How to Leverage Entrepreneurship as a Strength When Pivoting to the C-Suite

After running your own business, you see your next career move as taking you back to a leadership role at an established organization. You know the transferrable skills and experience you’ve gained as an entrepreneur will make you an asset to any company, and you’re confident in your ability to convey that value in interviews. But what about before you’ve reached the interview stage? Namely, as an entrepreneur going after more traditional, senior-level roles, how do you sell yourself on a resume?

Entrepreneurial experience, especially for hands-on business owners, can feel incredibly tricky to distill into a tidy, two-page resume. Additionally, there are some hiring managers who may see “founder” or “owner” on a resume as a liability — e.g. “Is this person too independent to fit within a traditional corporate structure?” — rather than as the selling point it is. And when you’re competing with candidates whose job history more conventionally ladders up into the role, that’s another challenge to tackle, as well.

These are obstacles that increasing numbers of people may face as they navigate career pathing during and after the pandemic. While there are many reasons to pivot career paths after gaining experience as an entrepreneur, the impact COVID-19 has had on small businesses is, for a lot of folks, a deciding factor.

If you’re among those whose business folded, because of the pandemic or for other reasons, that doesn’t mean you can’t still represent your experience in the most successful light possible. The key is in knowing how to strategically package that experience and leverage your role as a leader in a way that catches the attention of executive recruiters. 

Below, we talked to career coaches and other experts about the resume strategies that entrepreneurial executives can employ. Here’s what they advised. 

I’m applying for a senior-level role. How should I include entrepreneurship on my resume?

1. Get specific.

Career consultant Dawn Boyer advised avoiding generic descriptors like “founder” and instead getting as specific as possible. 

“I advise my resume clients who may have had a business as an entrepreneur to write their experience as if they ‘didn’t own the company’ so that it comes across with specific accomplishments other than ‘ran the company,’” Boyer said. “For instance, what do CEOs of any business do? They develop strategic goals, put plans into place to reach those goals, conduct business development, perform HR tasks, supervise and manage staff, and are in charge ultimately for the accounting, taxes, invoicing and bill paying.” 

The trick is in zeroing in on the part, or parts, of your experience that most directly relate to the role you’re after and curating your resume around those parts. As for your title, as the owner of your business, there’s flexibility (within reason) around how exactly you choose to present yourself. Knowing that recruiters are on the lookout for more specific job titles than “founder” or “CEO,” it may be worth including a title that’s in line with the new role you’re after, so long as it speaks honestly to your experience — for instance, “Head of Product and Founder at Company ABC.”

2. Use keywords.

As is true of resume writing at any career level, you’ll want to strategically include key buzzwords within your industry. Taking that advice a step further, Alex Keyan, CEO and Founder of goPure Beauty, recommended choosing buzzwords that specifically highlight executive-level experience.

“Make sure that you add the proper keywords and include core proficiencies that scream ‘executive,’” Keyan said. “While your strengths may include Excel and staff management proficiency, these skills don’t scream out executive. You want to highlight skills like global strategy, employee development, mergers and acquisitions, and so forth.”

3. Tell a story.

“When making a career change, it’s critical you build a narrative arc connecting your early career with your recent business as well as the role you’re seeking going forward so that the reader hooks in to your journey and ‘gets it,’” Avery Roth, an Ivy Exec career coach, said. 

One way of doing this? Including an objective at the top of your resume: “It’s a highly debated move, but one I think is critical for the career changer since it goes a long way to contextualize your career pivot,” she said.

Like Keyan, Roth also recommended including keywords in your objective, as well as peppering them throughout the resume.

“Scour the job description for the role you’re applying for or look at job descriptions for similar roles and take note not only of the hard skills requested but the adjectives, which is where transferable skills and values come into play,” she added.

4. Back it up with data.

As a former entrepreneur applying to executive roles, one of the most critical things you can do is use your resume to highlight quantifiable results, Karen Rubin, a career coach and founder of Princeton Corporate Coaching, said.

“Quantify results on your resume — for example, what was the increase in sales, production, customers or users, and efficiency?” she said. “Percentages can be a useful way to tell this story versus raw numbers, and be sure to indicate the impact of these accomplishments.”

5. Emphasize collaboration.

Given that some corporate hiring managers may mischaracterize entrepreneurs as too renegade for conventional reporting structures, you’ll want to highlight your successes in working alongside others.

“One thing you should emphasize is how you worked with your staff, partner or others in the business,” Jonathan Hill, CEO and Chairman of The Energists, explained. “There may be a stigma to overcome that you’ll be less amenable to working in a team environment now that you’ve spent some time being your own boss. Showing your ability to both lead and work with people effectively can put these fears to rest.”

When describing your (quantifiable!) impact in your work as an entrepreneur, pepper in references to the other titles who you’ve strategized and partnered with. It’ll demonstrate that you’re not an “ivory tower” leader in the C-Suite and help provide examples for the types of partnerships you’ll be able to conduct in your new role.

 

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