Head of GTM Enablement

About Us

Observe.AI is the AI Agents platform for customer experience, designed to help organizations deliver faster, smarter, and more efficient customer service at scale. The platform enables businesses to deploy specialized AI agents that autonomously execute work across the full CX lifecycle—from handling customer conversations to supporting frontline teams and optimizing operations.

Each AI agent is purpose-built for a specific role, equipped to understand context, make decisions, take action, and continuously improve outcomes. This allows organizations to increase resolution speed, elevate service quality, and reduce operational costs while empowering your frontline team to focus on higher-value work.

Built on a CX-native foundation, Observe.AI works with 300+ global brands in Financial Services, Insurance, Healthcare and Consumer Services, including brands like DoorDash, Affordable Care, to improve customer satisfaction, boost productivity, and deliver consistent, scalable performance across every customer interaction.

Why Join Us

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

What enablement must deliver

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

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. Choose the approach that best helps each audience apply and retain what they learn.

1. Market, ICP and persona knowledge. Keep the ideal customer profile, buying-center maps and persona playbooks current. Make sure every seller can tell a conversation-intelligence buyer from an agentic-automation buyer, and knows when one budget owner covers both.
2. Platform narrative and positioning. Teach one consistent story of how conversation intelligence shows what to automate and agentic AI then automates it. Own competitive positioning against AI-native entrants, platform rivals and the analytics bundled into contact-center suites.
3. 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. Run the demo, proof-of-value and certification programs. Lean on sales engineers and forward-deployed engineers as teachers, and protect their time for it.
4. 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. Partner with Revenue Operations on tooling.
5. Manager coaching and deal-review rigor. Equip frontline leaders to coach rather than step in and sell. Run structured deal reviews, call coaching and forecast inspection.
6. Enablement operations and AI-native tooling. Run enablement as a product: a content governance model, a release-to-field cadence, learning and enablement platforms, and workflows that use our own conversation data to find what top performers do, power coaching and role-play, and flag where deals stall.

Outcomes

The first 90 days build the foundation where the biggest win-rate gains sit; later phases add scale.

1. First 90 days. Listen to calls and talk to the field, then assess current enablement. Ship a new-hire onboarding path, the platform narrative, ICP and persona playbooks, and the methodology gates. Stand up a weekly release briefing so the field hears about product changes within days.
2. Months 4 to 9. Launch role-based certifications, including a gate before reps run technical-win or pricing conversations. Train frontline managers on coaching and deal review. Introduce AI-assisted call coaching and role-play.
3. Year 2. Extend enablement to partners and implementation teams, and build a customer academy that drives adoption and expansion. Run enablement as a measured, continuously improving system.

How Success is measured

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.

• 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 to build and deliver practical, scalable programs that improve field performance.

Must have

• 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. Understand adult learning principles and translate sales and AI expertise into engaging, interactive curricula, certifications and labs using a variety of learning tools. Demonstrate effective use of microlearning, experiential learning and learning embedded in employees’ daily workflows to drive adoption, knowledge retention and practical application.
• 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, 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

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

Why You’ll Love It Here

• 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: Our unlimited, flexible PTO policy empowers you to take the time you need to recharge, maintain balance, and perform at your best.
• Additional Time to Recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave to fully support life outside of work.
• 401(k) plan: Long-term financial planning support with tax-advantaged retirement savings
• Quarterly Lifestyle Spending Account: Flexible quarterly stipend to support wellness, learning and professional development, 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 for hybrid and in-office employees

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. Base pay is one part of the Total Package that is provided to compensate and recognize employees for their work, and this role may be eligible for additional discretionary bonuses/incentives and equity (in the form of options). This salary range is an estimate, and the actual salary may vary based on the Company’s compensation practices.

Our Commitment to Inclusion and Belonging

Observe.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Observe.AI does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Observe.AI also strives for a healthy and safe workplace and strictly prohibits harassment of any kind.

We welcome all people. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop, and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.

If you are ambitious, make an impact wherever you go, and you're ready to shape the future of Observe.AI, we encourage you to apply. For more information, visit www.observe.ai.

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