244: From Founder to CEO: Startup Rhythm and Leadership Lessons with Leslie Fine

Have you ever wondered what separates a great founder from a great CEO? Or how some startups seem to move effortlessly while others struggle to find their footing?

In this episode, I sit down with Leslie Fine, Managing Partner at Enjoy The Work, to unpack the transition from founder to CEO. Leslie shares hard-earned lessons from her own journey—starting in academia and moving into startup leadership—and reveals the essential skills every aspiring CEO needs. From mastering the rhythm of a startup to navigating fundraising and leadership challenges, this episode is packed with insights for women in tech who are ready to take the leap into leadership.

"Every CEO was a first-time CEO once. Leadership is a craft. It's a learnable skill. People talk about leadership like it's some mystical quality that you either have or you don't, but it's something you can learn and improve." – Leslie Fine

• The key differences between a founder and a CEO—and why mastering both is crucial
• The three pillars of leadership every startup CEO must develop
• How to set clear goals and lead with accountability
• Why understanding the rhythm of a startup is essential for scaling successfully
• The five major phases of a startup and how to act stage-appropriately
• How to decide if venture capital is the right fit for your business
• The three main jobs of a CEO that define long-term success

After listening to this episode, take a moment to reflect: Are you operating as a founder or truly stepping into the role of a CEO?

Write down the three biggest leadership skills you need to develop to take your startup to the next level. Share your insights with us on LinkedIn or Instagram, and tag me—I’d love to hear your takeaways!

**Useful links**

• Connect with today’s guest and sponsor, Leslie Fine:
  • LinkedIn: linkedin.com/in/lfine
  • Website: enjoythework.com
  • Enjoy The Work: 
    • https://www.linkedin.com/company/etw-advisors/
    • https://x.com/EnjoyTheWork
• Leslie’s current read: Quit by Annie Duke
• If you are ready to uplevel your career, get unstuck or you are simply ready to unlock those leadership time-management techniques then join us in my monthly career & leadership coaching program exclusively for women in tech: https://www.tonicollis.com/academy 
• Catch the show notes, and more details about today's episode here: https://tonicollis.com/episode244 
• Check us out on Youtube.
• Join the Leading Women in Tech community in Slack where we discuss all-the-things for women’s tech leadership, covering everything from early-career leadership to C-level executives.

This episode was sponsored by our guest, Leslie Fine of Enjoy The Work. Thank you Leslie for helping to bring Leading Women in Tech to this community!