Head of Strategic Finance

About Numeral

Numeral is transforming how taxes get done. Digital businesses are buried under a painful web of regulations across 47 states and 50+ countries. We're eliminating this burden so teams can focus on their core mission.

We're the largest and fastest-growing AI-native tax solution. Founded in 2023, Numeral serves more than 3,000 paying customers and has more than tripled revenue every year since launch. We've raised over $157M from investors including Insight Partners, Salesforce Ventures, Benchmark, Mayfield, and Y Combinator, most recently our Series C led by Insight Partners.

We're primarily hiring in our SF and NY offices but do hire remotely in some cases.

About the role

Numeral's finance function exists to make sure the company is set up to win over the long term, and strategic finance is where that work starts. We're looking for a Head of Strategic Finance to be the analytical force behind our most important decisions. We have more than tripled revenue every year of our existence, we just raised our Series C to grow faster, and the questions in front of us, how we price, where to invest, and which motions to double down on, come down to the numbers.

Here's what makes this seat different. Our strategic finance team already runs the core FP&A rhythm: the budget, the forecast, the reporting cadence. You will not be rebuilding the basics, and you will not be buried in month-end close. This role exists for the problems that don't have a playbook. We will drop you into the highest-stakes, least-defined questions in the company, and you will own them end to end: framing the problem, building the model, pressure-testing it with the people who own the number, and landing the recommendation leadership acts on.

One quarter that might mean rebuilding the economics behind a pricing decision or taking ownership of a piece of the operating model. The next it might mean implementing an AI planning system like Pigment or pressure-testing a new go-to-market motion. The common thread: we hand you something ambiguous and important, and we stop thinking about it. That is the job.

This is a high-trust, high-visibility role reporting directly to the VP of Finance, and it carries a clear path toward broader finance leadership as the company scales.

What you'll do

• Own the strategic finance projects behind our biggest decisions: pricing, capital allocation, and the economics of new products and motions, taking each from ambiguous question to a recommendation leadership acts on.

• Take ownership of discrete areas of the company operating model, from the revenue build to the long-range plan, and raise the bar for how they're built.

• Build the analyses that inform how we deploy the capital we've raised, treating each major investment as a capital allocation decision with a clear view of cost, expected return, and tradeoffs.

• Model the economics of sales compensation, including commission structures, accelerators, and payout curves, to inform how we design and fund our plans.

• Own GTM and funnel analytics and the SaaS metrics that define the business: pipeline-to-bookings conversion, marketing ROI, CAC, payback, retention, gross margin, and unit economics.

• Lead the build-out of our AI-native finance stack: implementing planning and analysis tools like Pigment, automating the work that shouldn't need a person, and setting the standard for how finance uses AI here.

• Support the systems work underneath it all, from our accounting and ERP migration (NetSuite, Campfire, Rillet, or similar) to consolidations across our international entities, in close partnership with our data team.

• Lead cross-functional work from the front, coordinating across teams with competing priorities, and pick up what needs doing even when it sits outside strategic finance.

What you'll bring

• 6+ years across investment banking, private equity, and high-growth startup finance. A common path is two to three years in investment banking, then private equity or growth equity, then a strategic finance seat at a fast-growing company.

• Expert financial modeling in Excel. You build multi-faceted, driver-based models that follow investment banking best practices, and you build them simply. The goal is to answer the question in front of you quickly, not to add complexity for its own sake.

• Real AI fluency. AI shows up in your finance work every day, you have built or automated something real with it, and you have a point of view on where it works and where it still fails. This is a requirement, not a nice-to-have.

• Range. You get to competent fast on problems you have never seen before, and you have a repeatable way of ramping on unfamiliar territory.

• A bias to own and to lead. You like running processes and communicating across an organization, and you're good at it. When priorities compete, you lead from the front, line up the resources you need, and get it done without waiting on others.

• Fluency in SaaS metrics and unit economics, with a real sense of when payback, LTV/CAC, burn multiple, and net retention matter and when they mislead.

• Sharp written and verbal communication. You can take a complex analysis and land the single insight that moves a decision. This role writes for the board.

Even better

• MBA from a top program.

• Hands-on experience with NetSuite, Campfire, Rillet, or a comparable ERP or accounting system implementation.

• Fluency with SQL and BI tools (Looker, Hex, Sigma, or similar) and modern planning software (Pigment, Anaplan, or similar).

• International and multi-entity experience, including consolidations.

• Experience supporting a fundraise from the finance seat: data rooms, investor models, and diligence. Helpful, not required.

• Experience in SaaS, fintech, payments, tax, or another subscription and usage-based revenue model.

What we offer

• Competitive salary and equity. You'll share directly in the company's success.

• Full medical, dental, and vision coverage

• Wellness perks like Headspace and the Peloton One App

• 401(k) to help you build long-term financial security

• Lunch and snacks when you're in the office

• Regular team offsites and company events as we grow

• A culture built on ownership. Your work matters and people will see it!