Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Sam Jacobs — founder and CEO of Pavilion, a global community of over 10,000 go-to-market executives — to examine what happens when a CEO loses sight of the model that made their company work. Jacobs’s answer is direct: he made every mistake he tells others not to make. The core lesson from Pavilion’s chapter two — a four-year period that Jacobs describes as “quite unpleasant” — is that growth capital does not produce growth. The CEO’s internal state does. When that state shifts from conviction to aspiration for status, the decisions shift too, and the business follows.
Pavilion is now in chapter three. Jacobs has hired a president, rebuilt his executive team, and returned to the admission standards and programming focus that defined Pavilion’s early success. He has also accepted something most CEOs resist accepting: the role he performs best is not the one that runs the company. It is the one that builds the community.
This episode is for CEOs of membership-driven or community businesses who have raised growth capital and are questioning whether the decisions that got them to scale are the same ones that will sustain it.
Key Takeaways
- Sam Jacobs, founder and CEO of Pavilion, identifies that CEOs who raise growth capital often trigger a shift in internal motivation — from mission-led conviction to status and wealth-chasing — and that shift produces strategic drift that undoes what made the company work in the first place.
- Jacobs reversed four years of strategic drift at Pavilion by identifying a single priority — hiring a president — and rebuilding his entire executive team around it; within six months, the business returned to the focused model that generated its original growth.
- Pavilion’s shift to open self-serve signup in 2022 demonstrated that membership organizations that lower admission standards to chase scale actively destroy the product they are selling; exclusivity is not a feature of the community — it is the community.
- Jacobs’s experience at Pavilion during chapter two shows that CEOs who lack self-awareness about where they add value create organizational bottlenecks without knowing it; decisions return to them not because they centralize power but because their team lacks the capability to execute without them.
- Pavilion’s chapter three is built on the same premise as chapter one: tight ICP focus, curated admission, depth over breadth of programming, and a CEO operating in the role that actually fits — external evangelist, content creator, course teacher — not day-to-day operator.
How Raising $25 Million Triggered Four Years of Strategic Drift at Pavilion
Sam Jacobs did not set out to raise institutional capital. Elephant Ventures approached him. The $25 million investment arrived while Pavilion was still running on the organic momentum of its founding years — what Jacobs calls chapter one, a period where “every decision, you somehow feel like you have the Midas touch, like you can’t make a bad decision.”
What changed was not the business. What changed was Jacobs’s relationship to it.
“I started chasing some ideas about myself that I had let go of in chapter one,” Jacobs says. “That I needed to be a certain status, that I needed to have a certain amount of wealth, that Pavilion was gonna be a certain kind of company, a big company, a billion dollar company.”
That internal shift produced concrete strategic decisions. Pavilion had always required every prospective member to go through an interview. In 2022, Jacobs removed that requirement. Anyone could join by signing up online. The logic was scale. The consequence was identity erosion. When Pavilion made joining easy, it made belonging less meaningful — and the value of the community declined with its exclusivity.
The pattern extended beyond admission. Jacobs found himself with a team that was not operating at the level the organization required, making decisions that contradicted his previous positions, and searching for a conviction he could not manufacture. “Strategy seemed to shift all the time. I was desperately in search of conviction.”
He describes conviction as something that arrives without being sought. “When I get a strong feeling and I’m not looking for it, it tends to be correct. When I start looking for conviction, all of a sudden my hit rate plummets.”
What Happens When Decisions Keep Coming Back to the CEO
Jacobs is precise about how the bottleneck formed at Pavilion during chapter two. It was not that he refused to delegate. It was that the team around him could not absorb delegation effectively.
“I thought I had a team, I thought I was delegating,” he says. “But I would focus on the wrong things. I would double-click on issues where I was actually contradicting myself from three months prior or six months prior.”
The result was a structure that looked like delegation but functioned like centralization. Every significant decision looped back to Jacobs — not because he demanded control but because the team lacked the capability to resolve it without him. The CEO becomes the bottleneck when the team cannot operate at the company’s required level, regardless of the CEO’s intentions.
This is the distinction Jacobs makes between the talent problem and the leadership problem. A CEO can believe they are building capability while actually managing around its absence. The signal is not conflict. It is recurrence — the same issues returning, the same decisions being revisited, the same strategy shifting.
Jacobs traces the moment of clarity to a mastermind retreat within Pavilion’s own Small Councils program. Every person in the room was a CEO. Every person pointed at Jacobs and said the same thing: fix the talent quality in your organization.
“That was the moment that forced me,” Jacobs says. “I said my number one priority is hiring a president and everything will flow from there.”
How Sam Jacobs Rebuilt Pavilion’s Executive Team and Returned to Chapter One’s Model
Six months after hiring a president and rebuilding the executive team, Jacobs reports Pavilion is “confidently moving in the right direction” for the first time in years. The direction is not new. It is a return.
Pavilion is removing self-signup. It is tightening admission criteria. It is reducing the number of programming experiences to increase depth. It is sharpening ICP focus. Every element of chapter three is a restoration of chapter one — the model that built Pavilion’s reputation before capital arrived and before the aspiration to become a billion-dollar company displaced the judgment that had made it worth investing in.
The difference now is structural. Jacobs has organized the company around what he does well and hired to cover what he does not.
“It’s really much more for the point of your listenership, content creation, being the external face and evangelist for the organization, hosting my podcast, writing newsletters, teaching courses,” Jacobs says. “That’s an area where I really shine. But the day-to-day disciplined management of the company — I thought I was good at it and I’m just not.”
This is not a concession. It is a structural insight that most CEOs arrive at too late, if they arrive at it at all. The companies that scale past their founder’s operational comfort zone are the ones where the CEO stops trying to be good at everything and starts hiring people who are already good at what the CEO is not.
Jacobs’s framework for identifying this moment is simple: when peers whose judgment you trust all point to the same problem, that is not feedback. That is a priority.
The Scaling Executive Framework: What Sam Jacobs’s Pavilion Reset Teaches CEOs
| Principle | What it means in practice | Named evidence from this interview |
| Capital triggers identity drift before it triggers strategic drift | When a CEO receives institutional investment, the internal motivation can shift from mission-led conviction to status and scale aspiration — and that shift produces bad strategic decisions long before a bad strategy can be identified on a spreadsheet | After Elephant Ventures invested $25 million in Pavilion, Jacobs removed the interview-based admission process — Pavilion’s core membership value driver — entirely within 12 months of the investment, eroding the community quality that the membership product depended on |
| The product of a membership organization is its exclusivity, not its content | Lowering admission standards to drive member growth destroys the asset members are actually paying for — the quality and credibility of the community they are joining | Pavilion’s shift to self-serve signup in 2022 admitted members without vetting and degraded community quality to the point that chapter three’s entire recovery plan is built around restoring the original interview-based admission model |
| Delegation fails when the team cannot absorb it | A CEO who believes they are delegating but keeps having decisions return to them does not have a delegation problem — they have a talent calibration problem that delegation cannot fix | At Pavilion during chapter two, Jacobs found himself revisiting decisions and contradicting prior positions across a four-year period, a pattern that persisted until he replaced the executive team rather than adjusting his own delegation approach |
| Conviction cannot be manufactured — it must be recognized | CEOs who search for conviction under pressure tend to find false signals; the same capacity for judgment that guided their founding decisions degrades when urgency or anxiety replaces pattern recognition | The self-serve signup decision in 2022 — removing the interview requirement that had defined Pavilion’s membership quality — is the named consequence of conviction-seeking rather than conviction-arrival; Jacobs describes it as a call made while he was “desperately in search of conviction,” not one driven by a clear signal |
| The CEO’s right role is the one that produces results, not the one that feels like leadership | Self-awareness about where a CEO adds distinct value — and restructuring the organization to keep them there — is the enabler of scale, not a retreat from responsibility | Jacobs identified content creation, external evangelism, and teaching as his high-performance zone, hired a president to own operations, and reports the first confident forward motion in four years within six months of that structural decision; no measurable revenue or retention figure was disclosed in the interview |
Quotes from This Episode
- “I’ve made pretty much every mistake at Pavilion that I tell other people not to make.” — Sam Jacobs, Founder and CEO, Pavilion
- “I started chasing some ideas about myself that I had let go of in chapter one, that I needed to be a certain status, that I needed to have a certain amount of wealth, that Pavilion was gonna be a certain kind of company, a big company, a billion dollar company.” — Sam Jacobs, Founder and CEO, Pavilion
- “You can’t just join skull and bones at Yale by walking up and knocking on the door.” — Sam Jacobs, Founder and CEO, Pavilion
- “That was the moment that forced me. I said my number one priority is hiring a president and everything will flow from there.” — Sam Jacobs, Founder and CEO, Pavilion
- “The day-to-day disciplined management of the company — I thought I was good at it and I’m just not.” — Sam Jacobs, Founder and CEO, Pavilion
Frequently Asked Questions
What causes CEOs to lose strategic clarity after raising growth capital?
Sam Jacobs, founder and CEO of Pavilion, identifies the root cause as a shift in internal motivation rather than a change in strategy. When Elephant Ventures invested $25 million in Pavilion, Jacobs found himself chasing status and scale aspirations that had not previously driven his decisions — the desire for a billion-dollar company displaced the mission-led conviction that had made Pavilion successful. That internal shift produced a cascade of strategic decisions optimized for growth metrics rather than community value, including removing the interview-based admission process that had defined Pavilion’s membership quality. CEOs who raise capital without examining how it changes their relationship to the company’s identity are at significant risk of this pattern.
How should a CEO identify when their team is the constraint on company scaling?
Sam Jacobs, founder and CEO of Pavilion, describes the signal as recurrence rather than conflict: the same decisions return, strategy shifts repeatedly, and the CEO finds themselves contradicting prior positions without resolving the underlying issue. At Pavilion during chapter two, Jacobs believed he was delegating but discovered the team was not capable of carrying decisions forward without looping back to him — not because he refused to let go, but because the talent level was not matched to the organization’s needs. The clearest diagnostic, in Jacobs’s experience, came from external peer input: at a Small Councils mastermind retreat, every CEO in the room identified the same problem independently. When multiple trusted peers converge on the same diagnosis, Jacobs holds that it is no longer feedback — it is a priority.
What is the first structural move a CEO should make to fix a scaling bottleneck?
Sam Jacobs, founder and CEO of Pavilion, made a single decision that he credits with turning Pavilion’s trajectory: hiring a president. Rather than attempting incremental improvements to delegation or strategy, Jacobs identified that installing the right operational leader would unlock every other fix — and then he rebuilt the entire executive team around that move. Within six months of making the president hire, Pavilion had returned to the focused model — curated admission, tight ICP, depth over breadth of programming — that had defined its founding success. Jacobs’s principle is that when you cannot find traction through iteration, the constraint is usually a single structural gap at the top of the org, not a collection of tactical failures distributed across the company.
CEOs Work with Glenn Gow to Scale Their Companies by Scaling Themselves First
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
