Account Executive - Chicago Office

WeTravel•Chicago, IL

5d•$65,000 - $65,000•Hybrid

About The Position

WeTravel is seeking a passionate and driven Account Executive to join our growing sales team in Chicago. This role is ideal for individuals who are enthusiastic about fintech, possess a natural curiosity, and excel at building relationships. As an Account Executive, you will own the full sales cycle, from prospecting and discovery calls to product demos and closing deals. You will focus on understanding client needs and demonstrating how WeTravel's solutions can help their businesses thrive. We value proactive, solution-oriented individuals who can move fast, collaborate, and celebrate wins. This position requires a hybrid work model, with 4 days per week in our Chicago office and 1 remote workday.

Requirements

Fluent in English.
Natural confidence on the phone and enjoyment of outbound sales activity.
Clear communication and presentation skills with energy and purpose.
Passion for 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

Fluency in other languages.
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 with uncapped commission.
Base Fulltime Salary: $65,000 (USD)
On Target Earnings: Year 1 OTE = $115,000, Year 2 OTE: $150,000
100% employer-covered HDHP medical, DHMO dental, and standard vision coverages or a choice of plans.
Generous "Time to Recharge" policy (unlimited paid time off).
Opportunity to visit HQ in Amsterdam for 2-4 weeks annually.
Work remotely for a maximum of 4 weeks per calendar year.
Extensive paid family leave.
Three paid volunteer days per year.
2-week cross-functional onboarding program.
Join an international, travel-loving team.
Employer-sponsored 401(k) plan with a 2% company match.