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Head of Enablement

US - Remote
Founded in 2017, Obsidian Security was created to close a critical gap: securing the SaaS applications where modern business happens—platforms like Microsoft 365, Salesforce, and hundreds more. 
 
Backed by top investors including Greylock, Norwest Venture Partners, and IVP, we’ve built a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source. Our team includes leaders who helped define the categories of endpoint and identity security at CrowdStrike, Okta, Cylance, and Carbon Black. 
 
Now, we’re transforming how SaaS is secured—in the era of agentic AI. 
 
Today, Obsidian is trusted by global enterprises like Snowflake, T-Mobile, and Pure Storage. We protect more than 200 organizations across North America, Europe, the Middle East, Southeast Asia, Australia, and New Zealand—including many of the world’s largest Fortune 1000 and Global 2000 companies.
 
With strong global momentum, a growing partner ecosystem including SentinelOne, Databricks, and Google Cloud, and a major fundraise on the horizon, we’re scaling quickly toward long-term growth and IPO readiness. Join us as we define the future of SaaS security!

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.

Key Responsibilities

Enablement Strategy & Leadership

  • 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.

Sales & Enterprise Go-To-Market Enablement

  • 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.

Technical & Security Enablement

  • 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.

Content, Programs & Tools

  • 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).

Coaching, Manager Enablement & Behavior Change

  • 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.

Measurement & Business Impact

  • 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.

Cross-Functional Partnership

  • 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.

Required Qualifications

  • 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.

Preferred Qualifications

  • 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.

Key Competencies

  • 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

What Success Looks Like at Obsidian

  • 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



Employee Benefits

Our competitive benefits packages are designed to support our employees' well-being, both at work and at home.  Our US based employees enjoy:

  • 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

For more details on our US benefits, or for information on our international benefits, please see here.

Pay Transparancy

Please note that the base pay range is a guideline and for candidates who receive an offer, the base pay will vary based on factors such as work location, as well as the knowledge, skills and experience of the candidate. In addition to a competitive base salary, this position is eligible for equity awards and may be eligible for sales commission or incentive compensation based on the role or function within the company.

At Obsidian, we are proud to be an equal-opportunity employer. We value diversity and hire for talent, passion, and compassion. In compliance with federal law, all persons hired will be required to submit satisfactory proof of identity and legal authorization.  If you have a need that requires accommodation, please contact accommodations@obsidiansecurity.com

Information collected and processed as part of any job applications you choose to submit is subject to Obsidian’s Applicant Privacy Policy.

Base Salary Range

$195,000 - $240,000 USD

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