Director of Commercial Operations

Hi! 👋 I'm Mark, VP of Finance and Operations here at WeTravel. I've spent my career building strong teams, optimizing operations, and driving meaningful impact across fast-growing SaaS environments. At WeTravel, I'm focused on empowering our teams, improving processes, and creating the foundations that help our partners and our organization grow with confidence.

Think of the most incredible adventures imaginable: trekking to Machu Picchu, cycling through Tuscany, or going on a safari in Kenya. For years, the small businesses and local experts who run these trips have been stuck using messy spreadsheets, countless emails, and complicated payment methods.

WeTravel is changing that. We build the tools that empower any entrepreneur to launch and grow their own travel business. Our platform makes it simple for organizers to create beautiful trip proposals, securely process payments, and manage their customers, so they can focus on what they do best: creating amazing experiences.

This is one of the last great frontiers of travel to come online, and as the category leader, we are at the forefront of this change. Last year alone, our platform was trusted by 8,000 organizers to lead over a million travelers on adventures in 150+ countries. Now, we’re on an exciting journey to grow from powering $1B to $10B in travel experiences per year.

We believe that every trip, when done right, can be a force for good - and we’re building the engine to make more of that possible.

As the operational backbone for our Go-to-Market (GTM) teams, you will own and evolve the end-to-end Commercial Operations strategy across Sales, Marketing, Account Management, and CX. Reporting to the VP of Finance & Operations and partnering closely with sales leadership, you will design, drive, and optimize scalable systems and processes that fuel predictable revenue growth.

You’ll be a force multiplier across the organization—connecting data, people, processes, and technology to unlock productivity and transparency across the revenue lifecycle. This includes optimizing our CRM, lead management and sales systems, leading multiple teams, building cross-functional visibility, and driving operational excellence in a high-growth, fast-paced fintech environment.
For candidates who are located near Chicago, IL: this role is a hybrid role (3 days a week on-site) in our new Chicago office, located in the Loop.

• Serve as a strategic advisor to the GTM leadership team, driving alignment across Sales, Marketing, Customer Success, Finance, and Product.

• Define and continuously improve our revenue operations strategy, with focus on scale, automation, and data integrity.

• Manage annual and quarterly GTM planning cycles: segmentation, quota modeling, territory design, pipeline health, forecasting, and performance tracking.

• Own and evolve the CRM (HubSpot preferred), ensuring accurate pipeline management, forecasting hygiene, and efficient workflow automation.

• Build and maintain robust reporting and dashboards that support real-time decision-making for sales reps, managers, and executives.

• Lead revenue analytics: funnel conversion, attribution, churn, win/loss, and cohort trends across self-serve and sales-led motions.

• Drive consistent, board-ready revenue insights and KPI tracking in partnership with Finance and Analytics.

• Ensure lead scoring, routing, and follow-up SLAs are aligned across Sales and Marketing to drive pipeline efficiency.

• Support the selection and integration of new GTM tools and tech stack (e.g., Gong, Aircall, Hubspot etc)

• 5+ years of experience in Revenue Operations, Sales Operations, or Strategy roles at a high-growth SaaS, fintech, or B2B tech company

• Proven success leading operational strategy across multi-functional GTM teams (Sales, Marketing, Customer Success)

• Expert in sales tech stack administration and optimization (HubSpot, Salesforce, Looker, Excel/Google Sheets, etc.)

• Strong business acumen and ability to distill complex operational problems into clear action plans

• Excellent communication and stakeholder management skills—able to influence cross-functionally and at the exec level

• Hands-on project management and prioritization skills in a dynamic, fast-paced environment

• Experience with high-volume sales models (inbound and outbound), as well as self-serve and hybrid growth motions

• Bonus: Experience supporting revenue forecasting, or business reviews at the leadership level

• 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.

• 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.

• Cutting-edge equipment and tools to set you up for success.

• Join an international, travel-loving team with a passion for adventure and innovation.

• For this role, we can only consider candidates with the legal right to work in the United States. 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!