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Sitemate is seeking a Head of People Operations to own and rebuild the People Operations function end-to-end for the AI era. The company builds software and AI agents for construction, infrastructure, and industrial sectors, with 200 people across 18+ countries and strong product-market fit backed by Blackbird.
You will lead a team of two (Senior Talent Acquisition Manager and People Operations Manager) and architect the next version of People Operations, designed for automation and AI agents to handle administrative work as the company scales. This is a hands-on, builder-first role where you personally design and build systems, agents, and playbooks.
Key responsibilities include:
- Designing the People Operations architecture across all entities, with automation as the default approach
- Building AI agents and automations for People processes, defining guardrails and data governance
- Creating frameworks and playbooks that enable managers to run people processes independently
- Owning People programs: career paths, leveling, compensation principles, L&D, performance and engagement cycles
- Establishing people data systems and engagement measurement for leadership decision-making
- Leading, coaching, and developing your team; making performance, promotion, and exit decisions
- Partnering with CEO on people strategy translation, Finance on payroll and compensation, Legal on compliance, and department leaders on org design and hiring
Day-to-day work includes personally building workflows and automations, designing how Rippling, Remote, and Ashby integrate, writing and maintaining playbooks, running the function's weekly cadence, coaching the team, handling complex employee relations cases, and owning calibration and promotion decisions.
Success metrics: By 90 days, map manual admin across People Operations and identify automation priorities; deploy first automation/agent in a live process; ensure all payroll runs close on time globally. By 6 months, finalize the next-version design, enable managers to run at least one full people cycle from playbook/agent, establish and report against SLAs and KPIs. By 12 months, calibration and promotion outcomes standardized across departments with supporting data; succession readiness for at least one key role.
The company operates on clear principles: build People Operations like a product with users and a roadmap; default to AI and automation; ship your org chart; avoid offloading thinking; assign single responsible owners; grow from within before hiring.
Requirements:
Must have:
- Operations or leadership experience through a comparable growth-stage transition (ideally 100–300 person scale-up)
- Systems architecture thinking: designing how multiple platforms and data work together so processes run without manual admin
- Hands-on experience personally building automations or AI agents
- Experience writing frameworks or playbooks that managers executed independently
- Comfort with ambiguity; ability to move fast on hypotheses and adjust as you learn
Nice to have:
- Series B or growth-stage scale-up experience
Essential tools:
- AI tools
- Project management and communication tools (Slack, Jira, Confluence)
Bonus tools:
- Zapier, Airtable, or similar no-code automation
- Rippling or comparable HRIS and global payroll platform
- Remote or comparable employer of record platform
- Ashby or comparable ATS
- AI coding tools (Claude, Claude Code)
Not a fit if: your instinct on broken processes is new policy/tools/headcount; you rely on IT/vendors to build details; you measure value by being the go-to person; you'd treat AI/automation as someone else's project; you need very stable, clearly defined reporting lines.
