Sales Training & Enablement Manager

Location: Concord, MA or Boston, MA (Hybrid) Preferred, Open to Remote

The Opportunity

We’re looking for a Sales Training & Enablement Manager to design, deliver, and continuously improve our sales onboarding and training programs across all segments—from SMB to Enterprise. Reporting to the VP of Revenue Operations & Strategy, this role sits at the intersection of sales, marketing, and people development. You’ll build the foundation for scalable onboarding, manage our learning management system (LMS), and drive measurable improvements in ramp time, sales velocity, and team productivity.

If you’re passionate about coaching sellers, building content that sticks, and partnering cross-functionally to create a world-class enablement experience, this is your opportunity to make a lasting impact.

🎯 What You’ll Own

🧩 New Hire Onboarding & Continuous Training

• Design and deliver a best-in-class onboarding experience for all sales roles across SMB, Mid-Market, and Enterprise.

• Own the onboarding calendar, curriculum, and certification process from pre-boarding through full ramp.

• Partner with Sales Leadership, People & Talent, and Marketing to ensure training aligns with GTM priorities and company values.

• Measure ramp time, productivity milestones, and skill acquisition—using data to continuously optimize the program.

📚 Learning Management System (LMS) Ownership

• Manage the end-to-end operation of the LMS (content library, user access, analytics, certification paths).

• Create and upload engaging, trackable modules covering product, process, and skill-based content.

• Partner with RevOps, Product Marketing, and Customer Success to ensure content is current, relevant, and accessible.

• Leverage usage analytics to measure adoption and ROI of learning programs.

🎭 Role Play, Coaching & Certification

• Lead regular role-play sessions focused on SPIN methodology, objection handling, storytelling, and consultative selling.

• Facilitate skill assessments and certifications to validate readiness and drive accountability.

• Deliver live and virtual enablement sessions on core competencies—product knowledge, competitive positioning, and GTM strategy.

📈 Performance Enablement & Metrics

• Build frameworks and scorecards to track onboarding performance, ramp-to-productivity, and training ROI.

• Collaborate with the Data & Insights team to analyze sales performance pre- and post-training.

• Identify trends, skill gaps, and enablement opportunities across teams and segments.

🤝 Cross-Functional Partnership

• Collaborate with Sales Leadership to align training with pipeline goals, quota attainment, and buyer journey needs.

• Partner with Marketing to roll out new campaigns, messaging, and product launches with clarity and consistency.

• Work with Customer Success and Hospitality teams to build training that supports the full customer lifecycle.

• Contribute to enablement initiatives that reinforce company culture and hospitality-driven selling.

🧠 Content Development & Communication

• Develop modular, scalable enablement content (playbooks, decks, cheat sheets, videos).

• Align content across teams to maintain a consistent narrative from prospecting to renewal.

• Ensure training programs reinforce both the art and science of sales—balancing soft skills with data-driven rigor.

✅ What We’re Looking For

• 3–6+ years in Sales Enablement, Training, or Sales Leadership within B2B SaaS or hospitality technology.

• Minimum 2 years direct selling experience—preferably in SaaS, tech, or hospitality sales.

• Strong understanding of sales methodologies (SPIN, Challenger, MEDDICC, or similar).

• Experience managing or implementing a Learning Management System (WorkRamp, Lessonly, Seismic, or equivalent).

• Ability to design and deliver engaging live and virtual training programs.

• Skilled in content creation (slides, video, documentation) and familiar with sales tech stacks (Salesforce, Outreach, Gong, DealHub, etc.).

• Data-driven mindset with the ability to analyze performance and recommend improvements.

• Exceptional communication, facilitation, and interpersonal skills—able to energize and inspire diverse teams.

📈 Success Looks Like:

• Decreased ramp time and faster time-to-first-deal across all sales roles.

• Consistent onboarding experience across segments, supported by measurable certification milestones.

• Increased adoption of sales processes, tools, and methodologies.

• Improved sales velocity and win rates through skill reinforcement and role-based enablement.

• A scalable enablement framework aligned with GTM strategy, product updates, and market trends.

• Engaged, confident sellers who deliver value-driven conversations at every stage of the funnel.

Base Compensation Range:

• $95,000 - $115,000 annually
  

Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission.
The above represents the expected base compensation range for this job requisition. Ultimately, in determining your pay, we’ll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.

What We Offer:

• Competitive compensation and comprehensive benefits including medical, dental, vision, life insurance, and 401(k) with company match.

• Flexible paid time off to promote work-life harmony.

• Pet insurance to take care of your furry friends.

• An open, inclusive culture that focuses on collaboration, innovation, and personal growth.

• The opportunity to work on a product that makes a real difference in the hospitality and event industries.