Self-funded part-time search: Best concurrent W2 job?

searcher profile

January 20, 2026

by a searcher from Dartmouth College - Tuck School of Business at Dartmouth in Chicago, IL, USA

I have a narrow buy box (~50-mile radius, specific industry segment, small EBITDA range, etc.), and there isn’t enough pipeline flow to justify a full-time search. I’m considering taking a full-time job while continuing to search on the side. What kind of job makes the most sense if my plan is to continue searching part-time and eventually buy and operate within five years? (1) “Fancy-title” roles at startups or large industry-leading companies (e.g., Chief of Staff, Strategy, Corporate Development, Program Manager, etc.) (2) Functional roles at large industry-leading companies (e.g., Sales, Marketing, Finance, Operations, etc.) (3) Leadership roles at small or medium-sized businesses (e.g., General Manager, Operations, Sales, Marketing, Finance, Corporate Development, etc.) My sense is that “fancy-title” roles don’t contribute much to long-term small business ownership or operating experience—beyond providing higher compensation that could later fund equity, outsourced search support, or transaction costs. They also tend to offer less flexibility and require longer hours. I’m still exploring the practical benefits of functional roles at large companies versus leadership roles in smaller businesses. The latter seems ideal if there’s strong industry overlap with a future acquisition, but perhaps less valuable if the eventual purchase is in a different industry. For operators: Does a functional leadership role in a medium-sized business actually equip you for ownership? I’ve often heard that “nothing can prepare you for ownership,” but is that really true for a role like sales leadership at a small or medium-sized business? For lenders, investors, or advisors: How do you think about the risk of funding someone coming from a large industry-leading company (in the same or a different industry) versus someone with functional leadership experience in an unrelated small business?
0
10
212
Replies
10
commentor profile
Reply by a searcher
from Thunderbird School of Global Management in Westport, CT, USA
I agree with ^redacted‌ , the way to go is to find a role in the specific industry segment you are looking for. This will give you skills and network to operate later on.
commentor profile
Reply by a searcher
from Duke University in Chicago, IL, USA
I like the unique take from Jason above! My gut says that something closer to the day to day reality of running an SMB is most useful...more responsibility at a smaller company to understand what it takes to run daily operations. functional role at a bigger company seems less helpful...
commentor profile
+8 more replies.
Join the discussion