Account Executive - Chicago Office

Hi! 👋 I’m Kaitlin, Director of Inside Sales at WeTravel.

My mission is to build a strong, talented, and mission-driven sales team that is passionate about helping group and multi-day travel businesses thrive. We’re growing fast, and I’m looking for someone who’s ready to roll up their sleeves, connect with amazing clients, and help us scale the US market even further.

If you’re someone who loves fintech, has a natural curiosity, and thrives on building relationships—you’ll fit right in. Together, we’re building more than just a team—we’re building the future of travel tech.

This role is primarily in-person (4 days per week) at our Chicago office in the Loop (20 N Wacker Dr), with one remote workday each week.

HOW WE WORK

At WeTravel, our Sales teams combine autonomy with strong collaboration. As an Account Executive, you'll own the full sales cycle — from initial outreach and discovery calls to product demos, closing deals, and smoothly handing off to onboarding.

We focus on understanding each client's unique needs and aligning our solutions to match. You won’t just sell — you’ll guide and support potential customers in discovering how WeTravel (products) can truly help their business thrive.

We value proactive, solution-oriented individuals who aren’t afraid to take initiative, spot opportunities, and act on them. Our teams move fast, support one another, and celebrate wins together — big and small. You’ll spend most of your time doing what actually moves the needle: prospecting, demoing, and following up with qualified leads.

WHY YOU SHOULD OR SHOULDN’T APPLY

You should apply if you:

- Are fluent in English (bonus points for other languages—list them on your resume!).

- Have a natural confidence on the phone and enjoy outbound sales activity.

- Communicate clearly and present with energy and purpose.

- Love helping small business owners scale their operations.

- Have some experience in inside sales via emails and calls.

- Thrive in ...