What are the responsibilities and job description for the Account Executive - Chicago Office position at WeTravel?
Hi! 👋 I’m Luke, from LA in the US 🇺🇸, Sales Director for the US, LATAM, and APAC markets here at WeTravel.
I’ve been with WeTravel since the early days and have had the chance to see the company grow through many exciting phases. It’s been an incredible journey — and I’m more excited than ever about what’s ahead. My mission is to build a strong, talented, and mission-driven sales team that’s 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 new Chicago office in the Loop (20 N Wacker Dr), with one remote workday each week.
How We Work
Our team thrives on energy, ownership, and results. As an Account Executive, you’ll manage the entire sales cycle: from initial outreach, to discovery calls and product demos, all the way through closing and handoff to onboarding.
We take a consultative approach, focused on understanding each client’s unique challenges. Our clients are small-to-medium-sized multi-day tour operators, often run by passionate entrepreneurs who wear many hats. That means you'll have a real impact—helping them grow and simplify their operations through our all-in-one platform.
We use tools like HubSpot to keep things organized and scalable, and we support each other through collaboration, feedback, and shared wins.
Why You Should or Shouldn’t Apply
You Should Apply If You
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!
I’ve been with WeTravel since the early days and have had the chance to see the company grow through many exciting phases. It’s been an incredible journey — and I’m more excited than ever about what’s ahead. My mission is to build a strong, talented, and mission-driven sales team that’s 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 new Chicago office in the Loop (20 N Wacker Dr), with one remote workday each week.
How We Work
Our team thrives on energy, ownership, and results. As an Account Executive, you’ll manage the entire sales cycle: from initial outreach, to discovery calls and product demos, all the way through closing and handoff to onboarding.
We take a consultative approach, focused on understanding each client’s unique challenges. Our clients are small-to-medium-sized multi-day tour operators, often run by passionate entrepreneurs who wear many hats. That means you'll have a real impact—helping them grow and simplify their operations through our all-in-one platform.
We use tools like HubSpot to keep things organized and scalable, and we support each other through collaboration, feedback, and shared wins.
Why You Should or Shouldn’t Apply
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!
- Don’t enjoy high-volume outreach or cold calling.
- Prefer reactive roles with minimal client interaction.
- 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, DHMO dental, and standard vision coverages or a choice of plans that suit your needs.
- Exciting new office location in downtown Chicago, with a requirement to be on-site 4 days per week.
- 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.
- Join an international, travel-loving team with a passion for adventure and innovation.
- At this time, we are only accepting applications from candidates who can join our downtown Chicago office by February 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!
Salary : $65,000 - $150,000