Account Executive - Chicago Office
Wetravel · Chicago Office
- On site
- Fulltime
- Chicago Office
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Subject: Interested in the Account Executive - Chicago Office role at Wetravel
Hi Alex â I came across the Account Executive - Chicago Office opening and wanted to reach out directly. I've spent the last few years doing exactly this kind of work, and Wetravel stood out becauseâŠ
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About the role
Hi! đ Iâm 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. Weâre growing fast, and Iâm looking for someone whoâs ready to roll up their sleeves, connect with amazing clients, and help us scale the US market even further.
If youâre someone who loves fintech, has a natural curiosity, and thrives on building relationshipsâyouâll fit right in. Together, weâre building more than just a teamâweâre 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.
How We Work
At WeTravel, our Sales teams combine autonomy with strong collaboration. As an Account Executive, you'll own the full sales cycle â 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 wonât just sell â youâll guide and support potential customers in discovering how WeTravel (products) can truly help their business thrive.
We value proactive, solution-oriented individuals who arenât afraid to take initiative, spot opportunities, and act on them. Our teams move fast, support one another, and celebrate wins together â big and small. Youâll spend most of your time doing what actually moves the needle: prospecting, demoing, and following up with qualified leads.
Why You Should or Shouldnât Apply
You should apply if you:
Are fluent in English (bonus points for other languagesâlist 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 industryâthatâs a big plus!
You might not be the right fit if you:
Donât 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.
On a Weekly Basis You Will Find Yourself
Reaching out to and building relationships with multi-day tour operators across the U.S.
Delivering engaging demos that showcase the value of WeTravelâs 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 - 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 â US team members get 100% employer-covered HDHP medical, DHMO 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.
Generous "Time to Recharge" policy â enjoy unlimited paid time off to rest, recharge, and show up as your best self.
Amsterdam Program â 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 â take time to give back to causes you care about, on us.
2-week cross-functional onboarding program.
Join an international, travel-loving team with a passion for adventure and innovation.
Employer-sponsored 401(k) plan with a 2% company match to support your long-term financial goals.
Please note
At this time, we are only accepting applications from candidates who can join our downtown Chicago office by July 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.
Equal Opportunities
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!