Please ensure Javascript is enabled for purposes of website accessibility

Alyssa Thomas, 34

Sarasota Sailing Squadron, manager

  • By
  • | 5:00 a.m. October 14, 2022
  • | 2 Free Articles Remaining!
  • Class of 2022
  • Share

Alyssa Thomas, 34

After a trip to Captiva in Sanibel Island six years ago, Alyssa Thomas became part of a community that changed the course of her career. 

While then living in Kansas City, Thomas visited Captiva on vacation — where she learned to sail. 

When asked about her plans to sail again, Thomas didn’t have a good answer. She was just planning to sail once or twice a year during vacations. Instead, the sailing teacher prompted Thomas to look into a local sailing club. While the thought of a sailing club in land-locked Kansas City seemed ridiculous to Thomas, she followed through.  

And she soon found a local sailing club. “We just wanted to cruise around on big boats,” she says, noting she ended up falling in love with the people in the community. 

As she became more invested, Thomas started racing more, eventually winning the Governor’s Cup in Kansas with a J22 Fleet sailboat. “It was fun and terrifying at the same time,” Thomas says. “Sailing is the most fun you’ll have at five mph.”

In 2021, Thomas turned her hobby into her career. After more than a decade as an engineer, as well as a civil structure manager for Kiewit, a construction company based in Nebraska, Thomas applied for a job with the Sarasota Sailing Squadron. Never believing they would take on an engineer, Thomas was surprised when she was hired as a manager.  

Maria West, her mentor, has been an inspiration for Thomas on how to manage a team. “She would coach you without it feeling like that,” she says. “She definitely has a good way of looking at people, seeing what makes them tick and (figuring out) the best way to help them.”

Thomas tries to replicate that in her leadership.  

“I enjoy using my team’s strengths and letting them take the ball and run with it,” she says, adding she will only make authoritative decisions if needed. 

Before Thomas, the landscaper at Sarasota Sailing Squadron was given a lot of direction on how to make the campus look, for example. But since Thomas has been there, she’s looked to the landscaper for ideas. Since then, she’s received a lot of positive feedback on how much better the squadron looks. 

“It would be silly to come in (and tell) people what to do,” she says. “It’s been great listening to their ideas.”

One theme consistent in Thomas’ career? Helping others. In engineering, for one, she notes there are few women. Sailing is more of the same. She spent time in Kansas City as a sailing instructor for the Jacomo Sailing Club hoping to make an impact. Now, a few of her former students are taking on leadership roles.  

“Everyone has an equal opportunity getting out on the water,” Thomas says. “I hope to help in a way that (students) stick with it for a long time."

Amanda Postma

City of Residence: Sarasota

Birthplace: St Louis, Missouri

Years in the area: One

Marital Status/Children: Married, no children

Alma Mater/Degree: University of Missouri - Columbia; Bachelor of Science - Civil Engineering

What community group or organization are you most involved with? Sarasota Sailing Squadron

Are you working from the company office, home office or hybrid? Company office

What's the weirdest job you've ever had? Or the weirdest task you've ever been assigned? Being asked how quickly I could fly to Poland to meet our power plant turbine vendor and convince them that I needed loads to design my foundation.

What's your top tip for being productive? Break down big projects into smaller tasks. It makes it easier to take the first step and hand off work to others. If in doubt, write it down!

If you could have a side hustle, what would it be? Be a biking Uber downtown with my new cargo bike, and Urban Arrow

What's your favorite off-hours activity? Biking to the Squadron to go sailing or kayaking

What's the most significant item on your life bucket list — and what's keeping you from completing it? Last thing on the bucket list was getting to Sarasota and being closer to sailing opportunities. I marked that complete much earlier than I thought I would!

What's your favorite podcast? "Manager Tools" - I haven't listened to it in a while, but when I became a manager I'd listen to their DISC profile podcasts during my commute and it was so helpful.

At what percentage on your phone do you start to get Low Battery Anxiety? If I'm out on the water taking pictures and tracking a sail, at about 30%. Otherwise at about 5%, since I can always communicate with my watch.

What are the top three apps used on your smartphone? I keep a close eye on the weather, so Weather Channel for basic weather, Windy for a wind forecast, and My Lightning Tracker for keeping an eye on lightning.

What books are you reading now? Sailing Smart, by Buddy Melges. On the drive down to Sarasota I re-listened to the Five Dysfunctions of a Team, by Patrick Lencioni. It's told through the perspective of a new CEO at an existing company.

What's your go-to music genre, band or act to be inspired? Drake

Who would play you in the movie of your life? Jennifer Lawrence

Where is your happy place? At the Sarasota Sailing Squadron, by A-Dock where you can look out over the bay and the city. It's beautiful.

Describe yourself in three words: Learner, Active, Tenacious

Who is your mentor for your career and why? Maria West coached me since I was a new hire at Kiewit. As a contract worker, she stepped into a difficult design and did so well we hired her a few years later! She always took the time to help me both professionally and technically.

What are the biggest lessons you have learned from your mentor? So many lessons! You can make anything a stretch assignment to grow and develop from it. Focus on the success of others, and help them find their next role. You can make it through anything if you have the right mentors and break it down into small pieces.

She always had a resource, like a book, a handout, a standard, or a detail from another project to help with whatever I faced. She taught me to be resourceful and find best practices from others.


Latest News


Special Offer: $5 for 2 Months!

Your free article limit has been reached this month.
Subscribe now for unlimited digital access to our award-winning business news.
Join thousands of executives who rely on us for insights spanning Tampa Bay to Naples.