Head of Finance

Shepherd • San Francisco, CA

6d • $275,000 - $400,000 • Onsite

About The Position

Shepherd is hiring a Head of Finance to own the company’s financial planning, accounting, controls, and reporting, while leading the operations teams that support its go-to-market engine. The role manages the Finance Lead and the Revenue Operations, Business Operations, and Analytics teams; works closely with the CEO; and partners with the Reinsurance and Capital Strategy leader as Shepherd adds risk-bearing capacity. It is based in Shepherd’s New York City or San Francisco offices.

The Head of Finance will own financial planning and forecasting, build product-level contribution margin analysis, and prepare reporting for the board, investors, carriers, and reinsurers. The role will partner on new risk-bearing structures and build the related entity, treasury, cash, payment-tracking, and reporting infrastructure. It will also oversee close, audit, tax, spend controls, and outsourced accounting, and lead operating functions spanning analytics, revenue operations, and business operations.

The base salary range is $275,000–$400,000, depending on location and experience, plus an annual performance bonus and equity. Shepherd describes its culture through four values: Think big, build big; Win together; Cross the aisle; and Go get it.

Requirements

• 10+ years of finance experience spanning FP&A, accounting, and strategic finance, including 4+ years leading teams at a venture-backed or high-growth company.
• Insurance finance experience at an MGA/MGU, carrier, reinsurer, or insurtech, including familiarity with commission and fee revenue, premium and claims flows, fiduciary accounts, bordereaux, and carrier and reinsurance reporting.
• Familiarity with risk-bearing structures such as captives, sidecars, quota shares, and fronting arrangements, and their accounting, cash, collateral, and regulatory requirements.
• Track record of running annual planning, forecasting, and budget-versus-actuals reviews on integrated models across revenue, headcount, operating expenses, and cash.
• Strong command of close, audit, tax, treasury, and internal controls, including management of outsourced accounting partners.
• Experience leading or partnering closely with revenue operations, business operations, and analytics teams.
• Executive presence with boards, investors, carriers, and reinsurers.
• Bias toward systems and automation, including building finance and payments infrastructure with engineering.
• Bachelor’s degree in finance, accounting, economics, or a related field.

Nice To Haves

• Fundraising experience.
• CPA, CFA, or MBA.

Responsibilities

• Own the annual operating plan, long-range model, monthly forecast, and budget-versus-actuals reviews across revenue, headcount, operating expenses, and cash.
• Build product-level contribution margin views to assess the economics of new product launches.
• Own reporting packages for the board, investors, carriers, and reinsurers, and support future fundraising.
• Partner with the Chief Insurance Officer and Reinsurance and Capital Strategy leader on the modeling, accounting treatment, capital and collateral needs, and reporting for risk-bearing structures, including captives, sidecars, quota shares, and fronting arrangements.
• Build entity, treasury, and cash infrastructure for risk-bearing structures, including premium trust and fiduciary accounts, collateral, intercompany flows, and regulatory filings.
• Build scalable carrier payment tracking and bordereaux reconciliation across carrier partners.
• Oversee close, audit, tax, and spend controls, and manage the outsourced accounting partner.
• Lead Analytics, Revenue Operations, and Business Operations across submission attribution, broker tiering, quota setting and compensation, underwriter enablement, partnerships, and marketing infrastructure.
• Connect plan, pipeline, and performance data in a unified operating cadence.
• Hire, coach, and develop the finance and operations teams.

Benefits

• 100% company contribution to health, dental, and vision coverage.
• Fertility benefits and family-building support.
• Unlimited PTO; another benefits section describes flexible PTO.
• Daily lunches, dinners, and snacks.
• Professional development, including access to premium coaching and leadership development.
• Competitive 401(k) plan.
• Dog-friendly office; dogs are specifically noted at the San Francisco office.
• Annual performance bonus and equity in Shepherd.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive