People Operations Lead at Withshepherd

You will be the first dedicated People Operations hire, building the entire HR function from scratch for a 75-person startup. This greenfield role involves designing performance frameworks, compensation bands, and manager development programs. You will partner directly with leadership to define the culture and operational infrastructure that supports scaling high-hazard industry insurance through autonomous underwriting.

• Design and implement Shepherd’s first performance management framework, including calibration methodologies, rating rubrics, and the rollout of tools like Lattice.
• Build a comprehensive manager development program from scratch to support first-time and early-career managers through playbooks, training, and feedback loops.
• Partner with Finance and Operations to establish company-wide job leveling frameworks and data-driven compensation bands across a multi-office footprint.

• 7+ years of People Operations experience, with a proven track record of building core HR programs from zero to one within high-growth startups (50-200 people).
• Expert-level capability in designing compensation structures, leveling frameworks, and organizational designs while managing day-to-day PEO relationships and payroll.
• A self-starter who excels in ambiguity, possesses exceptional communication skills for sensitive situations, and maintains a high bar for accountability and integrity.

• Take true greenfield ownership as the first People Ops lead, designing foundational systems for a high-growth startup that just secured a $42M Series B led by one of the world's largest insurers.
• Direct impact on company culture and organizational design, partnering with executive leadership to scale a team that is pioneering fully agentic, autonomous underwriting technology.
• Exceptional benefits including 100% healthcare coverage, fertility support, unlimited PTO, and professional coaching within a high-performance environment that blends technology and insurance expertise.