On Wednesday, June 17, 2026, the Entrepreneur Exchange Committee of CREW Boston welcomed members to Davis in Watertown for a Power Lunch featuring Cindy Schlessinger, Founding Principal of Epsilon Associates, Inc.
During this intimate conversation, Cindy reflected on her remarkable career and the vision that helped establish and grow Epsilon Associates following its founding in 1997. She shared the story of building the firm from seven founding principals into a team of more than 100 professionals, offering candid insights into the challenges, opportunities, and strategic decisions that shaped its continued growth throughout the Boston market.
Cindy spoke about the importance of strategic thinking, cultivating lasting relationships, empowering talented people with autonomy, and maintaining perseverance through changing market conditions. She also shared how her genuine passion for the work allowed her to build a fulfilling career while creating a rich home life, remaining deeply committed to leadership and mentorship within the firm.
The conversation explored Cindy's career journey, Epsilon's evolution, succession planning, and her thoughtful transition into retirement. It was an inspiring discussion that reminded us that long-term success is built through purpose, resilience, and investing in people.
Members left with meaningful takeaways on building a career with intention, sustaining growth through changing economic cycles, and preparing for the next chapter, both professionally and personally.
Thank you, Cindy, for your generosity in sharing your experience and wisdom, and thank you to everyone who joined us for such an engaging and thoughtful Herstory Power Lunch.
