:52 than I thought I had to spend to stay true to the thing of like it it's just

42:56 fair to give somebody the resources they need to do the job and so I understand

43:01 that there are financial repercussions of that or it's not what we forecasted

43:04 it to be but that's the consequence of being wrong so but we ought to do it we

43:11 ought to not do the alternative how do you how do you keep in check I agree

43:15 wholeheartedly I think I feel like maybe I have some judgment on when it's hey

43:22 this person's genuinely under resourced versus this person's just kingdom

43:27 building in the company and asking for the world and the results for their

43:31 coming I'm sure that there's a spectrum between those two things do you have any

43:36 way or questions you ask yourself to help discern if this person's asking for

43:42 stuff that's unreasonable or if it's a fair ask it's tricky right that part's

43:49 tricky yeah one symptom that seems like a problem to me is when when a leader

43:57 when every problem or new issue in it and that leaders organization can be

44:02 resolved by a new hire we have a problem mm-hmm okay so it's sort of like we

44:09 really need to do X Y & Z now for our customers okay we'll have to hire

44:13 somebody for that do you is that true right and then in it and it might not be

44:21 sort of like empire building but it might just be like the philosophy that

44:26 everything that needs to be done means incremental headcount I think is

44:30 somebody who's not solving to be efficient and effective they're solving

44:35 for you know the easiest path to success that way and without keeping sort of the

44:42 cost structure in mind so I think that's a that's kind of one of those red flags

44:48 for me is like is that is that true just because we have one more thing to do is

44:53 it true that we need an incremental headcount of a person to get it done so

44:59 that's not it's not the perfect self but that's one of those things that when I

45:03 see it I think hopefully hopefully that person's doing okay the other is like

45:07 when somebody's performance is starting when you're starting to worry you might

45:11 have had this experience where like this person has taken on a lot and it might

45:16 be possible they're getting close to being in over their head and they're

45:21 scrambling a little bit and the answer is always because they don't have enough

45:24 resources that's always the answer and your job as a VP is to manage resources

45:32 and to you know manage the strategy for your department that could be a sign of

45:38 a problem right so those are things I look for I think it's a delicate balance

45:44 admittedly I think when I get it right I call more by I actively call people I

45:50 did that this morning there's somebody who have a really really fantastic team

45:56 I mean that and I called somebody this morning because I know this person does

46:02 this person does anything and everything you ask mm-hmm and I I call more to say

46:10 how are you do you have everything you need yeah do you have do you feel like

46:16 you have everything you need to do everything you just told me do you have

46:20 that that's more of a concern for me any more than the than the opposite which is

46:26 probably which is a testament to them I think likely right yeah I think again

46:31 like when you're in a position where you have to hold people back versus needing

46:35 to push them I think that's that's us I've had I have had that too where I've

46:40 had to force people to take more resources like no you cannot take on

46:43 this other project you cannot take this other thing on you already have too many

46:46 things I already see that you're working all night and on weekends like I'm gonna

46:51 force you to take PTO you need to go on a vacation yeah like those which yes

46:57 fantastic people to have on your team but it is dangerous if you let them just

47:01 keep running they will burn themselves out too and yeah if they don't take

47:06 advantage of their kindness and goodwill and ambition - I think that's right and I

47:13 also think it's a good lesson in sort of helping the leader mature into their

47:19 role is like a thing I will say is just be careful you know people are gonna roll

47:25 roll balls to your feet just be careful which ones you pick up because people

47:30 roll them like balls come to my feet every time I just don't pick off pick

47:33 off them up because once I pick it up I own it right and so just be just be

47:37 careful that sometimes in an effort to be helpful you start picking a bunch of

47:41 things up and now you know their problems are your problems or what

47:46 somebody else could have done you're now responsible for and as a leader I

47:50 expect you to be able to have to be able to allocate your prioritize your life

47:56 prioritize your department allocate your resources appropriately and to the

48:00 degree that your priorities outweigh your resources that's also a managerial

48:05 thing that we have to work on right right and so that's fine that we need to

48:10 work on it but that is a part of the job so I know sometimes hero ball sounds like

48:16 a ton of fun but it's also maybe the sign that you know maybe maybe we're

48:21 over prioritized in your department and not necessarily under resourced and

48:26 that's a worthwhile conversation to have to absolutely you appreciate someone who

48:32 knows how to pass the ball to the fourth bucket that you had again sounds obvious

48:36 but I'm sure there's some depth to it everybody treated with respect are there

48:40 any non-obvious things that you see leaders doing management teams doing

48:47 that are really breaking that contract and they may not even realize they're

48:52 doing it I don't think being treated fairly means the same thing to everybody

49:02 right so it's sort of like am I fast well that's a relative term right and

49:09 maybe fair has some similarities to it and so I think you know I don't mind

49:17 Anthony friction okay I really don't sure um I I said before I like spirited

49:25 bait that's completely true I've you direct communication as a sign of trust

49:30Respect, friction, and the "no assholes policy" problem

49:30 so the faster I can be direct in my communication and you can with me I think

49:33 this is great we're starting to trust each other that's a good thing but I

49:38 think it's totally fair to be able to separate performance from somebody's

49:44 personality I think that's completely fair and so to objectively review your

49:50 performance independently to who you are as a person is fair so you can have bad

49:56 performance and still be a good person that's true good people have bad ideas

50:02 also that's that's also true and so I think conflating like maybe softer

50:11 things that are associated with fairness into that bucket is not really what I'm

50:15 talking about I think the thing I'm particularly excluding here is like I

50:20 don't like incivility I just don't like it so when people are not civil to one

50:27 another I that's not I don't like it it doesn't you should be fair to people in

50:34 in terms of etiquette and civility is important and I understand things are

50:38 gonna get the pressure is gonna mount okay and there gonna be times when we're

50:44 doing great and there's gonna be times where we feel like we're never doing

50:47 great and that's all baked in the cake that's all gonna be a part of the

50:50 experience we can control how we communicate to each other we can control

50:54 how we treat one another and we should not get so exercised that we start

50:59 treating each other unfairly that's not okay and so that's more the spirit of

51:05 what I'm talking about but I think it's not everybody gets treated like you're

51:11 nice to me a hundred percent of the time well that's not always true I'm not

51:17 unkind I would never humiliate you I would never you know I would never

51:23 demean who you are as a human as a brother as a son as a mother that's

51:28 completely out of bounds right but we can't we can't talk about your

51:32 performance objectively that's completely fair and consequently you

51:36 should be fair to me it's it's not always a one-way street you should be

51:41 fair as it as a worker in the our place of business and so that's a perfectly

51:48 reasonable bilateral contract to get into so that's more of what I mean I I

51:52 think people will take it to its true have you ever heard the term of like we

51:55 don't hire jerks sure yeah we have that we have a no ass no assholes policy you

52:01 ever hear that it's like the most common thing in the world that you're

52:03 absolutely and it's like with the fine asshole like it's um I'm open for

52:13 business for like a ton of interesting personalities you know what I mean I

52:17 really am I think I think it's like really interesting to work with people

52:22 with different viewpoints and different opinions and different I find it

52:25 fascinating and I'd love to hear it and then sometimes I'm prone to weighing in

52:30 and you should be open to that too that's fair so that's a little bit of

52:38 what I mean when there's should be like a standard of etiquette and treatment of

52:41 one another that reaches a level of civility that we all mutually agree is

52:46 above board and it's okay if it gets a little bit out of bounds it's okay but

52:51 you should take accountability and you said look at that was too much and I'm

52:55 sorry I got exercised and I probably shouldn't have said that and I apologize

53:01 and I do I do like a little bit of that too a little bit of that zest on the

53:06 team means you don't do that if you don't care so if you care whether it's

53:12 you care enough about yourself and your career and who are as a professional or

53:15 care about the company and what we're doing what we're building here and the

53:17 importance of it that's usually what drives out that type of passion that may

53:21 cross the line so yes that not all the time but but if it never happened

53:30 you're such a you're such a founder in this way I agree but I think I think the

53:36 the thing so I'll go back to like the the guy I was talking about in my first

53:41 job who I now I'm gonna reference him again right I told you I reference him a

53:44 bunch we're gonna have to have John on here next so John's a legend so so and if

53:53 he heard this he would be like mortified so he he would he would get very he

54:03 would be disappointed if we didn't advocate and pound the table for issues

54:07 that we were having interdepartmentally and with our customers why are you not

54:12 why are you guys not outraged that this is happening and why isn't anybody so

54:17 that's what you're that's not out of bounds at all that's fair this department

54:22 is not doing good enough to take care of my customers I'm not talking about the

54:25 leaders are bad people or they don't care I'm saying this that's not good

54:28 enough and it's hurting my business and it's hurting our business to reach our

54:31 customers needs and it's hurting sales and it's a problem that's completely

54:35 fair that's completely fair now you start insulting it well it's because so

54:40 and so is a jerk and he's a let okay well that's too much you don't need to

54:44 go after personal attacks inside of us assessing what the problem is and that's

54:48 more of what I mean around like the civility elements if it's helpful right

54:53 but you might just a little bit just a touch a dash yeah dash of incivility it's

54:59 kind of like if building a product and nothing ever broke going fast enough are

55:05 you pushing hard enough like you're not finding your limits then I think you're

55:09 leaving some some stuff on the table so on that note though what where we'll

55:15 find common ground on this is like I would really respect like if I would

55:19 really respect it from a leader if they're like look this is this is what we

55:23 tolerate I don't that's okay here you know what I mean now a little bit that's

55:28 fine so expect it good enough good enough the ambiguity is what I have a

55:34 problem with right yeah the ambiguity that like I probably curse a little bit

55:40 more than I should but when I talk to people who are potential applicants

55:44 sometimes I'll curse in the application process and I will say you know we curse

55:48 around here sometimes now if that's a problem for you probably shouldn't care

55:54 no that's so because you might hear it and that's kind of what's acceptable

55:59 around here and you can make a moral judgment on whether that's right or wrong

56:02 but that that's kind of the way it works and so that's that's what's gonna

56:06 happen and that's fine that's fine well one one thing we talked about a little

56:12 bit on the prep session I would never bring up anybody's kids unless they kind

56:17 of gave up an opportunity to do so but I know you have some kids that are

56:22 starting to enter their early career years they're just kind of starting off

56:27 and I do think I mean my goodness I think even the last five years so much

56:33 of how we work has changed and so I would love to hear your perspective on

56:40 the advice you're giving them and maybe also advice you might give someone who

56:46 aspires to be a CRO one day too yes so you're right I have two kids one she's

56:56 gonna go back to college next week which is both a bummer and really good a bummer

57:02 because she's it's great to have her in the house and it changes the whole like

57:07 ecosystem in the house having her so that part's a bummer and then also awesome

57:13 because she's like fired up to go back and it's cool that you know she loves

57:19 college and she's sort of her own woman and that means you know she's she's

57:26 good for the world so that makes me feel good so it's both good bet and then my

57:31 son is going into his last year of high school and he's the best so he is like

57:40 such a self-aware mature guy I learned stuff from him frequently because he's

57:47 he's a good dude so advice that I give them is sort of not necessarily it's

57:56 starting to be professional a little bit

58:01Dad Wisdom

58:01 this is I'm gonna tell you this and like regret it immediately I like my wife

58:10 doesn't even know this so I started I like started a little text thread with

58:15 them and I renamed it dad wisdom okay for posterity but that's so when I when

58:22 I think of something where I'm like I really hope they know this fired off

58:26 into the text thread and then they have it so they can always go back to dad

58:29 wisdom I don't know how valuable this is we're early in the experiment but I've

58:35 started well give it a couple years you plug that thing in a clod I mean they

58:42 won't miss a beat it's gonna be awesome

58:50 yeah they don't even need to talk to you anymore yeah yeah what have I done what

58:56 have I done no I wisdom is probably like overselling a little bit I think the

59:02 thing that I try to one of the things that I learned like later on in life

59:09 which I wish I would have known earlier is like I told you a little bit of the

59:15 story of my career where I like I didn't know anything about sales I wasn't

59:19 totally sure whether I wanted to be in sales or not I didn't know anything

59:23 about commercial loans far from it I certainly didn't know anything about

59:28 health care dentistry so I was off to a bad start Anthony I didn't know anything

59:32 and then I started to as I was telling before I started to really enjoy the

59:37 dynamic dynamic of I really like talking to people and I'm genuinely interested

59:41 and curious about people so I started to enjoy the job and I really liked how

59:45 self-directed I could be and how much agency I had over you know the outcome

59:49 of my performance and there's like an element of independence streak that's

59:53 always been a part of my life that certainly is valuable in a salesperson's

59:57 world right sort of traditionally I was into athletics and that kind of stuff

1:00:01 which is I know a little bit of a cliche but but the I I worked really hard to

1:00:09When a career stops being survival and becomes a choice

1:00:11 get to a point where my basic needs I was married young I've been married for

1:00:15 26 years and we were married very young and I was very eager to get us to a

1:00:20 point where our basic needs were met okay whatever that means whatever that

1:00:25 meant for us at the time which was like I want us to have a house or an

1:00:30 apartment that's nice nice I'm putting in quilts and you know a car that's nice

1:00:35 enough and food and the ability to like have some discretionary income for

1:00:41 vacations or entertainment and that kind of stuff or clothes these are basic needs

1:00:46 as I defined them as a young person and in sort of like classically I like every

1:00:56 next opportunity in my job was very obvious so if you're like an inside

1:01:01 salesperson being an outside person is an obvious progression and being an

1:01:04 outside salesperson and managing people is an obvious progression and then do

1:01:08 get it everything is sort of like very logical and very and and getting

1:01:12 promoted it's fun and you get paid more and getting the recognition is fun but

1:01:18 after my basic needs were met everything was kind of a choice I was making

1:01:23 between like job satisfaction and impact and you know whatever joy was being

1:01:30 derived from the work or not that I was doing and title and compensation those

1:01:36 were the compromises right right and and I didn't fully appreciate that I just

1:01:42 sort of like plotted through my career to get promoted promoted promoted and

1:01:45 then I was like do I still love this am I doing the thing that I still love

1:01:53 because I told you I set out not to be a salesperson I was one I met my basic

1:01:59 needs by being a salesperson and then I got promoted for having whatever talent

1:02:05 or good performance somebody perceived relatively in that and and I that was

1:02:11 what seemed like the right thing to do but more than my basic needs have been

1:02:14 met and then I sort of was in a position of like it feels like I've chosen a

1:02:18 career did I do it deliberately yes or no you're pretty deep on the game of

1:02:25 life you've got a lot of squares here so yes is this where you want to be or is

1:02:29 there a fork that you missed yes in it and it would have been valuable whether

1:02:35 I would have listened or not is a different story right but it would have

1:02:38 been valuable to have the perspective of like I'm choosing at this point I'm

1:02:42 choosing what to do I don't have to is this a choice I want to make relative to

1:02:47 an alternative choice and what are all my what are my alternative choices and

1:02:51 so it's so I'm clearly not advocating for like playing hopscotch with your

1:02:58 career in perpetuity although if that's what you want that's fine it was more

1:03:04 you know once you get 10 15 years into what you're doing you kind of have a

1:03:09 career in the switching cost might be meaningful for you right and so that

1:03:13 wasn't explained to me right sick because I went from survival having my

1:03:18 basic needs met to whatever relative success I I had or excess above my basic

1:03:23 needs was met and I found myself in a career now I'm a happy guy that's true

1:03:28 but I want my kids to feel like they're not in a race for survival they can be

1:03:37 deliberate about the decisions they make in their career and be thoughtful about

1:03:40 why they're doing something over an alternative and so and maybe in

1:03:45 answering the CRO question I think I've had to think a lot about this in my life

1:03:50 which is like outside of making money and having a title or whatever what is

1:03:57 it that I genuinely like about my job what what are the things that are

1:04:00The cocktail: comp, title, industry, people, impact

1:04:00 non-negotiable that I like doing and I'll give you some examples which is

1:04:06 like is it is it the compensation is it the title is it the industry right is it

1:04:13 the the leadership of people is it the job specifically that I'm doing you get

1:04:24 it there's a cocktail of things there so like is it true that I would be equally

1:04:28 happy if you just paid me more and gave me a better title and put me in a

1:04:31 different industry and I didn't lead people and I didn't feel like I had an

1:04:35 impact is it would that legitimately make me happy and it wouldn't right I'm

1:04:40 no different from anybody else like if you give me everything I want all the

1:04:43 time I get worse that's kind of the way human behavior works right if you have

1:04:49 young kids you learn this like really quickly which is like what's the best

1:04:52 way to make it unhappy two-year-old give them everything they want whenever they

1:04:55 want it it does not improve their behavior at all does this make sense so

1:05:01 far I am learning that counter intuition right now raising young kids so yes it's

1:05:09 resonating well it's also fun but inside of that I think the thing I've

1:05:16 challenged myself is like I I sincerely love leading people managing people I

1:05:22 love it and I have a huge amount of energy to direct at what I perceive to

1:05:29 be helping or developing people or using whatever knowledge and experience and

1:05:34 background I have to to maybe help somebody develop through their career

1:05:40 or achieve what they want to do I love it it makes me really really happy and

1:05:43 that has nothing to do with the industry that I'm in it just makes me happy doing

1:05:47 it and I would be genuinely miserable if I felt like I worked if I didn't have an

1:05:54 impact that I thought was positive on people it would make me really really

1:06:00 unhappy I would be a genuinely unsatisfied person and I want that to be

1:06:06 in the sense of like that's for me that's not for everybody else that's for

1:06:11 me to determine whether I think that I'm having an impact right it doesn't have to

1:06:15 be true for you might look at it and say you're not that's okay that's for me

1:06:19 right you would never do that but I think I think those are reasons why I

1:06:28 take a job or continue to work with a job and at this point in my career who I

1:06:33 do it with matters so much I mean in the more of those things I can compile

1:06:40 together I love to be selfish in this way which is like I want that and that

1:06:46 and that in that that's what I want and if I don't get it I don't want to do it

1:06:51 and that wasn't always true for me in my career there were parts there were times

1:06:54 of my career where I had to do jobs that I didn't think I was having an impact and

1:07:01 I didn't think I was doing about but I needed to get somewhere and so the fact

1:07:05 that I have some of that now is like a prized possession of mine and so anyway

1:07:12 that's the way I go about doing it today and I think that like matters for people

1:07:15 who are chiefs of whatever makes a ton of sense yeah I love it love the cameos

1:07:25 well and I think I think being intentional about the choices you're

1:07:30 making knowing the trade-offs that you have and then especially if you're early

1:07:33 in your career knowing hey something that you enjoy doing may have a slower

1:07:38 start that's okay play the long game if you're passionate about something if

1:07:42 there's a certain work style that you want to have or things you want to be

1:07:45 incorporated in that and I have found that too later I mean yes at the

1:07:50 beginning and like hey I have just survival and bills to pay so I'll pretty

1:07:54 much do whoever pays me the most at this point but then yes getting more

1:07:58 selective as you go you know with lean scale when you said who you work with

1:08:03 matters the most that's been the coolest experience for me I'm in a very

1:08:08 fortunate position to get to pick everybody works here or at least try to

1:08:12 get them to work here but I have like my childhood best friend is here my wife

1:08:18 and I work together I'm the oldest of five I and my youngest sister works here

1:08:23 and then just the people that we've been able to attract and the type of

1:08:29 culture you've been able to build I get fired up to work here today so I think

1:08:34 when you're building something like that you those become so valuable I would not

1:08:40 take more money to trade off all of those things that I have built in here I

1:08:48 love that and good for you for feeling that way and in you you might have had

1:08:54 this experience I know I have where people who haven't challenged that

1:09:00 priority for themselves can make decisions that aren't best for them so

1:09:06 you you might have a performer who's like I'm leaving or somebody in your

1:09:11 company that you think is it doesn't matter what you think their value or not

1:09:14 but they're they're leaving and the reason they're doing it might be I'm

1:09:20 gonna get paid more and they're giving me a new title right and you think well

1:09:24 have you considered the other elements have you considered the aspect of like

1:09:27 who you work with the impact you feel like you have in the organization you

1:09:32 know the the industry itself that you're doing and how you have you considered how

1:09:37 valuable those are to you and whether you're gonna get that or how likely you

1:09:40 are to get that at your new place and that doesn't land all that well with

1:09:44 some people who are determined but how frequently do you see them unhappy for

1:09:49 those reasons later on and learn that lesson and that's a painful lesson to

1:09:52 learn right sometimes I think you just have to go through it it's one that's

1:09:59 tough to teach but pretty obvious once you've actually been in that situation

1:10:03 where oh I have traded some things I value really highly for a bigger salary

1:10:11 bigger title whatever it is but I'm feeling empty or missing all these other

1:10:17 things that I know I've experienced in other places so but it's very hard I

1:10:22 think to explain that to someone I think you have to live it yeah I think you're

1:10:30 right I'm sure you're right it's one of those things that you can't convince

1:10:33 somebody to feel that way they kind of just have to to your point feel it and

1:10:39 go through it and learn the lesson themselves which is hard to watch but

1:10:43 part of maturing and growing up I guess so yeah I think about it a lot and I try

1:10:53 to I try to scrutinize and pressure test it every once in a while just to make

1:10:57 sure I'm right you know in a minute when I take a different job with people I

1:11:01 would you know just to see whether the priorities are in the right place and

1:11:05"Why do you want to be a CRO?"

1:11:05 that's I'll get I'll get people who ask me a little bit of like I think I want

1:11:10 to be a CRO how do I and that's one of those questions I'll ask is what what do

1:11:15 you think you want to be like why do you want to be a CRO like what is it and

1:11:19 that question for some people is like they don't almost understand the question

1:11:23 it's like what do you mean I'm in AE I just told you I want to be a CRO why is

1:11:26 that hard to understand but that's like fair enough but that there is like that's

1:11:32 like promotion for the sake of promotion and that's not always good this by point

1:11:36 and you made a really good point before which is like how frequently do you see

1:11:40 a really top performer get into management and struggle and it's like

1:11:44 yeah that happens that happens a lot I have a lot of respect for people have

1:11:49 the self-awareness to be like I think I'm good at this I don't think I'd be

1:11:51 good at leading people so I'm not gonna do it yeah and and I've seen a lot of

1:11:56 those people do really well too I mean they're there's top top ICs that are

1:12:02 making much more than managers or in it so you know just do your passion about

1:12:08 follow that along get great at your craft and then like those other accolades

1:12:14 and things can follow it doesn't only have to be a people management thing

1:12:19Wrap

1:12:19 totally cool thank you so much for everything you shared everything you

1:12:28 went through I love the contract that you have with people who are on your

1:12:32 team making sure that they're compensated fairly treated fairly have

1:12:38 the tools to be successful and know what good looks like I think anybody listening

1:12:43 this can learn quite a bit from following how tactical that can be and

1:12:47 then just the advice on how to think about your career and being intentional

1:12:51 with it and looking outside of just a small lens of your salary and title but

1:12:58 opening up that aperture to all these other things that you might value so

1:13:03 I'm probably gonna have to subscribe to the dad wisdom sub stack that I think

1:13:08 you're gonna launch and then I'll plug Claude into it make sure my kids don't

1:13:12 miss any beat either but I really appreciate everything can't wait to

1:13:15 follow what you're doing now and then see what you do next in your career I

1:13:19 really appreciate it it was great it was great talking to you and thanks for

1:13:23 having me on I really appreciate it