Head of GTM Enablement

atObserve.AIRemoteUS flagUnited StatesFull-timeProduct MarketingLead$215k – $235k/year

Posted 5 days ago

This is a fully remote position, open to applicants in United States.

📋 Description

• Take full responsibility for the enablement of all customer-facing roles, from initial outreach to deployment and expansion.

• Convert sales knowledge and AI insights into practical, scalable learning initiatives.

• Utilize adult learning principles to create engaging, interactive programs with defined objectives, opportunities for practice, feedback, and reinforcement.

• Maintain updated Ideal Customer Profiles (ICP), buying-center maps, and persona playbooks.

• Educate on platform narratives, positioning, and competitive differentiation.

• Develop tiered technical education on Large Language Models (LLMs), speech models, retrieval, evaluation, guardrails, integrations, security, and compliance.

• Conduct demo sessions, proof-of-value initiatives, and certification programs.

• Instruct and evaluate the sales process, qualification, technical and security victories, pricing strategies, negotiation, and CRM best practices.

• Empower managers to coach, perform deal reviews, conduct coaching calls, and review forecasts.

• Manage enablement through content governance, release-to-field schedules, learning platforms, and AI-native workflows.

• Develop onboarding materials, platform narratives, ICP/persona playbooks, and methodology gates within the first 90 days.

• Initiate role-based certifications, manager coaching, AI-supported call coaching, and role-playing exercises.

• Extend enablement efforts to partners and implementation teams, and create a customer academy.

• Evaluate metrics such as win rate, conversion, ramp time, productivity, forecast accuracy, pipeline hygiene, speed of content release, and the effectiveness of enablement.


⛳️ Requirements

• At least 8 years of experience in sales enablement, sales leadership, sales engineering, or solutions consulting within B2B SaaS, particularly with enterprise-level, multi-stakeholder deals.

• Minimum of 5 years of hands-on instructional design experience in creating and delivering enablement programs that demonstrably enhance field performance.

• Solid understanding of adult learning principles and the ability to convert sales and AI expertise into compelling, interactive curricula, certifications, and labs using various learning tools.

• Proficient in employing microlearning, experiential learning, and embedding learning within employees’ everyday workflows.

• Proven track record of significantly improving win rates, ramp times, or technical-win conversions.

• Technical proficiency in AI technologies, including LLMs, speech and conversation analytics, retrieval, evaluation, guardrails, security, and compliance.

• Experience in developing programs for multiple roles simultaneously, not limited to sales engineers alone.

• Excellent facilitation and executive communication abilities.

• Practical experience with enablement tools and Salesforce.

• A proactive approach towards creating workflows and automation solutions.


🏝️ Benefits

• Competitive base salary aligned with market standards.

• Performance-based incentives.

• Significant equity ownership opportunities.

• Comprehensive medical, dental, and vision coverage for employees and their eligible dependents.

• Unlimited and flexible paid time off.

• Ten designated company holidays.

• Annual company-wide winter break.

• Paid parental leave policy.

• 401(k) retirement plan.

• Quarterly Lifestyle Spending Account to promote wellness, learning, and professional development as well as personal growth.

• Monthly stipend for mobile and internet expenses.

• Pre-tax commuter benefits.

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