Strategic People Programs Lead

Jobtailor; San Francisco (CA); On-site; USD 140,000 - 190,000; Full time

Job summary

Jobtailor is seeking a senior People Operations / Chief of Staff to own the operating rhythm of the People team and drive multi-quarter initiatives, including AI/automation integrations. You will design scalable planning processes, lead headcount forecasting, and partner closely with senior leadership to align priorities and execute complex programs.

You will map workflows, conduct audits, and deliver scalable, data-driven solutions such as organizational health dashboards, while navigating

Qualifications

• 7+ years of varied experience across G&A functions, including HR, People Operations, HR technology, BizOps, special projects, or Chief of Staff roles.
• Ability to design, plan, and execute multi-quarter initiatives end-to-end.
• Strong business and process design skills, including requirements gathering, problem-solving, implementation, and change management.
• Experience managing across organizational boundaries without direct authority.
• Ability to align stakeholders, drive decisions, and measure impact.
• Comfort with ambiguity in a fast-moving, high-growth environment.
• Experience with technology evaluation, implementation, and vendor management.
• Exposure to ATS, HRIS, or People technology.
• Understanding of People data, reporting, and workflows.
• Interest in AI and automation for People processes.
• Program/project management skills and execution bias.
• Comfort acting as a thought partner to senior leaders and influencing without authority.
• Intellectual curiosity about People operations, technology, and AI.
• Adaptability between strategic thinking and tactical problem-solving.
• Track record of building scalable processes, systems, and solutions.

Responsibilities

• Own the People team's operating rhythm, including all-hands, leadership meetings, quarterly OKR planning, annual strategy planning, and offsites
• Design and implement a documented, repeatable planning process that reduces ad hoc coordination and SVP operational involvement
• Own headcount planning and forecasting, including scenarios and functional headcount needs
• Execute major multi-quarter initiatives, including the M&A integration playbook, UK equity/visa sponsorship infrastructure, Ashby ATS transition, HRIS evaluation, and ad hoc projects
• Partner with the Director of People Operations on prioritization, scope, and sequencing
• Map People workflows to identify AI and automation efficiencies
• Conduct a workflow audit within six months and identify 3–5 high-impact AI opportunities
• Build scalable, one-team solutions such as an organizational health dashboard
• Partner with IT and Legal on AI/Claude usage guardrails and advocate for a revised AI usage policy
• Serve as a thought partner and ideator to the SVP of People
• Lead execution and projects so the SVP can focus on strategy
• Lead through expertise, judgment, influence, and operating mechanisms without direct management authority

Skills

People Operations

Multi-Quarter Initiative

Stakeholder Alignment

Process Design

AI & Automation

Tools

ATS

HRIS

AI Tools

Automation Software

Job description

Jobtailor is seeking a senior People Operations / Chief of Staff to own the operating rhythm of the People team and drive multi-quarter initiatives, including AI/automation integrations. You will design scalable planning processes, lead headcount forecasting, and partner closely with senior leadership to align priorities and execute complex programs.

You will map workflows, conduct audits, and deliver scalable, data-driven solutions such as organizational health dashboards, while navigating