Head of Finance

The role

The Head of Finance will own financial planning, accounting, controls, and reporting. This person will also lead the operations teams that run the go-to-market engine.

What you will do

• Oversee the annual operating plan, long-range model, and monthly forecast and budget-versus-actuals reviews.
• Develop and improve product-level contribution margin views.
• Own reporting packages for the board, investors, carriers, and reinsurers.
• Support future fundraising.
• Partner on the finance side of new risk-bearing structures including modeling, accounting, and capital needs.
• Build entity, treasury, and cash infrastructure including premium trust and fiduciary accounts.
• Build scalable carrier payment tracking and bordereaux reconciliation.
• Oversee close, audit, tax, and spend controls and manage outsourced accounting partner.
• Lead Analytics, Revenue Operations, and Business Operations teams.
• Hire, coach, and grow the finance and operations teams.

Required qualifications

• 12+ years in finance, spanning FP&A, accounting, and strategic finance.
• 4+ years leading teams at a venture-backed or high-growth company.
• Insurance finance experience at an MGA/MGU, carrier, reinsurer, or insurtech.
• Knowledge of 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.
• Knowledge of accounting, cash, collateral, and regulatory requirements for risk-bearing structures.
• Track record of running annual planning, forecasting, and budget-versus-actuals reviews.
• Strong command of close, audit, tax, treasury, and internal controls.
• Experience leading or partnering closely with revenue operations, business operations, and analytics teams.
• Executive presence with a board, investors, carriers, and reinsurers.
• A bias toward systems and automation.
• Bachelor’s degree in finance, accounting, economics, or a related field.

Nice to have

• Fundraising experience
• CPA
• CFA
• MBA

Benefits

• 100% contribution to health, dental, and vision
• Fertility benefits and family building support
• Flexible PTO
• Daily lunches, dinners, and snacks
• Access to premium coaching, including leadership development
• Competitive 401(k) Plan
• Dog-friendly office

About the company

Shepherd rebuilds commercial insurance with software, data, AI, and deep underwriting expertise. The company is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.