About this role.
Obsidian Security is seeking a senior GTM enablement leader to build and operate enablement across sales, technical pre- and post-sales teams, and BDRs. The role owns onboarding, role-based ramp, ongoing development, call-based coaching, and the operating cadence that connects GTM strategy to field execution. Success is measured through business outcomes including reduced ramp time, higher productive sales participation, pipeline efficiency, and improved win rates. This leader will hire and develop an enablement team while partnering closely with Product Marketing, Product, Sales Engineering, Customer Success, RevOps, and GTM leadership. Cybersecurity domain knowledge, enterprise sales-motion expertise, MEDDIC/MEDDPICC fluency, analytics, and strong people leadership are central to the role.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Sample interview questions
I would begin by baselining ramp, pipeline, conversion, win-rate, and call-quality data by role and segment. I would then interview frontline leaders and review representative Gong calls to identify the highest-impact behavioral gaps. From there, I would implement a role-based cadence for onboarding, deal coaching, manager reinforcement, product launches, and quarterly skill development, with named owners and measurable outcomes for each program.
I use call intelligence to define observable behaviors rather than relying on course-completion metrics. For example, I would examine whether discovery calls establish business pain, quantify impact, identify decision criteria, and secure next steps; then I would create targeted coaching, manager scorecards, and practice sessions around the weakest behaviors. I would measure adoption through subsequent call samples and connect the change to stage conversion, pipeline quality, or win-rate movement.
I would create distinct competency maps and productivity milestones for each role, such as first qualified pipeline, first technical validation, first proof of value, or first closed deal. The ramp experience would combine essential product and security knowledge with scenario practice, observed field execution, manager coaching, and just-in-time resources. Progress would be based on demonstrated capability and live-deal outcomes rather than time spent in training.
I embed the methodology in the actual selling workflow: discovery preparation, call coaching, opportunity reviews, CRM inspection, deal strategy, and manager one-on-ones. I define a small set of observable behaviors for each stage, train managers to coach those behaviors consistently, and inspect both call evidence and opportunity data. Success is assessed through improved deal qualification, forecast quality, stage progression, and conversion—not certification scores alone.
I would align partners around a shared business problem, the target metric, and a clear decision process rather than around requests for training assets. For each initiative, I would document the audience, desired behavior change, owner, timeline, dependencies, and measurement plan. I would use regular operating reviews to surface tradeoffs early, confirm commitments, and keep work focused on the initiatives most likely to improve field execution and revenue outcomes.
Obsidian Security is the leading SaaS security platform, trusted by global enterprises like Snowflake, T-Mobile, and Algolia. We protect 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.
Founded in 2017 and backed by top investors like Greylock, Obsidian was built to close a critical gap: securing SaaS apps where business happens—Microsoft 365, Salesforce, and hundreds more. The company does this by offering a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source. Obsidian was built by leaders who redefined endpoint and identity security at CrowdStrike, Okta, Cylance, and Carbon Black. Now, they’re transforming how SaaS is secured.
With AI driving rapid SaaS growth and complexity, agentic AI tools gain privileged access to sensitive data through integrations, creating new risks most security tools miss. Obsidian uniquely detects anomalous OAuth token activity and manages integration risks. Major announcements are on the horizon. Recognizing that SaaS security needs to evolve, Obsidian enables growing organizations to start with a lightweight, prevention-focused browser extension and expand coverage over time.
With global momentum, a growing partner ecosystem including SentinelOne, Databricks, and Google Cloud, and a major fundraise ahead, Obsidian is scaling rapidly toward long-term growth and IPO readiness.
About The Role
Obsidian is looking for a Head of GTM Enablement to own how our customer-facing teams learn, apply, and win. This role leads enablement across the full go-to-market motion: sales, technical (both pre and post sale), and BDR. The mandate is simple. Drive higher sales participation and faster revenue by shrinking ramp time, getting more reps into productive motion, making pipeline generation more efficient, and improving win rates.
This is not a content librarian or LMS administrator role. You will build and run the enablement operating system that turns strategy into consistent field execution, and you’ll measure success in reps ramped, deals progressed, and quota attained rather than slides shipped or courses completed. You will report to leadership, be a trusted operating partner to the broader GTM leadership team, and partner closely with Product Marketing, Product, Sales Engineering, Customer Success, and RevOps to keep the field sharp as the market for AI Security evolves.
What You’ll Do
Build the enablement operating system
- 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.
Sharpen field skills and deal execution
- 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.
Coach from real conversations
- 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.
Work AI first
- 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.
Lead the function
- 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.
How You’ll Be Measured
We measure enablement on outcomes, not activity. Your primary indicators are:
- Ramp time: how quickly new reps reach productivity milestones such as first pipeline generated and first deal, trending down over time.
- Sales participation rate: the percentage of customer-facing reps in productive motion and hitting plan, and how that moves quarter over quarter.
- Pipeline generation efficiency: more qualified pipeline produced per rep and per motion.
- Win rates: better conversion through the funnel and at close.
Who You Are
- 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.
How You Operate
- You get your truth from real customer conversations and deal data, not from completion reports.
- You are a builder, not an administrator. You measure your work in behavior changed and deals progressed.
- You are a coach. You can listen to a discovery call and give a rep an audible they can use tomorrow.
- You see modern enablement as in the moment and systematized, not as a quarterly bootcamp or a static content page.
- You are proactive. You see what the field needs before it is asked for and drive alignment across functions to get ahead of it.
- You are commercially literate. You can read a forecast, spot an execution gap, and translate it into a coaching or content intervention.
- You hold a high bar but you don’t let perfect get in the way of impact.
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
$180,000—$230,000 USD
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