Haley Crum, 36

Haley Crum was totally fine with her career track soon after college, working 100-hour weeks as a chef in Clearwater. “I was having a blast,” she says.

Crum’s dad, Frank Crum, would come by and often ask her: When are you going to come work for the family business?

Far from a restaurant, the Crum family business is FrankCrum, a business-to-business entity, with work in insurance, benefits, human resource outsourcing, payroll and staffing. A pioneer in what’s now known as a professional employer organization sector, Crum and his father founded the business in 1981 with $25,000. It has since grown to $1.6 billion in annual revenue.  

Haley Crum, in her mid-20s a decade ago, had little desire to join the company. But her father was persistent, and when her grandfather got sick, she thought, finally, the timing was right. She had one caveat: She had to start from the bottom and work her way up on the merits.

The senior Crum agreed, and Haley Crum started in basically a clerk position, four levels removed from the C-suite. “It was a big benefit,” says Haley Crum, citing the training and getting-to-know the company phase. “If I had to do it all over again, I would do it the same way.”

Crum, now with a law degree, oversees the staffing unit in addition to operations on the PEO side at FrankCrum, from compliance to business affairs. With the company growing, from some 260 employees today, for example, to seeking to hire 50 more people over the next year, Crum is particularly focused on client relations. “We have to make sure that we maintain great customer service or it even gets better as we grow,” she says.

Another focus: continuing to work well with her dad and her brother, Matt Crum, a fellow top executive at FrankCrum. She says arguments among family tend to work out sooner than later. “It’s not perfect. We have our riffs,” says Crum. “But we have learned to work together for the greater good.”