# Head of GTM Enablement  at Observe AI

Observe AI is hiring a Head of GTM Enablement . It pays $215k-$235k a year and Level rates it Works on AI ●●●○; you can [apply on Observe AI](https://jobsbylevel.com/go/f5bfd3b3-725e-4e68-8c4f-f6054dcbcf26?utm_medium=ai-agent).

AI Level 3, AI centrality 67 out of 100. Remote (Remote-US).

## Details

- Company: [Observe AI](https://jobsbylevel.com/companies/observe-ai)
- AI level: AI Level 3 (score 67 out of 100)
- Location: Remote (Remote-US)
- Salary: $215k-$235k
- Posted: November 4, 2026
- Apply: https://jobsbylevel.com/go/f5bfd3b3-725e-4e68-8c4f-f6054dcbcf26?utm_medium=ai-agent
- Free CV review for this job: https://jobsbylevel.com/cv-review?job=head-of-gtm-enablement-at-observe-ai-fdde67

## Prepare for this job

The job page lists 3 likely interview questions for this offer, with a CV checklist: https://jobsbylevel.com/jobs/head-of-gtm-enablement-at-observe-ai-fdde67

## Description

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. 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. 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. 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. 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. Manager coaching and deal-review rigor. Equip frontline leaders to coach rather than step in and

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