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Director, Investment Finance

Kemper · Chicago, IL · $129,500–$215,700 a year · Full time

Posted Sep 2, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you built or improved a reporting process for a finance team.

What they are checking: Whether they can improve processes and controls, not just run existing ones.

How do you develop the people on your team while hitting tight reporting deadlines?

What they are checking: Whether they can lead and grow a team, not just produce work themselves.

What would you do

How do you work with Actuarial and Treasury to tie investment results back to the company's overall financial picture?

What they are checking: Whether they understand how investments support liabilities and capital in an insurance company.

Interest rates move sharply mid-quarter. How do you update your forecast and what do you tell leadership?

What they are checking: Whether they can react quickly and explain the impact on income, unrealized gains and capital.

About the work

Walk me through how you would lead the annual planning and quarterly forecast for an insurer's investment portfolio.

What they are checking: Whether they can run the full planning cycle, including assumptions and coordination with business leaders.

What assumptions drive a net investment income forecast, and which are hardest to get right?

What they are checking: Whether they understand yields, reinvestment rates, cash flows and the volatility in alternative returns.

How does the CECL process work for an insurer's investment portfolio, and what's your role been in it?

What they are checking: Whether they have real experience with credit loss estimation and the governance around it.

How do you present investment results to senior management in a way that highlights risks and forward-looking implications?

What they are checking: Whether they can lead with insight, not just tables, for executive audiences.

What role should the Valuation Committee play for hard-to-value assets like private credit?

What they are checking: Whether they understand fair value governance and the documentation it requires.

How do statutory accounting and risk-based capital considerations affect investment decisions at an insurer?

What they are checking: Whether they understand regulatory capital constraints that shape how an insurer invests.

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The full job description

As published by Kemper.

Location(s) Chicago, Illinois Details The Director, Investment Finance leads the financial analysis, planning, forecasting, and reporting activities supporting the organization’s investment portfolio. This role partners closely with Finance, Treasury, Actuarial, and Investment teams to provide strategic financial insights, support investment and business objectives, strengthen risk management, optimize capital deployment, and ensure alignment with regulatory requirements. Role Responsibilities: • Lead the annual investment portfolio financial planning and quarterly forecasting process, including development of key assumptions and coordination with business leaders • Partner with actuarial, finance treasury and other business functions to understand financial results and incorporate operating trends into forecasts and plans. • Lead preparation of monthly and quarterly financial reporting packages for senior management with clear and concise analysis of financial performance, including key trends, risks, opportunities, and forward-looking implications. • Establish and monitor key financial and operating metrics used to evaluate company and business-unit performance. • Key contributor to the company’s Current Expected Credit Losses (CECL) and Valuation Committee processes, including coordination of data, assumptions, analysis, documentation, and appropriate governance. • Serve as the owner of certain key SOX controls within Finance, ensuring controls are appropriately designed, executed, documented, and supported. Minimum Role Requirements: • Bachelor’s degree in Finance, Accounting, Economics, or a related field • MBA or relevant professional certification (e.g., CFA, CPA) preferred • At least 8 years of progressive finance, accounting, or related experience, including experience supporting investments or investment-related financial activities • At least 6 years of prior management or leadership experience leading teams • Previous experience in insurance, asset management, or another complex, regulated financial environment preferred • Strong understanding of financial statements, accounting principles, and the interaction between operating performance and financial results. • Knowledge of applicable financial and regulatory reporting standards, including GAAP and STAT The range for this position is $129,500 to $215,700. When determining candidate offers, we consider experience, skills, education, certifications, and geographic location among other factors. This job is eligible for an annual discretionary bonus and Kemper benefits (Medical, Dental, Vision, PTO, 401k, etc.) Kemper is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, disability status or any other status protected by the laws or regulations in the locations where we operate. We are committed to supporting diversity and equality across our organization and we work diligently to maintain a workplace free from discrimination. Kemper is focused on expanding our Diversity, Equity and Inclusion efforts to align with our vision, mission, and guiding principles. Kemper does not accept unsolicited resumes through or from search firms or staffing agencies. All unsolicited resumes will be considered the property of Kemper and Kemper will not be obligated to pay a placement fee. Kemper will never request personal information, such as your social security number or banking information, via text or email. Additionally, Kemper does not use external messaging applications like WireApp or Skype to communicate with candidates. If you receive such a message, delete it.

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