Hi! 👋 I’m Kaitlin, Sales Director of US Inside Sales at WeTravel. We’re currently hiring a motivated and people-first Sales Manager to lead a new Chicago Sales Team. In this role, you’ll be responsible for interviewing, hiring, training, coaching, mentoring, and scaling a high-performing sales team focused on selling to small and medium-sized wellness travel businesses. This isn’t just a management role—it’s a leadership opportunity rooted in how we Lead, Drive, and Grow at WeTravel:

• LEAD by being the guide, not the hero—your success is measured by how well your team succeeds.

• DRIVE momentum by making the right moves at the right time, always aligned with what truly moves the needle.

• GROW by developing people every day, embracing feedback, curiosity, and continuous learning.
  

Our mission is bold: We’re growing fast, and I’m looking for someone who’s ready to roll up their sleeves and help us scale the US market even further.

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

At WeTravel, we run lean, move fast, and support each other fiercely. Our Sales Managers spend roughly 80% of their time coaching reps, joining demos, reviewing call recordings, and holding pipeline and performance reviews. You’ll also handle full sales cycles and contribute to top-of-funnel activity where needed.

We use a consultative sales approach and rely on systems like HubSpot or Salesforce to stay organized and optimize performance. This is a remote-first role with high accountability, autonomy, and visibility. You'll help your team stay aligned to clear goals, smart risks, and constant improvement.

Why You Should or Shouldn’t Apply

You should apply if you:

• Have 2+ years of experience in a sales leadership role.

• Are energized by coaching, developing, and scaling sales reps.

• Thrive in driving an ambitious and engaging office environment.

• Have a track record of exceeding targets and building outbound sales discipline.

• Are comfortable working across cold calls, demos, and full sales cycles.

• Are experienced in CRM tools like Salesforce or HubSpot.

• Are passionate about the personal and professional development of your sellers.

You might not be the right fit if you:

• Don’t feel energized by coaching or developing Account Executives.

• Are unfamiliar with consultative sales or full-cycle outbound sales.

• Struggle with giving and receiving feedback.

• Prefer heavily structured corporate environments over a startup pace.

• Resist feedback or avoid stretching yourself — here, we grow 1% every day, and that starts at the top.

On a Weekly Basis You Will Find Yourself:

• Coaching sales reps through outbound strategy, objections, demos, and deal cycles.

• Managing and monitoring team KPIs and sales processes.

• Forecasting pipeline and reporting to senior sales leadership.

• Jumping into calls and presentations with clients across US/LATAM and beyond.

• Sharing product and market feedback across the business.

• Representing WeTravel at industry events (national and international).

Benefits

• Attractive compensation - uncapped commission. Base Full-Time Salary range is $80,000-$90,000 (USD) (On Target Earnings: Year 1 OTE = $121,000).

• 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.

Please note:

• At this time, we are only accepting applications from candidates who can join our downtown Chicago office in-person 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.
  
  

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!

Compensation Range: $80K - $90K