Why Can't the Former Entrepreneur Land a C-level Job?

Thank you for taking the time to answer questions! I’ve been an entrepreneur for 30 years and just sold my last small business. I seem to be painfully over-qualified for many jobs, or woefully short in requirements for most C-level businesses looking to hire for those positions. My skill set is best-suited for C-level positions, but I have no direct experience that they’re requiring. Any advice?

You may not be so happy about my advice after I share my thoughts on your question, but I would not be doing anyone any favors if I did not tell it like I see it.

We see this problem often, when candidates are transitioning from owning their own business and going into corporate America. There is no question that running a business involves a unique set of highly valuable soft skills, from the ability to multi- task, to not being risk adverse, and having confidence in one’s abilities. And certainly most small business owners are skilled in many different tangible skills as well, from bookkeeping and sales, to vendor management and operations. HOWEVER, just because someone has held a President or CEO title in their own company does not make them over-qualified for lower level jobs in the corporate sector.

I would suggest you make a conscious effort to forget about titles altogether, and strictly focus on skill sets when looking for a potential match. To be frank, I read and re-read your question a few times and it sounds like there is a discrepancy between your tangible skill set, and the jobs you are aiming for.

Case in point…you candidly cannot be best suited for C-level jobs but lacking in the specific experience they are requiring.

Everyone wants to be the CEO, but the fact is, you are only suited for the roles that you are qualified for.

My guess is you are hung up on the title, and that simply needs to stop in order to find fulfillment in a role that you will be hired for, and ultimately find satisfaction in.

Write down all of your skill sets that would fall under mandatory qualifications such as years of experience in XYZ, certifications, etc. Then do a search on ExecuNet for similar roles, totally disregarding titles. In all likelihood, you will be coming into a company below the C-level, but through hard work and calling upon the skills you learned and honed during your 30 years of running your own business, chances are you will be given the opportunity to advance.

I hope you take my advice to heart, and are able to let go of the title piece and instead look for a job that will match your skill set and give you room for advancement.

Over the years, we have worked with more candidates than I can count who have let their egos get in the way of finding a job. It is truly a shame when someone has a solid work history and valuable skills, but is so concerned about title that they pass up viable opportunities. Please be cognizant of that pitfall and do your best to avoid it.