Account Executive - Chicago Office

WeTravel•Chicago, IL

39d•$65,000 - $150,000•Hybrid

About The Position

Hi! 👋 I’m Luke, from LA in the US 🇺🇸, Sales Director for the US, LATAM, and APAC markets here at WeTravel. I’ve been with WeTravel since the early days and have had the chance to see the company grow through many exciting phases. It’s been an incredible journey — and I’m more excited than ever about what’s ahead. My mission is to build a strong, talented, and mission-driven sales team that’s 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 new Chicago office in the Loop (20 N Wacker Dr), with one remote workday each week. How We Work Our team thrives on energy, ownership, and results. As an Account Executive, you’ll manage the entire sales cycle: from initial outreach, to discovery calls and product demos, all the way through closing and handoff to onboarding. We take a consultative approach, focused on understanding each client’s unique challenges. Our clients are small-to-medium-sized multi-day tour operators, often run by passionate entrepreneurs who wear many hats. That means you'll have a real impact—helping them grow and simplify their operations through our all-in-one platform. We use tools like HubSpot to keep things organized and scalable, and we support each other through collaboration, feedback, and shared wins.

Requirements

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 an office environment.
Are willing to travel up to 10% for client visits.

Nice To Haves

Have some worked in B2B sales, especially selling to SMBs.
Have knowledge of HubSpot CRM or similar tools.
Have experience or a strong network in the travel industry—that’s a big plus!

Responsibilities

Reaching out to and building relationships with multi-day tour operators across the U.S.
Delivering engaging demos that showcase the value of WeTravel’s platform.
Managing your pipeline and tracking activity in HubSpot.
Following up with prospects and guiding them through to close.
Collaborating with onboarding and support teams to ensure a seamless client experience.
Sharing feedback with product and marketing based on client conversations.
Consistently meeting and exceeding outreach, demo, and sales targets.

Benefits

Attractive compensation - uncapped commission. Base Fulltime Salary is $65,000 (USD) (On Target Earnings: Year 1 OTE = $115,000, Year 2 OTE: $150,000).
Your health matters – US team members get 100% employer-covered HDHP medical, DHMO dental, and standard vision coverages or a choice of plans that suit your needs.
Exciting new office location in downtown Chicago, with a requirement to be on-site 4 days per week.
Generous "Time to Recharge" policy — enjoy unlimited paid time off to rest, recharge, and show up as your best self.
Amsterdam Program – visit us in Amsterdam (HQ) for 2-4 weeks every year, staying in one of our WeTravel apartments.
Work remotely for a maximum of 4 weeks per calendar year.
Annual team off-site (often somewhere sunny 🌊).
Extensive paid family leave.
Three paid volunteer days per year — take time to give back to causes you care about, on us.
2-week cross-functional onboarding program.
Join an international, travel-loving team with a passion for adventure and innovation.