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40 Under 40 Class of 2023

Chief Operations Officer, the Jamrog Group: Age 38

Jessica HollowayGrowing up, Jessica Holloway wasn’t exactly sure what she wanted to do for a living.

While earning a degree in finance at the Isenberg School of Management at UMass Amherst, she came to understand two things — she liked helping people, and she was good at math. And she desired a career that would marry those two attributes.

So, following an eye-opening internship at Northwestern Mutual that became a learning experience on many levels, she put herself on a path to a career in financial services … and her current role as chief operations officer for the Holyoke-based Jamrog Group. (Amy Jamrog is the founder and CEO of the company, and also Holloway’s mentor.)

While the business card says COO, Holloway says she’s primarily a financial planner, a role in which she can use her math skills (a little) and that ‘helping people’ trait to a much larger degree.

“What I really love about it is helping clients start to view money as a tool instead of a stressor,” she explained. “A lot of the work I do is helping clients get really tuned into what matters to them — who and what — and then aligning the money accordingly.”

As COO, she has a broad role, one that includes everything from building systems, processes, and workflows (work that has helped the company triple its revenue) to coaching and development of employees, to integrating health and wellness into the group’s culture, leading outside ‘walks and talks’ with staff, and even hosting Zoom Peloton rides with team members.

“As financial planners, we spend a lot of time at our computers, crunching numbers. So we started to integrate a lot more movement, just to encourage both ourselves but also our team members to get up and move during the day,” said Holloway, who, in her spare time, is a board member for the nonprofit Girls on the Run.

Jamrog, a 40 Under Forty honoree herself (in the inaugural class of 2007), nominated Holloway for the same honor.

“As my business partner over the past nine years, Jessica has shown extraordinary growth in her business acumen, leadership among our team, and financial planning expertise,” she said in that nomination. “She has done all this while raising three young boys, volunteering for her kids’ schools, volunteering for board work, and hosting an exchange student from Spain. She is generous, has unbelievable capacity to manage her home, work, and community, and is an overall rock star of a human being.”


—George O’Brien