The LeanScale Podcast · Episode 147

The CRO Who Wasn't in the Board Meeting

Christian Miller on why a CRO missing from the board meeting is a red flag, the 60-day diagnosis of a hidden payments business, reading pipeline coverage by segment and stage, the founder-led snapback, and keeping AI from turning your message into 50 versions of the same deck

Christian Miller · Partner, Revenue Growth, TechCXO · TechCXO Hosted by Anthony Enrico
Published Updated 00:54:09 53 min read 10658 words
Sales Leadership Revenue Operations Forecasting GTM Strategy AI in GTM
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Executive Summary

The one-paragraph brief, extended

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

Christian Miller is a partner in TechCXO's Revenue Growth practice, where he works as a fractional CRO with private equity and venture-backed companies, and the founder of Florian Growth Advisors. Per the show notes, he started his career carrying a bag at GE Capital, led corporate payments sales at U.S. Bank, and has been Chief Revenue Officer at Motus and Global CRO at HRS Group. He describes his usual assignment plainly: when a CRO is brought in, something is typically wrong, whether that is missed targets, poor reporting data, no visibility into the forecast or sellers leaving. He puts average CRO tenure in the private equity-backed world at about 18 months.

The episode opens with the run that shaped him. Recruited out of U.S. Bank into a payments business that host Anthony Enrico describes as one of 12 divisions at a logistics company, he was given 60 days to tell the CEO and CFO what they had and what to do with it. He came back with three options: invest and bring in growth leaders, take it private with private equity, or sell it to one of three or four named acquirers. They sold, and he went with it as general manager. The unit, at about $27 million in EBITDA, merged with a company of similar size to reach $54 million, grew to nearly $90 million in about 14 months, and sold for roughly $1.5 billion. The team knew the business down to the basis point, ceded travel and expense business to American Express in exchange for payment files ten times larger, and integrated into accounting software so one partnership could open up thousands of potential customers.

The core of the conversation is how a CRO earns the trust of the CEO and the board. Christian calls a CRO's absence from a private equity board meeting a massive red flag, because in his experience 80 percent of the conversation is about sales. Missing it means follow-up emails during the meeting, a week of board requests, and reporting that should have been in the deck. Anthony, who rode shotgun with the CRO at board meetings as an operator before founding LeanScale, agrees.

That trust rests on data, and Christian says his RevOps leader has always been his right hand. Pipeline coverage only means something by segment: three and a half to four times in enterprise can hide a mid-market segment at 2X that isn't converting. He spends his time on why deals fail between specific stages, using MEDDPICC gaps as the signal. With a 120-day sales cycle, a pipeline shortfall can be predicted months out. Ignoring it leads to being dependent on three or four deals, and to 20 to 30 percent discounts that teach customers to wait.

Christian also names the pattern he calls the founder-led snapback. A founder's sales process built on personal authority and connections doesn't replicate, new reps stall, and the founder returns to selling to hit the number promised to the board, with four people back on every call. The answer is onboarding, repetitions, authority for sellers, and a founder willing to step away. Where a turnaround takes longer than anyone wants, he lays out data-backed scenarios and resets expectations with the CEO and board.

On AI, Christian says the tools can lift an average seller to top tier, but he has watched good sellers get sloppy and executives arrive with new AI-built decks until a company has 50 versions of its basic pitch. The episode suits CROs, CEOs, founders and RevOps leaders at private equity and venture-backed companies.

Key Takeaways

15 things worth stealing

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

01

Sixty days, three options the executives could act on

The CEO and CFO asked Christian to evaluate the payments business and recommend what to do with it within 60 days. He offered three paths: invest and bring in growth leaders, take the entity private with private equity, or sell it to one of three or four companies he named. He had concluded the first was unlikely, since the fact the conversation was happening at all suggested they weren't interested in investing.

Why it matters: A diagnosis lands when it includes the option leadership will actually take. They reached out to one of the named companies, and about 90 days later Christian was told the business was being sold and that he would go with it as general manager.

Revenue ExecutivesFounders
02

Let the dominant brand keep what it's known for

EFS couldn't match American Express on brand, with its Super Bowl commercials and celebrity endorsers. So in competitive deals Christian's team offered to leave American Express the travel and expense business and take over the payments customers were making by ACH, wire and check. Those files turned out to be 10X the size of the T&E business they gave away.

Why it matters: A smaller competitor can make the buyer's cardholders happy, avoid the fight it would lose, and win the larger pool of spend. Christian says spend volume and revenue climbed as a result.

Sales LeadersRevenue ExecutivesFounders
03

Sellers who can structure the deal in the room beat bigger brands

Christian says everyone at EFS, including the CEO, knew the business down to the basis point, so the team could structure a deal on the spot and knew its ROI and margins going into meetings. Reps were highly trained and enabled to make deals within set parameters, while banks and legacy payment providers gave their salespeople less room.

Why it matters: Deep commercial knowledge plus defined authority is a speed advantage. Christian says it let an unknown brand outsell larger competitors when sitting across from customers.

Sales LeadersRevenue Executives
04

One partnership can replace thousands of logo hunts

Rather than trying to win 5,000 new logos a year, Christian looked for a handful of key accounting software providers in the right industries, where the team wasn't competing against name brands, and integrated into their products. He says one partnership could yield 5,000 potential customers, or hundreds, depending on the situation.

Why it matters: Embedding in software your buyers already use is a distribution strategy that avoids head-on brand competition, and it complemented partnerships with expense platforms.

FoundersRevenue Executives
05

A CRO missing from the board meeting is a red flag

Christian calls it a massive red flag when the CEO attends a board meeting and the CRO doesn't. In the private equity-backed board meetings he has been part of, 80 percent of the conversation is about sales: pipeline, where the company is winning, which segments and industries, how marketing campaigns are going. He allows that some VC-backed companies may not need the CRO at every monthly check-in.

Why it matters: Being removed from the process signals something might be wrong, whether or not it is. Anthony adds that the depth of data questions in these meetings needs someone who knows the numbers, and that having the head of RevOps there also helps.

Revenue ExecutivesFoundersRevOps Leaders
06

Skipping the meeting costs more than attending it

Christian says the board meetings he wasn't in often left him receiving 15 emails during the meeting, or a following week filled with board requests. Without the right people to explain the numbers, he says, you get 10X the questions, plus follow-up meetings and additional analysis.

Why it matters: He ends up spending the week on non-revenue-generating work and on board reporting that should have been in the deck in the first place. He adds that it can also dent sellers' confidence, since they feel their function should be represented.

Revenue ExecutivesRevOps Leaders
07

The CEO and CRO have to look at the same data

Christian's healthiest situations have clear expectations, transparent targets and incentives tied to them from the top down, in a single thread to the top-line number. The disconnect shows up when the CEO and CRO are two ships passing in the night, with a quick call before the board meeting and a pipeline number without detail.

Why it matters: Get the CEO what they need to make decisions, which can mean leaning into the sales organization, getting comfortable with the RevOps or sales ops team and joining some calls. And when a CEO says to just do what you need to do, Christian hears that as code for sending the dashboards that show things are on track.

Revenue ExecutivesFounders
08

RevOps is the CRO's right hand

At most of the companies Christian has worked at, his closest partner was his RevOps person, because they have all the data and can explain it. He describes working through a segment together: coverage, who is on track, average sales cycle and conversion rate, and the at-bats each person is getting by segment.

Why it matters: With a 30 percent conversion rate, for example, he says you can do the reverse math to see where you will land. A CRO and RevOps leader who truly know this can explain it to a CEO without boiling the ocean, and that is what should shine in a board meeting.

RevOps LeadersRevenue Executives
09

Pipeline coverage only means something by segment

When a CEO asks why the pipeline isn't there, Christian's answer is that it depends on the segment. A company might require three and a half or four times coverage and be hitting that in enterprise while winning nothing in the mid-market segment that is supposed to be its logo acquisition engine, where coverage is only 2X and conversion is poor.

Why it matters: An aggregate coverage number can look acceptable while the segment that matters is failing. The conversation should be about which segment needs more pipeline and whether conversion justifies the target.

Revenue ExecutivesRevOps LeadersSales Leaders
10

Find out why deals fail between specific stages

Christian says he has spent much of the last couple of years asking why deals fail between stages three and four or four and five. If you have parsed the data correctly, you know how much pipeline sits in each stage, from one through seven, and what the conversion rates are. Most companies he works with use MEDDPICC, and a stall usually points to a gap such as no champion or not understanding the paper process.

Why it matters: A gluttony of pipeline stuck in certain stages means deals need to be advanced or disqualified. Stage-level diagnosis gives the CRO a specific explanation rather than a general worry about pipeline.

Sales LeadersRevOps Leaders
11

Build pipeline a sales cycle ahead, or end up discounting

Activities are predictive indicators of future results, Christian says. With a 120-day sales cycle and little pipeline in the largest logo acquisition segment, he can predict a Q3 miss months out if marketing investment doesn't start in time. Left alone, the quarter comes down to three or four deals, and sellers become desperate and give discounts.

Why it matters: Those discounts condition customers to hold deals until the team offers 20 to 30 percent off. Sharing data early and having the relationship with the CEO to act on it avoids being deal dependent in the last two weeks of a quarter.

Revenue ExecutivesSales LeadersMarketing Leaders
12

The founder-led snapback stalls companies after they raise

A founder who sold to their first contacts creates a prescriptive process that often can't be replicated, sometimes with the CTO, product, a sales engineer and a seller all on one call. New reps can't run it, because the founder sold from a position of authority and knew the product better than anyone. Conversion drops, the founder's connections are no longer opening doors, and the founder goes back to selling to hit the number committed to the board.

Why it matters: Christian says companies where the founder won't step away linger and never get where they need to be. He contrasts this with the $1.5 billion outcome, where the CEO was a phenomenal salesperson but also put in place the structure that let the organization scale.

FoundersRevenue Executives
13

Turnarounds fail when sellers are thrown in too early

Companies under pressure shove new hires through onboarding to get bodies in seats. Christian calls this a recipe for disaster that prolongs the turnaround, because reps fail quickly and churn, and he has seen seller churn of 80-plus percent at companies needing big turnarounds. He says the long game takes discipline and patience.

Why it matters: When the plan won't be met, the CRO should tell the CEO and board why, lay out scenarios, and possibly revisit the year's goals, all backed by historical sales cycles, conversion rates and seller experience. Done well, it conveys a steady hand on the wheel even when results are poor.

Revenue ExecutivesSales LeadersRevOps Leaders
14

AI lifts average sellers and can make good ones sloppy

Christian says some AI solutions can take an average-level seller and make them a top-tier seller, and that there has never been a better time to be a seller. But he has also seen really good sellers get sloppy trying to scale too quickly, and could tell from a colleague's work that it didn't sound the way that person talks.

Why it matters: The fix is to keep the blocking and tackling veterans rely on, such as sales methodologies, and bring those disciplines into the new tools. Anthony's version: do A-plus work for a smaller group rather than B-level work across more people.

Sales LeadersRevenue Executives
15

Uncontrolled AI turns your message into 50 versions of one deck

Christian describes C-suite peers tinkering with different AI tools and showing up to top-customer meetings with new decks and new ways of presenting the data. Even where the data is right, the talk track differs. Other people see it win deals and copy it, until there are 50 versions of the basic deck and 80 variations of anything in the marketing library.

Why it matters: The test he uses: if he stepped out of a sales meeting, a colleague should run it just as he would. Anthony adds that if the message isn't clear internally, a prospect has no chance of understanding it. Christian ties it back to setting proper expectations internally and externally.

Revenue ExecutivesMarketing LeadersSales Leaders
Frameworks Discussed

9 named models

Every framework Jimmy names, defined and time-stamped.

Sixty-Day Diagnosis, Three Options

02:18

Evaluate a business within a fixed window, then give executives three distinct paths rather than one recommendation: invest and bring in growth leaders, take it private with private equity, or sell to named acquirers.

Christian sat in on a multi-million-dollar technology project, spent time with the people in the business on where their time and skills went, and found an established base being cross-sold with no aggressive go-to-market for new customers. He also found an unusual asset: the business was its own issuer and processor with open-loop and closed-loop systems. Because he suspected investing wasn't what they wanted, he made sure the options included ones they would act on.

Let the Incumbent Keep Its Category

09:35

When a competitor's brand is too strong to beat head-on, concede the business it is known for and take a larger adjacent pool of spend.

EFS told prospects American Express could keep their travel and expense business, since employees likely wanted an Amex card anyway, and asked to process the payments being made by ACH, wire and check. Those files were 10X the size of the T&E business the team gave away.

One-to-Many Partnerships

11:28

Instead of winning thousands of logos individually, integrate into a handful of key software platforms in the right industries, where you aren't competing against name brands, so each partnership reaches many potential customers.

Christian's team integrated its technology into accounting software, and he says one partnership could yield 5,000 potential customers or hundreds, depending on the situation. It sat alongside partnerships with expense platforms, where he says the team was agnostic about who it worked with.

Pipeline Coverage by Segment

15:53

Evaluate pipeline coverage separately for SMB, mid-market and enterprise, and read it alongside each segment's conversion rate rather than in aggregate.

Requirements of three and a half or four times can be met in enterprise while the mid-market segment, supposed to be the logo acquisition engine, sits at 2X with poor conversion. Christian's example of the working conversation: mid-market coverage is one and a half to two X, he needs three to four, and the team can work out who will reach the number from sales cycle, conversion rate and at-bats by segment.

Stage-to-Stage Failure Diagnosis

22:57

Know how much pipeline is in each stage and each stage's conversion rate, then ask why deals fail between specific stages, using MEDDPICC gaps to find the cause.

Christian says a stall usually means something is missing, such as no champion or no understanding of the paper process. A concentration of pipeline stuck in certain stages means deals should be advanced or disqualified. Delivered clearly, this is what a CRO and RevOps leader should bring to a board meeting.

GTM Telemetry as a Gold Mine

26:31

Anthony's metaphor: investing in go-to-market without telemetry is like spending tens of millions on mining equipment with no idea what the machines are yielding.

Telemetry means knowing which reps are doing well and why, why you win and lose, which channels produce pipeline, and whether you are in a place that has gold to mine or need to shift your ICP. Anthony says a missed quarter with a very good explanation and plan could save a leader a quarter or two, while a miss without answers might end the journey.

The Founder-Led Snapback

30:25

After a raise, a company hires salespeople to replace founder-led selling, the founder's process fails to replicate, conversion falls, and the founder returns to selling to hit the committed number.

The founder's authority, product knowledge and contacts don't transfer with a script. Taking the founder off calls can prolong deals, because reps have to check with the CEO on many of the customer's questions. Bringing the founder back restores four people on a call, which Christian says isn't efficient, scalable or repeatable. His fix is for the founder to step away and give sellers the authority to sell.

Data-Backed Scenario Reset

38:50

When the plan is out of reach, tell the CEO and board why you are in this spot and what happens if nothing changes, then lay out scenarios supported by historical data.

Christian's inputs are average sales cycle, conversion rate, how long sellers have been in seat, and experience differences, such as a mid-market seller now working longer enterprise deals. He says it can include relooking at goals for the year, and that it depends on data integrity.

The Step-Out-of-the-Room Test

46:50

If you had to leave a sales presentation for an emergency, the colleague beside you should be able to run it just as you would, because the message is the same.

Christian uses this to describe what message consistency should feel like, against a backdrop of AI-generated decks and talk tracks. He wants everyone in sales and marketing telling the story the same way, like cut and paste, so a prospect doesn't hear different versions from different people.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“If the CEO is attending a board meeting and the CRO is not in that meeting, which for me is massive red flag, right?”
Christian Miller 18:00
“They want to talk about sales. What is your pipeline? Where are you winning?”
Christian Miller 18:57
“The meetings that I haven't been in often end up being me receiving 15 emails either during the board meeting or text or my next week is absolutely filled with board requests to review.”
Christian Miller 19:11
“All of a sudden you're quickly realizing I'm spending my week doing non-revenue generating activities and then doing board reporting of stuff that should have been in the board deck in the first place.”
Christian Miller 25:14
“Everybody, including myself, CEO, and everybody that was involved in the business knew the business down to the basis point.”
Christian Miller 08:43
“Listen, American Express can keep their business.”
Christian Miller 10:02
“But in some segments, you're doing a really good job because you're hitting that three and a half to four times, maybe in the enterprise, but you're not winning any deals in what is supposed to be your logo acquisition monster of the business”
Christian Miller 16:19
“Most of the companies I worked at, it is like the right hand person to the CRO has always been my RevOps person because they're the person that's got all the data, can explain all the data as much as you need.”
Christian Miller 21:39
“Why am I failing between stages three and four or four and five and whatever?”
Christian Miller 22:57
“If you don't hit your numbers, but you have a very, very, very good explanation as to why, and you could diagnose it and say, "Here's the plan for next quarter," I think it could save you a quarter or two.”
Anthony Enrico 27:31
“I can predictably tell you that we will not make our Q3 numbers, and the worst thing you can get into is the game of chasing large logos to offset the risk that you had.”
Christian Miller 28:49
“It's not a good feeling to be deal dependent in the last two weeks of a quarter when everybody's numbers and incentives are riding on it.”
Christian Miller 29:42
“Yeah, but you're also the founder and the CEO, so one, you can sell from a position of authority, plus you know the product better than everybody else.”
Christian Miller 33:17
“If your founder has to be on every single sales call, you don't really have a true product, you have a seller that could sell, but you don't have a real company.”
Christian Miller 35:14
“Just lay out different scenarios but it all has to be backed by data that's why data integrity is so important”
Christian Miller 39:12
“You can take potentially an average level seller and make them a top tier seller.”
Christian Miller 41:54
“If you're trying to do B-level work across more people, just do A-plus work for a smaller group, and I think you're going to win.”
Anthony Enrico 44:55
“All of a sudden you get this massive amount of 50 versions of every deck that you might have, even though it's your basic one-on-one deck of what you do.”
Christian Miller 46:30
“If you're having trouble understanding what your message and brand is internally, there's no way in hell a prospect is going to understand it.”
Anthony Enrico 48:40
“If we're doing this correctly internally, it's gonna work externally.”
Christian Miller 49:48
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Revenue Executives

  • Treat a seat in the board meeting as part of the CRO job, and raise it early if you are being left out of private equity board meetings.
  • Give the CEO the data and dashboards to see whether you are on track, and invite them into the sales organization and RevOps team.
  • Tie incentives from the top down in a single thread to the top-line number so everyone knows what they are accountable for.
  • When the plan is out of reach, explain why, lay out scenarios backed by historical data, and be willing to revisit the year's goals.
  • Keep a network of people you have worked with. Christian says hiring from his network has not been a losing strategy.

RevOps Leaders

  • Report pipeline coverage by segment and by stage, alongside conversion rates, rather than as one aggregate number.
  • Build the stage-by-stage view that shows how much pipeline sits in each stage and where deals fail to advance.
  • Be ready to explain the data at board level, and work with the CRO so that detail is in the deck and doesn't turn into a week of follow-up.
  • Prioritize data integrity. The scenarios a CRO puts in front of a board depend on it.

Founders

  • Before scaling the sales team, check whether your sales process works without you and without four people on every call.
  • Hand selling over deliberately, step away from the process, and give sellers the authority to close deals.
  • Don't return to selling at the first missed quarter without asking why reps aren't converting.
  • Bring your CRO to the board meeting so revenue questions are answered in the room.

Sales Leaders

  • Make sure sellers have the repetitions and product knowledge before they get on a call, rather than rushing bodies into seats.
  • Give reps defined parameters for structuring deals so they can move faster than larger competitors.
  • Use MEDDPICC gaps, such as a missing champion or an unknown paper process, to explain why deals stall in a specific stage.
  • Avoid end-of-quarter discounting that teaches customers to wait for a better offer.
  • Keep the fundamentals of your methodology when adopting AI, and check that output still sounds like the seller.

Marketing Leaders

  • Plan pipeline investment at least a full sales cycle ahead for the segments that drive new logos.
  • Keep one controlled set of decks and messaging so the marketing library doesn't fill up with AI-generated variations.
AI Takeaways

How AI actually changes GTM

LeanScale's signature read on the AI-in-GTM question this episode wrestles with.

The thesis

AI can raise the level of an average seller, but only if it builds on the fundamentals. Without shared discipline, the same tools make good people sloppy and fragment a company's message across dozens of versions of the same deck.

Agent & automation ideas

  • A deck governance agent that compares new customer-facing presentations against the approved messaging and flags unsupported claims or new logos.
  • A pipeline coverage agent that reports coverage and conversion by segment and stage and flags where a shortfall will affect a future quarter given the sales cycle.
  • A MEDDPICC gap agent that identifies deals stuck between stages and names the missing element, such as a champion or the paper process.
Operations Takeaways

By function

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

Revenue Operations

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Pipeline & Marketing Ops

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Metrics Mentioned

The numbers, with context

60 days
Time given to diagnose the payments business

The mandate from the CEO and CFO to evaluate the business and recommend what to do with it.

$27M to close to $90M
EBITDA growth

Christian's business unit was at about $27M, merged with a company of similar size to reach $54M, then grew to close to $90M in about 14 months. The show notes cite $27M to $89M.

About $1.5B
Exit value

The sale of the payments company, per Christian and the show notes.

10X
Payment files versus T&E

The size of the payment files EFS took on compared with the T&E business it left to American Express.

5,000 potential customers, or hundreds
Reach of one software partnership

What Christian says a single accounting software integration could yield, depending on the situation.

About 18 months
Average CRO tenure in private equity-backed companies

Christian's estimate.

80%
Share of PE-backed board conversation about sales

Christian's estimate from the board meetings he has been part of.

15
Emails after a missed board meeting

Christian's example of what he receives, or a following week full of board requests, when he isn't in the room.

10X
Extra questions without the right people in the room

Christian's estimate of what happens when nobody present can explain an issue the board wants to explore.

3.5X to 4X
Pipeline coverage requirement

Christian's example of what some businesses require, against a mid-market segment at 2X or one and a half to 2X.

20–30%
End-of-quarter discounts

What Christian says customers learn to wait for when a team becomes dependent on a few deals at quarter end.

80%+
Seller churn in turnarounds

The worst Christian has seen at companies needing big turnarounds.

50 versions
Deck sprawl

Christian's description of the versions of a basic deck that accumulate as people use different AI tools. He also cites 80 variations of anything in a marketing library.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

TechCXOFractional Executive Services

Where Christian is a partner in the Revenue Growth practice, working with private equity-backed, VC-backed, privately held and publicly held companies on revenue transformation.

53:26Company →
Electronic Funds Source (EFS)Payments

The payments company at the center of Christian's story. Per the show notes it grew EBITDA from $27M to $89M ahead of a roughly $1.5B exit. Christian says the business unit he ran was at about $27M, merged with a company of similar size to reach $54M, and grew to close to $90M in about 14 months.

05:14 · 05:24 · 09:54 · 30:54Company →
U.S. BankBanking

Where Christian led the corporate payments sales organization before being recruited to the payments business. His network from U.S. Bank and the corporate payments space became the source for the talent he hired.

01:53 · 07:16Company →
American ExpressPayments

The dominant travel and expense brand EFS competed with. Christian's team conceded T&E to American Express in deals and took the payment files, which were 10X larger. Some of his hires came from competitors such as American Express.

07:25 · 09:35 · 10:02Company →
LeanScaleGTM Operations

Anthony's company, founded in 2021 after he worked as an operator at three startups.

19:51Company →

People

Christian Millerguest

Partner in TechCXO's Revenue Growth practice and fractional CRO, formerly Chief Revenue Officer at Motus and Global CRO at HRS Group.

Partner, Revenue Growth, TechCXOProfile →
Anthony Enricohost

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

Co-FounderProfile →

Tools & software

ClaudeAI Assistant

Named once by Christian as an example of what people are using when unfamiliar claims and materials show up in customer meetings.

Website ↗
Methodologies referenced MEDDPICCReverse-math pipeline planningSingle-thread incentivesCRO and RevOps at the boardNetwork-first hiring
Related LeanScale Services

Where this shows up in the work

Fractional RevOps

Embedded, field-facing RevOps leadership and execution — the operator model Jimmy describes, delivered as a service.

Christian's case rests on a RevOps partner who can parse pipeline by segment and stage, explain it to the CEO and board, and keep the data trustworthy.

Forecasting & ARR Definition

Define a raise-worthy ARR and build a reliable consumption forecast across finance, data science, and go-to-market.

The episode covers forecast visibility, reverse-math coverage planning, and data-backed scenarios for the board when a plan is out of reach.

Sales Enablement Build

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

Moving from founder-led sales to a repeatable motion takes onboarding, repetitions and a consistent message, which is what Christian says breaks in the snapback and in AI deck sprawl.

Frequently Asked Questions

Straight answers

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

Should the CRO attend board meetings?

Christian Miller, a partner in TechCXO's Revenue Growth practice, calls a CRO's absence from a private equity board meeting a massive red flag. In the private equity-backed board meetings he has been part of, 80 percent of the conversation is about sales, including pipeline, where the company is winning, and which segments and industries it is succeeding in. He says being left out often means 15 emails during the meeting or a following week full of board requests. He allows that some venture-backed companies may not need the CRO at every monthly check-in, but says a private equity meeting without the CRO is a warning sign.

What is the founder-led snapback?

The founder-led snapback is the pattern where a company raises money, hires salespeople to replace founder-led selling, and then drifts back to the founder selling. Christian Miller of TechCXO explains that founders create a prescriptive process built on their own authority, product knowledge and connections, often with several people on each call, and it doesn't replicate. New reps struggle, conversion falls, and the founder returns to hit the number promised to the board. He says the cycle continues until the founder steps away and sellers are trained and given authority to sell.

How should a company read pipeline coverage?

By segment and by stage, according to fractional CRO Christian Miller. A company might require three and a half or four times coverage and hit it in enterprise while winning no deals in the mid-market segment meant to drive new logos, where coverage is only 2X and conversion is poor. He recommends knowing how much pipeline sits in each stage, each stage's conversion rate and the average sales cycle, then asking why deals fail between specific stages. In his experience, MEDDPICC gaps such as no champion or an unclear paper process often explain the stall.

What is the relationship between the CRO and RevOps?

Christian Miller says that at most companies he has worked at, his RevOps person was his right hand, because that person has all the data and can explain it in as much detail as needed. Together they work out which segments are short on coverage and who will reach the number, using average sales cycle, conversion rate and at-bats by segment. He says this partnership is what should shine in a board meeting, and that a CRO without it risks ten times the follow-up questions.

How can a smaller company compete against a dominant brand like American Express?

At Electronic Funds Source, Christian Miller's team didn't fight American Express for travel and expense business, since employees often wanted an Amex card anyway. Instead it offered to leave that business in place and take over the payments customers were making by ACH, wire and check. Those payment files were 10X larger than the T&E business it left behind. The team also knew its economics down to the basis point, so sellers could structure deals on the spot, and it integrated with accounting software so one partnership could reach thousands of potential customers.

How do you run a turnaround when the sales plan is out of reach?

Christian Miller's approach is to be transparent with the CEO and board about why the company is in its current position, what will happen if nothing changes, and what different scenarios are available, supported by historical sales cycles, conversion rates and seller experience. He warns against rushing new hires through onboarding, which he has seen contribute to seller churn of more than 80 percent at companies in need of big turnarounds. He says the goals for the year may need to be revisited, and that a clear plan signals a steady hand even in a difficult environment.

How can AI hurt a sales organization's message?

Christian Miller says that when executives and sellers use different AI tools, new presentations and talk tracks appear that colleagues have never seen. Even when the data is right, the message changes, and companies end up with 50 versions of their basic deck. Other people copy what wins deals, and quality declines. He recommends keeping the message consistent, so anyone could run a sales meeting the same way, and using AI to improve work built on established sales fundamentals.

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00:00Intro 00:58Sixty days to diagnose a hidden payments business 18:00Why the CRO belongs in the board meeting 30:11The founder-led snapback 40:27Pipeline, AI tools and hiring in 2026 51:22Wrap
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00:00Intro

0:00 My guest today is Christian Miller, a CRO, who gets brought in when a company needs to go from missing targets, founder-led sales, or needs a true veteran to build a real revenue machine.

0:11 In two months, we had an absolute rocket ship in that we grew from $54 million in EBITDA up to $89 million, close to $90 million, and then sold to Warburg Pink as for a Billy Pot.

0:20 Time and time again, as soon as each company gets to a particular point of scale, but then hit some adversity,

0:27 you call it the founder-led snapback.

0:31 They just understand like this script. Just work the script, sell the script, it works, I've been doing it this the whole time.

0:37 Yeah, but you're also the founder and the CEO, so...

0:41 If you're having trouble understanding what your message and brand is internally, there's no way in hell a prospect is going to understand it.

0:47 If we're doing this correctly internally, it's going to work externally.

00:58Sixty days to diagnose a hidden payments business

0:58 Christian, you once walked into a payments business that was one of 12 divisions at a logistics company and had 60 days to tell the CEO and CFO what to do with it.

1:09 What did you actually see in those 60 days and how did you land three options they'd act on?

1:14 You know, it's actually a funny situation for me because if I could hit my driver in a six-iron straight,

1:21 I could literally hit their corporate office from where I live and I bring that up simply because they're a Fortune 500 global supply chain company

1:29 and I had no idea at all that they actually had a payments business to them.

1:33 But they created the payments and it makes a lot of sense in retrospect because they needed to give tools and solutions,

1:41 meaning corporate cars and travel cards to their supply chain customers, you know,

1:45 over-the-road truckers that need to procure goods and services and fuel and maintenance for the vehicles as well as their drivers too for food and hotel and so on.

1:53 But yeah, it was a unique situation where I was recruited out of US bank where I was leading their corporate payment sales organization and processing billions of dollars

2:02 because we're the largest issuer of Visa and MasterCard at that time.

2:06 And a recruiter reached out to me and said, hey, there's a unique opportunity here for a growth leader.

2:11 And I was brought in and interviewed. And the test that I had from the CEO and the CFO of the business was the following.

2:18 One is we want you to come in and do an evaluation of the business and tell us what we have.

2:24 And then in 60 days, we want to talk to you again and give us a recommendation what we should do with the business going forward.

2:29 So, you know, it was actually a pretty cool mandate to do, to come and be an advisor, consultant, but also lead the business.

2:36 So 60 days later, I did exactly that. I came back in and said, we said, hey, here's my recommendation on the business.

2:40 And three parts. One is invest in the business, bring growth leaders into the business because you may not realize it.

2:46 But you actually have something incredibly special that very few people in the payments industry have in that you are your own issuer and process your transaction

2:54 and have an open loop and closed loop system, open loop, meaning the business unit that I was running in.

2:59 And then people are most probably familiar with the corporate cards, travel cards, and those expense reporting for travel needs.

3:04 And then the open loop business, excuse me, the closed loop business, which is our overall transportation field.

3:09 So procuring over the road transportation fuel for trucks drop, you know, and semis and so on.

3:16 So at that time, that was nobody really had anything like that. Nobody went to market with that.

3:20 So they built something really special. I don't think in most cases, they realize how special a solution that they really had.

3:25 And I told the business that night. And I said, hey, I think what you really need to do is to bring in some additional growth leaders into this business and run this business and scale like you can.

3:34 And I think you're going to have something wonderful here inside the company and then outside the company as well.

3:39 But given the fact that we were having this conversation, it led me to believe that that was not what they were interested in doing because they had that solution all the time.

3:46 And the reason why they brought me in really be was because they have told different divisions of the company.

3:50 And the division, as they call them branches, was generating the second largest amount of cash for the business and for being a publicly traded company at that time.

3:58 It was a little unusual to have an entity that is not a core asset of your supply chain, produce business and logistics business kicking off that much cash.

4:06 So my second option for him at that time was, hey, I think again, you got something special here, but I think you need to treat the business a little bit differently.

4:15 Why don't you consider taking potentially this entity private, bringing private equity and this grow this business because it's again, you have something incredibly special here.

4:26 But again, you need to run the business a little bit differently and you need to run it more aggressively.

4:30 And then moreover, you can't be focused on your core transportation customers for the ongoing growth of business.

4:36 You need to diversify with some of the other solutions you have that are in market that you simply need a distribution model for that to happen.

4:43 And then three, third option to him, because I knew they weren't interested in potentially doing that, was here's the name of three or four different companies that are active in this space that I think would be in a choir for.

4:54 And then they took me, they actually went ahead with one of those and reached out and had some conversations.

5:00 And then I got a call probably 90 days later or so and said, hey, we are looking to make it a change in here.

5:07 We're going to sell this entity off and you're going to go with it and you are going to be the general manager there, their payments business itself.

5:14 So the business unit that I was running was roughly about $27 million in EBITDA. We were actually then actually merged into a company of like size for $54 million.

5:24 And then for about 14 months, we had an absolute rocket ship and that we grew from 54 million in EBITDA up to 89, close to $90 million.

5:32 And then sold to Warbird Pink is for ability five.

5:36 What an incredible run. Absolutely masterful run. I'm curious going back to the beginning because I think this is where people listening might make it a lot of value from.

5:46 How did you even begin to assess the situation, investigate what was going on and then start to come up with those recommendations?

5:56 What data were you looking at? What interviews were you having? How did you gather the intel needed to come to some of the options and conclusions that you made?

6:06 Yeah, I mean, very simply, we had a great team of people that had been in business for a long period of time.

6:12 We were doing a multi-million dollar tech enhancement at that time.

6:16 So I had a pretty good look and sat in the meetings as far as what was being built, how it was being built and the purpose for it being built.

6:22 Some of the solutions for not only our corporate card customers, but our over the road transportation customers as well.

6:29 And then the people that I spent a ton of time with as far as where they're spending their time, where their core focus in the business, what were their skill sets.

6:40 It was a lot of crossover and existing opportunities that we had within that established base at that time, but there wasn't really necessarily an aggressive outward go to market approach to acquiring new customers.

6:52 We had, as I mentioned, our over the road transportation was very specific.

6:56 You know, you're talking about class 78 trucks, diesel fuel, you know, at trucking sites was generating millions of dollars of spend volume through the platforms and our corporate card payments.

7:07 Although we did step out of our core base of customers outside of transportation, we were still reliant on cross-sell and up-sell into that space.

7:16 So we went in and largely through a Rolodex that I had working at US Bank and then being well networked into the corporate payment space itself.

7:25 We now acquired some really good talent that were very aggressive, that had worked at some leading competitors of ours, whether that be an American Express, some of the banks,

7:35 you know, different transportation companies that I would say was probably a little more ahead of the game than we are as far as where we wanted to get to, that had their own very, very strong playbook.

7:46 And because of that, you know, what we were doing wasn't rocket science, right?

7:51 You know, we were competing against banks, fintechs, corporate payment companies.

7:55 And this was in the day and age before, not long ago, but we're looking at roughly around 2012 where the corporate payments industry was just absolutely taking off.

8:05 Automated payments was there, received image capture of your expenses instead of scanning and faxing in your expense reports, people are just taking pictures of it.

8:13 And so it was kind of at that forefront of where things were getting just really ready to take off and boom.

8:19 Where we were at that inflection where we just had something really special, we had everything we needed to really kind of make it happen.

8:25 But we just needed people that were there that could help make it happen and then be fully supported from the executive team to enable these people to go out there and sell and kill it.

8:35 And we did. We had a pretty very specific plan in place on how we wanted to go to market, what our sales presentation was.

8:43 Everybody, including myself, CEO, and everybody that was involved in the business knew the business down to the basis point.

8:50 So when we engage with customers and clients, we could structure a deal right on spot, knew our ROI or metrics or margins when we went into these meetings.

8:59 And I think that allowed us to be so much more nimble than our competitors who are often, as I mentioned, some of the banks and some of these legacy payment providers that didn't enable a lot of their sales people to do what we were able to do.

9:12 And because of that, we were, you know, not the brand that people were aware of.

9:18 But when we sat across from our customers, we knew we could probably outsell most of them because they were highly trained.

9:24 They knew what they could do. They were enabled to kind of make deals get happened within certain parameters.

9:30 And we just killed it. And quite honestly, we took a unique approach to write.

9:35 So because we're not we were not American Express and American Express dominates the travel and expense industry, we would simply say when we would get in competitive matches where we knew might have been a little bit of our skis as far as, you know, who we're competing against and what they were and what their brand made because, you know, they're running Super Bowl commercials.

9:54 They're on the Wall Street Journal. They've got celebrity endorsers and we're just, you know, EFS and who's heard of these guys, right?

10:02 But we knew our product. We knew how to go to market. And the way that we did to them is like, you know, listen, American Express can keep their business.

10:10 They're great at T&E, their expenses because your people probably want an Amex card in their pocket anyway because it looks good at dinner and everything else.

10:17 But here's the deal. How about we do this? How about you give them the T&E business and I'll take all the accounts receivables that you have to pay instead of paper, excuse me, instead of ACH wire and check.

10:29 Why don't you just let us process that? Well, the approach quickly into is to the ADR files that they were sending us to automate and to pay via credit card or 10 X the size of their T&E.

10:40 So we would give them this business. We would make the seller happy because that's what made their cardholders happy.

10:45 But then the files that we were getting and automating the payment function were 10 X bigger than the other stuff that we gave away.

10:51 So our spend volume base just rocket shipped up and revenue increased. And it was a pretty good specific play plan that we had.

11:01 And then we're doing some pretty other unusual stuff in the market, too, because we had to be nimble and adaptive.

11:07 So we went together and partnered with a lot of expense platforms that we did previous have to make it.

11:13 I would say we were industry agnostic as far as who we partnered with because we just wanted to be in the game as wherever we can be game.

11:20 But then we actually came across some unique opportunities with some accounting software solutions where we integrated our technology into their accounting software.

11:28 So I called it the one and many approach instead of going out and winning 5000 new logos per year.

11:34 I would find a handful of the key accounting software in the right industries where, again, we weren't competing against the name brands.

11:41 And I would integrate my software solutions into those accounting software. So that one partnership was yielding me 5000 potential customers or hundreds of customers depending on the situation.

11:52 And we just ethically scale our business doing unique things like that marketplace.

11:57 Well, and I think a lot of those things. So the partnership track the approach to the go to market jujitsu.

12:04 You have to play against the bigger players and see exactly what that angle is.

12:07 You can win. And then also the velocity of execution and scaling the teams.

12:13 One of the things that you mentioned in our prep session that that was really interesting is that if you're a CRO,

12:18 the most important thing is having the tight relationship with the CEO and the board and having a seat at the table.

12:27 I'm assuming that enabled a lot of the execution and success that you had in that particular run.

12:35 But we'd love to hear what do you need to do in order to build that relationship or evaluate if it's even when you want to build.

12:43 Yeah, I think, you know, I think everybody's kind of been there.

12:46 It's been in the CRO seat where you've got, in some cases, just this wonderful relationship with your CEO between the CRO and everybody's very confident with the game plans.

12:57 Expectations are well understood. Targets and metrics are, you know, it clearly laid out and transparent and that incentive packages are tied to from the top down.

13:07 So there's a single thread to make sure that anybody in the organization is directly tied to the potential outcomes relative to their metrics and their accomplishments and what they need to do to hit that top line number that the business has set out for us.

13:21 But I think where the challenge really, and I think in those situations where people are all are all vested in because they understand the expectations of why we're driving for certain outcomes because they all tie to the top line of business.

13:34 I think within on the opposite side of that was where I see the disconnect is when there's not strong alignment between a CRO and a CEO where there's a little ambiguity as far as what we're trying to do and what we're trying to achieve and where it's going to come from and how it's going to get there.

13:50 I think that's oftentimes a little bit of challenge. And I'll give an example to this. I know in some of my peers I shared with me through some just conversations in the past is when there isn't alignment, goals aren't clearly defined.

14:08 There is a misunderstanding of the data and then reporting in analytics. It becomes a challenge because oftentimes when as your opening statement said, I'm often brought in situations where things are not performing well, right?

14:24 And the average age of a tenure of a CRO in today's private equity back world is like 18 months or something like that. So typically when a CRO was coming into a company, it's usually because something's wrong, right?

14:34 Because why would a CRO lead an organization where you know you're growing at high double digits, you know, or your rural Florida company, everybody's making their number, everybody's, you know, well incentivized and killing their OTE and their bonus and everybody's making presence clubs, right?

14:49 So typically when folks like me are brought into a situation is where things are not on track, right? And we're missing your sales targets. The data isn't there for reporting. There's no good visibility into the forecast.

15:02 And things don't seem to be on track. And oftentimes you get sellers leading, leaving the business as this is happening too. So, and I think where the challenge is, is there is getting the CEO what they need to have to make the proper decisions and then understand the business.

15:17 And oftentimes it means having him lean into the organization, the sales organization and understanding the business himself a little bit, getting very comfortable with the RevOps sales ops team, participating potentially on some calls and or just understanding what is it that you need to help for us to help you understand the business so that you can clearly see whether we're on track or off track.

15:43 And if we're not on track, we can give you all the information that shows you where we're off track. And then we need alignment as far as how we're actually going to get this thing turned around together.

15:53 Is it resources here? Are we in the wrong TAMP? Are we identifying the wrong ICP? Is it, hey, I don't get why, you know, your pipeline isn't there type of questions. Well, it depends on which segment are we talking about.

16:06 We're talking about the SMB side of it. We're talking about the middle market. We're talking about the enterprise portion of the business because in some of the business that worked out, for example, they can have requirements for like three and a half times or 4X pipeline coverage.

16:19 But in some segments, you're doing a really good job because you're hitting that three and a half to four times, maybe in the enterprise, but you're not winning any deals in what is supposed to be your logo acquisition monster of the business, which is your mid market, which is where some of those.

16:33 But because your pipeline is only 2X and the reality is our conversion rates are not very good. So I need more pipeline in this segment here to get me on track.

16:43 So, you know, it's having those that level of understanding as far as everybody needs to understand the business.

16:49 And if you've got certain CROs that want to lean a little bit more, which is fantastic, get some CR CEOs like, hey, you guys just do what you guys got to do.

16:58 I trust that you're going to get there. But keep me informed, which oftentimes is code for it.

17:03 Send me the dashboards and the reporting that I need to know to see on a daily basis to ensure that things are kind of exactly the way you're saying to be.

17:12 And that oftentimes creates that level of confidence. I think to go back to your original question is where I see the disconnect often with the CRO and the CEO is that when, you know, they're just two ships passing each other in the night.

17:24 They're having, you know, a quick call before board meeting on a Monday morning. So you're talking Sunday night. Here's the things you got to know about the business and here's where the deals are.

17:32 And so on. And the pipeline is this, but doesn't have the detail on it. So it makes it harder for him to have those jobs.

17:39 And I think that's probably where the disconnect I often see is when everybody's not on the same page, everybody's not looking at the same level of data.

17:48 Everybody doesn't have a total understanding of what the requirements that are going to meet to keep things on track for the business.

17:55 And I think that transparency is absolutely key. Everybody's got to be on the same page.

18:00Why the CRO belongs in the board meeting

18:00 Everybody's got to be honest on the situation because if the CEO is attending a board meeting and the CRO is not in that meeting, which for me is massive red flag, right?

18:10 Is that that CRO should be in that meeting because I'll tell you this, it's I've been in organizations in the past where the CRO is often left out of a meeting.

18:19 And there's no revenue representation at meetings that in some companies and VCs, you might not have the CRO attending a lot of different meetings because there's not a need for it.

18:30 In some cases, specifically for like a monthly check in meeting, but for a CRO monthly meeting at a private equity or quarterly meeting and there's not there, that to me is it's a red flag.

18:42 And I will tell you, you know, it is so solvable just by having the right people in the room to answer the right questions because they ultimately in the board meetings that I've been a part of, you know, at a PE back board meeting, 80% of the conversations relative to sales.

18:57 They want to talk about sales. What is your pipeline? Where are you winning? Who's doing what deals, what segments, what industries are you specializing?

19:05 How is your marketing campaigns going? You know, what is your, you know, all these things they want to see all that stuff.

19:11 And I'll tell you from living it is the meetings that I haven't been in often end up being me receiving 15 emails either during the board meeting or text or my next week is absolutely filled with board requests to review.

19:28 What is your pipeline? How does it work? We didn't cover to this. I noticed this and this and this.

19:32 You're better off just making sure that the CRO, the CEO is in the board meeting, clearly articulating it, giving level of confidence because I think is when you're removed from the process, it throws up a red flag because there might be something wrong.

19:45 In some cases there might be something wrong. Sometimes there might not be, but it's a red flag.

19:51 I think it's a red flag for sure. And I think the data is so important. My experience that it's an operator and three startups before doing before doing lean scale starting 2021.

20:04 But I always rode shotgun at the board meetings with the CRO because we knew the level of depth and detail that.

20:13 The numbers are going to get to in that meeting is going to require someone who knows it in and out, not just a strategy, not just high level ones, but.

20:21 The amount of detailed data questions that come up in those meetings. It's just absurd. So I was, I don't know, the go to market quant that would show up and just be ready to answer anything that was needed.

20:34 I do agree. I haven't been in a situation where the CRO wasn't in the board meetings. In fact, as I mentioned, like even having your head of rev ops there was helpful in that case.

20:44 But I'm curious for some of the CROs that have challenges building that relationship.

20:53 And in any relationship, it's both sides. Of course. What do you see sometimes if a CRO is spiraling and really letting that relationship kind of get out of control?

21:03 What are some of those fatal flaws that sometimes take place with the CRO?

21:07 Well, I think it always comes down to missing your sales targets. Right. And that not distilling the confidence that you're getting things on track.

21:16 And moreover, if you don't have a firm grasp on the data and the path that you put yourself in a position to get on track, meaning what is the forward leading indications that things are going to get you to where you need to be?

21:32 I think this is where the partnership between the CRO and the head of RevOps is so important.

21:39 In fact, most of the companies I worked at, it is like the right hand person to the CRO has always been my RevOps person because they're the person that's got all the data, can explain all the data as much as you need.

21:52 I'll give you an example. Like, hey, we're struggling in the middle market right now. Our pipeline coverage is one and a half to two X. I need three to four.

22:00 What is the, you know, who's on track? Who's going to get to the number?

22:04 And typically we can look, you know, a ways out based on if we have a firm understanding of the average sales cycle that we have, the average conversion rate that we have on a deal that's actually being sold.

22:16 You know, if we've got a 30 percent conversion rate, we can easily do the reverse math to get us to where we think we're going to be.

22:23 If somebody is going to be successful. And then moreover, is the opportunities and at bats that a person gets beaten by segment.

22:31 And if we can get all of that broken down either at a top of funnel level or in a in specific areas of the sales funnel, whether it's stage one, stage two, stage three.

22:44 I think if you have the data and have parsed it correctly and truly understand it, you know exactly how much of your pipeline is in stage ones all the way through stage seven, what your conversion rates are.

22:57 And then moreover, one of the things I end up learning, you know, and spending a lot of time on the last couple of years is why am I failing between stages three and four or four and five and whatever?

23:07 What are the issues that we have? You know, we have med picking pretty much as a sales philosophy and methodology and most of the companies I work with.

23:15 Typically, you know, that shows us a sign is like, hey, we're missing something here.

23:19 And chances are it's because we're not talking about we don't have a champion or we don't understand the paper process of the contract process or we're, you know, we're skipping through some of this stuff and taking stuff for granted.

23:30 And all of a sudden it comes and bite us because we've got a gluttony of our pipeline stuck in certain stages and we're not advancing them either that or disqualifying them or keep them in the sales stage.

23:40 If you can have that level of understanding of your sales cycle, you're going to be in a great spot.

23:47 And I think that's, you know, you don't need to boil the ocean to the CEO to get that individual to understand that.

23:53 But if you can easily convey this either with the data or somebody can easily explain it.

23:58 I think that's the type of stuff that a CRO, you know, in partnership with their RevOps leadership team shines at or should shine at in a board meeting is those types of things because they know the stuff inside out.

24:12 If they truly know it, they can articulate it in ways that people can easily understand.

24:16 But the challenge is I think oftentimes is people take for granted how actually complicated it is for but not for those that live it day in and out like you and I do.

24:28 And I think that's where all the question is.

24:30 And in my experience is, you know, you can go down a rabbit hole really, really, really fast when you're not making your number because oftentimes when you're making your number and you're cruising through the quarters and you're on track for your year, you know, coming out of Q2 or whatever.

24:46 There's not many as questions because everybody just feels good about it.

24:49 If you can show the ongoing trajectory of the business and things that continue to move in the pipeline building and people are making their numbers and you're adding new logos, you don't receive too many questions.

24:58 It's people when they go down the rabbit hole. It's like, hey, there's an issue here and I want to explore it.

25:02 The challenge is if you don't have the right people in the room to explain it, you're going to lead to 10 X the amount of questions that you wouldn't have to do, which candidly on the flip side and I've experienced this as well.

25:14 It leads to a lot of follow-up meetings, a lot of additional analysis, a lot of different reporting and all of a sudden you're quickly realizing I'm spending my week doing non-revenue generating activities and then doing board reporting of stuff that should have been in the board deck in the first place.

25:31 Then I think it kind of hurts the confidence a little bit of the sellers themselves, like, why aren't we there? We should be representing this. This is what we do day in and day out.

25:44 If you've got a good, strong partnership and there's the trust that is needed between the organization, you're great.

25:50 The one caveat I will say to this is if your CEO is a really, really strong seller themselves and has been in the industry a long time, maybe came out of the sales ranks or potentially a little bit of a unicorn in some cases, but I've worked with a couple of those folks that have been awesome.

26:11 I told them, "No, no, so-and-so has got this. It'll do great. I'm here to get support." But you know your Spidey senses go up pretty quickly when this person is taking this into this meeting.

26:23 I'm waiting for a lot of calls on the back end, which you know is going to come, but unfortunately it does happen.

26:31 Yeah, and I think going back to the data conversation, people do really underestimate what it takes, but I've always had the metaphor of, "Hey, if you were going to go set up a gold mining operation and you invested tens of millions of dollars into all of these machines and conveyors to get mine out of it and you had no idea how much your machines were yielding, that would sound completely absurd."

26:58 So, to not have the GTM telemetry in place, to understand which reps are doing well and why, why are we winning, why are we losing, which channels are producing pipeline or not producing pipeline, and are we in a place that actually has gold to go mine, or do we need to shift our ICP a little bit?

27:16 To not have that access, I have no idea how you do planning, and I don't want to say it will save you, because like you mentioned, you hit your numbers, not a lot of questions.

27:27 People just say, "Great job, do it again next quarter."

27:31 If you don't hit your numbers, but you have a very, very, very good explanation as to why, and you could diagnose it and say, "Here's the plan for next quarter," I think it could save you a quarter or two.

27:42 Now, of course, if you're consistently losing, then fine, but if you don't hit a quarter and then you don't have the answers, that might be the end of your journey.

27:52 Yeah, exactly, and I think it's kind of one of those things, too, is activities are predictive indicators of future results, too.

28:00 I've been in meetings where I think for six months prior, like, "Hey, we need to keep building the pipeline right now, because we have a 120-day sales cycle, and by Q3 or Q4, we should have had this pipeline to advance through the sales stages before, so we can sell these deals within quarter, whether that be Q3 or Q4."

28:21 But a lot of times there's disconnect, and you're not getting the audience you need potentially maybe from on the marketing side, which needs sometimes often the support of the CRO to put the investment in there, because we can tell, as you know very clearly, that, "Hey, if I'm sitting on very little pipeline in our largest logo acquisition segment of our business, and it's a 120-day sales cycle, and I didn't start investing into the marketing at that time,"

28:49 I can predictably tell you that we will not make our Q3 numbers, and the worst thing you can get into is the game of chasing large logos to offset the risk that you had.

29:00 And then we've all been there, right? Where, come to the end of the quarter, I don't have the levers to pull because my entire quarter is coming down to three or four deals that I need to get, and then become a little bit of a desperate seller given discounts, and then you condition your customers to understand,

29:16 "Hey, just wait till I'm going to hold this deal. I don't need to sign this by the 15th of the month because I know the team is going to be coming in here and giving me 20 to 30% off because they need to report into the board that they got these deals done, so I'm going to save myself."

29:28 So we've all been there. So I think it's kind of like having that open collaboration, sharing data, sharing insights well in advance to start to avoid those situations where nobody wants to find themselves, but we've all been there before.

29:42 And it's not a good feeling to be deal dependent in the last two weeks of a quarter when everybody's numbers and incentives are riding on it.

29:51 You can avoid a lot of that pain with open, easy conversation, clear transparency on what's going on. And if you have the relationship with your CEO, you can get out in front of that to avoid those downstream risks that always seem to come when you don't do any things proactively and early enough when they should be done.

30:11The founder-led snapback

30:11 One of the things that you talk about, which I'm really interested in because I feel like I have heard this narrative time and time again as soon as each company gets to a particular point of scale, but then hit some adversity.

30:25 You call it the founder-led snapback, and it always feels like things are going well, you're growing, you're scaling, you miss a quarter or two, and then everybody starts getting real reminiscent about the good old days and everything was working.

30:40 We must have been doing something better a couple years ago or when we started, how is that phenomena so ubiquitous across different companies? What's causing it and how do you deal with it as a Sierra?

30:54 You know, it's kind of a catch-22, right? As I mentioned before, one of the fastest and best-growing trajectories at Arizona is a company that sold for a billion five, and the CEO of the company is a phenomenal salesperson. Just great.

31:07 But I think the difference between that and the situation that you're talking about, the founder-led snapback, is that that CEO also put in place very good structure, so it wasn't a founder-led sales thing.

31:22 He enabled an organization to allow to scale out and to become more commercialized, right? Where I see the biggest challenge in founder-led organizations specifically in newer stage growth companies is that the person that started out was the best seller.

31:40 They had the brand, had the awareness, had all the initial connections in the industry where they can pick up the phone and go through their first 50 people that they know, maybe get 10 initially to sign up, and then all of a sudden you get your seed round, you get this, that, or the other, and things are going well.

31:58 And then all of a sudden you get your money, and now the expectation is that you're going to scale out the organization, you're going to take it from founder-led out to a scalable growth machine. And then invariably what happens is you continue to do that, but there's such a prescriptive sales process that the founder created that oftentimes is not replicable and doesn't scale.

32:19 Meaning you've got four people on a call because we're still, you know, flying the plane, you know, as we build it a little bit, so you got your CTU on a call, you got your product person on a call, you've got a sales engineer call and a seller on the call.

32:32 And for the bigger call, you might even have to bring on your sales leader to the call, and all of a sudden you have an over-engineered, you know, sales process that doesn't work because you can't scale it out because it's just the cost of sales are so heavy and there's too many people and trying to coordinate calendars.

32:47 And then I think that, you know, I think that for the initial transition as you bring on your initial sellers after the founder-led sales process, you can replicate that a little bit, but then when you need to start growing and scaling, it just doesn't work.

33:01 And then when it breaks, meaning your people that you brought into the sales organization that can't do the sales process because everybody has their own style, discipline, and then moreover, we're in the company from day one, so they don't understand all the nuances, what we can sell, what we can't sell, they just understand like this script.

33:17 Just work the script, sell the script, it works. I've been doing it this the whole time. Yeah, but you're also the founder and the CEO, so one, you can sell from a position of authority, plus you know the product better than everybody else.

33:30 And that, you know, when you take that person off a call, then every like three quarters of the responses or questions from the customer say, "Hey, I need to check with our CEO on this and that," so it just prolongates the sales process.

33:42 And then what happens invariably all of a sudden is like, "Oh goodness, we went out and hired a half a dozen new salespeople to take us to the next level."

33:49 And then, you know, sales process, it's not as efficient, you know, the pipeline isn't oftentimes growing as fast as you like it to be because now that founder that had all the connections that got you the first meeting and the second meeting is no longer available, and then your conversion rates are starting to tank.

34:05 So, and then all of a sudden, what do you end up with? Well, you end up with the founder back trying to sell again because he's got to get to his number that he committed to the board or whoever, you know, he committed to for the investment that they took into the business.

34:17 So then, all of a sudden, now you're back to four people on a sales call, you know, it's not efficient, it's not scalable, it's not repeatable, and I've seen it happen many times.

34:27 And I think that's one of the, I think one of the challenges from a CRO that's stepping into is it is oftentimes, it can be a blessing curse, having it transition from a founder-led salesperson that has willingness to hand this over and kind of, you know, and check in and work and support the sales organization.

34:44 But if the founder doesn't kind of step away and kind of remains in there in the sales process and then asserts himself or herself when they want, it just doesn't work and it doesn't scale.

34:55 And I think those are the companies that I would say that kind of just linger out there a little bit and never get where they need to be until something comes in.

35:03 So we said, hey, you got to change, you got to enable these people, you got to give them the authority to go out and sell these deals, but it can be a challenge.

35:14 And, you know, the sales, as somebody told me before, and I think it's a great line, if your founder has to be on every single sales call, you don't really have a true product, you have a seller that could sell, but you don't have a real company.

35:32 And there's, I think there's a lot of truth to that.

35:36 I'm curious, between the, on the spectrum of, hey, I'm involved in every single deal, and I'm an absentee CEO just giving you all of the weight to hit the number and no support.

35:51 What is, what is a healthy level of involvement look like with a CEO? And maybe speak to any founders or CEOs that are listening to this right now. Where would you say, hey, I would really like you to actually be involved in these types of situations.

36:05 I need support here. Here's where maybe you need to set up a boundary where you let your team fly a little bit. What would good look like?

36:12 Yeah, that's a great question. I think it's, I think it comes down to is everybody trained on onboard really well and knows the product inside out, and are they conveying in confidence that before they get on the call they've had the repetitions that they need to be to actually have a really good conversation

36:30 and a sales call with a prospect. Where I've seen it challenging oftentimes is when they're not there yet, haven't had the repetitions and don't understand the process and the technology as well as that they should, where I've seen a lot of issues.

36:48 And then moreover, in some environments when CROs are brought on board, it's often because there's a lot of seller churn because people aren't making their number, and that you're bringing people on so quickly that they haven't been onboarded.

37:00 They're not really unable to sell. But we're kind of, but they're being shoved through the onboarding process because you need to get the bodies and seat to make the calls to build the pipeline and do some of those things.

37:10 And I think that if when you have really good alignment, and you have all these processes in place, and you're doing the things that the blocking and tackling of what we all know needs to get done, and you should have in place and you're not forcing it and you're not reacting

37:25 and you're not creating environment where people aren't ready, but they're being thrown into it. I think there is usually a recipe for disaster and actually prolongs the turnaround from happening, because those sellers will fall and fail quickly because they're thrown into

37:45 the pool too quickly, and they won't make their numbers and they just churn so that sales, the sellers, you know, churn rate could be I've seen them as bad and companies that are need big time turnarounds is 80 plus percent.

37:59 You know, and then you've got to be patient with some of these folks and you can't rush it and you have to identify it is what it is, and then you just have to be disciplined that you're committed to the long game.

38:09 And I think the challenge is a lot of times when it comes to sales and revenue transformation is such a rush to change, obviously, because people need sales and you need to generate revenue and there's, you know, they're always that pressure and for obvious reasons.

38:23 I think it's you got to balance it and be understanding and where we really really at, and I think that the reality is, it goes back to transparency communication that CEO CRO relationship simply saying hey, we met might not be where we want to be, but we are where

38:39 we are, and it's going to take time. And I think we should probably have a really strong conversation relative to realize the expectations and what we are capable of.

38:50 And, you know, it might be, you know, let's think about things differently. Let's think about the approach, how are we doing this thing where was our forecast at, and where is their data tell us we're going to be, and just potentially even relook at your goals and aspirations

39:04 for the year, and then, and but in doing so you got to clearly communicate to the CEO and the board. Why are we in this spot.

39:12 We continue to go down the same path what is going to be the outcomes, but it all has to be have data to support these conversations, and then simply say, and then just lay out different scenarios but it all has to be backed by data that's why data integrity is so important

39:27 because you're like sales and read offs, and with the CRO, because if you can have these conversations, and you can back it by data by using, here's historical information about what would be done in the past here's the average sales cycle here's our conversion rate here's the

39:41 age of the seller that have been here. Some of these people have sales experience some of them don't have sales experience this person used to be a middle market sales person now trying to sell longer more complex and, you know, enterprise level deals that are no longer 90

39:53 or 120 180 days and you're working across matrix organization. I think if you can clearly articulate the challenges that you have, but the direction that you're going.

40:03 I think that even in some very difficult environments that will convey, okay, things aren't going the way we want to at this point, but, you know, they have a steady hand on the wheel, they have a plan, they know what needs get done.

40:18 We need just need to maybe potentially have a little bit more patience that we don't really want to have, but that's going to be the requirement for us to us to get to our end game here.

40:27Pipeline, AI tools and hiring in 2026

40:27 Now that you've been working across quite a few different companies probably various levels of scale.

40:34 I, I, not I think I know go to market looks very different in 2026 than it ever has in the past. And I was curious to pick your brain a little bit, what do you feel is working in terms of building pipeline, getting in front of new logos, getting

40:55 an opportunity to even have that deal because I feel like it's gotten very, very noisy, very difficult to break through. So I was curious from your perspective, what's working there.

41:05 And then the other part that always comes with scaling quickly is hiring and how do you get the best people for the roles you need in seat and what strategies have you deployed that have worked well there too.

41:19 There's a lot of noise out there. And for a lot of different reasons. One is there's so many really cool tools and innovations that have come out and play here that I think have made things equally easier.

41:32 You know, you're talking about CRM solutions, you're talking about note taking solutions, you're talking about usage of some of the AI tools that I just was commenting somebody here just this morning is like, oh my goodness, if AI didn't present this to me, I would have

41:46 never known that this was actually a follow up item that was on my I thought I was waiting for somebody else to do it. But I got the alarms like, hey, you need to go respond to so and so, which was awesome.

41:54 We didn't have tools like that. And then, you know, it could, I would say in many cases right now some of the AI solutions that are out there, you can take potentially an average level seller and make them a top tier seller.

42:06 Right. But what I've also seen is I've seen really good sellers trying to scale to quickly some of these solutions that have gotten sloppy to because I remember talking to a couple very close people that I worked with for a long period of time I'm like, come on, man.

42:22 You're using AI on all this stuff, aren't you? And he goes, well, how'd you know? And I said, because none of this sounds like the way you talk, the way you engage, and I could just tell you're doing, you know, a ton of different things right now, like probably getting a little loose on this because this isn't the standard

42:37 of the stuff that you're working on, you're just trying to scale right now. I get it, but I think everybody's going to get used to that. But I think there's never been a better time to be a seller, because I think there's just so many cool tools available that that are available.

42:51 So, but I think the challenge is to avoid taking the easy path and not doing the blocking the talent, the tackling that veteran salespeople have always used in their career that when times get tough, you get back to because you know it works and it's discipline, it's been tested through the systems, the platforms, the sales methodologies, whether it be med pick and/or others, you know, to use that.

43:15 And if you incorporate a lot of those old school disciplines, like I mentioned before, into the new AI solutions, oh my gosh, it takes two worlds and makes them even that much better if you can get them done right.

43:26 But you know, I have to use them right. Where I've been, to answer your question relative, like from sales hiring and where I've been finding people, I've been very fortunate to work with a lot of very good people for a long period of time.

43:38 And in many cases where I've come into CR role roles for different opportunities, I've always had a really good rolodex of people that I had that had skill sets that I've been able to closely pair with me.

43:52 And I've just been fortunate with some of the success that we had in the past, that the people who worked with me have been successful as well, and that, you know, we tend to kind of align back up on other deals that we worked on in the past.

44:04 So in fact, I just had a guy that I hired for another company, worked for a very large bank running a product saying, "Hey, what are you up to? Questions?"

44:12 I know it's coming. He's going to be asking me like, "Hey, what can we work on next together?"

44:16 Which is, it's a great feeling to work with people that have been great, you know, that you spend a lot of time with, you trust, and you know, success breeds success a little bit, I guess.

44:27 I think it's very tough to be having a good experience, hiring with a network that hasn't been a losing strategy for me, and it's worked very well.

44:37 And also, I really appreciate the perspective on the fundamentals, because I think a lot of people are leveraging AI to be more efficient.

44:47 I think if you're leveraging AI to do a higher quality job and a more thorough job, I think you're going to get more out of it.

44:55 And I think you're going to show up and differentiate more. But if you're trying to do B-level work across more people, just do A-plus work for a smaller group, and I think you're going to win.

45:06 Yeah, I totally agree with you. And I think where it gets, and I've seen this in the last year or two, where, you know, you say, having worked in the C-suite and all of a sudden you've got other C-suite partners that, you know, are tinkering around with AI tools.

45:22 Sometimes when you, in different AI solutions than most of the people that use in the company, and all of a sudden they show up to a meeting with a top customer with a brand new presentation and a brand new deck, presented the data, you know, represented in a way you've never seen it before.

45:40 And all of a sudden, unfortunately, sometimes you end up like 20 minutes to review before you get on board and like, "Hey, where did this come from? Where did this logo go on? Are we really doing this?"

45:49 And so on. So I think it's kind of one of those things where you can truly get out in front of your skis pretty, pretty quickly. And even though the data is right, it's presented differently, and the talk tracks differently.

46:01 And then if you keep doing that over and over and over again, your message gets lost. Moreover, it kind of goes back to everybody needs to be on the same page and articulate the value proposition and what we do and how we do it in a way that is convincing, and that you've got a firm grasp on it.

46:18 But when you start introducing new presentations, new PowerPoints or whatever decks that you're using, or you're changing your demo all the time because you found a new tool that you thought was cool.

46:30 But yet, some people in the C-suite are using it because they had access to it, and then other people get to it, and then all of a sudden you get this massive amount of 50 versions of every deck that you might have, even though it's your basic one-on-one deck of what you do.

46:44 But now you've got 50 different versions of it, people talking about what you do 10 different ways from Sunday.

46:50 And it just gets, you kind of, I hate to say, you lose your brand a little bit and then lose who you are from a value proposition because I've always said, hey, if I step out of this room, you know, it's a sales presentation, and I look at Anthony and say, hey, Anthony, man, I got to step out to make a call.

47:07 It's an emergency or whatever. You got it. I've got 100% confidence you're going to run that meeting just like I will because we're on the same page.

47:14 We've done this a million times. You know, you know your stuff inside out just like I do, and it's rinse, lather, and repeat.

47:21 But now I simply see with, you know, so many tools and these, you know, all these resources that people have, they're just going to market with them.

47:29 And then all of a sudden, it's kind of like people, I get calls from people all the time after these meetings, so we say, are we really doing that? Can I get that?

47:37 Where's that coming from? I'm like, I have no idea. Somebody's using Claude or doing something differently on it, but I don't know what's going on.

47:44 And, you know, I think invariably people win a couple of deals, you know, doing that.

47:48 And then all of a sudden, other people see it and want it. And then all of a sudden, you go to your marketing library and there's 80 different variations from anything, you know, and there's the quality is gone, you know, there's just slop all over the place.

47:58 And we're in a day and age, right? You know, I, you know, I think we thought about five years ago before all this stuff came out that we had a firm grasp on all this so you can lock this stuff down.

48:07 And I think now it's kind of opened Pandora's box a little bit. Now, some of the stuff is really cool.

48:12 And I think that things will get settled over a period of time. But yeah, it's a little bit of the wild west on some of that stuff.

48:20 Yeah, and I think you should absolutely use AI and you'd be a complete fool not to, but don't lead with your thinking, your brand, your strategy, make it consistent, make it concise, and then leverage AI to execute or do an A+ job for your customer or your prospect.

48:40 But to your point, if you're having trouble understanding what your message and brand is internally, there's no way in hell a prospect is going to understand it.

48:47 So if you can't get aligned, just imagine how much further removed they are from all the conversations that you're having internally, all the internal meetings, all the everything that you're consuming every single day.

48:57 They're seeing you one or two times, depending on what your sales cycle looks like. They're not gonna be able to follow. So I think you've got to get your house in order first, get it consistent.

49:07 And I just remember most people need to be reminded more than they need to be told something.

49:12 Yeah, yeah. And you're right, everybody in the sales organization, sales revenue, marketing or whatever should be telling the same way to the same person over and over again.

49:23 So you're not running into a situation, you go to a conference and they said, "Hey, I talked to Todd or Sally or somebody said you guys are doing these things."

49:30 And it's kind of like, "Well, kind of." You know what I mean? It should be very, very everybody. It's cut and paste. This is exactly what we do. Here's how we do.

49:38 So you set the proper, it always comes down to setting the proper expectations internally and externally. And I say this all the time to people.

49:48 If we're doing this correctly internally, it's gonna work externally. The problem is when you get people doing different things and then the expectations outside are wrong and you never want to be in that position because you always want to set the expectation with the customer properly.

50:04 So that if something were to go awry or something to work, it went to plan. Now, things may come up where you kind of have to adapt and change or pivot on.

50:13 But the reality is if they are clear and you're transparent and they trust you, you're giving them proper expectations.

50:19 And I've always, it's saved my butt so many different times. It's just, you know, I sell this way, this is how it works and it might not be perfect, but I'm telling you it will work over time if we commit to this thing.

50:33 And this is going to be the timeline. So that's and the product is there's no selling ghostware or anything else. It's here's what we do. Here's how we do it. Here's how the technology works. Here's what we're going to deliver in a time frame.

50:45 It's going to deliver. Do we have mutual understanding on this thing? Yes, great. Cool. Let's get a plan to get it in place and execute on it.

50:52 And I think if you can get down to that basic base, you know, it's it comes down to just basics and the fundamentals.

50:59 And I think that if you continue to do that in the day and age of AI and use it to 10 X your business, fantastic.

51:05 But I think is when, you know, you get a little too creative and you're not setting expectations, correct.

51:11 I think that's when instead of, you know, achieving your goal, you can get exponentially in the wrong direction really, really fast and lose trust with people right away.

51:22Wrap

51:22 Well, Christian, thank you so much for being on the podcast. You have so much experience from a go to market perspective.

51:27 You've kind of seen it at all stages. You work with a variety of companies. So you have that pattern recognition.

51:32 And I really, really appreciate you distilling it down to the things that are important.

51:37 Everyone on from the audience is going to be taken away like, hey, data is everything.

51:42 It's what bridges the transparency to build that relationship with the CEO and the board and enables you to run the business and make the bets you need to make.

51:51 And then also everything around executing through scaling go to market from hiring, getting the right tools in place and leveraging AI in the right way in this new age of go to market.

52:06 I think it's been really, really valuable. So I appreciate everything you shared and can't wait to see what you do next.

52:14 Now, I'm excited. You know, I think we're living in great times if you're a seller and and I'm very fortunate to work with a lot of great people, continue to meet wonderful people like yourself, doing really cool things and innovating.

52:28 And I'm on a daily just being shocked about people having such great success in the areas that I never thought and considered, which I think would be really, really cool.

52:38 So, yeah, if anybody, you know, is, you know, wants to reach out to me, please reach out to me.

52:44 Always happy to have a conversation. I love and live on building networks that are mutually beneficial.

52:54 And, you know, formats like this to get a greater audience, a greater presence, greater awareness of not only what you're doing, what I'm doing, what other cool people are doing and building themselves.

53:07 I think is absolutely phenomenal. So I appreciate, Anthony, that you have a format like this that you invited me.

53:13 So I'm very appreciative of that. And, you know, if there's anybody that is looking for a revenue transformation, needs to grow their business, whether they're missing their sales targets and can't figure out their forecast and the forecast isn't right.

53:26 So again, struggling to figuring out a way to move from founder led sales into building a sales machine, reach out happy to work with you and engage with you through Tech CXO, which I'm a partner in the revenue growth business.

53:42 And that's what we do for private equity back VC back companies as well as privately and publicly held companies.

53:47 If you want to have an engagement that way, same thing. And yeah, it's just absolutely static to be here with you today.

53:56 Well, I know there's plenty of companies that are in that situation and I'm sure you'll be getting some calls. So thank you, Christian. Appreciate it again.

54:03 Awesome, Anthony. Appreciate your time.