Role Overview
The Head of GTM Enablement reports to the Chief Revenue Officer and owns enablement for every customer-facing role, from first outreach through deployment and expansion. You are a builder with a foundation in instructional design: you translate sales expertise and AI knowledge into practical, scalable learning programs that help the field explain, demonstrate, price, deploy and support our products.
What You Will Do
Six areas, in order of impact on win rate and ramp time. Across all six, apply adult learning principles to design engaging, interactive programs with clear learning objectives, opportunities to practice, feedback and reinforcement. Use a variety of learning tools and formats, including microlearning, experiential learning through real deal scenarios and hands-on practice, and learning embedded in daily workflows.
Why It Might Be a Fit
You are measured on revenue outcomes, supported by evidence that employees retain and apply what they learn. Use practical assessments, observed field behaviors and adoption of new skills and workflows to improve programs alongside the business measures below.
Requirements
- 8+ years in sales enablement, sales leadership, sales engineering or solutions consulting in B2B SaaS, with enterprise, multi-stakeholder deals
- 5+ years of applied instructional design experience building and delivering enablement programs that measurably improve field performance
- Technical fluency in AI: you can explain LLMs, speech and conversation analytics, retrieval, evaluation and guardrails, and security and compliance to a buyer, and coach engineers to do the same
- Experience building programs for several roles at once, not just sales engineers
- Strong facilitation and executive communication skills
- Hands-on experience with enablement tools and Salesforce, and a bias toward building workflows and automation
Benefits
- Competitive compensation including equity
- Excellent medical, dental, and vision insurance options
- Flexible Paid Time Off
- Additional Time to Recharge
- 401(k) plan
- Quarterly Lifestyle Spending Account
- Monthly Mobile + Internet Stipend
- Pre-tax Commuter Benefits
To apply for this job please visit observe.ai.

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