[Remote] Strategic Finance Manager

Note: The job is a remote job and is open to candidates in USA. Jerry is hiring a Strategic Finance Manager to build the financial analysis that informs capital allocation as the company expands into new markets. The role owns the operating model and planning cycle, partners with leaders on new opportunities and spending decisions, and develops reporting for executive and investor audiences.

Responsibilities

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

Skills

• 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
• Executive-ready output: What you produce can go in front of the founders or the board without a rewrite — clear, precise, and honest about what the numbers do and do not show
• Owner: You take ownership of outcomes and are comfortable building process where none exists yet
• 4+ years of relevant experience, ideally combining 2+ years at a reputable investment bank, corporate development group, or private equity firm with 2+ years in strategic finance or FP&A at a high-growth company
• A bachelor's degree in finance, accounting, economics, or a similarly quantitative field
• Strong financial modeling skills: driver-based operating models, three-statement mechanics, scenario and sensitivity analysis, and a working command of accounting concepts and GAAP
• Experience with unit economics in a consumer or marketplace business, including CAC, LTV, payback, cohort retention, and contribution margin
• A track record of translating complex analysis into a clear narrative for an executive or investor audience
• Hands-on fluency with AI tools for analysis, research, and workflow automation
• Startup or high-growth experience strongly preferred, including building financial processes from scratch
• Insurance, insurtech, fintech, or marketplace experience
• CFA certification
• Vendor negotiation or procurement exposure
• Finance tech stack experience (NetSuite, Ramp, planning tools)

Benefits

• For regular employees: health, dental, and vision coverage; paid time off; paid parental leave; 401(K) plan with employer matching; wellness benefits.
• Equity opportunities may also be part of your total rewards package.
• Remote work is supported for most roles; offices are available in Palo Alto, New York City, Chicago, and Toronto for those who prefer in-person or hybrid work.

Company Overview

Company H1B Sponsorship