CEO Spotlight

How this CEO and Best-Selling Author Found Freedom, Success, and Empowers Others to Do the Same

Sure, running a business can be overwhelming – the demands are often as high as the margins are thin, and all the little tasks that go into the daily grind of entrepreneurship are anything but glamorous. But for Jessica Dennehy, there is nothing she would rather be doing.

The consultant, CEO and best-selling author has built an empire thanks to her business acumen and life experiences – two things that, she said, continue to push her forward to this day.

“I always say that your energy is the momentum that will take you forward into the next chapter, whether that’s in business or in your personal life, or with your family or other relationships,” she said. “That’s why I started Pivot & Slay – I wanted to help clients find the energy within themselves to build their career and craft their ideal lives on their own terms.”

From Side Hustle to Full-Time Visionary

Dennehy wasn’t always the self-made CEO you see before you today. In fact, her first career was as a Wall Street regulator – a glamorous job she had coveted since her early days in law school. When she decided to launch a barbershop on the side in 2012, it was a move toward diversifying her streams of income, not so much a business she wanted to focus on full-time.

But the business quickly gained traction and she realized the freedom of owning her own business was more appealing than working for someone else’s bottom line. As she stepped into the full-time role of founder and CEO, she put her legal and regulatory experience to good use, expanding her business threefold and opening an overseas location.

“That cliché ‘everything happens for a reason’ is no joke,” she said. “I don’t think I would’ve felt motivated to pursue all those business opportunities if I hadn’t had the legal and regulatory experience I had, and it definitely made me feel more equipped to pivot from working on Wall Street to working for myself.”

Dennehy would soon have to pivot again; in 2020, her barbershops closed due to the COVID-19 pandemic and Dennehy focused her attention on doing what she could to help those in her community. She used her small business contacts to send over 100,000 surgical masks to local businesses, first responders and healthcare workers. She also put on her business consulting hat and began helping other small business owners learn how to approach closures, restrictions, reopening protocols and more.

“It’s all about using adversity as a stepping stone for growth,” she said. “I realized that I have experience and perspective that some small business owners needed, and I knew I could help them survive such an unprecedented time in history. And from that, I realized that working with other business owners was a passion of mine, and Pivot & Slay was born.”

“You Need Someone In Your Corner”

What sets Pivot & Slay apart, Dennehy said, is her ability to “pivot” her consulting to the need of each individual client. No two journeys are going to be the same, she said, and her priority is making sure she is empowering each and every entrepreneur who comes through her door to build their best business.

“From resources to advice and everything between, every client gets personalized attention and actionable tasks that are right for them,” she said. “Business owners and entrepreneurs don’t have the time to listen to cookie-cutter advice, and they shouldn’t have to!”

While Dennehy tells her clients information like it is, she said she’s also focused on taking on a compassionate role in the process of business founding and ownership. It’s often extremely financially and emotionally taxing to get a new venture off the ground, and Pivot & Slay exists to provide that support, she said.

“I’m here for everyone, from digital media experts and authors to CEOs and more, because everyone has the same core emotional needs for support, encouragement, and advice,” she said. “Sometimes you need someone in your corner, and I’m proud to be that person.”

Determination, innovation, collaboration, and creativity – Dennehy knows those subconscious skills many people have inside them are the keys to their success. While most consultants focus on the nuts and bolts of business ownership, Dennehy concentrates on what her clients can bring to the table all on their own.

“Everyone has their own natural skillsets, and everyone is good at things that will empower them to find more success than they ever imagined,” she said. “For me, it’s leadership and consulting. When I harnessed that, the sky became the limit. Now I want to help other people find that same level of freedom because it’s absolutely worth it to put in the work. I’m living proof of that.”

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Anna Papadopoulos
Anna Papadopoulos is a senior money, wealth, and asset management reporter at CEOWORLD magazine, covering consumer issues, investing and financial communities + author of the CEOWORLD magazine newsletter, writing about money with an enthusiasm unknown to mankind. You can follow CEOWORLD magazine on Twitter, Facebook, Instagram, or connect on LinkedIn for musings on money, wealth, asset management, millionaires, and billionaires. Email her at