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One Woman's Purpose-Led Journey to Becoming a CEO

One Woman’s Purpose-Led Journey to Becoming a CEO

Guest: Jennifer Gressman, the CEO of Site Impact, a company that specializes in multichannel direct marketing services. Their clients range from Fortune 500 corporations to locally owned and operated small businesses.

Overview: No CEO is ever just handed the top job at a BIG business. Founders put all of their time, effort, and resources on the line. Successful hired guns spend years earning their reputations as fixers. And ambitious leaders who pursue a path to promotion have to set clear targets that build win-by-win towards that dream job. 

On today’s show, Jennifer Gressman talks about how she purposefully navigated her transition from Vice President of Operations to become Site Impact’s first female CEO.

Jennifer Gressman on setting her sights on becoming a CEO:
“I had my first performance review and I actually took that as an opportunity to be really methodical about what I wanted. I was really tenacious in my plan, what I wanted, and the goals that I was setting forth for myself. And more importantly, what I was asking for when I hit those goals and what success looked like for me.

I spoke with the CEO and president of the company, and I said, ’18 months from now. I want my seat.’ I gave myself some really, really lofty goals. I absolutely was accountable to ownership of the organization. I had the ownership coming to me and saying, ‘This is what you said you were going to do. We didn’t tell you that you had to do this. This is what you said you were going to do. Where are you in relation to that?’ It very much kept me on course. I was not going to waste this opportunity. I was not going to squander it by any stretch. It was being accountable. Being accountable to myself, and being accountable to the organization.”

Jennifer Gressman on managing the transition from VP to CEO:
“It took a fair amount of compartmentalizing things. I went from having people who were my coworkers and colleagues to now being my direct reports. I had people who were now my indirect reports who, the day prior, I’m sitting side by side with and we’re peers. Really taking a step back and understanding that switch was big for me. I’ve learned a ton about trust and delegation over the course of the last two years. Hiring really well and trusting the people that I hire to know that they can make the same decisions that I would’ve made. Setting the intention for what the end goal is rather than doing it myself. I often have to remind myself to sit on my hands because I’m no longer the one who has to do it. I have to guide and mentor and coach on how something should be done. I think a lot of it really has been mental and a lot of it has been just taking a step back and also saying, ‘What did I appreciate in a leader? What did I appreciate in a coach or a mentor?’ So I think it’s setting intentions, it’s teaching, it’s coaching.”

Jennifer Gressman on what it means to be her company’s first female CEO:
“At the time, it was an all-male executive team, all-male c-suite. You’d like to think that there is no difference. It’s 2022, it shouldn’t feel that way, it should just be, I got promoted. But there was a difference. It felt like a different accomplishment. I’d like to be a mentor to the women who are within our organization, within my personal and professional network, to say, ‘If you want it, go for it. If you want it, go and get it.’ There’s nothing that stops you from getting that except you. I’m not sure that a male counterpart would have that same kind of thought process or aha moment, but I do think that as women, we do have to be a little bit more intentional. We do have to be a little bit more, ‘I’m going to go for it and I’m going to get it.’ And I can only hope that what I’ve done in my journey can be inspiring to someone else. If you want something, the only person who’s going to stop you from getting that is you.”


Jennifer Gressman on LinkedIn

4 Women CEOs on What It Takes to Succeed Our partners and coaches — Asha Saxena, Ramona Cappello, Cynthia Cleveland, and Jacquie Hart — discuss their experiences as CEOs, how they approach coaching, and their advice for fellow women CEOs working to Make BIG Happen.

4 Keys to Kelly Wade’s Rise From Stacking Levi’s to Trailblazing CEO CEO Coaching International’s Kelly Wade on the accumulation of work and life experience that helped her grow into a successful CEO. 

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About CEO Coaching International

CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 1,000 CEOs and entrepreneurs in more than 60 countries and 45 industries. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have made BIG happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $10 billion, and many are founders that have led their companies through successful eight, nine, and ten-figure exits. Companies working with CEO Coaching International for two years or more have experienced an average EBITDA CAGR of 67.8% during their time as a client, nearly four times the U.S. average and a revenue CAGR of 25.5%, more than twice the U.S. average.

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