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Head of GTM Enablement

150k – 180kDenver, CONew York, NYOnsite5+ YOE
Summary

Design, build, and run a best-in-class enablement program for Sales and Customer Success teams at an early-stage B2B SaaS startup. Own onboarding, training, playbooks, and performance measurement to accelerate GTM ramp and productivity.

About the role

What You'll Do

Design and Deliver Enablement Programs

  • Build and deliver onboarding programs for Sales and Customer Success new hires that combines live facilitation, e-learning, and real-world application.
  • Create scalable playbooks, quizzes, talk tracks, and certification programs that evolve with our product and go-to-market strategy.
  • Apply adult learning principles and instructional design best practices to develop engaging, effective learning experiences.
  • Facilitate workshops and training sessions for team members across multiple experience levels.

Partner Strategically Across Teams

  • Collaborate with Sales and CS leaders to identify skill gaps, process bottlenecks, and enablement opportunities.
  • Translate frontline insights into actionable content, tools, and programs that drive results.
  • Ensure teams are equipped with the latest product knowledge, customer insights, and competitive positioning.

Measure and Optimize Enablement Impact

  • Define and track KPIs such as time-to-ramp, program adoption, and productivity to measure enablement effectiveness.
  • Leverage data and feedback to continuously improve content, delivery, and strategy.
  • Partner with internal stakeholders to maintain a centralized enablement hub and single source of truth for GTM teams.

What You Need

  • 5+ years of experience in Sales Enablement, Customer Success Enablement, or Learning & Development within high-growth B2B SaaS environments
  • Experience owning and running enablement programs — not just participating in large, pre-built enablement systems
  • Proven track record in building and delivering Sales Academy programs and upskilling initiatives that improve ramp, productivity, and retention
  • Strong facilitation, instructional design, and storytelling skills grounded in adult learning principles
  • Demonstrated success designing and delivering programs that improve ramp time, productivity, and retention
  • Excellent communication and presentation abilities across all levels of the organization
  • Familiarity with enablement and learning tools (e.g., Salesforce, Gong, Highspot, Seismic, or similar platforms)
  • A builder mindset: comfortable with ambiguity, proactive in creating clarity, and passionate about scaling programs from the ground up
  • Empathy for both Sales and Customer Success teams, with a deep understanding of the customer journey
  • Experience supporting channel sales or partner enablement is a plus

Compensation & Benefits

  • Competitive salary + equity
  • 3 weeks of PTO
  • Health, vision, and dental benefits
  • $1200/year education stipend
  • 401(k)
  • Free lunch daily
  • New MacBook and any equipment you need
Skills
Sales EnablementCustomer Success EnablementLearning & DevelopmentInstructional DesignSalesforceGongHighspotSeismicFacilitationAdult Learning Principles
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