PEOPLE OPERATIONS LEAD

About You People Operations at Shepherd is about building the infrastructure that allows us to scale without losing what makes us great. We’re looking for an experienced People Ops leader to build and own the systems and programs that shape how we hire, develop, and retain our team. This person will play a central role in ensuring that as we grow, the culture and standards we’ve built continue to strengthen. This is a unique opportunity to join a dynamic early‑stage startup and take true greenfield ownership across all three pillars of People Operations: day‑to‑day execution, systems and tooling, and strategic programs. About The Role As we scale rapidly across multiple offices and functions, we’re making deliberate investments in the people, programs, and systems needed to support a company of our ambition. This role will be central to that effort — designing and building the foundations of our People Operations function as Shepherd continues to grow. Design and own Shepherd’s performance management framework, including review cadence, calibration methodology, rating rubrics, and documentation standards Evaluate, select, and implement a performance management platform (e.g., Lattice), including configuration, rollout, enablement, and ongoing administration Build and scale a manager development program for Shepherd’s growing cohort of first‑time and early‑career managers, including training materials, playbooks, and feedback loops with leadership Develop and maintain a company‑wide job leveling framework, with clear career paths, scope expectations, and level criteria across functions Partner with Operations and Finance to design and maintain compensation bands by level and function, and own the structure and execution of the compensation review cycle Partner with leadership on headcount planning and org design, supporting annual planning, role design, and organisational structure decisions Own Shepherd’s onboarding and offboarding experience, including structured 30/60/90‑day check‑ins Ensure Shepherd’s employee handbook, policies, and HR documentation remain current as we scale Manage the day‑to‑day relationship with Shepherd’s PEO, including payroll, benefits administration, and compliance across a multi‑office footprint Serve as a trusted partner to managers and employees on day‑to‑day people questions, surfacing issues early and resolving them with the appropriate urgency You Would Be Our Dream Candidate If… You have 7+ years of HR / People Operations experience, including time at a high‑growth startup You’ve built core people programs from scratch, such as performance frameworks, compensation bands, or manager development You’ve designed and led training and enablement programs across an organization, from manager development to broader company‑wide initiatives You’re comfortable operating across the full People Ops stack, from day‑to‑day execution to systems and programme design You’ve partnered closely with senior leadership on compensation, org design, and culture You have experience working in PEO‑managed environments and with performance management tools like Lattice (or similar) You’re a self‑starter who thrives in ambiguity and takes ownership of defining and driving the work You’re highly organized and detail‑oriented, able to manage multiple priorities as the company scales You’re an excellent communicator, able to navigate complex or sensitive situations with clarity You lead with ownership, integrity, and accountability, and build people programmes that reflect those values Benefits Premium Healthcare – 100% contribution to top‑tier health, dental, and vision Fertility benefits and family building support Unlimited PTO – flexibility to take the time off, recharge, and perform Daily lunches, dinners, and snacks – we work together, and enjoy meals together too Locations: SF, NYC, Dallas‑Fort Worth, Chicago and LA offices Professional Development – access to premium coaching, including leadership development Competitive 401(k) plan Dog‑friendly office – plenty of dogs to play with and make friends with in the SF office Compensation Range: $160K - $210K #J-18808-Ljbffr Shepherd Insurance Agency