Senior Financial Analyst at We Insure Group in Chicago, IL

Who We Are.

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision.

As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.

What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.

We Insure is building a lean, high‑leverage finance organization to power both organic growth and mergers and acquisitions. As a Senior Financial Analyst, you will independently own and manage the full cycle of FP&A activities from start to finish, including budgeting, forecasting, financial reporting, variance analysis, and financial modeling. This role is responsible for connecting business performance to financial outcomes by providing data-driven analysis and insights that support operational and strategic decision-making. You will partner with cross-functional teams to evaluate initiatives, monitor financial performance, and identify opportunities to improve reporting, efficiency, and profitability.

Key Responsibilities

FP&A Ownership & Financial Strategy

• Independently own and manage the full FP&A function from start to finish, including budgeting, forecasting, financial reporting, variance analysis, and long-range planning.
• Lead monthly, quarterly, and annual financial reporting processes, delivering actionable insights on business performance, trends, and operational drivers.
• Develop and maintain financial models, dashboards, and forecasting tools that connect operational performance to financial outcomes.
• Partner with leadership to support strategic planning, capital allocation, profitability improvement, and business decision-making.
• Build ROI analyses and evaluate the financial impact of new initiatives, investments, and growth opportunities.

Financial Analysis, Modeling & Risk Management

• Analyze revenue, expense, and operational performance data to identify risks, trends, and opportunities for improvement.
• Develop scenario, sensitivity, and “what-if” models to evaluate assumptions, forecast outcomes, and assess business risk.
• Quantify the financial impact of sales performance, market conditions, operating costs, and strategic initiatives.
• Deliver concise reporting packages, dashboards, and executive-level presentations to support informed decision-making.
• Proactively identify financial gaps, performance issues, and operational inefficiencies, while recommending data-driven solutions.

Process Improvement & Cross-Functional Leadership

• Drive continuous improvement initiatives across FP&A processes, including automation, reporting efficiency, and scalability.
• Own optimization and ongoing enhancement of financial systems and planning tools, including NetSuite and Adaptive Insights.
• Identify process gaps and implement improvements that strengthen reporting accuracy, workflow efficiency, and financial visibility.
• Serve as a strategic business partner to Sales, Marketing, Operations, and Technology teams by providing financial guidance, ad hoc analysis, and performance insights.
• Independently manage priorities, reporting deliverables, and cross-functional initiatives with minimal oversight.

Qualifications

Required

• Bachelor’s degree in Finance, Accounting, Economics, or related field.
• 5-8 years of experience in FP&A, corporate finance, or a similar analytical role.
• Advanced Excel and strong financial modeling skills.
• Excellent communication and presentation abilities.

Preferred

• Experience with ERP or planning tools (NetSuite, Adaptive Insights).
• Familiarity with SQL, Python, Tableau, or Power BI.
• Background in insurance or financial services.

Our Values. The We Way.

At We Insure, Group our values shape how we work, how we lead, and how we grow—together. They’re more than just words—they guide every interaction, every decision, and every customer experience.

We Way Reflects Our Commitment to.

• We personalize protection at a price you can trust

• We hustle to find opportunity

• We care authentically

• We thrive in ambiguity

• We own our results

• We have fun along the way

• And—we’re just getting started

Our Total Rewards.

• Medical, Dental, Vision, Life, Pet; Flexible Spending Account

• Competitive Salaries

• 401K Match

• Work-Life Balance: Personal Days, PTO Days, 12 Paid Holidays, Two Paid Days for Volunteer Service, Paid Parental Leave

• Short and Long-Term Disability

• Employee Support Programs, Including Mental Health

• Tuition Reimbursement

• Matching Charitable Gift Program

• Lucrative Referral Program

This position is not able to be performed in California, Colorado, New York or Washington.

EEO

We Insure Group is an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.

Disability

We Insure Group is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hrinfo@peak6insurtech.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

Note to applicant: It is unlawful in Massachusetts and Maryland to require or administer a lie detector test as a condition of employment or continued employment. Please know that our company does not use lie detector tests in our hiring process.

Base Salary Range: $88,000-$110,000