Jenn Crenshaw: Leading People Strategy for High-Growth Startups

Sixteen-year-old Jenn Crenshaw was waiting tables at a steakhouse. It was her first job, and she watched on as her older and more experienced colleagues would fret and fuss when money wasn’t coming in how they had wished. The scene was a lasting lesson for Crenshaw in culture building: Never count your tips until the shift ends.

“I watched their attitude be determined by how their cash was tracking for the night,” Crenshaw, now the chief people officer at home-health provider Prospero Health, told Oz Rashid, the founder and CEO of MSH, on the “Hire Learning” podcast.

“I intuitively knew very early that if you have a bad attitude—and if you judge the next table by how the last table treated you—you’re just going to spiral,” Crenshaw added. “You’re not going to make good tips for the rest of the night because now you’re in a bad place.”

Finding employees who could understand that in the service industry was crucial to building a strong workforce, said Crenshaw, who began her human resources career in home health and hospice care. She has also worked for corporate giants such as Anthem Inc. (now Elevance Health Inc.), Burger King Corp. and Domino’s Pizza Inc.

Healthcare, like waiting tables, is “one interaction at a time,” she said.

Prospero Health offers home-based care for people with chronic conditions in their final years. As a patient-driven alternative to traditional health care settings, physicians and nurses make 60 to 90-minute house calls, eschewing the often rigid, process-oriented nature of clinics and hospitals.

“We need to rethink how healthcare is delivered,” Crenshaw said.

Since Boston-based Prospero Health was founded just prior to the Covid-19 pandemic, Crenshaw has helped guide the company’s growth from zero to more than a thousand employees in 30-months’ time.

So how does one go about identifying dozens of new workers nationwide every month, while also building a strong company culture of patient-focused care?

“Confidence, humility and work ethic,” said Crenshaw, detailing the crucial blend of traits she looks for when hiring.

“I ask a lot of questions around when you’ve encountered barriers and how did you work through those barriers?” Crenshaw told Oz. “How did you get around them? Did you break through them? Climb over them? Go under them?”