WeTravel-posted 1 day ago
$80,000 - $90,000/Yr
Full-time • Manager
Hybrid • Chicago, IL
101-250 employees

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.

  • 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).
  • 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.
  • 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.
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