Strategic Finance Manager

Jerry; Chicago (IL); On-site; USD 120,000 - 190,000; Full time

Job summary

Jerry in Chicago is seeking a Strategic Finance Manager to own the operating model, planning cadence, and spend discipline across the base business and new product lines. You will partner with functional leaders, report to the VP of Finance, and collaborate with the CFO and founders to drive accuracy, cadence, and externally ready insights.

The role emphasizes forecasting, budgeting, evaluating opportunities, framing make/buy decisions, and building compelling financial cases to support

Qualifications

• Strong financial modeling and scenario planning required.
• Experience with budgeting, forecasting and variance analysis.
• Excellent written and verbal communication for executive audiences.

Responsibilities

• Own Jerry's driver-based operating model for the base business and expand it as new products scale.
• Run the annual budget and long-range planning process end to end—cadence, assumptions, inputs, and consolidated plan.
• Own the monthly and quarterly forecast cycle and variance analysis, explaining movements post-close.
• Write the executive narrative translating results into clear business insights for leadership.
• Lead monthly business reviews with functional leaders to drive decisions.
• Evaluate and implement a planning system, assessing options and leading rollout.

Skills

Driver-based operating model

Budgeting and forecasting

Variance analysis

Executive storytelling

Cross-functional partnership

Education

Bachelor's degree in Finance/Accounting

MBA (preferred)

Tools

Excel

SQL

Financial modeling

Power BI

Job description

Why We Exist

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - buy/sell, insurance, maintenance, repairs - is fragmented, complicated, and expensive.

Why We Exist

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - buy/sell, insurance, maintenance, repairs - is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.
We've reached 5M+ customers, raised $240M+, and scaled revenue 70X. We're now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.

Why We're Hiring

Jerry is expanding into several new markets at the same time. Capital allocation is now one of the most consequential decisions we make: each dollar committed to a new product line, a marketing channel, or a headcount is a dollar not available elsewhere.
We are hiring a Strategic Finance Manager, reporting to our VP of Finance, to build the analysis those decisions rest on. You will own the operating model and the planning cycle, partner with functional leaders across the company, and work closely with the CFO and the founders.

What You'll Own

The operating core is the model, the planning cadence, and the spend discipline the company runs on. Alongside it, you are the analytical partner on new opportunities - the products, verticals, channels and partnerships we are deciding whether to back. And over your first year or two, as our newer products scale and the audience for our numbers widens beyond the people who already know the business, the reporting itself has to reach a standard that holds up to outside diligence.

Own The Operating Model And Forecast Cycle

• Own Jerry's driver-based operating model for the base business and expand it as we launch new insurance products and business lines.
• Run the annual budget and long-range planning process end to end - cadence, assumptions, stakeholder inputs, and the consolidated plan the executive team commits to.
• Own the monthly and quarterly forecast cycle and variance analysis: Once Accounting closes the books, explain what moved against plan and prior period, why it moved, and what it means for the forecast.
• Write the executive narrative: Translate the financial results into clear business insights for the CFO, the founders, the board, and our investors, at a standard that survives external diligence.
• Lead monthly business reviews: Work with functional leaders and turn what the numbers show into the business decisions that need to be made.
• Support the team in evaluating and implementing a planning system: Assess the options, make the recommendation, and own the rollout.

Build the financial case for new opportunities

• Build the financial model for new product, vertical, channel or partnership: Size the market, model the economics, evaluate capital commitment and return profile.
• Read results back against the case: Once something is live, compare the actual economics to what we underwrote and carry the lesson into the next decision. Monitor product and channel economics including CAC and payback, policy retention and lifetime value, contribution margin etc.
• Support corporate development: Capital markets and investor workstreams through diligence, modeling, and transaction analysis as the need arises.
• Frame build, buy or partner decisions: help refine the frameworks we use to compare the options and the return profile of each.

Underwrite Vendor Spend

• Build the business case before a commitment is made, support negotiation on terms, and give budget owners the visibility to manage their own numbers.

Who You Are

• Accurate under deadline: Your numbers are right the first time, and they stay right when the deadline compresses. You check your own work before anyone else has to.
• Picks the right question: No one hands you the workstream. You decide which analysis will actually change a decision, and leave the rest alone.
• Direct communicator: You form a view, communicate it directly, and revise it when the evidence changes.