From Start-Up to Grown-Up

#91: From Startup to Grown-up: Mike Seckler, CEO of Justworks — how to run a great board process, how to avoid self-inflicted wounds, and the value of taking big risks early in your career

• Alisa Cohn • Episode 91

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Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transitions. We dive into founder resilience, building high-functioning boards, scaling culture in a hybrid world, and why mission-driven support for small businesses matters now more than ever.

What You’ll Learn:

  • How Mike evolved from first-time founder to CEO of Justworks
  • The “self-inflicted wound quotient” every founder faces—and how to reduce it
  • How values shape Justworks’ culture and decision-making
  • The impact of structured, intentional board leadership
  • Why Justworks pulled its IPO and why it was the right call
  • Lessons from integrating a remote team post-acquisition
  • How to stay adaptable without losing momentum
  • Why stepping back (even for vacation) makes you a stronger leader
  • Balancing in-person U.S. operations with global remote teams
  • The importance of staying close to your end user

Key Takeaways:

 ➡️ Minimize your “self-inflicted wounds”: Founders often make early decisions—co-founder choices, board composition, capital structure—that can hinder growth. Mike calls this your “self-inflicted wound quotient.” Keep it low. 

➡️ Good governance starts with leadership: Don’t wait for your board to self-organize. Set norms, prep materials early, and lead it the way you’d lead your exec team. 

➡️ Clarity beats comfort: From acquisitions to layoffs, Mike emphasizes over-communicating the why and making decisions that would “look good on the front page of the Wall Street Journal.” 

➡️ Culture isn’t what you say—it’s what you do: Values like “comradery” and “grit” must be defined through behavior and reinforced through recognition, awards, and storytelling. 

➡️ Board building is strategic: Justworks’ board includes domain-specific experts—from healthcare to global payments. Choose members like you’d build your C-suite. 

➡️ Hard decisions made early pay off later: Fix the roof when it’s sunny. The cost of delay is always higher. 

➡️ Remote vs. in-person is not either/or: Justworks combines in-office culture in the U.S. with distributed international teams, intentionally designing for both. 

➡️ Real leadership means managing your energy: Mike learned from parenting that being the calmest person in the room is often your superpower. 

➡️ Mission attracts the right people: Employees at Justworks are deeply motivated by its purpose—to serve small businesses as heroes of the economy. 


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