What We Do

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 werent 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.

Were pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. Were 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. Were building:

• Faster decisions

• Smarter more accurate pricing

• Better risk outcomes for insureds who invest in safer practices

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

Our Investors

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 were building. Our investors:

• Intact Private Capital

• Spark Capital

• Costanoa Ventures

• Y Combinator

• Susa Ventures

• And several others

Our Team

Were a team of technologists and insurance enthusiasts bridging the two worlds together. Check out our 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. Were 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 weve 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 were 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 Shepherds 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 Shepherds 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 Shepherds onboarding and offboarding experience including structured 30/60/90-day check-ins

• Ensure Shepherds employee handbook policies and HR documentation remain current as we scale

• Manage the day-to-day relationship with Shepherds 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

• Youve built core people programs from scratch such as performance frameworks compensation bands or manager development

• Youve designed and led training and enablement programs across an organization from manager development to broader company-wide initiatives

• Youre comfortable operating across the full People Ops stack from day-to-day execution to systems and program design

• Youve 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)

• Youre a self-starter who thrives in ambiguity and takes ownership of defining and driving the work

• Youre highly organized and detail-oriented able to manage multiple priorities as the company scales

• Youre 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