Account Executive - Chicago Office

WeTravel; Chicago (IL); Hybrid; USD 65,000 - 150,000; Full time

Benefits offered by this job

Uncapped commission

Health insurance (US)

Downtown Chicago office onsite 4 days

Lunch and Learn

Commuting allowance

Unlimited PTO

Amsterdam Program – 2–4 weeks yearly

Remote work up to 4 weeks/yr

Paid family leave

Volunteer days

401(k) match

Global travel opportunities

Job summary

WeTravel is seeking a results-driven Account Executive to own the full sales cycle in the US market from Chicago. You will prospect, demo, and close deals, traveling up to 10% as needed and coordinating with onboarding to ensure client success.

The role emphasizes outbound outreach, strong communication, and relationship-building for SMBs in travel tech; HubSpot experience is a plus and will be used to manage the pipeline.

Qualifications

• Fluent English; other languages a plus.
• Proven experience in inside/outbound sales.
• Ability to manage full sales cycle from prospecting to close.
• Knowledge of HubSpot CRM or similar tools.
• Familiarity with B2B sales to SMBs in travel/tech is a plus.

Responsibilities

• Prospect and build relationships with multi-day tour operators in the U.S.
• Deliver engaging product demos to showcase WeTravel value.
• Manage pipeline and track activity in HubSpot.
• Follow up with prospects through to close.
• Collaborate with onboarding and support teams for a seamless client experience.
• Provide feedback to product and marketing from client conversations.
• Consistently meet and exceed outreach and sales targets.

Skills

Outbound sales

Communication

Relationship building

Travel industry knowledge

B2B sales

English fluency

Cold calling

Tools

HubSpot CRM

Job description

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.

How We Work

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.

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!

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.

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 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.

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 – 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.

Please Note

• 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.