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Sitemate is seeking a Director of People Operations to lead the complete rebuild of the People Operations function for the AI era. The company builds software and AI agents for construction, infrastructure, and industrial sectors, with 200 people across 18+ countries.
You will own People Operations end-to-end: global payroll, employee lifecycle, talent acquisition, IT provisioning, and all people programs including performance management, engagement, learning and development, leveling, and compensation. You lead a team of two: a Senior Talent Acquisition Manager and a People Operations Manager.
The core mandate is to architect the next version of People Operations built for automation and AI agents, keeping the team small as the company scales. This is a hands-on, builder-first role where you personally build systems, agents, and playbooks, setting the bar through your own work. You will design how Rippling, Remote, and Ashby work together; build and maintain frameworks and playbooks that managers run independently; personally build automations and AI agent workflows; and handle complex employee relations and compliance cases with Legal.
Key priorities in order: maintain payroll, recruitment, and compliance operations; map manual admin steps across all People processes and identify automation opportunities; design the next People Operations architecture; build the first agents and automations; convert people programs into self-serve playbooks; and establish clear priorities and SLAs for the People Operations Manager.
Success metrics at 90 days include mapping manual admin with a written automation roadmap, deploying the first live automation with measured impact, closing all global payroll runs on time, and assigning owners to all in-flight items. At 6 months, the new People Operations design is agreed and being built, managers can run at least one full people cycle from a playbook or agent, and function SLAs and KPIs are reported. At 12 months, calibration and promotion outcomes are standardized across departments with supporting data, and succession planning is in place.
You will work closely with the CEO on translating company strategy into people priorities, partner with Finance on payroll and compensation, coordinate with Legal on compliance, and partner with department leaders on org design and hiring.
Sitemate operates with transparency (monthly all-hands sharing metrics and financials), player-coach leadership at every level, and a global footprint. The company values building People Operations like a product, designing AI-native processes, shipping the org chart, and growing from within.
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 their 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 run 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 or vendors to build detail; you measure value by being the person everyone asks; you'd treat AI and automation as someone else's project; you need very stable, clearly defined reporting lines.
