The Journey from Mentor to Operations: A Career Reflected

What does it take to lead lasting change in an organization? Alan Masarek, a multi-time CEO with a track record of company turnarounds, shares the lessons he’s learned from transforming brands like Vonage and Avaya. 

In this in-depth conversation, Alan talks about building high-performing teams, the power of clear communication, succession planning, and how to lead authentically across companies of every size.

Takeaways:

• There’s No “One Thing” — But Culture Comes Close: Alan explains that success doesn’t come from a single action but a combination of choices: pursuing winnable markets, building strong teams, and creating cultures rooted in openness, honesty, and transparency.
• Clear, Simple, & Repetitive Communication: He emphasizes the necessity of repetitive messaging to reinforce confidence and direction within an organization. Regardless of the company size, developing the habit of effective communication early is crucial for long-term success.
• Transforming Vonage Meant Facing Reality: At Vonage, Alan led a shift from residential telephony to business communications. He dismantled internal divisions, repositioned the company, and made hard but necessary cultural changes by being direct about who was driving growth and who wasn’t.
• People Follow Leaders, Not Titles: Alan emphasizes hiring smart, high-integrity people and focusing on the top two layers of the organization. He looks for utility players with CEO potential, not just narrow specialists.
• Avoiding the Trap of Over-Reporting: When he arrived at Avaya, a 77-slide weekly report deck had become the norm. Alan reduced this dramatically, advocating for consistent, actionable metrics that focus on real business health rather than satisfying a process.
• Private Equity Dynamics Can Clash with Strategy: Alan reflects on the challenges of navigating fund timelines and liquidity needs, especially in private equity-backed companies. He notes that these dynamics can often push leaders toward short-term decisions at odds with long-term business goals.
• Leadership Isn’t About Work-Life Balance — It’s About Fulfillment: Alan shares his view that if you love what you do, work-life balance becomes irrelevant. He encourages young professionals to build wide foundations early in their careers by learning as much as they can, as fast as they can.

Quote of the Show:

• " Our job as leaders is to lay that picture out clearly... 'cause all too often we ask people to achieve what they can't imagine." - Alan Masarek

Links:

• LinkedIn: https://www.linkedin.com/in/alan-masarek-1aa1a8a8/
• Twitter (X): https://twitter.com/amasarek
• Website: https://www.avaya.com/en/
  
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Avaya

Chapters:

00:00 Intro

01:43 Alan Massek's Leadership Philosophy

05:45 The Importance of Communication in Leadership

07:20 Transforming Avaya: A Case Study

10:23 Challenges and Strategies in Business Transformation

17:03 Vonage Transformation: From Residential to Business Communications

28:50 Hiring and Building High-Performing Teams

40:22 The Importance of CEO Succession Planning

41:46 Navigating Acquisitions: Strategies and Insights

48:49 The Role of Private Equity in Modern Business

54:09 Life After Stepping Down as CEO

56:20 Leadership and Mentorship: Keys to Success

01:06:02 Work-Life Balance and Return to Office

01:14:28 Advice for Young Professionals

01:17:26 Outro