Senior Financial Analyst

We Insure • Chicago, Illinois • Full Time

Posted on Fri, May 22, 2026

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

Financial Analysis, Modeling & Risk Management

Process Improvement & Cross-Functional Leadership

Qualifications

Required

Preferred

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.  

Our Total Rewards.  

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

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