SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 65,000 - 0 / annual
WeTravel is seeking an Account Executive to join its sales team in Chicago. You will own the full sales cycle for group and multi-day travel businesses—from prospecting and discovery calls through product demos, closing deals, and client handoff to onboarding. The role is primarily in-person (4 days per week) at the downtown Chicago office (20 N Wacker Dr, the Loop), with one remote workday per week.
You will spend most of your time on high-impact activities: prospecting and outreach to multi-day tour operators across the US, delivering engaging product demos, managing your pipeline in HubSpot, following up with qualified leads, and collaborating with onboarding and support teams to ensure smooth client transitions. You'll also share feedback from client conversations with product and marketing teams, and consistently meet and exceed outreach, demo, and sales targets.
WeTravel values proactive, solution-oriented individuals who take initiative, spot opportunities, and act on them. The sales team combines autonomy with strong collaboration, moving fast and supporting one another. You'll focus on understanding each client's unique needs and aligning WeTravel's solutions to help their business thrive—not just selling, but guiding potential customers to discover real value.
Benefits include a base salary of $65,000 USD with uncapped commission (Year 1 OTE: $115,000; Year 2 OTE: $150,000), 100% employer-covered HDHP medical, PPO dental and vision coverage, commuting allowance, unlimited paid time off, an annual 2–4 week Amsterdam program at company apartments, up to 4 weeks remote work per year, extensive paid family leave, three paid volunteer days annually, a 2-week onboarding program, and a 401(k) plan with 2% company match. The office features weekly "Lunch and Learn" sessions and is located in an exciting downtown Chicago setting.
REQUIREMENTS:
- Fluent in English (bonus: multilingual)
- Natural confidence on the phone and genuine enjoyment of outbound sales activity
- Clear communication and ability to present with energy and purpose
- Passion for helping small business owners scale operations
- Demonstrated experience in inside sales via email and phone calls
- Ability to thrive in an office environment (4 days/week on-site requirement)
- Willingness to travel up to 10% for client visits
- Full legal right to work in the US (citizenship or residency; no visa sponsorship available)
- Ability to join the Chicago office by November 2026
- Bonus: B2B sales experience, especially selling to SMBs
- Bonus: Familiarity with HubSpot CRM or similar sales tools
- Bonus: Experience or strong network in the travel industry
