GTM Enablement Leader: Scale Revenue & Adoption

Observe.AI; United States; On-site; USD 215,000 - 235,000; Full time

Benefits offered by this job

Competitive compensation + equity

Medical/dental/vision insurance

Flexible PTO

Company holidays + winter break

401(k) retirement plan

Lifestyle spending account

Mobile + internet stipend

Commuter benefits

Job summary

Observe.AI is seeking a Head of GTM Enablement to design and scale learning programs across sales, engineering and customer success. You translate sales expertise and AI knowledge into practical training that drives adoption, alignment, and revenue growth.

Lead six program areas from market intel to enablement operations, coach frontline managers, deliver role-based certifications, and partner with Revenue Operations.

Qualifications

• 8+ years in B2B SaaS sales enablement or related roles with enterprise deals.
• 5+ years of instructional design translating sales and AI into curricula.
• Proven ability to measurably improve win rate, ramp time or tech wins.
• Technical fluency in AI: explain LLMs, speech analytics, retrieval and guardrails to buyers.
• Experience building enablement programs for multiple roles simultaneously.
• Strong facilitation and executive communication skills.
• Hands-on with enablement tools and Salesforce; ability to build workflows.

Responsibilities

• Design engaging, scalable enablement programs using adult learning principles.
• Develop market/ICP knowledge, platform narrative, and pricing guidance.
• Build product and technical fluency trainings for non-technical to technical roles.
• Create methodology, pricing, and process coaching; partner with Revenue Ops.
• Coach frontline managers; run deal reviews and calls coaching.
• Run enablement ops and AI-native tooling; treat enablement as a product.

Skills

Sales enablement

Sales leadership

Instructional design

AI fluency

LLMs & security

Multi-role programs

Facilitation skills

Salesforce experience

Tools

Salesforce

Job description

Observe.AI is seeking a Head of GTM Enablement to design and scale learning programs across sales, engineering and customer success. You translate sales expertise and AI knowledge into practical training that drives adoption, alignment, and revenue growth.

Lead six program areas from market intel to enablement operations, coach frontline managers, deliver role-based certifications, and partner with Revenue Operations.