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Opportunities in the LiveOak Portfolio

AI Enablement Engineer

Chainguard

Chainguard

Software Engineering, Data Science
United States · Remote
USD 157k-184k / year + Equity
Posted on Sep 26, 2025

About the Role

At Chainguard, culture isn’t an afterthought—it’s our operating system. Our Culture & Belonging team’s mission is to code a culture of belonging, where our values and voices set the vibe. We envision Chainguard as a place where culture fuels innovation, belonging drives performance, and every employee can do the best work of their career.

As we scale fast, we want our employee experience to scale just as smartly. That’s where this role comes in. We’re looking for our first AI Enablement Engineer—a builder who will design and launch AI-powered tools that make work easier, smarter, and more human for Chainguardians.

This is an engineering role with a product mindset, focused on internal enablement. You’ll work at the intersection of culture, learning, and technology—helping us use AI to automate workflows, create just-in-time enablement, and reduce admin friction so employees and managers can focus on impact.

What You’ll Do

  • Build, launch, and iterate on AI-powered internal tools for employee enablement (e.g., adaptive 1:1 prompts, just-in-time performance coaching, automated culture dashboards).
  • Integrate AI into Google Workspace, Slack, Salesforce, and other core tools via APIs and Google Apps Script.
  • Partner with the Culture & Belonging team to understand friction points in manager/employee workflows.
  • Pilot new products quickly, gather user feedback, and iterate toward adoption.
  • Ensure tools are ethical, opt-in, and transparent in how AI is used.
  • Document builds and create reusable frameworks so solutions can scale.
  • Own and co-lead 1-2 Culture & Belonging team programs each year (e.g., onboarding enhancements, recognition programs, or community-driven initiatives)—bringing both engineering and team-player skills to the work.

What Success Looks Like

  • 2+ AI-powered pilots shipped in your first 6 months (e.g., adaptive 1:1 assistant, AI-enabled performance assessment prototype).
  • High adoption (75%+ usage in pilot groups).
  • Measurable impact on employee/manager experience (time saved, improved eSAT).
  • A roadmap of AI opportunities aligned to Chainguard’s culture strategy.

What We’re Looking For

  • 3+ years in software engineering, automation, or product engineering.
  • Strong skills in Python, JavaScript/TypeScript, and Google Apps Script.
  • Experience with LLMs (OpenAI, Anthropic, etc.) and orchestration frameworks (LangChain, RAG pipelines).
  • Comfort working with APIs (Google, Salesforce, Slack, etc.).
  • Product mindset: able to scope MVPs, prioritize, and deliver iteratively.
  • Strong communicator—can explain technical concepts simply to non-technical teammates.
  • Passion for building tools that make work easier, more human, and more impactful.

And because you’ll be part of our Culture & Belonging team, we’re also looking for someone who:

  • Believes belonging is a business driver, not a bonus.
  • Collaborates with curiosity, kindness, and respect.
  • Thrives in co-creation with employees, not just building for them.
  • Values thoughtful growth—scaling quickly while staying rooted in who we are.
  • Uses data and feedback to celebrate wins and continuously improve.

Nice to Have

  • Experience in learning tech, HR tech, or employee experience tooling.
  • Familiarity with UX design principles.
  • Previous startup experience—comfortable shipping fast with scrappy solutions.

Why This Role Matters

As we grow past 500 employees, we can’t scale people programs with headcount alone. This role helps us leverage AI to scale belonging, learning, and enablement—making culture a competitive advantage for Chainguard.

Base Salary Range
$157,000$184,000 USD

About Us

Chainguard is the secure foundation for software development and deployment. By providing guarded open source software, built from source and updated continuously, Chainguard helps organizations eliminate threats in their software supply chains.

Founded by the industry's leading experts on open source software, security and cloud native development, Chainguard has built the largest library of open source software that is secure by default.

Chainguard’s mission is to be the safe source for open source.

We live and breathe our company values:

We are customer obsessed - We focus on delivering solutions to our customers that create value and make their lives better.

We have a bias for intentional action - We prioritize, plan, try things, and fail fast.

We don’t take ourselves too seriously (but we do serious work) - We are solving an important problem which takes focus, but we also like to enjoy the journey.

We trust each other and assume good intentions - We’re transparent with decisions to empower team members to make well informed decisions.

A few of the benefits we offer:

  • Flexible & Remote-First Culture: Work remotely with team meetup opportunities, bi-annual destination summits, and a monthly stipend for coworking spaces, phone and internet costs.
  • Our Approach to Equity: Receive stock options upon hire and promotion. Plus, you can participate in secondary offerings and have 10 years to exercise your options (yes, you read that correctly: 10 years!).
  • 100% Covered Health Insurance: We cover 100% of your health, vision and dental insurance premiums for you and your dependents. Nothing comes out of your paycheck.
  • ∞ Flexible Time Off: Take the time you need – to do our best work, we need to recharge and reset.
  • 18 Weeks Paid Parental Leave: We offer 18 weeks for birthing parents and 12 weeks for non-birthing parents, with the option to use it all at once or throughout your child's first year.
  • For a full list of our benefits and rewards, click here.

If your experience is close but doesn’t fulfill all requirements, please apply. We’re building the best team in technology and are focused on hiring “Chainguardians'' with unique backgrounds, perspectives, and experiences.

Chainguard is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law.

By submitting your application, you acknowledge that Chainguard will process your personal data in accordance with Chainguard’s Privacy Policy.

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