[Hiring] Head of GTM Enablement @Observe.AI

Role Description

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. You own how those programs are designed, delivered and improved to drive adoption, retention and field performance.

Audience

• Sales development: ICP and persona fluency, qualification discipline, outreach that earns a conversation
• Account executives: Platform narrative, discovery, methodology, pricing and negotiation, technical and security wins
• Sales engineers: Demo and proof-of-value standards, architecture fluency, competitive technical positioning
• Account managers and customer success: Expansion plays, value realization, adoption and renewal conversations
• Forward-deployed engineers: Customer-facing selling skills, scoping discipline, handoff to the commercial team
• Frontline managers: Coaching, deal inspection, forecasting rigor

What you’ll be doing

• Market, ICP and persona knowledge: Keep the ideal customer profile, buying-center maps and persona playbooks current.
• Platform narrative and positioning: Teach one consistent story of how conversation intelligence shows what to automate and agentic AI then automates it.
• Product and technical fluency: Build tiered learning for non-technical and technical roles on LLMs, speech models, retrieval, evaluation and guardrails, integrations, security and compliance.
• Methodology, pricing and process discipline: Teach and inspect the sales process: stage exit criteria, qualification, the technical and security win, pricing and negotiation under usage-based commitments, and CRM hygiene.
• Manager coaching and deal-review rigor: Equip frontline leaders to coach rather than step in and sell.
• Enablement operations and AI-native tooling: Run enablement as a product: a content governance model, a release-to-field cadence, learning and enablement platforms.

Outcomes

• First 90 days: Listen to calls and talk to the field, then assess current enablement.
• Months 4 to 9: Launch role-based certifications, including a gate before reps run technical-win or pricing conversations.
• Year 2: Extend enablement to partners and implementation teams, and build a customer academy that drives adoption and expansion.

How Success is measured

• Win rate and stage-to-stage conversion
• Time to first deal and time to full productivity for new hires
• Technical-win and proof-of-value conversion rates
• Forecast accuracy and pipeline hygiene
• Days from product release to field-ready content
• Manager coaching cadence and field rating of enablement usefulness

What you bring

• A hands-on enablement builder who combines sales domain expertise, AI fluency and a foundation in instructional design.
• 8+ years in sales enablement, sales leadership, sales engineering or solutions consulting in B2B SaaS.
• 5+ years of applied instructional design experience building and delivering enablement programs.
• A track record of measurably improving win rate, ramp time or technical-win conversion.
• Technical fluency in AI: you can explain LLMs, speech and conversation analytics.
• Strong facilitation and executive communication skills.
• Hands-on experience with enablement tools and Salesforce.

Nice to have

• 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
• Built an enablement function from scratch at a company in the $50M to $150M revenue range
• Experience managing a small team and managing through leaders rather than around them

Benefits

• Competitive compensation including equity: Market-aligned base pay, performance incentives, and meaningful equity ownership
• Excellent medical, dental, and vision insurance options: Comprehensive medical, dental and vision benefits for employees and eligible dependents
• Flexible Paid Time Off: Unlimited, flexible PTO policy
• Additional Time to Recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave
• 401(k) plan: Long-term financial planning support
• Quarterly Lifestyle Spending Account: Flexible quarterly stipend for wellness and personal growth
• Monthly Mobile + Internet Stipend: Support for remote and hybrid work connectivity needs
• Pre-tax Commuter Benefits: Tax-efficient transit and commuting support

Salary Range

The base salary compensation range targeted for this full-time position is $215,000- $235,000 per year. Compensation may vary outside of this range depending on a number of factors, including a candidate’s qualifications, skills, competencies and experience.

Our Commitment to Inclusion and Belonging

Observe.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. We welcome all people and celebrate diversity of all kinds.