Director Of People Jobs in Chicago, IL

Our People team is a high-performing group, deeply committed to our Karbonites and values. We are looking for an operations leader who is AI-native to their core, builds systems that scale, and treats agentic workflows as the foundation of how modern People Operations functions. Reporting to the VP of People, this role owns the operational backbone of how we hire, onboard, and support Karbonites across six countries, with a clear runway toward growing a pillar of the People function.

We are looking for someone unique. You're the right operations leader for us if your default instinct when you see a manual process is to ask "what agent should own this?" before "who should own this?". You don't just use AI tools — you architect the workflows, build the agents, and design the systems that let a lean People team operate at the scale of a much larger one. You're equally fluent in the mechanics of multi-country HR compliance and the mechanics of prompt engineering, integrations, and agentic orchestration.

This is not a coordinator role and it is not a ticket-closing role. You'll spend your time designing how work gets done, not doing the work itself wherever an agent can do it instead. You'll own the operational engine across People Ops, with a meaningful TA overlay (forecasting, reporting, data integrity) and benefits ownership embedded in the role. You'll be measured on how much of that engine runs without human intervention.

About the Role

• Architect and continuously improve the end-to-end People Ops and TA operational stack, embedding AI agents and agentic workflows as the default execution layer across onboarding, offboarding, employee lifecycle changes, and the recruiting funnel.
• Design and deploy AI agents to own routine operational work end-to-end, including onboarding task orchestration, compliance documentation, offer letter generation, interview scheduling, and tier-1 employee queries.
• Use AI to manage and monitor multi-country HR compliance across our six operating regions, building agentic checks that flag risk, surface regulatory changes, and keep our entity-level obligations current without manual tracking.
• Build AI-powered reporting and analytics across the People and TA function, producing real-time dashboards, hiring funnel insights, and operational health metrics that the VP of People and pillar leads can act on without requesting them.
• Run our HRIS, ATS, and broader People tech stack as an integrated, AI-augmented system, evaluating new tools through the lens of agent-readiness and API-first design rather than feature lists.
• Use AI to support the TA function with a focus on pipeline forecasting, recruiting data integrity, and funnel reporting, partnering with hiring managers to embed AI into how they track and interpret hiring data.
• Own benefits administration and vendor management across our US entity, using AI to streamline open enrollment, automate eligibility tracking, and surface utilization insights that inform future benefits strategy.
• Leverage AI to deliver a seamless, high-quality employee experience at scale, anticipating friction points across the lifecycle and deploying agents or workflows to resolve them before they become tickets.
• Drive AI-led process documentation and knowledge management across People Ops, ensuring every workflow is documented in a way that is both human-readable and agent-executable.
• Partner with Finance, IT, and Legal using AI-augmented workflows for cross-functional operations, including headcount planning, system access provisioning, and contract and policy management.
• Coach and uplift the broader People team on AI fluency, agent design, and operational automation, modeling what an AI-forward People Ops function looks like in practice.
• Own AI governance for the People function, ensuring our use of agents and AI tools is compliant, ethical, and aligned with how we handle sensitive employee and candidate data globally.

About You!

• 5+ years of progressive experience across People Operations or HR Ops, with at least some leadership or team lead experience.
• Prior SaaS or high-growth tech experience is essential. You understand how a global, multi-entity People function operates and what breaks at scale.
• Deep, hands-on fluency with AI tools, agent builders, and agentic workflows. You've personally built, deployed, and maintained agents that own real operational work, not just experimented with them.
• Strong technical instincts: comfortable with APIs, integrations, automation platforms (Zapier, Make, n8n, or similar), and prompt engineering as core craft, not adjacent skills.
• Multi-country HR Ops experience strongly preferred but not essential, ideally across some combination of the US, UK, Australia/NZ, Canada, and the Philippines.
• Proven ability to redesign operational processes from the ground up rather than incrementally improve them, with a clear bias toward automation over headcount.
• Working knowledge of US benefits administration, including open enrollment, carrier management, and compliance (ACA, ERISA basics).
• Working knowledge of HR compliance across multiple jurisdictions, with the judgment to know when AI can own a compliance task and when a human must.
• Data fluency: you build operational dashboards, you read funnel metrics natively, and you use AI to go deeper and faster than the tools alone allow.
• A systems thinker who can hold the full operational picture across People Ops, TA, and Benefits simultaneously, and design how they interlock.
• Player-coach mindset: senior enough to operate independently, willing to build and ship the work yourself, with the trajectory and appetite to grow a pillar as we scale.
• Unquestioned integrity, high EQ, and discretion with sensitive employee and candidate data.
• Genuine excitement about where AI is taking the People function, and a strong point of view on what an AI-native HR operation should look like.

Why work at Karbon?

• Gain global experience across the USA, Australia, New Zealand, UK, Canada and the Philippines
• Excellent benefits package including:
• • Paid Flexible Time Off with an encouraged 3 weeks use per year
  • Company paid medical for you and eligible spouse/partner and dependents
  • Company paid dental and vision and eligible spouse/partner and dependents
  • Fully company funded short and long term disability
  • Fully company paid life insurance
  • 401(k) with company matching
  • Flexible Spending Account
  • Up to 8 weeks paid parental leave
  • Work-from-home stipend
• Work with (and learn from) an experienced, high-performing team
• A collaborative, team-oriented culture that embraces diversity, invests in development and provides consistent feedback
• Be part of a fast-growing company that firmly believes in promoting high performers from within