Head of Finance (Chicago)

About Occulytics

Occulytics is a market intelligence and data company built for senior living.

We help operators, owners and capital partners understand who actually lives in and moves into their communities, and what that means for their market. Our Data Platform (Market Intel, Lead Intel and Lead Gen) turns that into decisions about where to market, which leads to prioritize and where to grow. Our Advisory practice works alongside clients on the harder strategic questions.

We've grown to more than 20 operator and investor clients since launching in 2024, entirely self-funded. We're a small team, and everyone here ships real work and sees the impact of it.

The role

We're hiring our first finance leader.

We've reached the point where finance needs a dedicated owner. You'll start by taking over billing, collections and the monthly close. Then you'll build the function the company will run on for the next five years: the close, the controls, the metrics, the model and, eventually, the team.

You'll report directly to Rahul, our Founder and CEO. This is a role for someone ready to step up. You'll own the full finance function from day one, and the role is designed to grow into CFO as the company scales.

Why this role

• Your first chance to own a finance function end to end, not a slice of one
• Direct partnership with the CEO on pricing, hiring and growth decisions
• Meaningful equity and a defined path to CFO
• A growing business with real clients, real revenue and real data to work with

What you'll own

• Billing and cash. Run monthly invoicing across subscription, data and consulting revenue. Own collections, payment application and cash forecasting.
• The close. Deliver a clean, on-time monthly close in Xero. Get revenue recognition right for subscriptions, setup fees, deferred revenue and milestone-based consulting work.
• Business line economics. Show exactly how the Data Platform and Advisory each make money, including gross margin, contribution and where each dollar of payroll goes.
• SaaS and data metrics. Own the numbers that matter: ARR, net and gross revenue retention, customer concentration, CAC payback, burn and runway. Build them from the ledger so they hold up to scrutiny.
• Planning. Build our operating model and budget, and make the forecast something leadership actually uses to make decisions.
• Systems and controls. Design processes that scale without you in the middle of every transaction. Coordinate payroll (Gusto), equity (Carta), our outside CPA, tax, 409A and multi-state compliance. Decide what to automate, what to outsource and who to hire.

What success looks like

First 30 days: Learn our products, contracts and revenue models. Take over invoicing, collections and payment posting completely.

First 90 days: The monthly close runs on a predictable calendar. We have a monthly metrics package and business-line P&L that leadership trusts. You've documented the core processes and have a plan for what to hand off.

Ongoing, we'll measure you on:

• Speed and accuracy of the monthly close
• Days sales outstanding and cash predictability
• Forecast accuracy
• Quality of the financial insight behind major decisions
• A finance function that scales without adding founder time

Who you are

Required:

• 5+ years in finance or accounting, including time at a high-growth B2B SaaS or tech company
• Hands-on experience with the monthly close, revenue recognition (ASC 606) and financial reporting
• SaaS metrics fluency. You can build NRR from raw ledger data and explain what moves it.
• Ambitious and ready for more ownership than your current role gives you
• You can explain the numbers to anyone, from a client to a CEO to an outside partner
• Comfortable as both operator and strategist. You'll post a payment in the morning and build the operating model in the afternoon.
• You ship without being chased. Clear priorities are enough.

Nice to have:

• CPA or Big 4 background
• Experience with Xero, Gusto and Carta
• Exposure to senior living, healthcare, real estate or vertical SaaS

Details

• Location: Chicago, hybrid (2 to 3 days a week)
• Reports to: Rahul Bhangare, Founder & CEO
• Compensation: $120,000 to $130,000 base, plus performance-based variable and meaningful equity
• Benefits: Healthcare, dental, vision, 401(k) + matching