What We Do

• Complex commercial construction projects routinely wait weeks for a single quote
• Legacy carriers rely on static applications and disconnected systems
• Brokers chase carriers through calls, emails, and resubmissions
• Faster decisions
• Smarter, more accurate pricing
• Better risk outcomes for insureds who invest in safer practices

Our Investors

• Intact Private Capital https://www.intactfc.com/about-us/intact-ventures
• Spark Capital https://www.sparkcapital.com/
• Costanoa Ventures https://costanoa.vc/
• Y Combinator https://www.ycombinator.com/
• Susa Ventures https://www.susaventures.com/
• And several others

Our Team

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About https://www.shepherdinsurance.com/about page to learn more.

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

• 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 organizational 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 program 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 programs 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

🖥️ 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