VP of Finance
About The Position
DIGIDECK is a profitable, founder-led SaaS company at an inflection point. DIGIDECK, our cloud-based presentation and content platform, is used by over 500 professional and collegiate teams, venues, and enterprise brands. We are now building an AI product line on top of that platform, and the economics of that shift (pricing, margin, cost of inference, revenue recognition) will be decided in the next 18 months. We are looking for a VP of Finance to own financial operations end to end and to be the analytical partner to the CEO on the two questions that matter most: how we grow profitably from here, and how we position the company for a future capital event. This is a hands-on role at a company of our size. You will build the model, close the books, redline the contract, and present to the board. You will also be expected to use AI to do all of it faster than a traditional finance org would. We are an AI-forward company, and that isn't a slogan about our product roadmap. It's how we expect this function to operate: You will use AI agents connected to Salesforce, QuickBooks, and Maxio to pull, reconcile, and analyze rather than waiting on manual exports and hand-built spreadsheets. You will use AI to accelerate first-pass contract review and redlining, then apply your own judgment on risk and revenue treatment. You will automate recurring reporting, variance commentary, and board package prep so your time goes to analysis and negotiation, not assembly. You will build and own the unit economics of our AI products, including inference and infrastructure cost per account, gross margin under usage growth, and pricing structures that hold margin as adoption scales. If your instinct is to solve a reporting problem by adding headcount, this isn't the right fit. If your instinct is to solve it by building a workflow, keep reading.
Requirements
- 10+ years in finance, including 5+ years in a leadership role
- 5+ years in SaaS, ideally in a company between $5M and $50M ARR
- Demonstrated fluency with AI tools in a finance context. You should be able to describe specific workflows you have automated or accelerated, and what it saved
- Proven experience in customer contract review, redlining, and negotiation
- Deep command of SaaS metrics, revenue recognition (including usage-based and consumption models), and compliance standards
- Hands-on experience preparing a SaaS company for a sale, recapitalization, or growth investment
- M&A experience on both sides of the table, including post-close integration
- Strong analytical and modeling skills, with advanced budgeting and audit experience
- Comfort in a hands-on environment where you are both the strategist and the operator
- Credible presence with customers, partners, employees, investors, and boards
- Bachelor's degree in Finance, Accounting, Business, or a related field
Nice To Haves
- MBA and/or CPA
- Experience with QuickBooks Online, Maxio (formerly SaaSOptics), AvaTax, and Salesforce
- Experience owning the financial model for an AI or consumption-priced product line
Responsibilities
- Own budgeting, forecasting, and long-range planning, with a focus on the SaaS metrics that drive valuation: ARR growth, GRR, NRR, CAC payback, LTV/CAC, and Rule of 40
- Build and maintain the operating model that supports the company's growth plan and the decision gates within it
- Partner with the CEO, CTO, and go-to-market leadership on resource allocation and investment tradeoffs
- Model pricing and packaging decisions, including AI feature pricing, usage-based and hybrid structures, and their impact on revenue recognition and margin
- Lead customer contract review, redlining, and negotiation, optimizing revenue recognition and cash collection while managing risk
- Balance deal velocity against risk. Sales cycles should not stall in finance
- Own all financial reporting, month-end and year-end close, and compliance with GAAP and applicable regulatory standards
- Oversee accounting operations, including billing, A/P, A/R, GL, cost accounting, and revenue recognition
- Ensure timely, accurate tax and financial filings, and manage internal and external audits
- Maintain controls and reporting standards that hold up to buyer, investor, and lender scrutiny
- Report actuals against plan with clear variance analysis and recommended corrective action
- Keep the company diligence-ready on a standing basis: clean data room, defensible ARR and retention reporting, and quality-of-earnings-ready financials
- Assemble the financial models, materials, and narrative required for a sale process, growth investment, or debt facility
- Work with external advisors, bankers, and legal counsel, and serve as the finance lead in transaction negotiations
- Evaluate and execute acquisitions where they accelerate the plan, from diligence through integration
- Build a small, high-leverage finance function where tooling and automation do the work that headcount used to
- Collaborate across the executive team to drive company initiatives, and bring client and commercial insight back into product prioritization
- Foster accountability, transparency, and continuous improvement
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What This Job Offers
Job Type
Full-time
Career Level
Senior
