Head of Finance

Topsort•Somerville, MA

About The Position

We're looking for a Head of Finance who has been here before — not at a Fortune 500, but at a fast-moving, high-growth startup navigating the messy, exciting stretch from $10M to $100M ARR. You've built the financial infrastructure that lets a company scale without losing control. You've sat in the room when hard decisions were made and given leadership the data to make them confidently. This is not a bookkeeping or reporting role. This is a company-building role. You will own financial strategy, planning, and operations as we scale from where we are today to a company ready for a major liquidity event.

Requirements

Bachelor’s, Master’s degree or MBA from a top-tier academic institution (e.g., Ivy League, Oxbridge, top global business/engineering schools)
8+ years in finance, with meaningful experience at a high-growth B2B SaaS or marketplace company
Proven track record of scaling a company from the $10M–$100M ARR range — you know what breaks at each stage and how to get ahead of it
Deep fluency in SaaS metrics and business model economics
Strong financial modeling skills — you build models that drive decisions, not just decks
Experience managing accounting operations and working with external auditors
Exposure to fundraising, investor relations, or M&A processes
High ownership mentality — you run toward ambiguity, not away from it

Nice To Haves

Experience preparing for or navigating a Series B/C fundraise or pre-IPO readiness
Background in investment banking, venture-backed startups, or high-growth SaaS
Familiarity with ad tech, marketplace, or e-commerce business models
CPA or MBA (preferred, not required)

Responsibilities

Own the company's financial model, annual plan, and multi-year outlook
Drive the FP&A function — forecasting, scenario modeling, and board-level financial reporting
Partner with the CEO and leadership team on strategic decisions: pricing, unit economics, resource allocation, and growth investments
Build and maintain a real-time pulse on the business through dashboards and KPIs that actually get used
Own ARR tracking, cohort analysis, and SaaS metrics (NRR, CAC, LTV, payback period)
Partner with Sales and Customer Success on deal structuring, pricing strategy, and revenue recognition
Build the infrastructure to understand where we make money and where we don't
Prepare materials and data packages for investors, board meetings, and future fundraising processes
Manage relationships with existing investors and support due diligence processes as needed
Own cash management and runway visibility at all times
Oversee accounting operations and ensure GAAP-compliant financials
Own audit readiness and manage relationships with external auditors and tax advisors
Build scalable internal controls and financial processes that won't break as we grow
Build and lead a lean, high-output finance team
Own the finance tech stack: ERP, billing, expense management, and reporting tools