Alyssa Rapp is a woman whose name could be associated with a number of hashtag-worthy phrases: girl boss, biz author, woman-led, wife, mom. She’s the author of Leadership & Life Hacks, and currently CEO of Healthwell Acquisition Corporation I. Rapp is someone who seemingly embodies the 80’s feminist ideal of a woman who has it ‘all’: a career, a marriage, and some kids.
She began by founding Bottlenotes in 2005 with Kim Donaldson, a site originally conceived as a “Netflix-for-wine idea.” But due to regulatory shifts impacting the sale of wine, Bottlenotes was soon forced to transition to a media company. After a ten-year run with Bottlenotes, Rapp decided she didn’t want to be known as “the wine girl” forever.
“I loved what I learned about technology development after a decade-plus in Silicon Valley,” Rapp explained in a recent interview. “But I also liked the idea of leveraging that and applying it to other industries, not just wine.”
She dabbled in some advisory work before stepping in as turnaround CEO of the healthcare company Surgical Solutions in January 2018. Rapp’s passion for talent development helped her find success in an industry with which she had no prior experience.
“I came in with no healthcare experience, but a lot of experience running my own company,” she explains. “My greatest superpower was bringing in young green talent and giving them a tremendous amount of responsibility, coaching and watching them rise to the occasion and the roles.”
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Developing organizational talent quickly became a key aspect of Rapp’s turnaround strategy for Surgical Solutions. In addition to establishing programs in leadership and HR, Rapp personally identified qualified talent to foster and develop.
“I put on scrubs and I walked the halls of the hospitals,” she said. “I looked at which team members looked me in the eye. And I looked at who interacted with the customers the best. And I got a sense for the depth of the organization by doing that.”
She also led Zoom seminars, an hour and a half each week, for six weeks. Connecting top talent directly to the CEO, Rapp said, spoke volumes to employees. And it’s something she thinks organizations can be doing more of.
“It feels good when people invest in you. And for the company to invest in you,” she says. “It takes time. It takes effort. And it doesn’t just happen. These people don’t just come down the chimney. You have to invest in getting to know them and understanding them. And the more career ladders we create, the more people rise in the organization, the more they pull others up with them. It becomes a positive virtuous cycle.”
C-level leaders may balk at this level of involvement in talent development down the ranks. But in Rapp’s experience, “there’s no substitute for shoe leather.”
“I just don’t believe you can skate on top of an organization and be as effective as you need to be. It’s being on top of a business versus in a business. And you can’t do the work of running a company, at any level, without being in the business. You can’t afford to not roll up your sleeves at least to your elbows.”
Rapp’s advice to others who want to push themselves further in their careers while still having it all? Have it all, just not all at once.
“If I woke up every day and try to be the perfect wife, the perfect mother, the perfect CEO, the perfect lecturer, the perfect board member, best friend, mentor, daughter, sister—it’s just overwhelming,” she says. “Pick a couple of stakeholders each day and then give it all you’ve got. Whatever roles you’re playing that day, be present, do the best. You cannot try to be a little bit of everything to everyone in any given day.”
It’s also important, she stresses, to pursue opportunities that will truly foster growth.
“If your dreams don’t scare you, they’re not big enough,” she says. “If it doesn’t feel scary, I don’t feel it’s enough of a growth stretch.”
And leaders and managers should be doing their part to provide those opportunities, too.
“Give people jobs, not just titles, a full shoe size bigger than they’re ready for. And say, ‘I think you can get it done. I believe in you. And what do I need to do to set you up for success?’ That’s what people have done for me.”