Accounting

Build the insurance behind the physical world.

The world is building data centers, energy projects, hospitals, schools, and critical infrastructure. Every one of those projects needs insurance to move forward. Yet the process of getting that insurance still depends on scattered documents, manual work, and weeks of back-and-forth.

Shepherd is rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. We started in construction and energy, where understanding the specifics of a project matters and better decisions have consequences far beyond a screen.

We develop insurance products, decide which risks to insure and how to price them, and partner with established insurers to back the coverage. We own the platform our team uses to turn complex submissions into coverage for the builders and operators shaping the world around us.

Real problems. Real ownership.

Our engineers, designers, underwriters, CX, and actuaries build together. The problems span turning messy documents into reliable data, making pricing more precise, and designing AI agents that can take on increasingly complex underwriting work.

The ambition is a platform where experts spend more time on judgment and relationships, supported by software that handles the work around them. Join us to build systems whose decisions help real projects get built.

630+ customers / $500B+ insured project value

Capital to build. Partners to grow with.

$67M total funding / $42M Series B in March 2026

Shepherd is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. In March 2026, we announced a $42M Series B led by Intact Private Capital, bringing our total funding to $67M.

Intact is also a capacity partner. Alongside its investment, Intact works with Shepherd to bring insurance products to market. That relationship connects our platform and underwriting expertise with the resources of a global insurer.

A bigger opportunity ahead

We are investing in new insurance products, our underwriting team, and the path toward autonomous underwriting. For the people joining Shepherd, that means the chance to shape both the technology and the business it makes possible.

Our backing brings together investors who build technology companies and partners who understand insurance. We are building a company that earns the confidence of both.

Accounting

About you

You're a hands-on accountant who likes building the process as much as running it. You have closed the books yourself, you know what an auditor will ask for, and you'd rather fix a reconciliation at the source than patch it every month.

You’d be a great fit if you have:

• 4 to 7 years in accounting, including time in public accounting (audit preferred) and time in industry running a monthly close

• Insurance accounting experience at an MGA/MGU, broker, carrier, or insurtech, including commission revenue, premium receivables, carrier payables, and fiduciary or premium trust accounts

• Experience moving a close in house from an outsourced firm, or building a close at a company that hadn't had one

• Supported a financial statement audit, including preparing schedules and working through the PBC list

• Strong knowledge of US GAAP, especially ASC 606

• Comfort working with large data sets in Excel or Google Sheets, and willingness to learn SQL or work with our data team to pull from our platform

• An active CPA is a plus

About the Role

You will be Shepherd’s first in-house accountant. Today our books are kept by an outsourced partner, and our carrier remittances and premium balances are tracked in spreadsheets. You’ll own the accounting function and work alongside our external partners. They’ll continue to handle much of the transactional work, and you’ll own the close, the insurance accounting, and the policies and reconciliations that need to hold up to an audit and to diligence.

You'll report to our Finance Lead. You'll also partner with underwriting operations, our actuarial team, and engineering, since much of our accounting data starts in our own platform.

In this role, you will:

Monthly close

• Own the monthly close and manage our outsourced accounting firm through it, cutting the close from 30 days to 15, with periods locked once they’re closed

• Apply our revenue recognition policies for commission, policy and risk engineering fees, and contingent commission every month

• Prepare balance sheet reconciliations, including premium receivable, carrier payable, and fiduciary cash, and tie them to the bordereaux and remittance advice

Accounts receivable / Accounts payable

• Reconcile premium remittances received from broker partners and apply each payment to the correct policy and account

• Maintain the receivable aging, flag discrepancies and late payments to Customer Experience team, and see them through to resolution

• Own vendor AP and Brex card review, including GL coding rules, so spend is coded correctly before close

Treasury, special projects, and etc.

• Reconcile every incoming and outgoing transaction in our operating and fiduciary bank accounts so all payments are cleared and accounted for

• Set up the accounting for new products and carrier partners, from GL mapping to remittance workflow

• Support the Finance Lead on board materials, investor diligence, and carrier and reinsurer reporting requests

This is a position based in our San Francisco office

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. Come set a standard the rest of the team inherits.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

🏥 Premium Healthcare
100% contribution to health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Flexible 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