Operators Who Transitioned from Large Companies?

September 16, 2025

by a searcher from Massachusetts Institute of Technology - MIT Sloan School of Management in Boston, MA, USA

I’m hoping to connect with searchers or CEOs who successfully made the leap from leadership roles in large organizations to running smaller companies. Specifically, I’d love to learn from those who were mid-career in middle- or upper-management at Fortune 500s (or similar) and transitioned into search/CEO roles. What was the hardest part of the shift? What translated well? What didn’t? Would you do it again? If you’ve been through this transition—or know someone who has—I’d greatly value your insights. Please feel free to comment here or DM me directly. Thank you!

8 Likes

29 Replies

388 Views

Replies

Reply by a searcher
from The University of Chicago in Nashville, TN, USA

Once you go high enough in big companies, in my experience, your day is spent deep in a narrow niche, having your team prep data, dealing with the politics of big companies, and managing communication more than actually doing work. When an issue does arise, you already are an expert on that topic or have someone on staff who is. Ownership is basically the opposite, you are fighting fires that vary from HR to IT, to truck maintenance to customer service all in the same day. My roles earlier in my career working in manufacturing plants prepared me far more than my mid career roles at big companies. Feel free to reach out.

Reply by a searcher
from University of Georgia in St. Louis, MO, USA

I did this transition. Success in Corporate America is more political navigation vs value creation. It's the opposite in SMB-land. You also have to be much more of a generalist running a company because you have to know a little about tax, and HR, and billing, and... I also think I struggled with the pace of decision-making. I previously ran innovation for the Mercy health system. For me to get a major initiative done in a year, it would require Jesus himself to come down on a cloud to demand it. Even still IT would drag their feet... In my agency, I can make a decision this morning and we can have it implemented by the afternoon. That takes time to get used to. I'm glad to get more specific if you want to shoot me a DM or email me (scott @ jairusmarketing.com)

+27 more replies.

Join the discussion