Leadership Lessons - Tough Calls and Thriving in the Long Game | Sam Jacobs | S3:E7

Leadership Lessons - Tough Calls and Thriving in the Long Game 

In this episode of Force and Friction, we sat down with Sam Jacobs, CEO of Pavilion, Wall Street Journal bestselling author of Kind Folks Finish First, and a trailblazer in professional development for GTM leaders.

Sam’s journey, from managing a record label to building Pavilion into a global powerhouse, offers invaluable insights for leaders navigating today’s complex business landscape.

Sam Jacobs

The Revenue Table

Sam Jacobs is a trailblazer in professional development and community building for revenue leaders.

As the founder and CEO of Pavilion, he grew the organization (formerly Revenue Collective) from a bootstrap startup to $10M in annual recurring revenue (ARR) before securing a $25M growth financing round led by Elephant Ventures and GTM Fund.

Before Pavilion, Sam spent 15 years in senior revenue roles at notable VC-backed companies, including Gerson Lehrman Group, Axial, Livestream/Vimeo, The Muse, and Behavox.

He is also a Wall Street Journal bestselling author of Kind Folks Finish First, a guide to leading with kindness while achieving success, and co-host of the Topline Podcast. Sam resides in Manhattan’s West Village with his two dogs, Oswald and Abraham.

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Here’s what we uncovered during this candid conversation with Sam:

From Record Labels to Revenue Leadership:

Sam’s path to success is far from conventional. He began his career in the music industry, managing bands and running a record label, before transitioning into startups and eventually founding Pavilion.

“The music industry was collapsing, and I realized my calling wasn’t in managing bands, it was in building something that truly helps people succeed.”

This unique background shaped Sam’s leadership philosophy, emphasizing authenticity, resilience, and creativity.

Building Pavilion: From Bootstrap to $10M ARR:

Pavilion’s growth from a bootstrap startup to a $10M ARR business is testament to Sams leadership. He attributes the success to understanding his audience deeply and building a clear value proposition for revenue leaders.

“I was the customer. Pavilion wasn’t about what I needed to build, it was about what the market truly needed.”

Key milestones included launching local chapters, encouraging members to showcase their affiliation on LinkedIn, and pivoting to digital events during the pandemic.

The Power of Playing the Long Game:

Sam emphasized the importance of taking a long-term view in business and life. His advice? Build relationships, not transactions, and focus on creating lasting value rather than chasing quick wins.

“Desperation pushes away your goals. Success comes from patience, persistence, and playing the long game.”

This mindset has been instrumental in Pavilion’s sustained growth and community impact.

Tough Calls: Lessons from Letting Go of an Engineering Team:

One of Sam’s most challenging moments was the decision to let go of Pavilion’s engineering team in 2023 to ensure the company’s survival. He shared his thought process behind this tough call:

“I’d rather have people think I’m an idiot and save the company than let it fail out of pride.”

This story highlights the difficult decisions leaders must make to protect their organizations and the importance of acting decisively in tough situations.

Self-Compassion and Authenticity in Leadership:

At the heart of Sam’s leadership philosophy is the idea of self-compassion. He believes that the stories we tell ourselves shape our reality, and leaders must be kind to themselves to thrive.

“Life isn’t about being perfect, it’s about learning from your experiences and taking care of yourself along the way.”

This principle also underpins his book, Kind Folks Finish First, which explores how kindness and authenticity can drive success.

The Future of Pavilion and GTM Leadership:

Looking ahead, Sam is committed to building Pavilion into a long-term, sustainable organization. He believes in creating meaningful value for members while fostering a culture of collaboration and continuous learning.

“We’re not for sale. Pavilion is about building something that lasts and helps people, not flipping a company for a quick exit.”

For GTM leaders, this serves as a powerful reminder to focus on purpose over profit.

Final Thoughts:

Sam Jacobs’ journey is a testament to the power of authenticity, resilience, and playing the long game.

Whether you’re a SaaS founder, a revenue leader, or an aspiring entrepreneur, his insights offer a roadmap for navigating the highs and lows of leadership.

Purchase Sam's book on Amazon here: 

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A little about the 6teen30 Digital team who host and contribute to the show.  Please connect with us on LinkedIn we would love to have you as part of our professional networks.

Mike Midgley is the CEO at 6teen30 Digital, Inc. and a dynamic digital entrepreneur, nxd, strategist, public speaker and host of TheOpenMike Podcast show & Host at The Force & Friction Podcast.

Mike has achieved successful six and seven-figure exits over a 30-year career, raised in excess of £1.6m [$2.5m] in Venture Capital and franchised his businesses 68 times.

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