Vice President Sentry Io Jobs (NOW HIRING)

Hybrid — 3 days/week in office, downtown San Francisco

Billables AI is building the AI-powered operating layer for professional service firms, and we're starting where the pain is deepest: the legal industry. Our platform automates the manual overhead that slows lawyers down, bringing together intelligent timekeeping, work activity capture, and operational visibility so firms can understand how work happens and build a more efficient, profitable practice. The best work happens when people aren't buried in administrative burden, and that's exactly the problem we're solving.

Named Legal Tech Company of the Year by Law.com in 2026, Billables AI is one of the fastest-growing companies at the intersection of AI and legal technology. Our team brings together expert AI researchers and veteran startup builders who know how to move fast, build with conviction, and deliver software that sits at the core of how our customers work and generate revenue. Based in San Francisco, we empower everyone on the team to drive meaningful work end-to-end.

We’re hiring our first VP of Finance to be the financial and strategic right hand to our CEO. This is a hands‑on, high‑leverage role: you’ll take Finance, RevOps, and partner deal‑making off the CEO’s plate, systematize how we report and forecast, and help steer the strategic decisions that drive growth.

Important: our CEO is a deeply technical founder. This role is explicitly designed to complement that. We’re looking for someone who has partnered closely with a technical founder before, has a proven track record doing it well, and genuinely loves that kind of partnership — bringing a complimentary lens and altitude to the numbers.

The role is a healthy blend of tactics and strategy. You’re a builder who is happy in the weeds getting the financial foundation into excellent shape — and equally comfortable operating as a strategic partner on growth, partnerships, pricing, and planning.

• Own the full financial infrastructure end to end — Mercury (banking), QuickBooks (accounting), Stripe (revenue/payments) — and make the pieces connect cleanly and automatically.

• Manage the contract accounting/bookkeeping relationship, taxes, and a clean monthly close, so nothing falls through the cracks (incl. correct revenue recognition).

• Run the reporting cadence the business now needs: monthly reporting, budget to actuals, flux analysis, board materials & reporting, and an annual budget — always in a report‑ready state.

• Keep a precise, real‑time eye on burn and runway, and make spend both strategic and intentional.

• Own the economics of our partner, reseller, and referral channels — rev shares, attach, commissions — and stand up the PRM tooling (e.g., partner.io) to manage and pay them.

• Set the guardrails: define what we’re willing to do commercially today, in 6 months, and in 12 months, in partnership with the CEO.

• Run point on negotiating partner and referral deals directly, working with our legal team. This volume is growing and we want it owned.

• Build excellent business analytics on top of our data (HubSpot RevOps, Stripe, QuickBooks) and turn them into strategic decisions.

• Lead annual planning — starting from strategy, then translating it into the financial plan — and run it in close partnership with the CEO.

• Partner with go‑to‑market on pricing & packaging, commission structures, and whether we’re selling the product the right way.

• Prioritize investments (hires, channels, partner programs) on payback and ROI.

• Be the CEO’s primary thought partner on the business — the hard parts, what’s working, and how to resource it.

• Bring a complementary, numbers‑first perspective that strengthens a technical founder’s decision‑making.

• Done it before: prior VP of Finance experience having scaled a company through roughly $2M–$20M in ARR at least once. The foundational building blocks should be second nature.

• A builder: you know how a finance function should evolve from lean‑and‑scrappy upward, and you’re hands‑on building it.

• Proven with technical founders: a clear track record partnering with highly technical/analytical CEOs — and you love doing it.

• AI‑native mindset: you already believe AI is central to how this function will be built and run, and you have demonstrated it. We’re all in; this is non‑negotiable.

• Startup‑native: you thrive in a small, fast company. Common strong paths: banking/investing/consulting → head of FP&A → VP Finance; or grown up in the finance function across stages.

• Fluent in SaaS & the foundation: ARR, NDR, payback, cohorts; strong modeling; comfortable running GAAP and ASC 606.

• Bonus: legal tech, building partner ecosystems, or pricing & packaging experience.

This is a rare first‑finance‑hire seat with real strategic scope: you’ll build the foundation, own a growing partnership motion, and be a genuine right hand to the founder at a fast‑growing, AI‑native company, with the autonomy to shape how the function evolves.

Apply Now