Senior AI & Product Enablement Specialist Job Washington area,District of Columbia USA,IT/Tech

In the cloud, every second counts. On the leading edge of security, Sysdig stops attacks in real-time by instantly detecting changes in cloud security risk with runtime insights and open source Falco. Trusted by a large enterprise customer base, we are a well-funded startup, passionate open source enthusiasts at heart, and problem-solvers who are building and delivering powerful solutions to secure cloud-native applications.

We have an organizational focus on delivering value to customers. We appreciate diverse opinions and open dialogue to spur ideas and we believe in working together to achieve our goals. We're an international company that understands how to cultivate an inclusive environment across all teams.

And we're a great place to work too - we've been named a "Best Places to Work" by Inc, the San Francisco Business Time, and Built In, with recognitions ranging from "Best Benefits" to a "Best Company for Happiness".

We are looking for driven team members who want to join us on our mission to lead cloud security globally. Does this sound like the right place for you?

What you will do:

Design and build complex, hands-on lab scenarios that showcase Sysdig across containers, Kubernetes, Linux and public cloud, realistic enough to mirror what customers actually run.
Own the automation and reliability of the training platform (e.g. Instruqt, LMS and supporting tooling): provisioning, scripting, and troubleshooting environments so sessions never fall over.
Design and deliver engaging technical training, workshops and demos for diverse audiences, adapting your approach to each audience’s maturity level.
Apply instructional design principles to turn Sysdig’s solutions into structured learning journeys with clear outcomes, and author clear courseware and technical documentation (YAML- and Markdown-based content).
Use AI coding/agent clients (e.g. Claude Code, Codex, or equivalents) to accelerate lab creation, scripting, content drafting and troubleshooting, applying sound judgment on when to verify or refine their output.
Drive projects from inception to delivery autonomously, making sound decisions within broad parameters and escalating risks appropriately.
Partner with Product, Customer Success and Marketing to keep training relevant and aligned to feature value propositions, and represent Sysdig in customer and partner sessions.
Translate customer and internal feedback into content and process improvements, help define best practices and teaching standards, and mentor more junior team members.

What you will bring with you:

Deep, hands-on expertise in containers, orchestration (Kubernetes), Linux and/or public cloud services, plus a solid grasp of the cloud-native ecosystem (Cloud Native, CIEM, CNAPP) and Dev Ops tools and methodologies.
Fluent coding in 1–2 languages (Bash, Python, Go) and comfort authoring YAML- and Markdown-based content and working with APIs.
3+ years instructing and breaking complex concepts down for the target audience, with a strong track record of engaging delivery and clear, comprehensive technical writing.
The ability to both build training and deliver it confidently; you are strong on the technical craft and the communication craft, not just one.
Comfort working with AI coding/agent CLI clients (Claude Code, Codex, or similar) as part of your daily workflow.
Fluent English, written and spoken, for delivering global training.

What we look for:

Advanced, wide-ranging experience used to develop and refine learning solutions, with the creativity and structure to solve complex problems and the communication skill to make them land.
An analytical approach that uses feedback, data and metrics to improve labs, content and delivery.
Someone who helps define new best practices, mentors others, and works autonomously under broad direction.

When you join Sysdig, you can expect:

Extra days off to prioritize your well-being
Mental health support for you and your family through the Modern Health app
Great compensation package

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.