Account Executive - Chicago Office
WeTravel· Commercial
Chicago Office$65k+Full-timePosted 3w ago
About the role
Account Executive role based in Chicago, responsible for full sales cycle with multi-day tour operators across the U.S., primarily in-person (4 days/week) with one remote day. Focus on prospecting, demos, and pipeline management to drive growth for WeTravel in the US market.
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.
Qualifications
- Fluent in English; additional languages are a plus
- Natural confidence on the phone and enjoyment of outbound sales activities
- Clear communication with energy and purpose
- Love helping small business owners scale operations
- Experience in inside sales via emails and calls
- Thrives in an office environment
- Willingness to travel up to 10% for client visits
- Bonus: B2B sales experience, especially with SMBs
- Bonus: Knowledge of HubSpot CRM or similar tools
- Bonus: Experience or strong network in travel industry
Skills
Required:Sales lifecycle managementDemos and product demonstrations
Nice to have:HubSpot CRM
Benefits
- Base full-time salary $65,000 USD
- Uncapped commission (Year 1 OTE $115,000; Year 2 OTE $150,000)
- Health: 100% employer-covered HDHP medical, PPO dental, and vision or equivalent plans
- On-site work requirement: 4 days/week in Chicago office
- Weekly “Lunch and Learn”
- Commuting allowance
- Unlimited paid time off (Time to Recharge)
- Amsterdam Program: 2-4 weeks/year in Amsterdam (HQ) staying in WeTravel apartments
- Remote work up to 4 weeks/year
- Extensive paid family leave
- Three paid volunteer days per year
- 2-week cross-functional onboarding
- Employer-sponsored 401(k) with 2% company match
- Access to discounted personal travel on Booking Marketplace
Last updated Oct 14, 2026. Interested? Apply on the company site.
About WeTravel
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