Episode 20

Redefining Success: Building Resilient Communities and Careers in SaaS

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About This Episode

This episode of Revenue Renegades explores the changing landscape for go-to-market leaders in high-growth SaaS, spotlighting the shrinking tenure of CROs and CMOs and the need for new career resilience strategies. The conversation delves into the pivotal role of professional communities, the importance of founder-operator alignment, negotiation tactics, and the psychology behind building lasting membership organizations. Gain insight into optimizing for learning over compensation, sustaining authentic relationships, and nurturing personal brands in a noisy digital world—all while embracing vulnerability and long-term thinking to propel both your business and personal success.

About The Guest

Sam Jacobs

Founder and CEO, Pavilion

Sam Jacobs is the founder and CEO of Pavilion. He launched Pavilion as Revenue Collective in 2016 and bootstrapped the company to $10M in ARR before taking on a $25M growth financing round in early 2021, led by Elephant Ventures and GTM Fund.

Prior to Pavilion, Sam spent 15 years as a senior revenue leader at VC-backed companies in the New York area, including Gerson Lehrman Group, Axial, Livestream/Vimeo, The Muse, and Behavox.

He resides in Barcelona with his partner and their two dogs, Oswald and Abraham.

Transcript

Doug Camplejohn
(00:01)

Hello everyone. This is Doug Camplejohn, and welcome to this week’s episode of Revenue Renegades. I’m pleased to welcome Sam Jacobs to the show—the founder and CEO of Pavilion, bestselling author of Kind Folks Finish First, co-host of the Topline podcast, and a relatively new father. Welcome to the show, Sam.

Sam Jacobs
(00:21)

Thanks, Doug. I’m excited to be here.

Doug Camplejohn
(00:24)

We could talk about living in Barcelona and all kinds of fun stuff. But why don’t we start with what Pavilion is — and what’s the founding story?

Sam Jacobs
(00:34)

Pavilion is the largest—and we hope the best—community for go-to-market executives at high-growth companies. We’re a global, chapter-based membership organization with about 10,000 people in places like San Francisco, London, and New York. Our mission is to help build the modern go-to-market executive.

The world today is incredibly uncertain; it changes constantly. No one has experience being a CRO or CMO in 2026 yet—we’re all figuring it out in real time. Pavilion exists to provide education, community, and in-person experiences to help people lead with confidence and build great companies.

I started Pavilion after a 15-year career as a CRO at early-stage companies from 2003 to 2018. As my career advanced, I noticed my job security decreasing. There wasn’t an operator-focused org that truly championed CROs, CMOs, or CCOs. We popularized the stat that the average CRO tenure is only 18 months. I recently looked at my network—among sales and marketing execs, that number is now around 13 months. So we created Pavilion to equip people for this new world.

Doug Camplejohn
(02:43)

That shrinking tenure is alarming. What’s driving it—bad leadership, company culture, or just the startup model?

Sam Jacobs
(02:54)

The top reason is the macro environment. It’s not purely a failure of leadership; it’s how we now build companies—global workforces, remote teams, rapid shifts. Initially, I blamed inexperienced CEOs and quick-trigger investors (and they’re definitely a factor), but that’s only part of it.

We’re also seeing fractionals, consultants, founders—it’s a fragmented world. The traditional career path no longer exists. The real problem is a lack of development and education for go-to-market leaders. That’s the void we fill.

Doug Camplejohn
(04:10)

Tell me about this “Bill of Rights” you’ve developed for GTM executives.

Sam Jacobs
(04:15)

Yes! It’s a framework of five “rights” — really just best practices for negotiating your role.

  1. The Right to Due Diligence: Executives deserve a clear picture of company health before they commit—what’s the ARR, the capital structure, are there 3x liquidation prefs?
  2. The Right to Aligned Compensation: CROs shouldn’t be paid like AEs. Long-term leadership shouldn’t be incentivized with a 50/50 split. I recommend 2/3 base, 1/3 variable.
  3. The Right to Liquidity: You should negotiate for extended exercise windows on your options. Not getting that screwed me multiple times financially.
  4. The Right to Severance: These roles are risky—there should be a parachute.
  5. The Right to Consult/Fractional Work: If we’re constantly getting fired, we should be allowed to build other monetizable work streams.

Doug Camplejohn
(07:14)

I love that. At my company, we offer ten-year option exercise windows to eliminate unnecessary friction.

Sam Jacobs
(07:21)

That’s incredibly generous. We give two years at Pavilion.

Doug Camplejohn
(07:52)

We also do a 90-day check-in meeting—it forces clarity early and prevents B players from coasting too long.

Sam Jacobs
(08:19)

That’s smart. I’m rethinking the traditional 25% per year vesting model too. Some executives leave after a year and walk away with 1% of equity—nine years later that feels out of whack.

Doug Camplejohn
(09:05)

So what’s your preferred vesting schedule?

Sam Jacobs
(09:08)

Start with a one-year cliff. Then maybe backload a four-year vesting schedule. But the key thing is: give people time to decide post-departure, especially emotionally.

Doug Camplejohn
(10:22)

Right—solving the information asymmetry problem. Startups today have so much more knowledge available than when I launched my first.

Sam Jacobs
(10:56)

Exactly. We try to arm GTM leaders with that same depth. And sometimes people assume I’m like a union boss, fighting CEOs. But I mostly coach for alignment with CEOs and founders—not just squeezing more comp.

Doug Camplejohn
(12:02)

What’s the most common coaching issue you hear?

Sam Jacobs
(12:16)

Easily: “Should I quit?” I tell most people: stay. Unless it’s toxic, you’re generally just trading one set of problems for another. Longevity has value. Of course, there are exceptions. But most of the time? Stay and play the long game.

Doug Camplejohn
(13:48)

Reminds me of Jeff Weiner: “Seek first to understand.” That mindset is everything.

Sam Jacobs
(14:53)

Absolutely. Another common scenario is: “Should I take this job?” And the answer is: you often can’t know. It’s a startup. Do the diligence, then trust your gut.

Doug Camplejohn
(15:31)

I use the “love or fear” test. If I joined for love—the people, the mission—it worked out. If I joined for fear—a quick exit—disaster.

Sam Jacobs
(15:55)

Totally agree. The best situations were handshake deals with people I liked. Many of my current successes trace back to relationships I made 10 years ago.

Doug Camplejohn
(16:31)

My advice: optimize for learning, not title or comp.

Sam Jacobs
(16:47)

Exactly. Time builds your personal equity. Every failure adds to it.

Doug Camplejohn
(17:14)

That’s one of Silicon Valley’s superpowers. Failure here isn’t stigmatized—it’s capitalized.

Sam Jacobs
(17:35)

And it breeds optimism. Maybe your startup will be the next OpenAI—we just don’t know.

Doug Camplejohn
(17:52)

Let’s talk about community building. You’ve nailed it with Pavilion—10,000 members, no traditional marketing. What’s your secret?

Sam Jacobs
(18:20)

Quality beats speed. Most communities fail because they grow too fast and dilute the culture. Also, have a clear “why.” We built Pavilion to help GTM leaders grow—not to sell something.

We were hyper-focused on our ICP (ideal customer persona), but when we raised VC, we got distracted by expansion—Pavilion for legal, for HR, etc. Bad idea. It diluted exclusivity. If I could do it again: laser focus on the core audience.

Doug Camplejohn
(20:36)

So what else have you learned?

Sam Jacobs
(20:36)

Recognize status. Early supporters—the ones who helped build the community—want to be acknowledged. Think of community like college: there’s a “graduation.” Alumni don’t want to pay tuition, but they still want to be part of the legacy and mentor others.

Doug Camplejohn
(22:21)

You had hyper-growth during the pandemic, right?

Sam Jacobs
(22:27)

Yes—from late 2020 into 2022. Then came the tech recession. We over-hired, diluted talent, and had to go into rebuilding mode. But now, I’m excited again.

Doug Camplejohn
(23:53)

What’s next for Pavilion?

Sam Jacobs
(24:00)

We’re redesigning our offerings:

  1. Alumni Tier: For past members who want to give back but not engage full time.
  2. Pavilion Gold: Exclusive for operators at $100M–$3B+ ARR.
  3. Small Councils: Peer mastermind groups of 8–10 members.
  4. Deep Investment in Content: Custom offerings based on career stage.

We’re also testing positioning—people are more responsive when a membership has a mission: contribute to the community, not just pay dues.

Doug Camplejohn
(27:08)

In-person is more important than ever.

Sam Jacobs
(27:33)

Totally. In a world flooded with AI, IRL stands out. I flew from Barcelona to SF for one dinner—and it was worth it. Magic happens in person.

Doug Camplejohn
(30:13)

Let’s talk about LinkedIn. You’ve built a huge personal presence.

Sam Jacobs
(30:39)

I got serious in 2022. I defined my niche: empower executives, share practical startup advice. I worked with Alec Paul as an advisor. Clarity, consistency, and authenticity were key. I posted daily—and it paid off.

But LinkedIn’s algorithm shifts constantly. Reach is lower now. Still, personal brand—especially in a world of AI—is a massive asset. I even built Pavilion on that brand foundation. We’re now spinning off Topline podcast into its own company for this reason—distribution is a moat.

Doug Camplejohn
(37:26)

Amazing. Speaking of Topline, what makes a good podcast?

Sam Jacobs
(37:35)

Rapport. I co-host it with AJ Bruno and Asad Zaman—we have chemistry. Also: consistency. We haven’t missed a week in two years. And content matters. You have to say something interesting.

Doug Camplejohn
(39:32)

Let’s talk about your book. Two biggest takeaways?

Sam Jacobs
(39:38)

  1. Kindness is a strategic edge, especially over time.
  2. Play the long game. Helping others accumulates influence—just like Vito Corleone in The Godfather, but without the violence. Do good things, and your network becomes your superpower.

Doug Camplejohn
(41:47)

Kind leadership is underrated. You don’t have to be a jerk to win.

Sam Jacobs
(42:29)

Exactly. Maybe to be a billionaire, but not to be a centimillionaire—and that’s still pretty good.

Doug Camplejohn
(42:44)

Let’s go personal. What do you do for fun?

Sam Jacobs
(43:12)

I hang out with my baby daughter in Barcelona, run to the beach, read, and listen to vinyl. I even worked with a DJ from Ibiza to set up a record player. Also, I used to run a record label and have music on Spotify—it’s called The Flying Change.

Doug Camplejohn
(45:02)

Any tools you love?

Sam Jacobs
(45:19)

I use ChatGPT daily. Otter is great too—I upload transcripts, ask GPT to evaluate contributions, and get insights. The data is powerful—and I’m exploring ways to build GPTs informed by high-quality Pavilion conversations.

Doug Camplejohn
(48:28)

Amazing. How can our listeners connect with you?

Sam Jacobs
(48:36)

Follow me on LinkedIn: linkedin.com/in/samfjacobs. Subscribe to Topline. Or just join Pavilion—the pool is warm.