GTM Enablement Leader – AI-Smart Sales Training

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

Benefits offered by this job

Competitive compensation including by‑

equity

Excellent medical, dental, and vision

Flexible Paid Time Off

Company holidays

401(k) plan

Lifestyle Spending Account

Monthly Mobile + Internet Stipend

Pre‑tax Commuter Benefits

Job summary

Observe.AI is hiring a Head of GTM Enablement to lead enablement across all customer‑facing roles. This remote role reports to the Chief Revenue Officer and drives scalable programs for sales development, account executives, engineers, and customer success.

You’ll translate sales expertise and AI knowledge into practical learning experiences, build playbooks, certifications, and simulations, and partner with Revenue Operations to optimize tooling and CRM hygiene.

Qualifications

• 8+ years in sales enablement, sales leadership or related roles in B2B SaaS.
• 5+ years in instructional design building measurable enablement programs.
• Proven ability to improve win rate, ramp time or technical‑win metrics.
• Technical fluency in AI, LLMs, and security/compliance concepts.
• Experience building multi‑role enablement programs.
• Strong facilitation and executive communication.
• Hands‑on with enablement tools and Salesforce; process automation.

Responsibilities

• Design engaging, scalable programs across six areas with learning objectives and practice.
• Develop market, ICP and persona knowledge with playbooks for sales roles.
• Craft platform narrative and competitive positioning for the GTM motion.
• Build product/technical fluency training, demos and cert programs.
• Teach methodology, pricing and process discipline with CRM hygiene.
• Coach frontline leaders and run structured deal reviews and AI‑assisted coaching.

Skills

Sales Enablement

Instructional Design

Executive communication

Facilitation

Sales coaching

Sales leadership

Sales tools

Enablement tooling

Tools

Salesforce

CRM tooling

Job description

Observe.AI is hiring a Head of GTM Enablement to lead enablement across all customer‑facing roles. This remote role reports to the Chief Revenue Officer and drives scalable programs for sales development, account executives, engineers, and customer success.

You’ll translate sales expertise and AI knowledge into practical learning experiences, build playbooks, certifications, and simulations, and partner with Revenue Operations to optimize tooling and CRM hygiene.