---
title: "What Needs to Be True? The Question That Changed How a CRO Leads"
episode: 148
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Nick Reyes"
guest_title: "Chief Revenue Officer"
date_published: 2026-10-29
date_modified: 2026-11-09
duration: 00:55:12
word_count: 9348
topics: ["sales-leadership", "revenue-operations", "gtm-strategy", "outbound-sales", "ai-in-gtm"]
canonical_url: https://www.leanscale.team/knowledge/podcast/nick-reyes-pushpress-what-needs-to-be-true/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# What Needs to Be True? The Question That Changed How a CRO Leads

_Nick Reyes on going from the Marine Corps to first salesperson at PushPress, the RevOps hire he wishes he'd made years earlier, why RevOps now builds guardrails instead of castles, the 5 a.m. habit that taught him the financial model, and the one question that changed how his team solves problems_

**Episode 148 · The LeanScale Podcast**  
Nick Reyes, Chief Revenue Officer (PushPress) · Hosted by Anthony Enrico  
Published October 29, 2026 · Updated November 9, 2026 · 00:55:12  
Canonical: https://www.leanscale.team/knowledge/podcast/nick-reyes-pushpress-what-needs-to-be-true/

**Topics:** Sales Leadership · Revenue Operations · GTM Strategy · Outbound & Sales Development · AI in GTM


## Executive summary

Nick Reyes is Chief Revenue Officer at PushPress, the gym management platform built by gym owners for gym owners. He joined as its first salesperson, for equity and almost no salary, and over nearly a decade has owned sales, customer experience and marketing on the way to CRO. Host Anthony Enrico sets that against the 18 months he gives as the average CRO tenure in SaaS.

His route was unusual. Burned out by the pressure of a top prep school and wanting to go against the grain, he skipped college and enlisted in the Marine Corps. Mission accomplishment made sales a natural fit: first at Sprint, then public-sector sales of in-car digital video systems to police chiefs and sheriffs, then Caterpillar's rail division, where he grew an inherited territory of about $500K a year past $20M in hardware and software. A local CrossFit gym ended his back pain from the military, and when it was about to close he stepped in to run the business side, which is how he met the three PushPress founders. He decided the move was not a one-way door, and that if he was as good at selling as he thought, there was no risk.

The early years meant cold calls, walking into gyms in other cities, and a Google Hangout connecting him in Kansas City to founders coding in a gym office in LA. The market was what he calls a grungy, we-don't-use-software crowd with low margins, and some owners were still chasing members for physical cash. Ease of use turned out to be the value proposition, because a gym owner wants to be on the coaching floor, not in the software.

The operating lessons start with a regret. A sales leader he consulted told Nick to invest in RevOps way sooner than he thought, and he didn't listen. He now says he would have had a data-fluent operator before the seed round, or, running lean with AI, after a couple of reps. The signal that you are past due is spending too much time learning infrastructure yourself. He expects RevOps to shift from building tools to building the guardrails that let everyone else build, and argues the modern CRO has to be both builder and seller. Financial fluency is part of that: for a stretch he sat down at 5 a.m. every day to study one line of the company's financial model.

The through-line is a question. Instead of asking how to get from 100 demos a month to 200, Nick asks what needs to be true for 200 to happen. He says the wording opens the imagination, removes the assumption that you are limited to the resources in front of you, and takes the accusation out of asking a team to go faster. Anthony supplies the origin story from his own career: a growth model built to prove a doubling target impossible, which his CEO loved. The episode suits CROs, founders and RevOps leaders deciding when to invest in operations and how to plan against ambitious targets.


## Key takeaways

1. **"What needs to be true?" opens options that "how do we get there?" closes** — Nick's example is a team booking 100 demos a month that needs 200. Asking how to get to 200 doesn't open his imagination. Asking what needs to be true for 200 lets you list everything, including options like a $0 price, knowing not everything should stick. He calls it essentially first principles thinking.
   _Why it matters:_ Organizations tend to take a goal and work only with the box of toys they already have. The question assumes the box does not exist, so the team starts by imagining what the goal requires and then decides what is worth doing.
   _For:_ Revenue Executives, Founders, Sales Leaders

2. **The question takes the accusation out of asking for more** — A team member told Nick a project could be done in late April or early May. Telling them to get it done in January would be almost an indictment of the work behind the original date. Asking what needs to be true to finish by year-end invites an answer such as a million dollars or 10 people.
   _Why it matters:_ Once the cost is on the table, finance and the CEO can have an open discussion about whether it is worth it. Nick wants to see that someone has thought past what they currently have to play with, and an April date may be perfectly acceptable under those constraints.
   _For:_ Revenue Executives, Founders

3. **Argue about the inputs, then see what output they produce** — Anthony was head of RevOps at Emailage at $20M in ARR when CEO Ray rejected a plan and asked to double again, having just gone from about $12M to $20M. To prove it impossible, Anthony modeled the reps, conversion rates, pipeline, channels and churn that $40M would take. Ray's response was that this was everything he had been hoping for.
   _Why it matters:_ Backing into the requirements moves the debate from the target to the inputs. Nick adds that the question repeats at each level: if you need to hire 200 reps, what needs to be true to hire 200 reps? You back into the whole plan piece by piece.
   _For:_ RevOps Leaders, Revenue Executives, Founders

4. **Invest in RevOps way sooner than you think** — While looking for coaches and mentors among sales leaders, Nick was told by one of them to invest in RevOps immediately. He didn't listen, and spent several years funding roles that could close a deal or support a customer instead. He says he waded through the mud as a result.
   _Why it matters:_ Since investing heavily in RevOps, Nick has gained data fluency, an early warning signal, a partner on sales compensation and a large amount of mental bandwidth back. Anthony acknowledges how hard it is at an early stage to trade away another quota carrier or marketer for that.
   _For:_ Founders, Revenue Executives, RevOps Leaders

5. **Start RevOps on sales, marketing and attribution** — Looking back, Nick says he would have had someone far more data fluent before PushPress raised its seed round, starting on the sales and marketing side, because distribution is everything once you have product-market fit. Asked about team size, he says that if you are running lean, especially with AI today, you can probably wait until you have a couple of reps.
   _Why it matters:_ The first hire should be able to build the infrastructure that makes a sales team click and to understand attribution, which amplifies the output of both sales and marketing.
   _For:_ Founders, RevOps Leaders

6. **You're past due if you're learning how to do the RevOps job yourself** — Nick sees some benefit in figuring things out yourself. He had never set up a vertical SaaS sales comp plan and studied it. But if that goes on too long you are doing the organization a disservice, because you are doing the job of RevOps instead of leading the revenue function.
   _Why it matters:_ The signal is simple: if a revenue leader is spending too much time learning about infrastructure or how to do the job, it is time to bring someone in, and probably past time.
   _For:_ Revenue Executives, Founders, Sales Leaders

7. **RevOps is moving from building the castle to building the guardrails** — Nick says RevOps has the same mission but will execute it differently. If everyone is operating their own agent, building tools or making their own dashboards, RevOps stops leading the creation of those tools and instead builds the guardrails that let experts play in the sandbox.
   _Why it matters:_ Anthony sees the same shift in scope. When he started LeanScale in 2021 he says 60 to 70% of the work was in Salesforce. Now some clients have 30-plus go-to-market tools, run AI workflows across the stack, and manage a data warehouse so agents can run on top of it.
   _For:_ RevOps Leaders, Revenue Executives

8. **The modern CRO has to be both builder and seller** — Nick's CEO told him people need to be either builders or sellers. Nick's reaction was that a CRO has to be both. Anthony agrees and calls the CRO the most difficult position in a company: a pure RevOps career will struggle to own a number in front of a board, and someone who has only carried a bag may not know how to get more leverage from the system.
   _Why it matters:_ Anyone aiming at the CRO seat should take side quests to get the full breadth of the role. Nick also points technical sellers who like to tinker toward RevOps, where knowing the craft and the technology together can make someone dangerous.
   _For:_ Revenue Executives, Sales Leaders, RevOps Leaders

9. **A CRO has to go to finance's language, not the other way around** — Nick built PushPress's early bottoms-up and top-down models, enough that a strong finance leader later found the company wasn't completely flying blind. He does not expect finance to speak pure sales and marketing language, so the CRO has to learn theirs.
   _Why it matters:_ He doesn't know how you build comp plans or launch a new campaign without understanding LTV to CAC, CAC payback and what goes into each variable. Anthony points to the CRO and CFO partnership as an overlooked source of leverage, a point he says Pavilion founder Sam Jacobs makes often.
   _For:_ Revenue Executives, Sales Leaders

10. **Study one line of the financial model every morning** — When PushPress rolled out its latest financial model, Nick found terms and benchmarks he didn't know well enough. So every morning at 5 a.m., with a cup of coffee, he picked one data point and spent an hour on it: what are the benchmarks, what does good look like, what does great look like, what is ours.
   _Why it matters:_ He kept going until he understood all of it. The payoff came in pitches and diligence, when questions were being fired at him and he had all the confidence in the world.
   _For:_ Revenue Executives, Sales Leaders, Founders

11. **Endurance only works if you're on the right mission** — Endurance is one of the Marine Corps leadership traits, and Nick calls it one of the most underrated, at least in a growth role. He connects it to PushPress investor Altos Ventures and its preference for hedgehogs, people about the mission rather than chasing an outcome. In all his years he says he has never questioned the mission of helping gym owners.
   _Why it matters:_ If you want to quit when it gets tough, it may simply be tough or you may be on the wrong mission. Without being locked in when the system goes down on a Sunday, he says you cannot be there for the long haul.
   _For:_ Revenue Executives, Founders

12. **Hiring your customers as reps is a gift and a curse** — PushPress's early sellers were gym owners and clients. They knew the industry and the system very well, had near-zero ramp time and came with a strong network. But they are entrepreneurs who don't like staying within a tightly confined space, and they may not be natural or polished sellers.
   _Why it matters:_ Customer-turned-rep hiring is a strong source of early traction in a vertical market. Nick calls it a possibly unique advantage that everyone in the fitness space believes in coaching.
   _For:_ Founders, Sales Leaders

13. **Build the AE bench from your SDR team** — PushPress couldn't get outbound to work for years. It now has a very strong cold SDR motion that Nick wishes it had landed on forever ago, and that team is the source of future account executives. He says he doesn't think he will ever bring anyone in externally to sit straight in the AE seat.
   _Why it matters:_ Anthony likes the bullpen model for the commitment it earns compared with bringing in mercenary AEs. Nick's caveat is that the bench depends on the channel, so anything that kills outbound would also remove the talent pipeline.
   _For:_ Sales Leaders, Revenue Executives

14. **Don't be beholden to one channel** — Over the years, PushPress went from mostly inbound leads and no outbound success, to learning paid ads during a period when Meta had amazing ROI, to a strong outbound motion. Nick says you have to pounce on a channel while it works and keep experimenting with what didn't work last time.
   _Why it matters:_ He imagines AI voice agents flooding the market and killing outbound. Then you would have two problems: replacing the channel and replacing the bench of sales talent. He approaches almost every go-to-market motion the same way: untangle the factors, solve one, rinse and repeat.
   _For:_ Sales Leaders, Marketing Leaders, Revenue Executives

15. **In a low-tech market, ease of use is the value proposition** — Nick says ease of use can sound like a hollow value prop. But a gym owner wants to be on the coaching floor delivering a fitness result, and almost wants the software to disappear. Legacy systems at the time looked archaic and were bloated with toggles.
   _Why it matters:_ PushPress's early conviction was that it did billing and scheduling with more simplicity than any other tool and believed in integrations rather than marketing itself as an all-in-one. Nick says it took longer than most to learn how to build a SaaS company, in part because the team came from the fitness industry rather than from SaaS.
   _For:_ Founders, Marketing Leaders


## Frameworks

### What Needs to Be True? (44:15)

**Definition:** Replace "how do we get there?" with "what needs to be true for this to happen?", list every condition without limiting yourself to current resources, then decide which are worth pursuing.

Nick says he first uttered the phrase about a year before recording but has always thought that way. He calls it essentially first principles thinking and a way to unlock imagination. It also makes a harder target less pointed, because the answer can be a request for money or people that finance and the CEO can weigh. He says AI makes it more relevant, since ideas no longer have to go through engineering.

### Argue About the Inputs (52:07)

**Definition:** Take the target as given, spell out what it would require, and move the debate to the inputs rather than the outcome.

Anthony's story from Emailage: the model he built to show that going from $20M to $40M was impossible listed the reps, conversion rates, pipeline, channels and churn it would take, and his CEO loved it. Nick extends the logic down the chain: if the answer is 200 reps, what needs to be true to hire 200 reps?

### The RevOps Past-Due Signal (27:01)

**Definition:** If a revenue leader is spending too much time learning infrastructure or how to do the RevOps job, it is time to bring someone in, and probably past time.

Nick sees value in figuring some of it out yourself, such as a first sales comp plan. Left too long, the leader stops leading the revenue function and starts doing RevOps, which he calls a disservice to the organization.

### Guardrails, Not Castles (28:15)

**Definition:** RevOps keeps its mission of giving the go-to-market organization leverage, but builds the technical infrastructure and guardrails that let others build, rather than building the castle for everyone to look at.

Nick expects people across go-to-market to operate their own agents and build their own tools and dashboards as experts in their craft. RevOps' job becomes understanding the technical infrastructure that makes that safe and useful.

### The Builder-and-Seller CRO (31:21)

**Definition:** A CRO needs to be able to carry a number and build the systems behind it, and financial literacy rounds out the role.

Nick's CEO framed people as builders or sellers. Nick says a CRO has to be both. Anthony argues a pure systems background struggles with being accountable for a number at the board, and that a pure sales background misses leverage from the system, so aspiring CROs should take side quests.

### One Data Point at 5 a.m. (34:17)

**Definition:** Study one line of the company's financial model each day: its benchmarks, what good looks like, what great looks like, and where your own number sits.

Nick spent an hour each morning at 5 a.m. until he understood the whole model, which later gave him confidence in pitches and diligence.

### Endurance as a Leadership Trait (35:32)

**Definition:** Endurance, one of the Marine Corps leadership traits in the JJ DID TIE BUCKLE acronym, is underrated in growth roles and depends on being on a mission you never question.

Nick says there will be times when the system goes down on a Sunday after a week on the road. If you can't look at the mission and stay locked in when it gets tough, you can't be there for the long haul.

### Hedgehogs Versus Foxes (36:05)

**Definition:** The framing Nick attributes to an Altos Ventures article: the firm invests in hedgehogs, long-term people about the mission rather than about just chasing an outcome.

Altos led PushPress's A and B rounds, according to Nick, and he and his CEO keep little hedgehogs on their desks. He uses the idea to explain why being on the right mission is what makes endurance possible.


## Quotes

_Speakers inferred from an undiarized transcript — verify before attributing._

> "How do I get it to 200? For whatever reason, those words don't open my imagination the way that what needs to be true for us to have 200 does."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (44:49)

> "It really is just a way, I think, to force yourself to unlock your imagination to all of the potential that could exist."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (45:23)

> "Well, the box doesn't exist. The toys don't exist. Imagine the toys."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (46:03)

> "Now everyone can be a builder. So now what's the excuse?"
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (46:45)

> "Show me that you've gone through the thinking, not just of what you have to play with."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (49:03)

> "And it's like, see Ray, it's impossible. And he goes, this is everything I've been hoping for."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 148 (51:27)

> "Let's argue about the inputs. And then we'll see what output that'll produce."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 148 (52:10)

> "You need to invest in RevOps immediately, way sooner than you think. And I didn't listen."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (23:14)

> "I feel like I waded through the mud for several years, choosing maybe investing in other areas because they could close a deal or they could support a customer rather than they could support me and the entire go-to-market team."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (24:30)

> "If you're spending too much time learning about infrastructure or how to do the job, then you need to bring in someone and you're probably past due bringing in someone at that point."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (27:10)

> "I think they're gonna be building the guardrails that allows everyone else to play in the sandbox as the experts in their craft."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (28:15)

> "I actually think it's more about understanding the technical infrastructure that allows people to play in the sandbox than it is actually building the castle in the sandbox and then having everyone look at the castle."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (28:32)

> "I'm thinking as a CRO, you have to be both a builder and a seller at this point."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (31:31)

> "I just don't know how you can do the job effectively day in and day out, where partnering with finance is so critical to doing the CRO job well, if you're not speaking the same language."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (33:24)

> "I don't know how you build comp plans without it. And I don't know how you can launch a new campaign without understanding, LTV to CAC, CAC payback, what goes into each of those variables."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (33:50)

> "I made a point to every single morning, sit down at 5 a.m., cup of coffee, look at our model, dig into one data point."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (34:17)

> "If you can't, I think, look at the mission and go, no, this is still important and I'm still locked into it, even when it gets tough, you can't be there for the long haul."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (37:59)

> "I can't see a world where I would hire anyone that's not on that team to be an account executive."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (41:55)

> "If you're really that damn good, then it's an automatic yes, because the only thing this company is missing is you."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (14:07)

> "A gym owner wants to be on the coaching floor with their members, delivering a fitness result, and they don't wanna have to clickety-clack in a software. They almost want the software to disappear."
>
> — Nick Reyes, The LeanScale Podcast Ep. 148 (20:56)


## Practical advice by role

### Revenue Executives

- Replace "how do we hit this?" with "what needs to be true for this to happen?" in planning meetings, and allow answers that fall outside current resources.
- When a date or target is too slow, ask what it would take to move it rather than asking the team to compress its own estimate.
- Learn the financial model one line at a time: the benchmark, what good and great look like, and your own number.
- Learn finance's language rather than expecting finance to learn sales and marketing's. Understand LTV to CAC and CAC payback before building comp plans or launching campaigns.
- If you are spending too much time on infrastructure or on how to do the job, bring in RevOps now.

### Founders

- Plan for RevOps earlier than feels comfortable. Nick would have had a data-fluent operator before his seed round, or, running lean with AI, after a couple of reps.
- Point the first RevOps hire at sales, marketing and attribution, because distribution is everything once you have product-market fit.
- In a vertical market, consider hiring customers as early reps for their network and near-zero ramp, and expect them to need coaching and some tolerance for structure.
- Check whether the mission would hold you through the worst weeks. If it wouldn't, Nick suggests you may be on the wrong one.

### RevOps Leaders

- Plan for a world where go-to-market people operate their own agents and build their own dashboards, and define the guardrails they work inside.
- Build an understanding of the technical infrastructure, including the data layer agents run on, as well as the CRM.
- Take a target you think is unreachable and model exactly what it would require. Use that to move the debate to the inputs.
- Spend time carrying a number if you aim to be a CRO, so you know what it takes to be accountable for one at the board.

### Sales Leaders

- Treat the SDR team as the AE bench and promote from within rather than hiring AEs externally.
- Do not rely on one channel. Pounce on what is working and keep testing what didn't work last time.
- Consider what happens to your talent pipeline as well as your pipeline if outbound stops working.
- If you have technical sellers who like to tinker, point them toward RevOps as a career path.


## AI takeaways

**Thesis:** Nick sees AI as removing the excuse that good ideas have to wait for engineering. If everyone can build, the planning question becomes what needs to be true, and RevOps' job becomes the guardrails around what people build.

- **** — 
- **** — 
- **** — 
- **** — 
- **** — 
- **** — 

**Agent & automation ideas**

- A what-needs-to-be-true planning agent that takes a target and lists the reps, conversion rates, pipeline, channels and churn it would require, then flags which inputs are assumptions.
- A financial-model tutor that picks one line of the company's model each morning and returns its benchmarks, what good and great look like, and the company's own number.
- A guardrail checker that validates agent-built dashboards and tools against RevOps-owned definitions and permissions.


## Operations takeaways

### Revenue operations

- **.** 
- **.** 
- **.** 
- **.** 
- **.** 

### Pipeline & marketing ops

- **.** 
- **.** 
- **.** 
- **.** 


## Metrics mentioned

| Value | Metric | Context |
| --- | --- | --- |
| About $500K to over $20M a year | Caterpillar rail territory | The territory Nick inherited and grew across hardware and software sales. |
| 18 months | Average CRO tenure in SaaS | Anthony's figure, set against his description of Nick having almost a decade in the role. |
| 100 to 200 a month | Demo target example | Nick's illustration of a growth problem framed as what needs to be true for demos to double. |
| One hour at 5 a.m. | Daily finance study | Nick's routine of digging into one data point in the financial model every day. |
| 60–70% | Salesforce share of early LeanScale work | Anthony's estimate of how much of the work was in Salesforce when he started LeanScale in 2021. |
| 30+ | Go-to-market tools at some clients | Anthony's description of companies LeanScale works with that have point solutions for everything and run AI workflows across the stack. |
| About $12M to $20M, with a target of $40M | Emailage ARR | Anthony's recollection of where the company stood when his CEO asked the team to double again. |
| Half a billion dollars | Emailage exit | Anthony's description of the company's outcome. |


## Entities mentioned

- **PushPress** (company) — Nick's employer, the gym management platform built by gym owners for gym owners. Started by three founders in LA, it hired Nick as its first salesperson in Kansas City. He describes years of learning how to build a SaaS company, RevOps investment he wishes had come sooner, and a move from gym-owner reps to a cold SDR motion. · https://www.leanscale.team/knowledge/company/pushpress/
- **Caterpillar** (company) — Where Nick moved into enterprise sales. He inherited a territory at its rail division doing around $500K a year, selling hardware and software for bearing detection systems on rail lines, and grew it to over $20M a year. · https://www.leanscale.team/knowledge/company/caterpillar/
- **Sprint** (company) — Nick's first tech sales job after the Marine Corps, working in a retail store. He then moved to a Sprint partner for public-sector sales. · https://www.leanscale.team/knowledge/company/sprint/
- **CrossFit** (company) — Nick stumbled into a new CrossFit gym with back pain from the military, was free of painkillers within months, and later helped run the gym's business side. He says CrossFit laid the foundation for today's group fitness market and is the community PushPress first sold into. · https://www.leanscale.team/knowledge/company/crossfit/
- **Mindbody** (company) — Named as a behemoth in the space that was light years ahead of PushPress early on and thrived in yoga and Pilates. · https://www.leanscale.team/knowledge/company/mindbody/
- **Altos Ventures** (company) — PushPress's lead investor in both its A and B rounds, according to Nick, who cites its article on hedgehogs versus foxes and says it invests in long-term, mission-driven founders. · https://www.leanscale.team/knowledge/company/altos-ventures/
- **Emailage** (company) — Where Anthony was head of RevOps. He tells the story of building a growth model to show CEO Ray that doubling from $20M to $40M in ARR in one year was impossible, and says the company later had a half-billion-dollar exit. · https://www.leanscale.team/knowledge/company/emailage/
- **LeanScale** (company) — Anthony's company, started in 2021. He says that at the time 60 to 70% of its work was in Salesforce, and that it now works with companies running 30-plus go-to-market tools. · https://www.leanscale.team/knowledge/company/leanscale/
- **Meta** (company) — Nick's example of a channel that for a time had amazing ROI and that he says you should pounce on without becoming beholden to it. · https://www.leanscale.team/knowledge/company/meta/
- **Pavilion** (company) — Anthony cites founder Sam Jacobs as often talking about the CRO and CFO partnership and the financial literacy it requires. · https://www.leanscale.team/knowledge/company/pavilion/
- **ZoomInfo** (company) — Named by Anthony among the small set of tools that made up a typical stack when he started LeanScale in 2021. · https://www.leanscale.team/knowledge/company/zoominfo/
- **Nick Reyes** (person, guest) — Chief Revenue Officer at PushPress and its first salesperson; Marine Corps veteran who grew a Caterpillar rail territory from about $500K to over $20M a year. · https://www.leanscale.team/knowledge/guest/nick-reyes/
- **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://www.leanscale.team/knowledge/guest/anthony-enrico/
- **Salesforce** (tool, CRM) — Anthony says that when he started LeanScale in 2021, 60 to 70% of the work was in Salesforce.
- **HubSpot** (tool, CRM) — Named by Anthony alongside Salesforce as the other CRM in the typical 2021 stack.
- **Outreach** (tool, Sales Engagement) — Named by Anthony as the sequencing tool in the typical 2021 stack.
- **Wispr Flow** (tool, AI Dictation / Voice) — Anthony says one of his favorite things to do is dictate ideas into a Google Doc with it, then ask AI to turn them into something that makes sense.


## FAQ

**Q: What does asking "what needs to be true?" do that "how do we get there?" doesn't?**

A: PushPress CRO Nick Reyes says "how do I get it to 200?" doesn't open his imagination the way "what needs to be true for us to have 200?" does. The first question usually means working with the resources you already have. The second lets a team list every condition that would make the goal happen, even ones like a $0 price, and then decide what is worth doing. Nick calls it essentially first principles thinking. It also makes pushing a team less pointed: rather than demanding an earlier date, a leader asks what it would take, and finance and the CEO can weigh the answer.

**Q: When should a company make its first RevOps hire?**

A: Nick Reyes, CRO at PushPress, says he regrets waiting. Looking back he would have had someone far more data fluent before raising the seed round, starting on the sales and marketing side and attribution because distribution is everything once you have product-market fit. If a company is running lean, especially with AI today, he thinks it can probably wait until it has a couple of reps. LeanScale co-founder Anthony Enrico acknowledges the trade is hard at an early stage, since it can mean one fewer quota carrier or marketer.

**Q: What is the signal that you waited too long to hire RevOps?**

A: According to PushPress CRO Nick Reyes, the signal is a revenue leader spending too much time learning about infrastructure or how to do the job. There are benefits to figuring some of it out yourself, such as a first vertical SaaS sales comp plan, but if that goes on too long you are doing the job of RevOps instead of leading the revenue function. At that point he says you probably are past due.

**Q: How is AI changing the role of RevOps?**

A: Nick Reyes, CRO at PushPress, says the mission of giving the go-to-market organization more leverage doesn't change, but the execution does. If people are operating their own agents or building their own tools and dashboards, RevOps builds the guardrails that let those experts work safely, rather than building the castle for everyone to look at. LeanScale's Anthony Enrico says the work has also become more technical, with some companies running 30-plus go-to-market tools, AI workflows across the stack, and data warehouses that agents run on top of.

**Q: Why does a CRO need financial literacy?**

A: Nick Reyes says he doesn't know how a CRO can do the job well without speaking the same language as finance. Comp plans and new campaigns both depend on understanding LTV to CAC, CAC payback and the variables behind them, and he says fundraising and board reporting require the same fluency. To get there he spent an hour at 5 a.m. every day on one data point in PushPress's financial model, asking what the benchmarks were, what good and great looked like, and where the company stood.

**Q: Should you hire account executives externally or promote from SDR teams?**

A: PushPress CRO Nick Reyes says he can't see hiring anyone from outside its SDR team to be an account executive. The company early on hired gym owners, which brought near-zero ramp and strong networks but also entrepreneurs who disliked tight structure. It now has a strong cold outbound SDR motion that doubles as its sales talent pipeline. His caution is that if outbound ever stopped working, a company would have to replace both the channel and its bench of sales talent.

**Q: How do you sell software to a market that doesn't want software?**

A: Nick Reyes was the first salesperson at PushPress, selling gym management software to a CrossFit community he describes as a grungy, we-don't-use-software crowd with low margins and low technical aptitude. He says ease of use was the value proposition all along, because a gym owner wants to be on the coaching floor and almost wants the software to disappear. Early on, the company focused on doing billing and scheduling simply and believed in integrations rather than selling an all-in-one.


## Timeline

- **00:00** — Cold open + intro
- **01:18** — Skipping college for the Marine Corps
- **14:47** — Early days: selling software to a "we don't use software" market
- **25:06** — When to invest in RevOps — and the signal you're past due
- **27:30** — How RevOps is changing: guardrails, not castles
- **44:16** — "What needs to be true?"
- **53:09** — Wrap + Nick's ask: drop into a local gym


## Related episodes

- **Ep. 83: The Lie Behind Failed Quarters** (Andrew Geisse (Pallet)) — Anthony tells the same Emailage growth-model story here, and Andrew takes from it a what-would-it-take exercise close to asking what needs to be true. · https://www.leanscale.team/knowledge/podcast/andrew-geisse-failed-quarters-gtm-planning/
- **Ep. 115: What RevOps Should Look Like at Every Stage** (Hassan Irshad (Unify)) — A stage-by-stage build order for RevOps, which answers the question of when to invest that Nick says he got wrong.
- **Ep. 85: Why AI + GTM Engineers Can't Replace RevOps** (Tessa Whittaker (ZoomInfo)) — Tests the same claim as Nick's guardrails argument: what stays with RevOps when AI and GTM engineers can build. · https://www.leanscale.team/knowledge/podcast/tessa-whittaker-ai-gtm-engineers-revops/
- **Ep. 123: Stop Hiring GTM Engineers. They Already Work For You.** (Ryan Vanshur (Handle)) — Finding builders inside each department, which fits Nick's view that everyone can now be a builder.
- **Ep. 82: How an Ops Guy Became CRO of a $3B Company** (Joshua Trott (Patch)) — An operations-first route to CRO, the counterpart to Nick and Anthony's case that the role needs both systems and a number. · https://www.leanscale.team/knowledge/podcast/joshua-trott-ops-guy-cro/
- **Ep. 125: COO or CRO? Where the RevOps Career Actually Ends Up** (Thurman Sneed (Marigold)) — A finance-trained CRO on board credibility, alongside Nick's habit of learning the financial model to speak finance's language.
- **Ep. 143: A Decade in One CRO Seat: Make More Money Than You Spend** (David Cady (Virtuous)) — Another long-tenured revenue leader at a mission-driven vertical software company, describing how go-to-market changed with the same product and market.
- **Ep. 114: Outbound Isn't Dying. Yours Is.** (Joey Gilkey (TitanX)) — A detailed case for cold outbound, which pairs with Nick's late-landing SDR motion and his worry about AI voice agents ruining the channel.


## Full transcript

_Machine-transcribed and not diarized; speaker attribution is inferred._  
_Transcript only, as a separate file: https://www.leanscale.team/knowledge/podcast/nick-reyes-pushpress-what-needs-to-be-true/transcript.md_

### 00:00 — Cold open + intro

**[0:00]** - Any time you feel yourself wanting to quit,

**[0:02]** you might be on the, it might be tough,

**[0:04]** or you might have the wrong mission.

**[0:06]** And I don't think in all these years,

**[0:09]** I don't think I've ever questioned the mission.

**[0:11]** - My guest today is Nick Reyes,

**[0:13]** Chief Revenue Officer at Push Press,

**[0:15]** the gym operating system that powers

**[0:17]** thousands of fitness businesses.

**[0:20]** - So I think even just looking back then,

**[0:22]** there was a little bit of like, go against the grain,

**[0:25]** don't just conform to what everyone's doing,

**[0:27]** because that's what you're supposed to do.

**[0:30]** - One thing you mentioned in our prep call

**[0:31]** that I thought was really interesting,

**[0:33]** speaks to my heart as a RevOps professional.

**[0:36]** You regret not hiring RevOps earlier.

**[0:41]** - I feel like I waded through the mud for several years,

**[0:45]** rather than they could support me

**[0:48]** and the entire go-to-market team.

**[0:50]** - So if you wanna get to 40 million,

**[0:51]** you're gonna need this many reps,

**[0:53]** we're gonna have to convert at this rate,

**[0:54]** you're gonna have to build this pipeline,

**[0:55]** the pipeline needs to come in right now,

**[0:56]** we're gonna need to activate these channels,

**[0:58]** churn's gonna have to be here.

**[1:00]** It's like, "C-Ray, it's impossible."

**[1:03]** And he goes, "This is everything I've been hoping for."

**[1:07]** (laughing)

**[1:10]** I was like, "What did I just do?"

**[1:12]** (upbeat music)

### 01:18 — Skipping college for the Marine Corps

**[1:18]** - Nick, you were the one kid out of one of the best

**[1:22]** prep schools in the country who said no to college

**[1:25]** and went to the Marine Corps instead.

**[1:27]** What was going on in your head at 18

**[1:29]** and what did that choice set up for everything after?

**[1:35]** - Well, this is a little bit of a blast from the past

**[1:38]** to start the episode with and Anthony,

**[1:40]** I really appreciate you having me here.

**[1:43]** You know, I think back then,

**[1:44]** there was so much pressure to make amazing grades,

**[1:50]** be in the top of the class, choose the right college.

**[1:54]** And I think over time of just studying

**[1:56]** throughout the summer, doing summer assignments,

**[1:58]** seemingly going to school year round,

**[2:00]** there was a combination of both burnout

**[2:02]** and then also like everyone else

**[2:04]** was doing the exact same thing.

**[2:07]** I grew up wrestling, I was a little kid,

**[2:09]** I wrestled 125 pounds, yep, yep, in high school.

**[2:14]** And there was a little bit of like,

**[2:16]** you know, you can't go and do hard things,

**[2:19]** you're a little guy.

**[2:21]** So naturally ended up choosing

**[2:23]** one of the more difficult military services to enlist in.

**[2:27]** So I think even just looking back then,

**[2:29]** there was a little bit of like, go against the grain,

**[2:31]** don't just conform to what everyone's doing

**[2:34]** because that's what you're supposed to do,

**[2:36]** kind of maybe in my DNA

**[2:38]** or maybe I picked it up somewhere at a younger age,

**[2:40]** but you know, largely that was what was going through my head

**[2:43]** was maybe compensate a little bit

**[2:45]** for a shortcoming of being small

**[2:46]** and don't follow the norm, you know.

**[2:50]** - I love it.

**[2:51]** Well, I have a wrestling background too,

**[2:52]** I don't think there's a better sport to teach,

**[2:54]** discipline, perseverance, endurance.

**[2:56]** And then I didn't take the Marine Corps out,

**[2:59]** but I feel like that just takes it

**[3:00]** to an absolute next level.

**[3:03]** - Yeah, yeah.

**[3:04]** Oh, the discipline that you get from wrestling

**[3:06]** certainly served me in my military years

**[3:09]** and then the, you know,

**[3:11]** building on that discipline in the Marine Corps.

**[3:13]** The Marine Corps really shaped me as an adult

**[3:15]** at a, you know, at a really young age.

**[3:18]** You know, you're a teenager,

**[3:19]** but you're given a ton of responsibility.

**[3:22]** Coming out of the Marine Corps,

**[3:23]** it was like, well, what do I do now?

**[3:26]** I think that's a lot of things

**[3:27]** that anyone who's leaving the military service

**[3:29]** kind of falls into is, you know, what's next?

**[3:31]** And I found myself kind of gravitating towards sales.

**[3:36]** I had done some, you know,

**[3:37]** part-time sales jobs in high school and stuff like that,

**[3:40]** but like I really enjoyed interacting with people.

**[3:43]** I really enjoyed hitting a target.

**[3:46]** And, you know, the Marine Corps is like all around mission

**[3:49]** accomplishment.

**[3:50]** And so when given a target to hit,

**[3:52]** it was like, that's my objective in life

**[3:55]** is to hit that target.

**[3:56]** And so sales was just a natural fit.

**[3:58]** And I'm sure there's plenty of people

**[3:59]** with military backgrounds that are in sales

**[4:01]** and they're just like, absolutely, this fits me.

**[4:04]** So from there, got into tech sales,

**[4:08]** but not the tech sales you might think

**[4:10]** as an entry-level rep.

**[4:11]** I started doing sales for Sprint,

**[4:13]** which was the company that T-Mobile acquired.

**[4:17]** They're a mobile phone provider, you know,

**[4:19]** back in the day, I'm probably showing my age.

**[4:22]** So working in a retail store from there,

**[4:25]** went over to one of their partners

**[4:28]** and started doing public sector sales,

**[4:30]** which was one of the first digital video systems.

**[4:33]** You know, like you would see on COPS, the TV show,

**[4:36]** they went from having the VHS tapes in their cars

**[4:38]** to actually doing digital video systems.

**[4:42]** And that was a pretty massive step up

**[4:45]** in terms of like who you're selling to.

**[4:48]** You're talking to police chiefs,

**[4:50]** you're talking to sheriffs.

**[4:52]** And I learned so much around selling.

**[4:55]** There's RFP process, I didn't even know existed.

**[4:58]** It was just like a complete headfirst dive

**[5:02]** into the unknown of what does grownup sales really look like.

**[5:08]** And super small company based here in Kansas City.

**[5:13]** And one of the technical, the CTO left,

**[5:17]** and he went to a company called GE.

**[5:22]** And they were- - I think I've heard of them.

**[5:24]** They do a few things, right? - They only do a few things.

**[5:28]** And so GE had a rail arm to it.

**[5:32]** And Caterpillar had started trying to get

**[5:34]** into the rail business and they acquired,

**[5:37]** they were acquiring basically supplemental businesses

**[5:40]** in the rail industry so that they could begin

**[5:43]** selling locomotives to the big class one railroads

**[5:47]** in the United States.

**[5:48]** This CTO that I had worked with was challenged

**[5:51]** after this acquisition from GE to spin up a sales team,

**[5:56]** a technical leader challenged to spin up a sales team.

**[5:59]** And so he called me and he said,

**[6:01]** do you know anyone that might be interested?

**[6:03]** And I thought, damn, yes, I am.

**[6:06]** I'm absolutely interested.

**[6:07]** Let's go try something new.

**[6:09]** Let's continue to kind of see what this enterprise game

**[6:12]** can really look like.

**[6:13]** And so inherited a territory at Caterpillar's rail division

**[6:19]** that was doing around 500K a year.

**[6:22]** Super, super small in the grand scheme of things.

**[6:25]** They were actually selling declassified

**[6:29]** heat seeking missile technology

**[6:31]** to put bearing detect systems all throughout rail lines

**[6:35]** in North America in order to predict

**[6:38]** when a derailment might happen.

**[6:40]** So there was a hardware piece to that business.

**[6:44]** There was a software piece to that business.

**[6:46]** There was a lot of meeting individuals

**[6:49]** that had been in the rail industry for their entire careers.

**[6:55]** It was just, again, another headfirst.

**[6:57]** I don't know how this is gonna work type of moment

**[7:00]** in my career that then I had the fortunate

**[7:06]** ability to learn from just a lot of people

**[7:08]** who were willing to kind of take me under their wing,

**[7:10]** teach me, they saw something in me.

**[7:13]** Maybe it was that mission accomplishment attitude,

**[7:15]** but that is what the catalyst was

**[7:17]** that got me into enterprise sales

**[7:19]** and really learning how to drive toward a goal,

**[7:22]** carry a number, don't take no for an answer,

**[7:26]** whatever is needed in order to hit the target,

**[7:28]** which is kind of still with me today.

**[7:31]** - And I think sometimes people,

**[7:33]** I think make an assumption that,

**[7:35]** oh, that's totally different than maybe SaaS

**[7:38]** or software sales, but I would argue not at all.

**[7:42]** I think it's still, it's a B2B process.

**[7:44]** You gotta build a business case.

**[7:45]** It's multi-threading, it's networking.

**[7:47]** It's not a transactional sale.

**[7:49]** There's a relationship and partnership involved

**[7:51]** in the whole thing.

**[7:53]** So I think that probably teed you up really well

**[7:57]** for the next step, if I'm not mistaken.

**[8:01]** - It did, it did.

**[8:02]** I think there's a, in the enterprise space,

**[8:05]** there's probably even more so of an expectation

**[8:08]** of owning the result with the customer,

**[8:12]** because especially in something like there's not,

**[8:15]** railroads don't just grow on trees.

**[8:17]** So you don't burn relationships.

**[8:19]** If you sell something, it better damn well deliver.

**[8:21]** And I know that's not always the case

**[8:23]** in a lot of B2B sales, but that's very much the case

**[8:26]** in like the higher end enterprise sales,

**[8:29]** the relationships and your ability

**[8:30]** to follow through are paramount.

**[8:32]** And so that's probably one of those underlying traits

**[8:35]** of like, here at PushPress, our customers are so critical

**[8:39]** to like, we view them as being the lifeblood

**[8:42]** of the organization.

**[8:42]** If they're not the center of every decision,

**[8:44]** if we don't drive results for them,

**[8:46]** you can't grow the company.

**[8:48]** And so same thing, but now it's just expanded.

**[8:52]** And I think the way that I ended up getting even

**[8:54]** to PushPress from there, if I wanna maybe take a step back

**[8:57]** and expand on the story for a minute,

**[8:59]** when I was at CAP, I was having back pain from the military.

**[9:04]** I stumbled into a CrossFit gym that was brand new.

**[9:07]** This was like right as CrossFit was hitting the market

**[9:09]** and people had no idea what it was.

**[9:11]** They had a mascot that was everywhere

**[9:13]** that people criticized.

**[9:14]** It was Puke the clown.

**[9:16]** This was like the OG CrossFit days.

**[9:21]** And people were in baggy shorts.

**[9:23]** It was a whole thing.

**[9:25]** So I was having back pain.

**[9:27]** My wife said, you know, you should go and try

**[9:30]** this new CrossFit affiliate that is opening up

**[9:32]** down the street.

**[9:33]** If you're going to be miserable,

**[9:36]** you may as well be miserable and fit.

**[9:38]** And I thought, okay, you know what?

**[9:41]** I've missed out on fitness for a while.

**[9:43]** You're absolutely right.

**[9:44]** I'm in pain nonstop.

**[9:47]** I'm in.

**[9:48]** It was about three or four months in.

**[9:52]** The two founders of that gym, T.J. Kiblin and Brady Mora,

**[9:56]** they got me deadlifting, squatting, moving well.

**[10:00]** And within a few months, I was free of painkillers.

**[10:05]** Slept through the night for the first time.

**[10:07]** Everything immediately started to click.

**[10:10]** I could start actually improving my physical appearance.

**[10:13]** Next thing you know, I'm off to the races feeling good

**[10:16]** and have never had back pain ever since then.

**[10:19]** And about a year after I started there,

**[10:23]** they came to me and they said,

**[10:24]** hey, I think we're going to have to close the gym.

**[10:26]** And it was like just a punch to the gut.

**[10:30]** I was like, you guys can't, you guys saved me.

**[10:33]** You cannot close this gym.

**[10:35]** And so we worked through like, well, how can I help?

**[10:39]** What can I do to give you a hand?

**[10:41]** And we worked out a deal where I came on just to run

**[10:45]** the business side of things for them.

**[10:47]** And that's how I ended up meeting Dan, Chris and Brian,

**[10:51]** the three founders of Push Press.

**[10:53]** They were in Los Angeles and we ended up working out a deal.

**[10:58]** We can go into that detail if you're curious.

**[10:59]** But yeah, I ended up working out a deal

**[11:00]** for me to leave Caterpillar, believe it or not.

**[11:03]** Somehow, probably the best sale ever,

**[11:05]** besides getting my wife to marry me,

**[11:07]** was talking her into letting me leave

**[11:09]** an enterprise sales job to go take a bet

**[11:11]** on this little startup out of three guys in LA

**[11:13]** that I had only met once.

**[11:16]** - I'm always curious in that moment.

**[11:19]** And by the way, when I started Lean Scale,

**[11:21]** I started in 2021.

**[11:23]** You better believe I had a full PowerPoint presentation

**[11:26]** for my wife as to why I needed to do this.

**[11:28]** She's like, wait, 'cause at that point,

**[11:31]** I had jumped from a few SaaS companies.

**[11:33]** I've been doing really, really well.

**[11:34]** I had an amazing exit at one of them.

**[11:36]** It was really good for everyone on the team there.

**[11:39]** Great relationships with VCs.

**[11:41]** I was being like flown in as the RevOps operator

**[11:45]** for all of these really, really exciting companies.

**[11:48]** And she's like, so you're gonna leave all of that.

**[11:51]** And I haven't shared this with too many people.

**[11:55]** And I don't talk about this moment a lot,

**[11:58]** but I actually had an offer to be the COO

**[12:01]** of one of the companies.

**[12:03]** It was a big job and something

**[12:04]** that I always kind of aspired to.

**[12:06]** And I had to do the same thing.

**[12:08]** I was like, hey, yeah, we're gonna leave all that.

**[12:10]** Lean Scale, how much revenue are we making?

**[12:11]** Yeah, nothing yet.

**[12:12]** How many kids do we have?

**[12:13]** One, one more on the way soon.

**[12:16]** Okay, and wife's not working either.

**[12:18]** It's like, okay, so you're gonna bet everything on this?

**[12:21]** I said, absolutely.

**[12:22]** But yes, biggest sales rep I had as well.

**[12:25]** What conviction did you have though?

**[12:27]** Because there's gotta be something that was like

**[12:29]** so compelling that made you make that move.

**[12:34]** - It was twofold.

**[12:38]** The territory at Cat, I ended up growing

**[12:40]** to over $20 million a year

**[12:43]** between both hardware and software sales.

**[12:46]** So I had developed, I think, a strong enough reputation

**[12:48]** that it didn't feel like a one-way door.

**[12:51]** It felt like if I went and I was gone for a year

**[12:53]** and this thing plummeted and went to nothing,

**[12:56]** then I could go crawling back

**[12:58]** and everyone would be like, hey, welcome back.

**[13:00]** We're glad to have you, we missed you.

**[13:01]** That's honestly how it felt.

**[13:03]** So it was like exit, but do it, maintain the relationship.

**[13:07]** So again, it didn't feel as risky at the time.

**[13:12]** The other piece is I, as a user of the product,

**[13:18]** I thought that one of its key value props

**[13:21]** was actually that it was only really good at one thing,

**[13:24]** which was being a single application for a gym owner.

**[13:28]** They didn't try to be everything that a gym owner need.

**[13:31]** At the time in those very early days,

**[13:33]** we did not market ourselves as an all-in-one.

**[13:37]** We in fact believed strongly in the integration framework.

**[13:41]** And the thing that it did well,

**[13:42]** the billing and the scheduling,

**[13:43]** it absolutely nailed with more simplicity

**[13:46]** than any other tool in the market.

**[13:48]** And I remember looking in the mirror,

**[13:53]** trying to determine whether or not this was the right move.

**[13:56]** And I was, I had a moment where I'm like,

**[13:59]** if you're as good as you think you are at selling,

**[14:03]** there is no risk here.

**[14:06]** You've evaluated all the tools on the market.

**[14:07]** So if you're really that damn good,

**[14:10]** then it's an automatic yes,

**[14:12]** because the only thing this company is missing is you.

**[14:14]** So it was like a little bit of like,

**[14:16]** are you full of it or not moment?

**[14:18]** And that was the push off the bridge.

**[14:23]** - Yeah, not to bring it back to our wrestling background,

**[14:26]** but it feels like the moment the whistle blows.

**[14:29]** It's like, okay, now it's game time.

**[14:31]** - It's time.

**[14:32]** - So, and all the thought, the stress,

**[14:35]** everything, the anxiety coming up now,

**[14:37]** but when you're there, you get in the zone.

**[14:39]** So what happened after you jumped in?

**[14:42]** How did you approach it?

**[14:44]** What did those early days look like?

### 14:47 — Early days: selling software to a "we don't use software" market

**[14:47]** - Yeah, the early days were a lot of whatever you have to do

**[14:50]** in order to get product market fit.

**[14:51]** It was cold calling, dropping into gyms

**[14:54]** that I had never visited before,

**[14:58]** driving to gyms in St. Louis or Tulsa.

**[15:03]** It was basically just like,

**[15:05]** what are all the different ways

**[15:06]** that you can get in touch with gym owners,

**[15:09]** build your contact list,

**[15:11]** try to understand what the market needs

**[15:14]** as much as possible.

**[15:15]** And at the same time, it was set up to CRM,

**[15:18]** understand the funnel,

**[15:21]** and it's the three founders and me,

**[15:23]** and they're in LA together.

**[15:24]** And so they were working out of Torrance Training Lab,

**[15:27]** which was the gym that Dan owned at the time.

**[15:29]** And they would set up a, we had a Google Hangout,

**[15:33]** and I'm the only guy in Kansas City on an island,

**[15:36]** and there's a TV, and I can see them,

**[15:38]** and they're coding away in the gym,

**[15:40]** and there's weights banging,

**[15:42]** and they're literally in a gym office,

**[15:45]** a CrossFit gym office,

**[15:46]** and there's people yelling,

**[15:48]** and they would go to lunch on Pacific time.

**[15:51]** I'm still working on Kansas City time.

**[15:53]** And it was a lot of just like,

**[15:55]** what are you guys building?

**[15:56]** Oh, you're building this?

**[15:57]** Cool, I think I can sell that.

**[16:00]** Why did you build it that way?

**[16:01]** There were some of those advantages,

**[16:02]** I think, in the early days of understanding

**[16:06]** how we, as a team, were thinking about

**[16:09]** attacking the market, that I look back,

**[16:12]** and it's like, those were things that I didn't understand

**[16:15]** how important they were at the time.

**[16:18]** And if we wouldn't have had that,

**[16:20]** just that little Google Hangout,

**[16:22]** I don't think we would have been as successful.

**[16:24]** Obviously, if you're in a physical environment office space,

**[16:28]** then you have that advantage.

**[16:29]** But just being remote, we never,

**[16:31]** if it wasn't for that one little thing,

**[16:33]** I don't think we would have,

**[16:34]** which is funny to look back on.

**[16:37]** I love the humble beginnings during that time.

**[16:42]** And I think I can just picture that,

**[16:44]** them coding next to Wade slamming all over the place.

**[16:49]** So from there, there had to be a point where it felt like,

**[16:52]** okay, we're actually getting some traction here.

**[16:55]** Maybe your wife is starting to gain

**[16:56]** a little bit of confidence in this decision that you made.

**[16:59]** Where did you start really getting aggressive

**[17:02]** and really pushing and trying to accelerate the growth?

**[17:08]** - Yeah, it was probably, oh gosh.

**[17:13]** The first probably year and a half, two years maybe,

**[17:20]** I'm trying to rewind my brain there as best I can.

**[17:22]** Year and a half, two years was largely about

**[17:25]** understand the market, what are we building?

**[17:28]** And there are some big behemoths in this space,

**[17:30]** like MindBody, which everyone knows,

**[17:32]** which were light years ahead of us.

**[17:35]** And there were companies that had started building

**[17:37]** these all-in-one tools.

**[17:39]** And so it was a little bit of like,

**[17:40]** what's the market really gonna need?

**[17:42]** If you're not familiar with the group fitness market,

**[17:45]** CrossFit really helped lay the foundation

**[17:49]** for what exists today in like the Orange Theories

**[17:53]** and the Barry's Bootcamps and the F45s.

**[17:56]** There wasn't a big flock to group fitness.

**[17:59]** Yoga existed and Pilates certainly existed

**[18:03]** and that's why MindBody thrived in those early days.

**[18:06]** But otherwise, the CrossFit space

**[18:09]** was really the pioneer there

**[18:10]** and they were the grungy, we don't use software crowd.

**[18:15]** And so it was a very immature B2B market

**[18:20]** where the customer had low margins,

**[18:25]** not a high tech aptitude.

**[18:27]** And so trying to boil down like, what is your value prop?

**[18:31]** How do you demo this software?

**[18:34]** It took a good amount of time for the industry to go,

**[18:38]** oh yeah, maybe we could use some tools

**[18:41]** to actually help us understand billing

**[18:43]** rather than trying to chase people down for cash,

**[18:45]** which in 2026, this even sounds crazy to say,

**[18:49]** but that's how long we've been at the game.

**[18:51]** And I guess maybe in how late the market was

**[18:53]** to actually exist and then mature over time.

**[18:57]** - When you say cash, you're talking physical cash.

**[18:59]** - Literally physical cash, yes, yes.

**[19:01]** - I didn't know they still made that, but yeah.

**[19:06]** - So, but that was the kind of the genesis

**[19:10]** of the first several years and then it was like,

**[19:11]** well, we only have one or two people in support

**[19:15]** and it's figuring out the hiring

**[19:18]** and it's figuring out the staffing

**[19:19]** and in your capacity models across what do you need where

**[19:22]** and you've only got a few people and they're all remote.

**[19:25]** And so how do you get these people together?

**[19:27]** And it was just, it took us a long time to figure out

**[19:31]** how to build a SaaS company, longer than most.

**[19:37]** And I think a big part of that is we grew,

**[19:39]** we all came from within the fitness industry.

**[19:42]** We didn't come from SaaS looking for a problem to solve.

**[19:45]** We came from the industry with a problem and said,

**[19:48]** I think we can probably solve this

**[19:50]** if we put our heads together.

**[19:52]** Dan will tell you this, if you were to ask him,

**[19:55]** it was a much bigger thing

**[19:57]** than he ever thought it would be.

**[20:00]** He thought it was like a simple coding project.

**[20:01]** He'd be good to go.

**[20:02]** And it's just grown into like this massive piece of software

**[20:06]** in order to support small businesses all around the world.

**[20:09]** - I actually think that's where the best ideas come from.

**[20:12]** People who have deep, deep empathy for the problem

**[20:16]** that their customers are going through.

**[20:19]** I'm curious 'cause maybe you were a little bit forward thinking

**[20:22]** and how you would operate maybe one of those gyms.

**[20:24]** Was there an inflection point or point in time

**[20:27]** or a way that you changed the messaging

**[20:30]** and the value proposition for a gym owner

**[20:32]** where it felt like, oh, this is when it clicked

**[20:35]** and people started really resonating

**[20:36]** with what we're trying to do here.

**[20:40]** - I think ease of use has always been that.

**[20:43]** And I don't know that we recognized it in the early days

**[20:47]** or we didn't say it that way.

**[20:49]** And it feels like, in some ways,

**[20:51]** it feels like a little hollow of a value prop.

**[20:54]** But if you just think that like at the end of the day,

**[20:56]** a gym owner wants to be on the coaching floor

**[20:59]** with their members, delivering a fitness result,

**[21:02]** and they don't wanna have to clickety-clack in a software.

**[21:06]** They almost want the software to disappear.

**[21:08]** I just want to do this thing,

**[21:11]** which is to make people in my local community healthier.

**[21:14]** Then ease of use becomes the most critical piece

**[21:18]** of the entire stack for them,

**[21:20]** especially in a world where the legacy systems

**[21:23]** have been around for decades.

**[21:24]** And they, at least back then, they look like Windows 98.

**[21:28]** Again, I'm showing my age, but they look archaic.

**[21:31]** And so they were bloated, tons of toggles everywhere,

**[21:35]** couldn't figure them out.

**[21:37]** It's just not friendly to the coach

**[21:39]** who needs to have their attention on the member

**[21:40]** that's in front of them, not on the piece of software.

**[21:43]** - Yeah, I think sometimes that's what happens though.

**[21:45]** When you're a little early, you just have to kind of endure

**[21:48]** and make it to that point

**[21:49]** where it starts to become obvious for everybody else.

**[21:51]** And then once you start getting that adoption,

**[21:54]** you could start fine-tuning that messaging

**[21:55]** and getting in front of people that you need.

**[21:57]** - Yeah, absolutely, absolutely.

**[22:00]** - One thing you mentioned in our prep call

**[22:02]** that I thought was really interesting,

**[22:04]** speaks to my heart as a RevOps professional,

**[22:07]** is you regret not hiring RevOps earlier in the cycle.

**[22:15]** Can you walk me through the pains that you felt,

**[22:18]** when you wish you would have hired RevOps,

**[22:21]** and what you think you could have done

**[22:22]** if you made that investment earlier?

**[22:24]** - You know, one of the things that I really,

**[22:29]** really appreciate about our CEO, Dan Wymera,

**[22:33]** and what he built is he's always been a champion for,

**[22:37]** we don't know what we don't know.

**[22:39]** That includes me at the top as a CEO,

**[22:42]** and therefore we all need to be willing to learn,

**[22:45]** and we should all have coaches and mentors.

**[22:47]** We serve an industry of coaches,

**[22:50]** coaching people to get healthier,

**[22:52]** and we need to do the same

**[22:54]** when it comes to growing a company.

**[22:56]** That regret actually comes from some of the early discussions

**[22:59]** I had with other leadership, sales leadership,

**[23:03]** VPs of sales, CROs, trying to figure out who I wanted

**[23:07]** to lead me in coaching and learn from.

**[23:11]** And one of the individuals that I spoke with said,

**[23:14]** you need to invest in RevOps immediately,

**[23:17]** way sooner than you think.

**[23:19]** And I didn't listen.

**[23:22]** And in hindsight, I'm like, oh, you're such an idiot.

**[23:24]** Why didn't you do it?

**[23:25]** And there's been so many things.

**[23:27]** It's like data fluency,

**[23:29]** having someone to be an early warning signal,

**[23:32]** someone to partner with in sales comp.

**[23:36]** Like since we've invested heavily into RevOps,

**[23:39]** so obviously for a while now,

**[23:44]** the amount of mental bandwidth that I've received back

**[23:49]** that they take so much off of my plate,

**[23:52]** I think as the business grows,

**[23:54]** it's just impossible to mentally be everywhere.

**[23:57]** I almost look at it as like,

**[23:59]** look at your financial model

**[24:01]** and it's 2,000 rows and a million columns

**[24:05]** and they have the ability to stand up

**[24:08]** all of the tooling and data

**[24:10]** to where you don't have to study every cell

**[24:12]** as if your life depends on it.

**[24:13]** Because at the end of the day,

**[24:16]** there's a million ways to grow a company

**[24:19]** and there are some underlying metrics that you'll miss

**[24:22]** unless you have a partner that understands

**[24:24]** how you think, where the leverage is at

**[24:27]** and RevOps has done that for me in spades

**[24:30]** and I feel like I waded through the mud for several years,

**[24:35]** choosing maybe investing in other areas

**[24:39]** because they could close a deal

**[24:41]** or they could support a customer

**[24:43]** rather than they could support me

**[24:46]** and the entire go-to-market team.

**[24:48]** - I'm curious 'cause I always feel like

**[24:50]** it's such a struggle at the early phase

**[24:52]** and even though I know the value of RevOps

**[24:55]** to its core down to every detail,

**[24:58]** I understand where it can be difficult to trade

**[25:01]** maybe another quota carrier or somebody doing marketing.

**[25:05]** From your perspective, if you were to go back,

### 25:06 — When to invest in RevOps — and the signal you're past due

**[25:08]** and I know everyone will have a little bit

**[25:10]** of a different story, but if you were to go back,

**[25:12]** when would you have invested in RevOps?

**[25:15]** - Before we raised our seed round,

**[25:17]** I'd probably have someone who was way more data fluent

**[25:25]** and I think RevOps is changing,

**[25:27]** which it could be a whole 'nother podcast,

**[25:29]** but definitely someone who could help build

**[25:32]** the infrastructure to make a sales team really click,

**[25:36]** understand attribution.

**[25:38]** I would say I'd probably start more

**[25:40]** on the sales and marketing upside of things

**[25:43]** in the early days because distribution is everything.

**[25:47]** Once you have product market fit

**[25:49]** and so having a strong partner that's really cut their teeth

**[25:52]** in those areas and can help you,

**[25:54]** will only amplify the output of both your sales team

**[25:59]** and your marketing team.

**[26:00]** - No, it makes a ton of sense.

**[26:02]** Do you have a sense of how many reps

**[26:05]** maybe you had on the team?

**[26:06]** Is it like, get two reps,

**[26:09]** then get some sales ops, marketing ops in the door?

**[26:11]** Is it, hey, bring that on before you even bring on reps

**[26:14]** and you just run those front facing functions

**[26:16]** for a little bit?

**[26:17]** - I think if you're gonna operate lean,

**[26:20]** and especially in today's world of AI,

**[26:22]** I think you can probably wait till you have a couple of reps.

**[26:28]** Certainly the benefits of figuring it out yourself,

**[26:31]** like I had never set up a vertical SaaS sales comp plan,

**[26:34]** so there was a fair amount of studying there

**[26:36]** and if you would have been on my team,

**[26:38]** it would have been a completely different story.

**[26:40]** I would have been like, hey, whatever you think is best,

**[26:41]** Anthony, like let's make some adjustments and you know,

**[26:45]** or whatever, but I think there's some benefits

**[26:48]** to figuring it out yourself to some degree,

**[26:50]** but if you let that go on too long,

**[26:52]** then you're just doing the organization a disservice

**[26:56]** because you're not doing the job

**[26:58]** of leading the revenue function,

**[27:00]** you're doing the job of rev ops.

**[27:01]** And so there's probably a signal

**[27:05]** if I sat down and thought about it,

**[27:06]** but certainly if you're spending too much time,

**[27:09]** and maybe this is the signal,

**[27:10]** if you're spending too much time learning

**[27:12]** about infrastructure or how to do the job,

**[27:16]** then you need to bring in someone

**[27:18]** and you're probably past due bringing in someone

**[27:21]** at that point.

**[27:23]** - I think it makes a ton of sense.

**[27:25]** I'm curious, we don't have to spend a whole hour on it,

**[27:28]** but I would like your perspective.

### 27:30 — How RevOps is changing: guardrails, not castles

**[27:30]** You mentioned rev ops is changing.

**[27:33]** How do you think it's changing and why?

**[27:37]** - I think rev ops today is probably shifting more

**[27:42]** towards the infrastructure that allows the entire GTM org

**[27:47]** to function with more leverage than they have in the past.

**[27:51]** That's actually no different of a mission

**[27:52]** than they had before,

**[27:54]** but the way that they execute that mission is different.

**[27:57]** I think about moving forward

**[28:00]** where everyone is either operating their own agent

**[28:05]** or they are building tools themselves.

**[28:08]** Maybe it's dashboarding themselves.

**[28:10]** So rather than rev ops actually leading

**[28:13]** the creation of those tools,

**[28:15]** I think they're gonna be building the guardrails

**[28:17]** that allows everyone else to play in the sandbox

**[28:19]** as the experts in their craft.

**[28:22]** And so I just think it looks different.

**[28:23]** The mission doesn't change,

**[28:24]** but then how they go about the mission

**[28:26]** is probably different.

**[28:27]** They're probably, I know the term like go to market engineer

**[28:31]** has been thrown around for years,

**[28:32]** but I actually think it's more about understanding

**[28:35]** the technical infrastructure

**[28:36]** that allows people to play in the sandbox

**[28:38]** than it is actually building the castle in the sandbox

**[28:41]** and then having everyone look at the castle.

**[28:44]** - Yeah, I think we're seeing that too.

**[28:46]** And I agree, mission's the same.

**[28:48]** Get the highest yield out of the go to market team

**[28:50]** as possible, give visibility to the team

**[28:53]** so you can make excellent decisions

**[28:54]** and increase the likelihood that your bets will pay off

**[28:59]** and you'll put capital

**[28:59]** where you're gonna get the most return.

**[29:01]** But it is getting more technical

**[29:03]** and the tools that are available

**[29:05]** are getting more dynamic and interesting.

**[29:08]** When I started LeanScale in 2021,

**[29:11]** I'd say 60 to 70% of the work was in Salesforce.

**[29:17]** And then a little bit of HubSpot,

**[29:19]** maybe you're plugging in Zoom info for some things

**[29:21]** and an outreach for sequencing.

**[29:23]** So either your tech stack is a handful of tools.

**[29:26]** We work with some companies

**[29:27]** that have 30 plus go to market tools,

**[29:29]** point solutions for every single little thing.

**[29:31]** They're running AI workflows across the entire stack.

**[29:33]** We're not talking about just managing the data in the CRM,

**[29:36]** but we're talking about managing a data warehouse

**[29:38]** so you can run agents on top of it.

**[29:40]** I mean, the depth and breadth of RevOps

**[29:43]** has just expanded tremendously in the last five years.

**[29:47]** And I don't see that slowing down.

**[29:50]** - I don't either.

**[29:50]** I actually think it's a really interesting place

**[29:54]** for your more technical sellers to look at.

**[30:00]** If you have a nap for, you wanna experiment,

**[30:03]** you wanna tinker and you also know selling.

**[30:08]** RevOps has always been like an adjacent path

**[30:11]** for individuals in sales or in marketing,

**[30:14]** but if you find yourself really liking

**[30:17]** to be on the forefront of technology

**[30:19]** and you know your craft

**[30:20]** and you can be a dangerous individual

**[30:22]** in this new generation, it's kinda cool to see.

**[30:26]** - I think so too.

**[30:27]** And I think if you have that combo of,

**[30:29]** hey, go carry a bag.

**[30:31]** Go see exactly what it takes to go hit a number

**[30:33]** and own it and be accountable for it.

**[30:36]** Then spend some time learning the systems,

**[30:39]** building its scale.

**[30:40]** I think it's a really strong combo

**[30:42]** if you aspire to be a CRO one day.

**[30:44]** And I really think it requires both.

**[30:47]** I think it's very tough.

**[30:49]** A pure RevOps person coming up from like an analyst,

**[30:53]** a systems admin to running RevOps and doing that,

**[30:56]** I think you'll really struggle in a position

**[30:58]** where you have to be accountable for a number

**[31:01]** and bring it to a board every quarter.

**[31:04]** And then likewise, I think if you've only carried a bag

**[31:06]** and you're not familiar with like

**[31:09]** how you can get more leverage out of the system,

**[31:11]** I think a CRO role is gonna be very challenging

**[31:12]** for that person too.

**[31:14]** So I almost think you kinda need to take some side quests

**[31:17]** and side missions to get the full breadth of the role.

**[31:21]** - Completely agree.

**[31:23]** Dan and I were talking the other day

**[31:26]** and he was saying people either need to be builders

**[31:30]** or sellers.

**[31:31]** And it's like, I'm thinking as a CRO,

**[31:35]** you have to be both a builder and a seller at this point.

**[31:38]** It's in one move in my opinion.

**[31:41]** - It's absolutely where we're going.

**[31:42]** You have to do both.

**[31:43]** And that's why I think the CRO position

**[31:46]** is the most difficult position in a company.

**[31:50]** You have been in the role for almost a decade,

**[31:54]** which I think is incredible.

**[31:56]** The average tenure and lifespan of a CRO in SAS is 18 months.

**[32:01]** And it's either because the company's not doing well,

**[32:03]** but usually it's also, they're the first sacrificial lamb

**[32:06]** if you don't hit a number.

**[32:08]** And I think it's a very, very challenging role,

**[32:11]** especially if you're working in a high-growth company.

**[32:14]** Another thing I think gives the CRO some leverage

**[32:17]** and I think it's overlooked.

**[32:21]** Sam Jacobs, founder of Pavilion,

**[32:22]** talks about this quite a bit too.

**[32:24]** The partnership between the CRO and the CFO

**[32:28]** and having some financial literacy

**[32:30]** to be able to work together,

**[32:32]** I think is another angle that's really,

**[32:34]** really important to round out the role.

**[32:38]** - It's one that I think I understood the impact

**[32:42]** that it had in those early days.

**[32:43]** In the early days of push press,

**[32:45]** I built like our bottoms up model.

**[32:47]** I built a tops down model.

**[32:49]** I fit with you figuring out,

**[32:50]** how are we gonna hit growth targets

**[32:52]** to the point where, when our finance leader

**[32:56]** joined the org and I showed her everything,

**[32:59]** it was a lot of like, okay,

**[33:02]** we have our crap together to some degree.

**[33:05]** Okay, I'll take that as a compliment

**[33:06]** that we actually weren't completely flying blind

**[33:10]** when you get in a really strong finance leader in the seat.

**[33:12]** But even now, and through the fundraising process,

**[33:16]** it was critical to have financial acumen

**[33:18]** of understanding where the company's at.

**[33:21]** Obviously reporting to the board,

**[33:23]** that's important to have.

**[33:24]** I just don't know how you can do the job effectively

**[33:28]** day in and day out,

**[33:29]** where partnering with finance is so critical

**[33:32]** to doing the CRO job well,

**[33:37]** if you're not speaking the same language.

**[33:40]** And I just don't expect them to speak

**[33:43]** pure sales and marketing language,

**[33:46]** which means you need to go to them.

**[33:48]** And to that extent,

**[33:50]** I don't know how you build comp plans without it.

**[33:52]** And I don't know how you can launch a new campaign

**[33:55]** without understanding, LTV to CAC, CAC payback,

**[33:58]** what goes into each of those variables.

**[34:01]** It's all a requirement of the job.

**[34:03]** And I remember at one point,

**[34:07]** whenever they rolled out the latest financial model,

**[34:09]** it was like, oh, there's some of these terms

**[34:11]** that I don't know as well as I should.

**[34:14]** Or I don't know the benchmarks as well as I should.

**[34:17]** And I made a point to every single morning,

**[34:19]** sit down at 5 a.m., cup of coffee, look at our model,

**[34:23]** dig into one data point.

**[34:26]** What's the benchmarks for this?

**[34:27]** What does good look like?

**[34:28]** What does great look like?

**[34:31]** What is ours?

**[34:32]** And just spent an hour.

**[34:33]** And I did it every single day,

**[34:36]** until you just get to a point where you understand it all.

**[34:39]** And then when you're in a fundraising,

**[34:41]** when you're either you're in a pitch or you're in diligence

**[34:44]** and there's questions being fired at you,

**[34:46]** all the confidence in the world.

**[34:47]** But it took that like that day in and day out studying

**[34:49]** and work in order to get to that point.

**[34:52]** - Man, I just love hearing what your endurance

**[34:57]** and discipline is throughout pretty much every aspect

**[35:00]** of your life.

**[35:01]** I brought it up earlier.

**[35:05]** And I think this is another amazing example of it,

**[35:07]** but you've been in the CRO position for 10 years.

**[35:12]** And what does it take?

**[35:15]** What type of endurance does it take to stick to the mission,

**[35:22]** get through adversity?

**[35:23]** And what have some of those hardest moments been like

**[35:26]** throughout this journey?

**[35:27]** And how did you stay so focused?

**[35:32]** - One of the things that the Marine Corps does,

**[35:34]** they use an acronym for the leadership traits.

**[35:37]** You guys can look it up.

**[35:38]** It's called JJ Did Ty Buckle.

**[35:41]** I won't go through all of them,

**[35:42]** but one of the E's stands for endurance.

**[35:45]** I actually think it's probably one of the most

**[35:47]** underrated leadership traits, at least in a growth role,

**[35:51]** but probably in every role.

**[35:52]** And I'll give you an example of this actually.

**[35:55]** You can look up Altos Ventures.

**[35:59]** They are our lead investor in both our A round and our B

**[36:01]** round.

**[36:03]** I think it's altos.vc.

**[36:05]** You can look, they wrote an article.

**[36:06]** It's like super famous in the Valley of like

**[36:09]** hedgehogs versus foxes.

**[36:11]** And they invest in hedgehogs.

**[36:14]** Hedgehogs are very much Dan, myself.

**[36:18]** We have like little hedgehogs on our desks

**[36:20]** and stuff like that, right?

**[36:21]** Like, and it's people who are about the mission,

**[36:24]** not about the just chasing an outcome.

**[36:30]** They invest in long-term founders.

**[36:31]** And so I think the reason I weave that in here

**[36:34]** is because I think that's so important to having endurance

**[36:37]** is that you have to be on the right mission.

**[36:41]** And anytime you feel yourself wanting to quit

**[36:44]** because it gets tough, you might be on the,

**[36:47]** it might be tough or you might be on the wrong mission.

**[36:50]** And I don't think in all these years,

**[36:52]** I don't think I've ever questioned the mission.

**[36:54]** I've never questioned helping gym owners because my life,

**[36:58]** I credit Brady and TJ and CrossFit to saving my life

**[37:04]** and making me a renewed adult human and functional.

**[37:08]** And so the mission will always be this

**[37:11]** until I feel like running a gym is no longer a struggle

**[37:15]** and that the gym owners are able to serve their community

**[37:18]** in a way that's profitable, gives them a happy home life

**[37:22]** and is not a drain or a chore like it is

**[37:26]** and has been for years.

**[37:28]** And so the endurance piece of it though comes into like,

**[37:32]** you do have a number to turn in.

**[37:34]** You do have a target to hit.

**[37:36]** Leading people is tough and growing a SaaS company

**[37:39]** is insanely difficult and there's gonna be those times

**[37:42]** where system goes down on a Sunday and you're like,

**[37:47]** oh my God, what are we doing?

**[37:50]** And you're just trying to enjoy lunch with the family

**[37:54]** because maybe you've been on the road for a week straight

**[37:57]** and now you're back at work.

**[37:59]** And so if you can't, I think, look at the mission and go,

**[38:03]** no, this is still important and I'm still locked into it,

**[38:07]** even when it gets tough, you can't be there

**[38:10]** for the long haul.

**[38:12]** And I guess maybe you shouldn't be, I don't know.

**[38:15]** The endurance piece is mission critical

**[38:17]** or is absolutely paramount in my opinion.

**[38:21]** - Hi, I'm curious too with your long tenure.

**[38:25]** And I mean, I can tell it takes an immense amount

**[38:30]** of endurance to go through where you were

**[38:33]** in the beginning to where you are now.

**[38:35]** But one thing that I love is this is actually

**[38:37]** a very interesting case study of how GoToMarket has changed

**[38:41]** because you actually have a lot of control

**[38:43]** over the variables, same company, same mission,

**[38:45]** same ICP, relatively similar solution, I'm assuming.

**[38:51]** I obviously like iterating and advancing over time,

**[38:53]** but solving a similar problem.

**[38:56]** I'm curious your perspective on how GoToMarket has changed

**[39:01]** from 10 years ago to today.

**[39:04]** And when I say that, I mean, how do you build pipeline?

**[39:08]** How are you finding sellers?

**[39:10]** How are you training sellers?

**[39:12]** What techniques, tools, methodologies are you using?

**[39:16]** What's some of the wisdom that's maybe held true?

**[39:19]** And then what are some of the things

**[39:20]** that have adjusted over time?

**[39:23]** - Yeah, I think generally there's a lot of,

**[39:27]** you have to be nimble or you have to pay attention

**[39:30]** to what, where does your market pay attention to?

**[39:36]** And how does that change?

**[39:38]** What are the latest, I don't wanna say trends

**[39:40]** 'cause that would be a bad way to phrase it,

**[39:41]** but like there was a time period

**[39:43]** where I couldn't get outbound to work

**[39:46]** and the majority of our leads were inbound.

**[39:50]** And we didn't know how to do paid ads.

**[39:52]** And then we found out how to do paid ads.

**[39:54]** And it's like, there's a time period

**[39:57]** where Meta had amazing ROI and you gotta be able

**[40:00]** to pounce on that when you have it

**[40:02]** and when you have the opportunity,

**[40:04]** but you shouldn't be beholden to one channel.

**[40:06]** So then you're looking for like,

**[40:08]** well, what are the other channels

**[40:09]** and what didn't work last time?

**[40:10]** So there's like this constant experimentation

**[40:14]** that I think needs to be done in order to,

**[40:18]** or capture attention enough to actually convert it

**[40:21]** to something, a customer, something meaningful.

**[40:24]** And so when you ask like, how do we find sellers?

**[40:27]** Even that's changed.

**[40:28]** And it changed because early we hired gym owners.

**[40:32]** We hired our clients, which is a gift and a curse.

**[40:37]** One of the gifts are, they know the industry insanely well.

**[40:41]** They know your system very, very well.

**[40:45]** They have near zero ramp time because of those things

**[40:50]** and they have a strong network.

**[40:51]** So all great advantages for getting early traction.

**[40:56]** They generally are entrepreneurs, which is a benefit,

**[41:00]** but they don't like staying within tightly confined space

**[41:04]** and executing in the way

**[41:05]** 'cause they're an entrepreneur for a reason.

**[41:08]** There also may not be natural sellers or polished sellers.

**[41:13]** So that can be a little difficult at times,

**[41:17]** but thankfully in our space, everyone believes in coaching.

**[41:21]** And so that was maybe a unique advantage

**[41:24]** that we had at the time.

**[41:26]** And so we leaned heavily into that in those early years

**[41:28]** and we couldn't get outbound to work.

**[41:31]** But now we're at the stage in our company

**[41:32]** where we have a very strong outbound motion,

**[41:36]** very strong cold SDR outbound motion that,

**[41:40]** God, I wish we would have landed on forever ago.

**[41:43]** And our SDR team and our SDR leader

**[41:46]** have done an amazing job.

**[41:49]** And now that's the future sales talent,

**[41:52]** account executive talent that we have in the team.

**[41:55]** And I can't see a world where I would hire

**[41:58]** anyone that's not on that team to be an account executive.

**[42:01]** I don't think I'll bring anyone in external

**[42:04]** to sit straight to the account executive seat ever.

**[42:08]** - I love that.

**[42:09]** I love the bullpen and then giving people a path.

**[42:11]** And I'm sure there's a level of commitment that you can get

**[42:17]** when you have given those people opportunities

**[42:20]** as they've moved along rather than trying to find out

**[42:23]** or find mercenaries to bring into to be AEs.

**[42:28]** And I think it's a testament to the culture

**[42:31]** that you're building as well.

**[42:34]** - A hundred percent.

**[42:34]** I think the way that you find sellers,

**[42:39]** and it may change again, right?

**[42:41]** Like certainly, you could maybe fast forward time,

**[42:47]** see a world where AI voice agents ruin outbound.

**[42:54]** They always say marketers ruin everything, right?

**[42:56]** So we ruin outbound because we flood the market

**[42:59]** with AI voice agents.

**[43:00]** And then all of a sudden outbound is dead.

**[43:02]** Now you have to solve two problems.

**[43:04]** How do I replace this channel?

**[43:05]** And how do I replace my bench of sales talent?

**[43:09]** So that's generally how I look at solving

**[43:15]** almost every GTM motion is there's a series of factors

**[43:19]** that you have to kind of untangle,

**[43:21]** solve one, rinse and repeat.

**[43:26]** - You mentioned something in our prep session

**[43:28]** that I have completely stolen

**[43:32]** and used in all of my leadership meetings.

**[43:35]** So thank you.

**[43:36]** I'll pay you the royalties

**[43:37]** and you should get a nice check from that.

**[43:40]** But throughout your time,

**[43:42]** there are many bets and decisions and experiments

**[43:46]** and things that you have to make judgments on.

**[43:49]** You're not gonna have perfect data.

**[43:51]** You might have data as a signal,

**[43:52]** but there's no guarantees and go to market

**[43:56]** and there's no guarantees in SaaS.

**[43:58]** And the phrase that I cannot stop repeating

**[44:02]** is what needs to be true.

**[44:06]** I would love to hear the origin of that

**[44:10]** and how you have used that throughout your role.

**[44:15]** - You know, the origin,

### 44:16 — "What needs to be true?"

**[44:17]** I think I've probably first uttered it a year ago,

**[44:23]** but I feel like I've always thought that way,

**[44:25]** which is you see a problem

**[44:28]** and maybe this is where it came from.

**[44:30]** It's like you would see a problem in growth

**[44:32]** and it would be like,

**[44:34]** well, you've only got a hundred demos

**[44:39]** being booked of your software in a month.

**[44:41]** And what needs to be true for us to get that to 200?

**[44:46]** And the inverse way is go,

**[44:47]** how do I get it to 200, right?

**[44:49]** But how do I get it to 200?

**[44:51]** For whatever reason,

**[44:52]** those words don't open my imagination

**[44:56]** the way that what needs to be true for us to have 200 does.

**[45:00]** And so now all of a sudden

**[45:03]** you can just start throwing everything at the wall.

**[45:07]** Everything.

**[45:07]** It's like, well, certainly if it was $0,

**[45:11]** we'd have a lot of demand.

**[45:13]** Okay, that's one.

**[45:14]** Doesn't mean that everything you throw at the wall

**[45:16]** should stick,

**[45:18]** but it just lists out everything.

**[45:20]** I mean, it's essentially first principles thinking,

**[45:23]** but it really is just a way, I think,

**[45:25]** to force yourself to unlock your imagination

**[45:29]** to all of the potential that could exist.

**[45:33]** And it's so easy to get like the narrow focus

**[45:37]** in any organization around.

**[45:42]** Go accomplish this.

**[45:43]** And you immediately go to,

**[45:45]** okay, I have this box of things.

**[45:48]** I have the toys that I have to build this thing

**[45:52]** are confined into this box.

**[45:55]** So let me go accomplish that,

**[45:56]** but only with these pieces instead of the inverse,

**[46:00]** which is just what needs to be true

**[46:01]** for this mission to be accomplished.

**[46:03]** And you go, well, the box doesn't exist.

**[46:06]** The toys don't exist.

**[46:08]** Imagine the toys.

**[46:09]** And you can build from infinite possibilities, right?

**[46:14]** So I think to me the reason why we've used it so much,

**[46:19]** especially recently at Push Press,

**[46:22]** and the reason why it's always top of mind today

**[46:26]** more than ever is because AI has actually allowed

**[46:30]** even that imagination and that creativity

**[46:33]** to come to life in a way that it didn't three years ago

**[46:37]** or before where maybe it did have constraints.

**[46:40]** And in order to do something,

**[46:41]** it needed to go through engineering or something else,

**[46:45]** but now everyone can be a builder.

**[46:47]** So now what's the excuse?

**[46:51]** So if you're not thinking that way,

**[46:54]** I don't know how you get anything done.

**[46:56]** - I don't take you as a person

**[46:57]** who gave yourself many excuses in the past,

**[46:59]** but I do also feel like the ceiling of what's possible

**[47:03]** has just been completely lifted.

**[47:07]** And for people like you mentioned,

**[47:09]** hey, maybe there were some barriers.

**[47:11]** I'm not a developer.

**[47:12]** I wasn't even a very good Salesforce admin.

**[47:14]** I needed some systems admins just to make RevOps work.

**[47:18]** But now we can build applications, build systems,

**[47:22]** even just getting your ideas on paper.

**[47:24]** Like one of my favorite things to do

**[47:26]** is just whisper flow into a giant Google Doc

**[47:30]** and just be like,

**[47:31]** can you turn this into something that makes sense?

**[47:35]** So there really are no excuses now

**[47:37]** and you have access to the most powerful technology

**[47:42]** that's ever been built and you can build it.

**[47:45]** You can do it today.

**[47:46]** - Absolutely, absolutely.

**[47:48]** The other thing about that statement

**[47:50]** that I think has resonated in our organization,

**[47:54]** I think it tears down some of the pointedness

**[47:59]** that like, can you go do this?

**[48:01]** Can you go do more might bring.

**[48:03]** So this actually came up the other day.

**[48:05]** One of the members on our team said,

**[48:08]** we can get this done probably April, late April, early May.

**[48:14]** And it's like, that's an eternity in today's age.

**[48:20]** And so rather than say like,

**[48:22]** hey, can you figure out a way to just move it forward?

**[48:25]** Like figure out a way to get it done in January,

**[48:28]** which is almost an indictment on the work

**[48:33]** that was done to put the previous date out there.

**[48:37]** And instead, what needs to be true

**[48:40]** for us to have it done by the end of the year?

**[48:44]** If you tell me it's a million dollars,

**[48:47]** that might be okay,

**[48:49]** depending on whatever the initiative is.

**[48:51]** If you tell me it's gonna take 10 people,

**[48:53]** you can tell me it's gonna take infinite cloud credits.

**[48:56]** Whatever it is.

**[48:57]** And then as an organization,

**[48:59]** we can at least have an open and honest discussion

**[49:01]** around is it worth that?

**[49:03]** But show me that you've gone through the thinking,

**[49:06]** not just of what you have to play with,

**[49:08]** which might legit be,

**[49:10]** if I only confined you to using these things,

**[49:14]** then maybe April's an acceptable timeframe.

**[49:17]** But if it's really the biggest bottleneck to our growth

**[49:19]** and it's really that important,

**[49:21]** then put it out there and let finance and our CEO,

**[49:26]** like let other people come to the table and go,

**[49:29]** you know what, I'm in.

**[49:31]** That's what it takes to get it done.

**[49:32]** Damn right, let's do it.

**[49:34]** But you gotta invite that conversation.

**[49:35]** I think you gotta do it in a way that opens up creativity

**[49:37]** and doesn't stifle it.

**[49:42]** - The most memorable example of this I have in my career,

**[49:47]** I was head of RevOps for a company called Email Edge,

**[49:50]** CEO, founder, Ray.

**[49:53]** Ray's a tough dude.

**[49:57]** He has very high expectations.

**[50:00]** He has no appetite for mediocrity and very, very ambitious,

**[50:06]** which is probably why he built a company

**[50:08]** that had a half a billion dollar exit.

**[50:12]** But I was head of RevOps to that company.

**[50:14]** I was in charge of building the operating plan,

**[50:18]** the growth model.

**[50:19]** And I remember our head of sales or head of marketing

**[50:23]** or head of customer success at the time.

**[50:24]** We all got in the room or like,

**[50:26]** this is what we think we can do next year.

**[50:27]** This is the plan, this is where we can go.

**[50:30]** Go to an offsite meeting, present it to Ray,

**[50:32]** and he's like angry.

**[50:34]** He's like, it's not ambitious, it's nothing.

**[50:36]** We can't do that.

**[50:37]** We need to be able to double again.

**[50:38]** At this point, we were at 20 million in ARR.

**[50:41]** We're like, we cannot conceive a way to go

**[50:45]** from 20 to 40 in one year.

**[50:47]** Like, what are you talking about?

**[50:50]** We just kind of went from I think 12 to 20

**[50:53]** at this point in time.

**[50:54]** So how are we gonna do that all over again?

**[50:57]** And we had a couple of meetings with him

**[51:00]** and I started to get frustrated

**[51:03]** and it almost felt like this weird Mr. Miyagi moment.

**[51:05]** I was like, you know what, fine.

**[51:07]** Ray, you wanna know how crazy your idea

**[51:09]** of doubling is this year?

**[51:10]** I'm gonna show you exactly what it's gonna take

**[51:13]** and I'm gonna show you that this is the stupidest idea

**[51:16]** you've ever had.

**[51:17]** So if you wanna get to 40 million,

**[51:19]** you're gonna need this many reps.

**[51:20]** We're gonna have to convert it this rate.

**[51:21]** You're gonna have to build this pipeline.

**[51:22]** The pipeline needs to come in right now.

**[51:24]** We're gonna need to activate these channels.

**[51:26]** Churn's gonna have to be here.

**[51:27]** And it's like, see Ray, it's impossible.

**[51:30]** And he goes, this is everything I've been hoping for.

**[51:35]** (laughing)

**[51:37]** I was like, what did I just do?

**[51:41]** - You just did it.

**[51:43]** - I was like, oh, this is it.

**[51:45]** And I didn't have the words for it,

**[51:46]** but the what needs to be true.

**[51:50]** That's exactly where my mind was going.

**[51:52]** Like, okay, like it may sound ridiculous.

**[51:55]** Like, hey, Ray, you gotta hire 200 salespeople by January

**[51:59]** or else we ain't getting there.

**[52:01]** Fine, okay, well, let's start with that.

**[52:03]** And then if we need to pare that down.

**[52:05]** But then I love how it moves the conversation,

**[52:07]** just like you mentioned, to the inputs.

**[52:10]** Let's argue about the inputs.

**[52:13]** And then we'll see what output that'll produce.

**[52:16]** - Right, right.

**[52:18]** And the example you just gave is perfect

**[52:24]** because from there, if you have to hire 200 reps,

**[52:26]** it's like, okay, well, what needs to be true

**[52:28]** for us to hire 200 reps?

**[52:30]** Well, we better have a damn good recruiting process.

**[52:32]** (laughing)

**[52:34]** You back into the entire plan to make it happen,

**[52:38]** piece by piece.

**[52:39]** And so to me, it's one of those things

**[52:42]** I wish I would have even maybe put into words earlier.

**[52:46]** But again, it's just one of the ways

**[52:48]** I've thought about things over,

**[52:50]** for as long as I can remember,

**[52:53]** and then landing on the words about a year ago, I think,

**[52:56]** and now echoing them probably to the point

**[52:58]** where it makes my team sick.

**[53:01]** But it's always a signal of,

**[53:03]** I wanna see a little more at this point,

**[53:06]** for better or for worse.

### 53:09 — Wrap + Nick's ask: drop into a local gym

**[53:09]** - Well, Nick, this has been incredible.

**[53:12]** Thanks for sharing everything.

**[53:13]** First of all, your story.

**[53:14]** I just love the commitment and risks

**[53:17]** and betting on yourself

**[53:19]** and the relentless endurance

**[53:24]** that you've displayed throughout your entire career.

**[53:27]** I think it's something that anybody interested

**[53:29]** in aspiring to be a CRO

**[53:30]** or aspiring to be in this type of leadership position

**[53:33]** should be taking notes from.

**[53:35]** And I also really appreciate your approach

**[53:39]** to how to build, go to market, where RevOps fits

**[53:43]** in things you wish you would have done earlier.

**[53:45]** I think you can help someone skip a bunch of potholes

**[53:49]** on their way to their next stage of growth.

**[53:52]** And then I don't think I will ever forget the phrase

**[53:55]** that you've left me with, what needs to be true?

**[53:58]** And I think if anybody's listening,

**[54:00]** you need to ask yourself and others

**[54:02]** that exact question more often.

**[54:05]** And I think it'll unlock all kinds of opportunities

**[54:07]** you never imagined.

**[54:08]** So Nick, thank you so much for being on the podcast

**[54:10]** and I can't wait to see what you do next.

**[54:15]** - Well, thanks a ton.

**[54:16]** Really appreciate you having me on.

**[54:18]** Appreciate everything you're doing for growth leaders

**[54:21]** and SaaS founders everywhere.

**[54:24]** My one ask is to anyone in the audience,

**[54:26]** go find a local gym, go find a local gym, take a class,

**[54:33]** see what they're doing.

**[54:33]** I think their gym owners all around the world

**[54:36]** are solving both a health crisis,

**[54:40]** making us all fitter, healthier humans,

**[54:42]** and they're solving a loneliness epidemic

**[54:45]** that I often don't think gets enough discussion.

**[54:49]** And so between that, making mental health better,

**[54:52]** they really are doing a ton of work to make our communities

**[54:56]** more powerful, healthier mentally and physically.

**[54:59]** So that's my ask for the audience.

**[55:01]** Go drop into a CrossFit affiliate,

**[55:03]** go drop into a HiRocks affiliate,

**[55:05]** go drop into, take a group class,

**[55:07]** promise you won't regret it.


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_LeanScale Knowledge Hub. Free to quote and cite with attribution to The LeanScale Podcast (https://www.leanscale.team)._