Sysdig

Cloud-native security and monitoring for apps

Enablement and Learning Program Manager

Sales OperationsConfirmed live in the last 24 hours

Full-timeRemote in USARemote

About the Job

Requirements

5–8+ years of experience in sales, revenue, or go-to-market enablement, including experience building or significantly rebuilding an enablement program.
Experience designing measurement frameworks.
Hands-on fluency with modern go-to-market and enablement tooling, including learning management systems, content platforms, conversation intelligence, AI-native go-to-market tools, and enterprise AI assistants.
Experience with a sales methodology framework such as MEDDPICC or Command of the Message and reinforcing it through coaching.
Ability to align Sales, Customer Success, Revenue Operations, and Product Marketing around a shared enablement plan without owning their functions.
Ability to define charter and structure where none exists and be evaluated on adoption and business metrics.

Responsibilities

Author the enablement charter and operating model, define enablement ownership and success measures, and obtain sign-off from Sales, Customer Success, and Revenue Operations leadership.
Own new-hire onboarding and the certification framework for go-to-market roles, including a measured path to productivity.
Build and maintain the ongoing recertification cadence as the team and product evolve.
Drive adoption and reinforcement of the sales methodology and equip managers to coach it day to day.
Coordinate delivery for major go-to-market moments such as sales kickoffs and product launches, partnering with Product Marketing on the underlying content.
Own the enablement technology stack, including the learning management system and conversation intelligence tools.
Drive structured adoption of AI-native go-to-market tools and enterprise AI assistants across the revenue organization through role-based training and champions programs.
Build and maintain the enablement KPI scorecard, including training completion, certification pass rates, ramp time, and win rate, and use it to evaluate business impact.
Partner with Product Marketing on content adoption, Revenue Operations on systems and reporting, and Sales and Customer Success leadership to align the roadmap with pipeline and retention priorities.

Desired Qualifications

Prior enablement experience in cybersecurity, cloud security, or infrastructure software.
Experience standing up or significantly evolving an enablement function at a company undergoing a platform or go-to-market transformation.
Experience running AI adoption or change-management programs using usage metrics, champions programs, and structured rollouts.

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.

We would love for you to join us! Please reach out even if your experience doesn't perfectly match the job description. We can always explore other options after starting the conversation. Your background and passion will set you apart, especially if your career path is different.

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.

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About the Company

Sysdig

Cloud-native security and monitoring for apps

Sysdig provides cloud-native security and monitoring solutions for applications running in containers and Kubernetes. It offers products like Sysdig Secure for security and Sysdig Monitor for performance monitoring, delivering data collection from cloud-native environments to help enterprises manage compliance, security, and performance. The platform typically uses agents and a SaaS or on-premises interface to collect telemetry, run security checks, and present dashboards, enabling real-time visibility and risk management across complex IT stacks. What sets Sysdig apart is its integrated approach that combines security, monitoring, and compliance tooling in one platform with scalable tiers, targeting large organizations across technology, finance, healthcare, and government sectors. The company’s goal is to help customers securely run cloud-native applications with continuous visibility and control, reducing risk while maintaining high performance.

Company size: 501-1,000
Company stage: Growth Equity (Non-Venture Capital)
Total funding: $729.5M
Headquarters: Raleigh, NC
Founded: 2013

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