Growing Pains: What CEOs Need to Know About Navigating the 50-Employee Inflection Point
We’re excited to invite you to an exclusive webinar hosted by Overlap Holdings:
“Growing Pains: What Startup CEOs Need to Know About Navigating the 50-Employee Inflection Point.”
Scaling past 50 employees is a milestone worth celebrating—and one of the most disorienting transitions a founder will face. Obviously, there are new legal requirements and compliance obligations that come with the territory. But the harder challenge lies in what happens to your culture once you can no longer hire every person yourself—and when maintaining that culture depends on leaders you’ve developed, not just decisions you’ve made.
Join us on Tuesday, April 14, at 12 pm PT / 3 pm ET for a practical session where Justin Stevens, Overlap Founder & CEO, will interview Trisha Earls, Overlap’s fractional CHRO and a practicing employment attorney with deep experience leading and advising talent strategies for organizations large and small, and Josh DeFonzo, CEO of Mendaera and an accomplished healthcare robotics executive with deep experience growing organizations of all sizes.
Trisha, Josh, and Justin will cover:
Why 50 employees is a genuine inflection point—culturally, operationally, and legally—and what changes fast
How to preserve what makes your company great as hiring decisions move further from the founder
How to develop leaders who can carry your culture forward—including what it takes to lead a workforce where Gen-Z expectations are shaping the rules
The compliance and policy foundations you need to have in place, and how to build them without breaking your culture in the process
What founders can do now, before they hit these thresholds, to get ahead of the growing pains
The majority of the session will be reserved for live Q&A.
Tuesday, April 14, 2026
12 pm PT / 3 pm ET
RSVP via Luma by April 7th.
We look forward to seeing you there! Justin, Trisha, and Team Overlap
ABOUT OVERLAP:
Overlap is a Frontier Tech venture firm founded by Justin Stevens, who was previously a Senior Partner at Apollo Management (where he spent nearly two decades). The firm brings a Wall Street financing mindset to this capital-intensive ecosystem, as detailed in this exclusive article from The Wall Street Journal.
Overlap has three business lines: (1) Our Investing business invests in Seed, A, and B rounds of Frontier Tech companies. Overlap does not lead rounds, but prefers to follow great VCs and brings an unparalleled level of expertise and relationships to help our PortCos secure the optimal financing to scale growth; (2) Our Capital Solutions business helps Frontier Tech companies raise debt capital through external providers, leveraging 30+ years of capital markets expertise and a network of over 250 lender relationships; and (3) Our Government Solutions business helps frontier tech companies determine the best non-dilutive government funding for their needs, and connects them with the right service providers to pursue those funding opportunities.