How Can Former Entrepreneurs Get Back to a More Traditional Career Path?

I’ve been through a few hiring/recruiter processes, as I continue to run an independent strategic marketing and communications consultancy with an ever-growing client list. Recently, in mid-career, I earned an executive business master’s degree so that I might transition from sole proprietor consultant to senior staff of a company or professional organization known for innovation and sustainability.

I have previously held staff positions reporting to and shaping communications of nonprofit chief executives. How might I best make the case that I’m a self-aware entrepreneur ready to work on a bigger team who will be an asset at the C-level of an innovative company?

Statistics indicate that people 50+ are being funneled into the gig economy even after they’ve up-skilled for a career pivot. What further advice do you have on Why Can’t the Former Entrepreneur Land a C-level Job? Some former entrepreneurs want to progress on a more traditional career ladder.

Ann-Z-newWell, first of all congratulations on obtaining your master’s degree; that is just wonderful! The first step should be to reach out to current clients, and inquire if they have any needs for someone of your caliber on a full-time basis.

I would also follow the same tried and true steps that we always encourage anyone when attempting to look for a new role to follow: Invest the time in crafting a compelling resume and cover sheet. With your marketing background, that should be a snap. Consider sending out individual or at the very least a blind mass email so it appears to be individualized to all of your current clients, expressing your interest in gaining a C-level role and asking for their recommendations and suggestions. Create Google alerts for the types of roles you want to pursue. Set up alerts on the careers page of all of your targeted companies. Find all members of the executive teams of your targeted companies on social media, primarily LinkedIn, and start to engage with them. Like, comment and share their posts, and offer interesting insights in your comments with them, and also on your own page. Be innovative, and figure out a way to highlight some of your work on your various social media pages, again focusing on LinkedIn. Ask your clients to take a few moments to write you a recommendation to be posted on LinkedIn as well as on your website, if you have one. Consider writing articles that can be posted on LinkedIn and also submit to any and all publications that you can think of that accept submittals of your type of work.

The higher your profile when someone searches for experts in your line of work, the better. Reach out to recruiters who place CMO and high-level communication executives, and ask if you can send them your resume. You may also want to consider contracting with an employment agency, which differs from an executive recruiting firm because their primary focus is finding jobs for people as opposed to finding people for jobs. And it should be noted that as recruiters, the hiring managers pay our fees. Employment agencies charge the candidate. While you continue to do good work and build a solid reputation, you are bound to come across a company that has a need for someone of your caliber for a C-level role. Good luck!


Ask Ann,

Have a question you’d like a recruiter to answer? Write to me at AskAnn@execunet.com



Ann Zaslow-Rethaber

Ann Zaslow-Rethaber

A recruiter since 1996, Ann Zaslow-Rethaber is the president of International Search Consultants, a global executive recruiting firm launched in 1999.

ISC has become one of the country’s most reputable search firms, earning more recommendations on Linked In than any other 3rd party recruiting agency in the entire country. With a team of 15 talented recruiters, utilizing the very best high- tech tools available, ISC can produce highly qualified candidates for companies with hi-volume recruiting needs.

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