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Salary: USD 275,000 - 400,000 / annual
Shepherd is a Managing General Underwriter (MGU) rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. The company started in construction and energy—two of the most complex segments in commercial insurance—and is planning to expand to additional industries and products, targeting $1B+ in premiums by end of 2028. Backed by $67M in funding (including a $42M Series B led by Intact Private Capital in March 2026), Shepherd partners with established insurers to provide coverage while owning the platform that turns complex submissions into fast, accurate underwriting decisions.
As Head of Finance, you will own the complete financial engine for this fast-growing insurance company. You'll lead the Finance function and oversee Revenue Operations, Business Operations, and Analytics teams. Your responsibilities span three core areas:
**Finance & Planning:** Own the annual operating plan, long-range financial model, and monthly forecast and budget-versus-actuals reviews across revenue, headcount, OpEx, and cash. Build product-level contribution margin views to evaluate the economics of each new insurance product launch. Own reporting packages for the board, investors, carriers, and reinsurers, and support future fundraising efforts.
**Capital, Accounting & Controls:** Partner with the Chief Insurance Officer and Reinsurance & Capital Strategy leader on the finance side of new risk-bearing structures (captives, sidecars, quota shares, fronting arrangements), including modeling, accounting treatment, capital and collateral requirements, and regulatory reporting. Build the entity, treasury, and cash infrastructure needed for these structures, including premium trust and fiduciary accounts, collateral management, 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 outsourced accounting partners.
**Operations Leadership:** Lead Analytics, Revenue Operations, and Business Operations teams across submission attribution, broker tiering, quota setting and compensation, underwriter enablement, partnerships, and marketing infrastructure. Tie plan, pipeline, and performance data together in one integrated operating cadence. Hire, coach, and grow the finance and operations teams.
You'll work closely with the CEO and set the standard for how the company plans, spends, and measures results. The role is based in either the San Francisco or New York City office.
**Requirements:**
- 10+ years in finance, 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; 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, and the accounting, cash, collateral, and regulatory requirements that come with them
- Track record of running annual planning, forecasting, and budget-versus-actuals reviews on integrated models across revenue, headcount, OpEx, and cash
- Strong command of close, audit, tax, treasury, and internal controls, including managing outsourced accounting partners
- Experience leading or partnering closely with revenue operations, business operations, and analytics teams
- Executive presence with a board, investors, carriers, and reinsurers; fundraising experience is a plus
- Bias toward systems and automation, including building finance and payments infrastructure with engineering
- Bachelor's degree in finance, accounting, economics, or a related field; CPA, CFA, or MBA is a plus
