People Operations Lead

Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. Our mission is to make risk frictionless for the builders and operators shaping the physical world — protecting progress from concept through construction and into decades of operation.

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:

• 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

We built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real-time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.

We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.

With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:

• Faster decisions

• Smarter, more accurate pricing

• Better risk outcomes for insureds who invest in safer practices

We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.

In March 2026, Shepherd raised a $42M Series B — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

• Intact Private Capital

• Spark Capital

• Costanoa Ventures

• Y Combinator

• Susa Ventures

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

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.

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 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 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

🏥 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