Head of GTM Enablement
About The Position
Observe.AI is hiring a Head of GTM Enablement to own enablement for every customer-facing role, from first outreach through deployment and expansion. Reporting to the Chief Revenue Officer, this hands-on builder combines sales domain expertise, AI fluency, and instructional design to create practical, scalable learning programs that improve adoption, retention, and field performance. The role owns how enablement programs are designed, delivered, and improved. The position builds and maintains market, ideal customer profile, and persona knowledge; teaches a consistent platform narrative and competitive positioning; develops role-tiered product and technical fluency; and establishes methodology, pricing, and process discipline. It also equips managers to coach and inspect deals, and operates enablement as a product through content governance, release-to-field processes, learning platforms, and AI-native workflows using conversation data. In the first 90 days, the role assesses existing enablement, listens to calls and consults the field, and launches new-hire onboarding, the platform narrative, ICP and persona playbooks, methodology gates, and weekly product release briefings. In months 4–9, it launches role-based certifications, manager coaching and deal-review training, and AI-assisted call coaching and role-play. In year two, it extends enablement to partners and implementation teams and develops a customer academy for adoption and expansion. Success is measured by revenue outcomes and evidence that employees retain and apply learning, including win rate, stage conversion, new-hire ramp, technical-win and proof-of-value conversion, forecast accuracy, pipeline hygiene, release-to-field speed, manager coaching cadence, and field ratings of enablement usefulness.
Requirements
- At least 8 years in sales enablement, sales leadership, sales engineering, or solutions consulting in B2B SaaS, including enterprise, multi-stakeholder deals.
- At least 5 years of applied instructional design experience building and delivering enablement programs that measurably improve field performance.
- Understand adult learning principles and translate sales and AI expertise into engaging, interactive curricula, certifications, and labs using varied learning tools.
- Demonstrated effective use of microlearning, experiential learning, and learning embedded in daily workflows to drive adoption, retention, and practical application.
- Track record of measurably improving win rate, ramp time, or technical-win conversion.
- Technical fluency in AI, including the ability to explain LLMs, speech and conversation analytics, retrieval, evaluation, guardrails, security, and compliance to buyers and coach engineers to do so.
- Experience building programs for multiple roles, not only sales engineers.
- Strong facilitation and executive communication skills.
- Hands-on experience with enablement tools and Salesforce, and a bias toward building workflows and automation.
Nice To Haves
- Contact-center, customer experience, or AI/ML product experience.
- Experience teaching a structured methodology such as MEDDPICC.
- Formal education or certification in instructional design or adult learning.
- Experience building an enablement function from scratch at a company with $50M to $150M in revenue.
- Experience managing a small team and managing through leaders rather than around them.
Responsibilities
- Own enablement for all customer-facing roles from initial outreach through deployment and expansion.
- Apply adult learning principles to design interactive programs with clear objectives, practice, feedback, and reinforcement, using formats suited to each audience.
- Maintain current ideal customer profile materials, buying-center maps, and persona playbooks.
- Teach a consistent platform narrative and own competitive positioning against AI-native entrants, platform rivals, and analytics bundled into contact-center suites.
- Build tiered product and technical learning for technical and non-technical roles covering AI concepts, integrations, security, and compliance.
- Run demo, proof-of-value, and certification programs, partnering with sales engineers and forward-deployed engineers as instructors while protecting their time.
- Teach and inspect sales process discipline, including stage exit criteria, qualification, technical and security wins, pricing and negotiation under usage-based commitments, and CRM hygiene.
- Partner with Revenue Operations on enablement tooling.
- Equip frontline leaders to coach, conduct structured deal reviews and call coaching, and inspect forecasts rather than taking over sales.
- Operate enablement as a product with content governance, a release-to-field cadence, learning platforms, and workflows using company conversation data for coaching, role-play, and identifying stalled deals.
- Assess existing enablement by listening to calls and consulting the field; establish onboarding, platform narrative, ICP and persona playbooks, methodology gates, and weekly release briefings.
- Launch role-based certifications, including gates before technical-win or pricing conversations; train frontline managers; introduce AI-assisted call coaching and role-play.
- Extend enablement to partners and implementation teams and build a customer academy that drives adoption and expansion.
- Measure and improve programs using learning retention and application evidence, field behaviors, and business outcomes.
Benefits
- Competitive compensation including market-aligned base pay, performance incentives, and meaningful equity ownership.
- Medical, dental, and vision insurance options for employees and eligible dependents.
- Unlimited, flexible paid time off.
- 10 company holidays and an annual company-wide Winter Break.
- Paid parental leave.
- 401(k) plan.
- Quarterly Lifestyle Spending Account for wellness, learning and professional development, and personal growth.
- Monthly mobile and internet stipend for remote and hybrid work connectivity needs.
- Pre-tax commuter benefits for hybrid and in-office employees.
- May be eligible for additional discretionary bonuses or incentives and equity in the form of options.
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
