Enablement and Learning Program Manager

Sysdig, Inc.; Northern (KY); Hybrid; USD 128,000 - 160,000; Full time

Benefits offered by this job

401(k) Retirement Savings Plan

Maternity and Parental Leave

Mental health support

Full health benefits

Job summary

Sysdig, Inc. is seeking an experienced enablement leader to design and run our GTM enablement program. You will own onboarding, certification, and ongoing Mic and adoption analytics, coordinating with Product Marketing, RevOps, Sales and CS to tie enablement to pipeline and retention.

The role requires building scalable enablement processes, using LMS, Gong, Clay, and Claude to drive measurable outcomes and AI-driven improvements across the revenue teams.

Qualifications

• Experience designing and managing enablement programs.
• Ability to design and implement measurement frameworks.
• Strong cross-functional collaboration across Sales, CS, RevOps and Marketing.
• Hands-on fluency with modern GTM tooling and AI-native platforms.

Responsibilities

• Author enablement charter and operating model with sign-off from leadership.
• Own onboarding and certification framework for GTM roles, plus recertification cadence.
• Drive adoption of MEDDPICC and coordinate GTM moments with Marketing and Product teams.
• Own enablement tech stack and AI-native GTM tools with role-based training.

Skills

Enablement strategy

Measurement frameworks

Cross-functional collaboration

GTM tooling

AI adoption

Tools

LMS

Gong

Clay

Claude

Job description

At Sysdig, we believe cloud security isn't a compromise - it's a promise. From the start, our mission has been clear: to help organizations secure innovation in the cloud, the right way.

We created Falco, the open standard for cloud threat detection, and continue to lead the cloud security market with runtime insights, open innovation, and agentic Al. Creators of technology trusted by over 60% of the Fortune 500, Sysdig gives teams the real-time clarity to move fast and defend what matters most.

Culture matters here. We believe diversity fuels stronger ideas, and open dialogue drives sharper decisions. Recognized as a Best Place to Work and one of Deloitte's fastest-growing companies for the past 5 years, we're here to raise the standard for what cloud security and workplace culture should be.

If you have the passion to dig deeper, the desire to challenge convention, and the curiosity to build something better, Sysdig is the right place for you.

What you will do

• Author Sysdig's enablement charter and operating model — what enablement owns, how success is measured, and how it's inspected — and get sign-off from Sales, CS, and RevOps leadership.
• Own new-hire onboarding and the certification framework for GTM roles, with a clear, measured path to productivity. Build the ongoing recertification cadence so the program holds up as the team and product evolve.
• Drive adoption and reinforcement of our sales methodology (e.g., MEDDPICC) and equip managers to coach it day-to-day. Coordinate delivery for major GTM moments like SKO and product launches, partnering with Product Marketing, who owns the underlying content.
• Own the enablement tech stack (LMS, conversation intelligence) and drive structured adoption of AI-native GTM tools like Clay and enterprise Claude across the revenue org — role-based training and champions, not one-off demos.
• Build and maintain the enablement KPI scorecard — leading indicators like training completion and certification pass rates, lagging indicators like ramp time and win rate — and use it to show where programs are and aren't moving the business.
• Partner with Product Marketing on content adoption (they create, including battlecards; you drive field usage), RevOps on systems and reporting, and Sales/CS leadership to keep the roadmap tied to real pipeline and retention priorities.

What you will bring with you

• 5–8+ years in sales, revenue, or GTM enablement, including experience building or significantly rebuilding a program (not just running an existing one).
• A track record of designing measurement frameworks
• Hands-on fluency with modern GTM and enablement tooling: LMS/content platforms, conversation intelligence (e.g., Gong), and AI-native GTM tools (e.g., Clay) and enterprise AI assistants (e.g., Claude) — you direct these tools and drive adoption, not just use them yourself.
• Experience with a sales methodology framework (e.g., MEDDPICC, Command of the Message) and reinforcing it through coaching, not just a slide deck.
• Excellent cross-functional collaboration skills — you can align Sales, CS, RevOps, and Product Marketing around a shared enablement plan without owning their turf.
• A builder's mindset: comfortable defining charter and structure where none exists yet, and comfortable being judged on adoption and business metrics, not activity.

What we look for

• Prior enablement experience in cybersecurity, cloud security, or infrastructure software.
• Experience standing up or significantly evolving an enablement function at a company going through a platform or GTM transformation.
• Experience running AI adoption/change-management programs (usage metrics, champions programs, structured rollout) rather than ad hoc tool training.

When you join Sysdig, you can expect

• Extra days off to prioritize your well-being
• 401(k) Retirement Savings Plan with a 3% company match
• Maternity and Parental Leave
• Mental health support for you and your family through the Modern Health app
• Full health benefits package for you and your family

The U.S. annual salary range for this full-time position is between 128,000 and 160,000 USD/year. Actual offers may be higher or lower than this range based on a variety of factors, including your work location, job-related experience and education.

Sysdig values a diverse workplace and encourages women, people of color, LGBTQIA+ individuals, people with disabilities, members of ethnic minorities, foreign-born residents, and veterans to apply. Sysdig is an equal-opportunity employer. Sysdig does not discriminate on the basis of race, color, religion, sex, national origin, age, disability, genetic information, sexual orientation, gender identity, or any other legally protected status.