Head of GTM Enablement

Obsidian Security

Head of GTM Enablement responsible for training customer-facing teams for SaaS security leader Obsidian Security. Driving higher sales participation and faster revenue through effective enablement strategies.

Posted 7/14/2026full-timeRemote • 🇺🇸 United StatesLead💰 $180,000 - $230,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in building and scaling revenue enablement functions within high-growth technology companies, with a strong focus on metrics-driven performance and modern sales methodologies. Proven ability to lead and develop enablement teams while driving cross-functional alignment and effective coaching strategies.

Highest-signal resume keywords

Revenue Enablement Function DevelopmentCybersecurity Industry KnowledgeModern Sales Methodology ImplementationMetrics-Driven Performance ManagementProgram Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Onboarding Program DesignRole-Based Ramp ProgramsCoaching and InterventionsAI-Driven WorkflowsPerformance Data AnalysisSales Methodology FluencyPipeline Generation EnablementDeal Motion UnderstandingCompetitive PositioningCustomer Conversations Analysis

Soft Skills

People LeadershipCross-Functional AlignmentProactive AnticipationCoaching Frontline LeadersCommunication

Tools & Technologies

GongAI ToolsPerformance Dashboards

Industry Keywords

CybersecurityEnterprise Deal MotionSecurity BuyerHigh-Growth Technology

Tech Stack

Tools & technologies

Cyber Security

About the role

Key responsibilities & impact

Own the strategy, structure, cadence, and execution of enablement across sales, technical, and BDR, covering onboarding, ramp, and ongoing development.
Design and run onboarding and personalized, role-based ramp programs built to measurably shorten the time it takes new AEs, SEs, TAMs, and BDRs to become productive.
Run enablement as a system with a consistent weekly, monthly, and quarterly rhythm, so the right people absorb the right knowledge at the right moment.
Enable the field on the fundamentals that move deals: relevant security and product knowledge, persona-based pain discovery, new business meeting excellence (identifying use cases, bringing social proof, and quantifying pain), competitive positioning, and closing, including how to build durable champions inside accounts.
Equip technical talent across pre and post sale to win the technical evaluation and drive successful proofs of value.
Enable the BDR motion to generate more and better qualified pipeline.
Ground enablement in what is actually happening in deals. Use call intelligence such as Gong and real customer conversations, rather than certification pass rates or content engagement dashboards, as your primary signal for what is working, where reps are stuck, and what to coach next.
Turn those observations into specific coaching and interventions, and coach the frontline leaders so they reinforce the same behaviors.
Bring fluency in AI-driven workflows to make enablement faster and more efficient, and to systematize routine practices instead of doing them by hand.
Use AI and performance data to build personalized enablement tracks that meet each rep where they are, instead of one size fits all training.
Hire, develop, and lead the enablement team, and set the standard by leading from the front.
Drive cross-functional alignment proactively, anticipating what the field will need and getting ahead of it rather than reacting to inbound requests, and hold partners to clear commitments.
Bring strong program management: named owners, clear timelines, refresh cadences, and follow through.

Requirements

What you’ll need

You have built and scaled a GTM or revenue enablement function inside a high-growth technology company, ideally through a scaling phase.
You have deep experience enabling the full customer-facing org, including AEs, technical pre and post sale, and BDR or pipeline generation teams.
Cybersecurity industry knowledge is strongly preferred. You understand the security buyer, the enterprise deal motion, and the competitive landscape.
You are fluent in modern sales methodology such as MEDDIC or MEDDPICC and value-based messaging, and you have implemented it, coached leaders to it, and measured the behavior change it produces.
You are metrics-driven. You set baselines, instrument the motion, and manage to leading and lagging indicators.
You are a proven people leader who has hired, developed, and retained enablement talent.
You are a strong program manager who ships on time and follows through.

Benefits

Comp & perks

Competitive compensation with equity and 401k
Comprehensive healthcare with dental and vision coverage
Flexible paid time off and paid holiday time off
12 weeks of new parent or family leave
Personal and professional development resources