# Head of Finance at Shepherd

- Company: Shepherd
- What the company does: The all-in-one learning co-pilot. Backed by Y Combinator.
- Company website: https://www.shepherd.study
- Type: Startups (AI role)
- Level: Principal and up
- Location: San Francisco
- Work setup: On-site
- Pay: $275K to $400K base salary per year (USD)
- Posted: 2026-10-21
- Apply by: 2026-12-05
- Apply: https://jobs.ashbyhq.com/shepherd/8637577b-1e6d-43f3-ae6e-f3c2fce2a3ed?utm_source=1752vc&utm_medium=careers
- Page: https://www.1752.vc/careers/jobs/shepherd-head-of-finance/

## About the role

As Head of Finance, you will own Shepherd’s financial planning, accounting, controls, and reporting, as well as the operations teams that run our go-to-market engine. You’ll manage our Finance Lead and the Revenue Operations, Business Operations, and Analytics teams, report to the CEO, and partner with our Reinsurance and Capital Strategy leader as we add risk-bearing capacity. The Head of Finance is responsible for several strategic functions including: Found on 1752vc Careers, the job board for startup and VC roles.

## What they're looking for

- 12+ 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. You know 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
- A 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

Tags: Operations

Source: 1752vc Careers, https://www.1752.vc/careers/jobs/shepherd-head-of-finance/