Head of Enablement

Obsidian Security is seeking a Head of Enablement to build and scale a best-in-class enablement function that supports our mission to secure identity-driven cloud applications. This leader will be responsible for ensuring that Sales, Customer Success, Solutions Engineering, and partners are fully enabled to articulate Obsidian’s differentiated value, execute effectively in complex enterprise sales cycles, and drive durable customer outcomes.

The Head of Enablement will operate as a strategic partner to Revenue, Product, and Marketing leadership, translating Obsidian’s product innovation and market positioning into consistent, high-impact execution across the customer lifecycle.

• Define and own Obsidian’s end-to-end enablement strategy across Sales, Solutions Engineering, Customer Success, and relevant Partner motions.
• Align enablement priorities to company objectives, revenue targets, and market expansion goals.
• Build, lead, and scale the enablement team, establishing clear operating rhythms, standards, and accountability.

• Design and maintain structured onboarding programs for new hires, with a focus on enterprise sales readiness and security domain fluency.
• Develop role-based curricula covering:
• Obsidian’s platform, use cases, and technical differentiation
• Identity security, SaaS posture management, and cloud security concepts
• Enterprise buying personas and complex deal navigation
• Sales methodology, qualification, and value-based selling
• Partner with Sales Leadership to support forecast accuracy, pipeline progression, and deal execution.

• Partner closely with Solutions Engineering and Product teams to ensure technical sellers and customer-facing teams are deeply enabled on:
• Product architecture and integrations
• Competitive differentiation in the identity and SaaS security landscape
• Proof-of-value and customer validation strategies
• Value Engineering and Selling
• Ensure enablement programs keep pace with a rapidly evolving threat and technology environment.

• Own the enablement content ecosystem, ensuring materials are current, high quality, and easily consumable.
• Partner with Product Marketing on messaging, launches, competitive intelligence, and field feedback loops.
• Evaluate, implement, and optimize enablement technologies (LMS, content platforms, coaching tools, analytics).

• Establish scalable coaching frameworks that empower frontline managers to drive performance and skill development.
• Reinforce consistent sales and customer engagement methodologies across teams.
• Enable leaders with data, tools, and best practices to coach effectively in enterprise security sales contexts.

• Define and track enablement KPIs tied to business outcomes, including ramp time, quota attainment, win rates, deal velocity, retention, and expansion.
• Use data and qualitative feedback to continuously improve programs and demonstrate ROI to executive stakeholders.
• Proactively identify skill gaps and readiness risks as Obsidian scales.

• Act as a connective layer between Revenue, Product, Marketing, and Customer Success to ensure alignment and execution.
• Represent the voice of the field, feeding insights back into product roadmap, messaging, and GTM strategy.

• 10+ years of experience in enablement, sales, customer success, or related go-to-market roles, with 5+ years in a leadership role.
• Proven experience building and scaling enablement programs in a high-growth B2B SaaS environment.
• Strong understanding of enterprise sales motions and long, multi-stakeholder buying cycles.
• Experience partnering closely with executive leadership and influencing at the C-suite level.
• Demonstrated ability to drive measurable improvements in productivity and performance.

• Experience in cybersecurity, cloud security, identity security, or adjacent enterprise security domains.
• Familiarity with modern sales methodologies (e.g., MEDDICC, Challenger).
• Experience enabling technical sellers (SEs) and security practitioners.
• Background in organizational change management or learning and development.

• Strategic and systems-level thinking
• Executive presence and strong stakeholder management
• Data-driven decision making
• Exceptional communication, facilitation, and storytelling skills
• Ability to drive adoption, behavior change, and consistency at scale

• Faster ramp and higher productivity across Sales, SE, and CS teams
• Confident, credible field teams who can clearly articulate Obsidian’s differentiated value
• Consistent execution across enterprise deals and customer engagements
• Strong alignment between enablement efforts and revenue outcomes
• A culture of continuous learning in a fast-moving security landscape