Jessica Kaplin


Jessica (Jess) claims she has the best of both worlds having been born in Bozeman, Montana but now living near the beach in sunny San Diego. 

Jess first joined the young and growing Swing team in 2014 when the company had just opened the Oakland, CA office. Jess focused on team build-outs with some of our early (and among our favorites!) clients: Glint, Xamarin, Wunderland, Wizeline. She left Swing to move to San Diego (the beach called!) before we had adapted to the world of remote work. Fast forward seven years and Jess is back and a member of our growing WFH team. 

Between her time at Swing, Jessica kept her research chops strong as an Economic Research Specialist working on projects for the Department of Defense (DoD) and National Nuclear Security Administration (NNSA). She has also spent time as an AP Psychology teacher, a traveling sales woman hitting the grind at the trade show circuits and as a business coach. She is glad to be back in the world of recruiting and building relationships with candidates. 

The team is thrilled to have her (and her adorable daughter) back in the Swing family!


Jessica’s bread and butter is first sales hire, Account Executive build-outs, Director of Sales, Sales Dev Leadership, and Talent teams.

Notable Placements:

Head of Sales, Freshpaint
Head of Sales, Documate
Head of Sales Development, Syndio
Enterprise Account Executive (x5), Syndio
MM Account Executive (x2), Syndio
Enterprise Account Executive, Ketch
Enterprise Account Executive, Freshpaint
MM Account Executive, Freshpaint
MM Account Executive (x2), SimpleLegal
Director Strategic AccountsFirstup
Sales Directors (x5), FirstUp
Strategic Sales Executive (x2)Extend
MM Account Executive (x2)Extend
Enterprise Account Executive, Instabug 

If I had one motto to live by:

“Do the best you can until you know better. Then when you know better, do better.” — Maya Angelou

Fun Facts:

I was a bit of a rebel growing up, just ask 😉

My first full marathon was the San Diego Rock ‘n’ Roll marathon.