By Michelle Solomon * Lead photo by Eduardo Schneider

Jennifer Gressman might have been able to tell you what her typical day at the office was like a few months ago, when she was vice president of operations at digital marketing company Site Impact. Not that there ever was a typical day for the past seven years since she started. But since being named president of the once-small, family-grown company, headquartered in Coconut Creek, she has found life at the top has a different rhythm.

“In this business, I learned early that you have to be a few steps ahead of everyone,” she says. “I wanted to understand it, I wanted to learn it, and I wanted to be really good at it.

“This was the promotion of a lifetime that I’ve been waiting for.”

Her promotion was also a defining moment for the company. When it was announced on March 1, it was the first time in 10 years a woman had taken the reins in a C-level role at Site Impact, which personalizes email marketing campaigns and digital advertising across new media platforms for all types of businesses. Just two years before, the company purchased a building in Coconut Creek for almost $2.5 million and then invested $600,000 in upgrades of the 11,616-square-foot offices, located on Lyons Road.

Describing herself as a “follow it through to the end” type, she’s overseeing Site Impact’s upward track here and at its offices in Orlando and Overland Park, Kansas, where all together she oversees about 100 employees. So, how’s the new typical day shaping up? Here, Gressman shares glimpses of her CEO mindset and career path.

Morning routine: She starts every morning at 5:30 a.m. with an Audible book on the way to her early morning workout at the gym. Mondays begin with a “leadership listen” to get her week started. “What I have on my calendar for the day dictates what I’m listening to.” Good to Great: Why Some Companies Make the Leap … and Others Don’t by Jim Collins is on her current Monday playlist. One of her recent favorites was Powerful: Building a Culture of Freedom and Responsibility by Netflix’s former chief talent officer, Patty McCord.

Finding her path: Gressman grew up on the south shore of Long Island in Bellmore, New York, and graduated from John F. Kennedy High School, where a class assignment got her interested in documentary film. Eventually, she attended the University of Florida as a telecommunications production major.

When she graduated, she moved to New York City to get into the film industry, but the 22-year-old realized “how difficult it was going to be.” She ended up taking a job at an advertising agency assisting media buyers. But when she took a job at an internet marketing company, she was hooked. “It was a straight lateral move, but I was 24, and it was time to try something different, to see what’s going on,” she says.

“There wasn’t even mobile advertising then. I had a flip phone. It wasn’t a conscious decision for me to arrive at where I am today, but I’m humbled and thrilled that things worked out the way they have.”

Paradigm shift: Lifestyle changes were happening in Gressman’s world even before the promotion. Gearing up for a milestone 40th birthday at the end of March, Gressman decided to shake things up.

“I wasn’t unhappy; I just want to do some things differently,” she says. “So last summer I quit smoking, I joined a gym, got a personal trainer, and bought a house in Coconut Creek. To be honest, I hate exercise, but I found a trainer I like so I’m sticking to it. I’m going to turn the extra bedroom into a gym as a birthday present instead of buying myself jewelry or a new handbag.”

Current obsession: “I am mildly obsessed with my dog, Lola,” she says, The 9-year-old Yorkie was a rescue. “I know it’s clichéd when people say that you may have rescued them, but they rescued you. But in my case, it’s true. This dog is my everything.”

On her leadership style: Gressman had a revelation when watching a TED Talk about leadership styles with her office’s book club, which also discusses videos. “[The speaker, Adam Grant,] started to describe a personality, and about 25% to 30% of the people in the room looked at me and were smirking when the type was ‘disagreeable giver.’ No one wants to hear that they are disagreeable. But the definition of this style was defined as the person who gives critical feedback that no one wants to hear, but everyone needs to hear. Someone looked at me and said, ‘That’s you. You are tough, but fair.’ Said that way, I was OK with being the disagreeable giver.”

Taking charge: Only 5% of S&P 500 CEOs are women, according to Catalyst, a company that focuses on women-in-the-workplace research. “I’ve been doing this for over 15 years and I’ve worked for many companies, from very small startups to larger mature organizations, and I can think of only one that has any female leadership,” Gressman says. “I think we are still missing some of that female perspective at that leadership level.”

She says her appointment marks “a change of guard” for Site Impact. “For us, times are changing,” she says. “It’s like we’re saying, ‘Whoever has the good ideas, whoever can lead the ship, that’s who leads the ship, regardless of gender.’ ”

Guilty pleasures: “Red wine, good bourbon and bad reality television,” she says. ♦