Account Executive - Chicago Office
WeTravel is a growing company focused on helping group and multi-day travel businesses thrive. The Account Executive will own the full sales cycle, from outreach to closing deals, while building relationships with clients and ensuring their unique needs are met.
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
Skills
- Are fluent in English
- 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
- Don't enjoy high-volume outreach or cold calling
- Prefer reactive roles with minimal client interaction
- Are not self-driven and need lots of guidance
- Lack experience managing the full sales cycle
- Bonus points for other languages—list them on your resume!
- Bonus: Have some worked in B2B sales, especially selling to SMBs
- Bonus: Have knowledge of HubSpot CRM or similar tools
- Bonus: Have experience or a strong network in the travel industry—that's a big plus!
Benefits
- 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.
- 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.
Company Overview