Account Executive - Chicago Office

WeTravel•Chicago, IL

2d•$65,000 - $65,000•Hybrid

About The Position

WeTravel is seeking a motivated Account Executive to join their sales team in Chicago. This role is focused on building relationships with group and multi-day travel businesses, helping them thrive by leveraging WeTravel's fintech solutions. The ideal candidate will be passionate about travel tech, possess natural curiosity, and excel at building relationships. This position involves owning the full sales cycle, from prospecting and discovery calls to product demos, closing deals, and collaborating with onboarding teams. WeTravel values proactive, solution-oriented individuals who can take initiative and drive results in a fast-paced, collaborative environment. The role requires a strong focus on prospecting, demoing, and following up with qualified leads to move the needle on sales targets.

Requirements

Fluent in English
Natural confidence on the phone and enjoyment of outbound sales activity.
Clear communication and presentation skills with energy and purpose.
Love helping small business owners scale their operations.
Some experience in inside sales via emails and calls.
Thrive in an office environment.
Willing to travel up to 10% for client visits.
Full legal right to work in the US (citizenship or residency).

Nice To Haves

Other languages (listed on resume)
Experience in B2B sales, especially selling to SMBs.
Knowledge of HubSpot CRM or similar tools.
Experience or a strong network in the travel industry.

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).
100% employer-covered HDHP medical, PPO dental, and standard vision coverages or a choice of plans that suit your needs.
Exciting office location in downtown Chicago, with a requirement to be on-site 4 days per week.
Weekly “Lunch and Learn”
Commuting allowance.
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.
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.
Employer-sponsored 401(k) plan with a 2% company match to support your long-term financial goals.
Join an international, travel-loving team with a passion for adventure and innovation.