Head of GTM Enablement

Observe.AI

. Own enablement for every customer-facing role from first outreach through deployment and expansion .

Posted 11/4/2026full-timeRemote • United StatesLead💰 $215,000 - $235,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in sales enablement and instructional design, with a strong focus on applying adult learning principles to create engaging and effective training programs. Proficient in leveraging AI technologies and enablement tools to enhance sales performance and operational efficiency.

Highest-signal resume keywords

Sales EnablementInstructional DesignAI Technical FluencyFacilitation SkillsSalesforce Experience

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Adult Learning PrinciplesMicrolearningExperiential LearningCurriculum DevelopmentProgram MeasurementTechnical-Win ConversionB2B SaaS SalesMulti-Stakeholder DealsRole-Based CertificationsContent Governance

Soft Skills

Executive CommunicationCoaching SkillsFacilitation

Tools & Technologies

Enablement ToolsSalesforceLearning PlatformsAI-Native Workflows

Industry Keywords

Sales EngineeringSolutions ConsultingEnterprise SalesCustomer AcademyPipeline Hygiene

About the role

Key responsibilities & impact

Own enablement for every customer-facing role from first outreach through deployment and expansion
Translate sales expertise and AI knowledge into practical, scalable learning programs
Apply adult learning principles to design engaging, interactive programs with clear objectives, practice, feedback and reinforcement
Keep ICP, buying-center maps and persona playbooks current
Teach platform narrative, positioning and competitive differentiation
Build tiered technical learning on LLMs, speech models, retrieval, evaluation, guardrails, integrations, security and compliance
Run demo, proof-of-value and certification programs
Teach and inspect sales process, qualification, technical and security wins, pricing, negotiation and CRM hygiene
Equip managers to coach, conduct deal reviews, coach calls and inspect forecasts
Operate enablement through content governance, release-to-field cadence, learning platforms and AI-native workflows
Build onboarding, platform narrative, ICP/persona playbooks and methodology gates in the first 90 days
Launch role-based certifications, manager coaching, AI-assisted call coaching and role-play
Extend enablement to partners and implementation teams and build a customer academy
Measure win rate, conversion, ramp time, productivity, forecast accuracy, pipeline hygiene, release-to-content speed and enablement usefulness

Requirements

What you’ll need

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
Understanding of adult learning principles and ability to translate sales and AI expertise into engaging, interactive curricula, certifications and labs using a variety of learning tools
Effective use of microlearning, experiential learning and learning embedded in employees’ daily workflows
Track record of measurably improving win rate, ramp time or technical-win conversion
Technical fluency in AI, including LLMs, speech and conversation analytics, retrieval, evaluation, guardrails, security and compliance
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
Bias toward building workflows and automation

Benefits

Comp & perks

Market-aligned base pay
Performance incentives
Meaningful equity ownership
Comprehensive medical, dental and vision benefits for employees and eligible dependents
Unlimited, flexible PTO
10 company holidays
Annual company-wide Winter Break
Paid parental leave
401(k) plan
Quarterly Lifestyle Spending Account supporting wellness, learning and professional development, and personal growth
Monthly Mobile + Internet Stipend
Pre-tax Commuter Benefits