Build and lead Sysdig’s GTM enablement function, including onboarding, certifications, sales methodology reinforcement, AI-tool adoption, enablement technology, KPI measurement, and major GTM events. Partner with Sales, Customer Success, Revenue Operations, and Product Marketing to improve ramp time, field adoption, pipeline performance, and retention. The role requires experience creating or significantly transforming enablement programs, preferably in cybersecurity, cloud security, or infrastructure software.
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.
#LI-MC1
#LI-Remote
Similar Jobs
Artificial Intelligence • Fintech • Hardware • Information Technology • Sales • Software • Transportation
Leads Motive’s internal communications strategy, narrative, and cadence across company-wide forums, executive messaging, video, Slack, intranet, email, and other channels. Advises executives, supports crisis and change communications, aligns internal and external messaging, measures employee sentiment, and improves engagement programs. The role also partners with Corporate Communications, Legal, and People teams and mentors communications talent while remaining an individual contributor.
Top Skills:
Ai-Enabled ToolsEmailIntranetSlackVideo Communications
Beauty • Robotics • Design • Appliances • Manufacturing
Provides Tier 1 IT support for global associates, troubleshooting Windows and macOS endpoints, networks, identity and access, Microsoft 365, and software issues. Manages onboarding, offboarding, endpoint provisioning, and device administration using Intune, Autopilot, and Jamf. Documents resolutions, supports major incidents, escalates complex issues, and improves support processes. Requires up to 10% domestic and international travel and occasional after-hours support.
Top Skills:
Active DirectoryConfluenceiOSJAMFJira Service ManagementmacOSMicrosoft 365Microsoft Entra IdMicrosoft IntuneWifiWindowsWindows Autopilot
Blockchain • Fintech • Payments • Consulting • Cryptocurrency • Cybersecurity • Quantum Computing
Owns new-logo acquisition and expansion across enterprise accounts for Mastercard Identity’s fraud and identity data products. The role prospectively builds pipeline, manages consultative and technical sales cycles, engages fraud, payment risk, trust and safety, data science, and engineering stakeholders, represents the company at industry events, and accurately forecasts against quota.
Top Skills:
APIsData ScienceFraud ModelsIdentity DataWeb-Based Portals
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
