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Chicago, Illinois, United States
Onsite
Available
Hi! 👋 I’m Kaitlin, Director of Inside Sales at WeTravel.
My mission is to build a strong, talented, and mission-driven sales team that is passionate about helping group and multi-day travel businesses thrive. We’re growing fast, and I’m looking for someone who’s ready to roll up their sleeves, connect with amazing clients, and help us scale the US market even further.
If you’re someone who loves fintech, has a natural curiosity, and thrives on building relationships—you’ll fit right in. Together, we’re building more than just a team—we’re building the future of travel tech.
This role is primarily in-person (4 days per week) at our Chicago office in the Loop (20 N Wacker Dr), with one remote workday each week.
At WeTravel, our Sales teams combine autonomy with strong collaboration. As an Account Executive, you'll own the full sales cycle — from initial outreach and discovery calls to product demos, closing deals, and smoothly handing off to onboarding.
We focus on understanding each client's unique needs and aligning our solutions to match. You won’t just sell — you’ll guide and support potential customers in discovering how WeTravel (products) can truly help their business thrive.
We value proactive, solution-oriented individuals who aren’t afraid to take initiative, spot opportunities, and act on them. Our teams move fast, support one another, and celebrate wins together — big and small. You’ll spend most of your time doing what actually moves the needle: prospecting, demoing, and following up with qualified leads.
You should apply if you:
Are fluent in English (bonus points for other languages—list them on your resume!).
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.
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!
You might not be the right fit if you:
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.
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.
Attractive compensation - uncapped commission. Base Fulltime Salary is $65,000 (USD) (On Target Earnings: Year 1 OTE = $115,000, Year 2 OTE: $150,000).
Your health matters – US team members get 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.
Access to our Booking Marketplace: Book hotels and flights for personal travel at exclusive discounted rates.
At this time, we are only accepting applications from candidates who can join our downtown Chicago office by November 2026.
For this role, we can only consider candidates who have the full legal right to work in the US (citizenship or residency). Unfortunately, WeTravel is not able to offer visa sponsorship or relocation assistance at this time.
WeTravel is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome applicants from all backgrounds, experiences, and perspectives. If you're excited about this opportunity and believe you're a good fit, we encourage you to apply and join us in transforming the travel industry!
