Sales Enablement Trainer

Hi! 👋 I’m Keri, I lead Account Management and Commercial Enablement at WeTravel. I’m building a mighty team focused on helping our Sales, Account Management, and Onboarding teams succeed through meaningful training, smart tools, and ongoing support.

If you’re excited about empowering others to do their best work, love working across teams, and have a knack for creating engaging, effective training programs—then I’d love to meet you.

How We Work

Our Enablement team empowers our global Commercial teams—Sales, Account Management, and Onboarding—to succeed through world-class training, tools, and resources. As our Commercial Enablement Trainer (English and Spanish), you’ll join a small but mighty team and play a pivotal role in onboarding, upskilling, and supporting our go-to-market teams, with a heavy focus on Sales in 2025.

You’ll collaborate cross-functionally with team leads, content creators, and product stakeholders to deliver effective, engaging training experiences that drive performance and knowledge retention. If you’re a bilingual facilitator who thrives in a remote, fast-paced environment and loves building programs from the ground up—this one’s for you.

Why You Should or Shouldn’t Apply

You should apply if you:

• Are fluent in English and Spanish, with experience training in both languages.(required)

• Have 2–3 years of experience in enablement, learning & development, or training roles—ideally within SaaS, tech, or travel companies serving 75+ team members.

• Have worked in a revenue-driven role before (Sales, Account Management, or similar).

• Are a confident virtual facilitator who can energize and engage teams across time zones and cultures.

• Are passionate about education, performance improvement, and commercial success.

• Are organized, proactive, and comfortable working independently in a remote-first environment.

Bonus points if you:

• Have experience in travel tech or SMB-focused SaaS.

• Are familiar with HubSpot or other CRM tools.

• Have worked with enablement and LMS tools like Confluence, Seismic, Loom, or similar.

• Have experience creating role-based training paths or certification programs from scratch.

You might not be the right fit if you:

• Prefer roles that are mostly reactive or lack a proactive training component.

• Are uncomfortable facilitating virtual training sessions across multiple departments.

• Don’t have experience building structured enablement content or collaborating cross-functionally.

On a Weekly Basis You Will Find Yourself

• Delivering live and recorded training sessions in English and Spanish for Sales, Onboarding, and Account Management teams across global markets.

• Developing and maintaining enablement content such as playbooks, certification paths, and product walkthroughs.

• Partnering with commercial team leads to identify skill gaps and adjust training initiatives accordingly.

• Working with Product Marketing and cross-functional stakeholders to ensure content reflects the latest product capabilities and go-to-market strategy.

• Tracking training participation and performance metrics to evaluate effectiveness.

• Supporting new hire onboarding, ensuring Sales team members ramp quickly and confidently.

Bonus Points If You Have

• Experience in travel tech or SMB-focused SaaS.

• Familiarity with HubSpot or other CRM tools.

• Familiar with enablement and LMS tools such as Confluence, Siesmic, Loom, or similar.

• Experience building certification or role-based enablement paths from scratch.

Benefits

• Full-time - Fixed Term Contract

• 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. Coverage for certain work-from-home (WFH) equipment.

• Cambly for colleagues for whom English is not their first language.

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

Please note: For this role, we can only consider candidates who have the full legal right to work in US (citizenship or residency). Unfortunately, WeTravel is not able to offer visa sponsorship or relocation assistance at this time.

About WeTravel

Founded in 2016, WeTravel aims to be the Operating System of any multi-day and group tour operator.

Travel gives people new experiences and brings them together, sometimes in life-changing ways. That’s especially the case for group travel and multi-day travel where the trip participants (travellers) get to really immerse themselves. Passionate travel organizers make this magic happen and WeTravel is here to support those travel companies. We help them publish their trip offerings, generate leads and follow through to convert them to bookings, process payments around the world, pay suppliers/vendors, and digitise their operations. This helps multi-day travel organizers get more bookings, save time, and save money. 

We are a global, diverse, fun team with high ambitions but no ego. Our team is driven to continuously improve our technology; ensuring that our clients always have the best possible solutions at their fingertips. We have offices in San Francisco, Amsterdam, Boston, Sydney, and Baku.

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!