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Senior Financial Analyst
Senior Financial AnalystWe Insure • Chicago, IL, US
Senior Financial Analyst

Senior Financial Analyst

We Insure • Chicago, IL, US
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Senior Financial Analyst

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 Senior Financial Analyst, you will become the analytical engine behind the numbers, linking operational drivers to enterprise value and equipping leaders with clear, data-backed insights. You will own core FP&A deliverables, build ROI models for new initiatives, and partner directly with senior executives on high-impact projects, from launching in new markets to screening acquisition targets.

Cross-functional collaboration is central to the mandate. You will work closely with stakeholders in Sales, Marketing, Customer Experience, and Technology, translating raw data and financial results into actionable strategies that move the business forward.

The role sits at the intersection of finance and data. You will help shape performance dashboards, and automate recurring analyses, so decision makers always have the right information at the right time. Success requires intellectual curiosity, precision, and the confidence to explain complex financial concepts to non-finance audiences. In return, you will receive hands-on mentorship and a clear path to accelerated responsibility.

Key Responsibilities

Financial Planning and Analysis :

  • Produce monthly, quarterly, and ad hoc reporting packages with variance analysis, commentary, and KPI dashboards.
  • Maintain budgets, rolling forecasts, and long-range plans that connect operational metrics to EBITDA and free cash flow.
  • Support annual budgeting, reforecasting processes, and periodic business reviews with actionable insights and recommendations.

ROI and Decision Support :

  • Build and refine unit economics, payback, and hurdle rate models for new segments, customer acquisition channels, and technology investments.
  • Deliver clear recommendations that help leaders prioritize capital and resources.
  • M&A and Integration Support :

  • Support deal screening, financial due diligence, synergy sizing, and post-close integration tracking.
  • Develop valuation sensitivities and scenario analyses for live and pipeline opportunities.
  • Data Analysis :

  • Analyze and interpret large datasets related to premiums, sales, cost structure, profitability, and other operational metrics, identifying key business trends and improvement opportunities.
  • Recommend strategies for cost reduction, efficiency improvements, and revenue opportunities.
  • Manipulate large data sets to analyze historical performance, track industry trends, determine results, and reveal trends.
  • Risk and Scenario Modeling :

  • Quantify sensitivities (loss ratios, macro drivers, reinsurance costs) and present stress test results to senior stakeholders.
  • Process Improvement and Systems :

  • Champion finance best practices; help implement and optimize NetSuite, Adaptive Insights, and related automation tools.
  • Ensure all financial analyses and models align with GAAP / IFRS standards and insurance industry best practices.
  • Business Partnership and Cross Functional Collaboration :

  • Act as a finance liaison to Sales, Marketing, Customer Experience, and Technology, Carrier Relations, and Human Resources - translating financial impacts into operational language.
  • Provide rapid, consultative analysis with a "hands-on operator" mentality.
  • Qualifications

    Required :

  • Bachelor's degree in Finance, Accounting, Economics, Mathematics, Data Analytics, or a related field.
  • 3+ years in FP&A, investment banking, consulting, equity research, private equity, corporate development, or a similar analytical role.
  • Strong grasp of how business actions flow through to enterprise value. Mastery of financial modeling, DCF, and valuation techniques.
  • Advanced proficiency in Excel and financial modeling.
  • Experience with an ERP and / or planning tool (NetSuite, Adaptive Insights, or similar).
  • Exceptional written and verbal communication skills; able to turn complex analyses into crisp narratives for all levels of the organization.
  • Preferred :

  • Progress toward or completion of CFA, CPA.
  • Hands-on SQL and / or Python for data analysis and scenario simulation.
  • Familiarity with Tableau, Power BI, or Looker; ability to design data models and visualizations.
  • Exposure to insurance brokerage, MGA, or other financial services businesses.
  • Prior involvement in transaction diligence or post-merger integration.
  • Our Values. The We Way.

    At We Insure Group our values shape how we work, how we lead, and how we growtogether. They're more than just wordsthey guide every interaction, every decision, and every customer experience.

  • 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
  • Andwe'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

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