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This position has closed. Baird removed this listing from their careers page on Oct 3, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Senior Annuity & Insurance Supervision Officer

Baird · Milwaukee, WI · Full time

Posted Aug 6, 2026 · We last checked this listing on Oct 1, 2026

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

The posting asks you to be solutions-oriented with advisors while still supervising them. How do you hold both at once?

What they are checking: The central tension of a supervision role named directly in the posting.

You monitor recurring issues and identify trends in transaction quality or advisor behavior. Tell me about a pattern you spotted and what came of it.

What they are checking: Moving from transaction review to systemic improvement.

How do you keep current on annuity and insurance regulation?

What they are checking: Habits in a field where the rules move.

This requires the Securities Industry Essentials exam, Series 7, Series 63 or 66, Series 24 or Series 9 and 10, and a life and health insurance licence, with a Certified Annuity Specialist designation preferred or obtained within twelve months, in Milwaukee. Where are you on those?

What they are checking: That they read an unusually heavy licensing list and can answer plainly.

What would you do

Walk me through how you review a transaction with a documentation gap.

What they are checking: Method for the most common daily task.

You escalate higher-risk or sensitive matters to management, senior supervisory officers or compliance. Where is that line for you?

What they are checking: Escalation judgment, which defines the role's risk.

An advisor pushes back hard on a concern you have raised. How do you handle it?

What they are checking: Composure and firmness with a revenue producer.

What would make you decline a transaction outright rather than ask for more information?

What they are checking: Where they will actually stop something.

About the work

This role reviews daily annuity and insurance transactions for suitability and best interest considerations. What makes an annuity recommendation unsuitable for a particular client?

What they are checking: Real suitability knowledge — surrender periods, liquidity, age, income need.

You document reviews and decisions to support regulatory defensibility. What does a regulator want to see in that documentation?

What they are checking: Writing for the examination that may come years later.

Practice this interview out loud.

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The full job description

As published by Baird.

About the Role: We’re looking for a collaborative and solutions-oriented professional with deep expertise in annuity and insurance supervision, regulatory requirements and risk management. In this role, you’ll review annuity and insurance transactions to help ensure business is conducted in accordance with firm policies, supervisory standards and regulatory expectations while supporting a culture of integrity, compliance and client-focused decision making. You’ll serve as a trusted partner to Financial Advisors, branch associates, branch leadership, and internal business partners, helping navigate supervisory requirements in a practical and business-minded way. You’ll evaluate transaction suitability, identify documentation gaps or supervisory concerns, provide guidance on regulatory expectations and collaborate across teams to resolve complex or sensitive matters while maintaining firm and industry standards. Success in this role comes from your ability to exercise sound judgment, communicate with confidence and manage competing priorities in a highly regulated environment. You’ll serve as a subject matter expert on annuity and insurance products, industry regulations and supervisory practices, while identifying trends, recommending process improvements and helping strengthen the quality and consistency of supervisory outcomes across the business. The Impact You’ll Make: • Review daily annuity and insurance transactions to evaluate completeness, product suitability, best interest considerations, and alignment with firm policies and supervisory standards • Identify missing information, documentation gaps, inconsistencies, or supervisory concerns, and work directly with Financial Advisors and branch associates to obtain clarification, corrections, or additional support needed to complete the review • Escalate higher-risk, complex, or sensitive matters to management, regional Senior Supervisory Officers, Compliance, or other control partners, and follow issues through resolution • Serve as a subject matter resource for advisors, branch leadership, and internal partners on annuity and insurance supervisory requirements, documentation expectations, and transaction-related questions • Work as a partner to the field by helping advisors and branch teams navigate supervisory requirements in a practical, solutions-oriented way that supports the business while maintaining firm and regulatory standards • Document supervisory reviews, decisions and follow-up in a clear and timely manner to support regulatory defensibility, internal transparency and consistent supervisory outcomes • Monitor recurring issues, identify trends in transaction quality or advisor behavior and partner with leadership to recommend training, process improvements or control enhancements • Participate in departmental initiatives, testing, training and other special projects that support the continued evolution of annuity and insurance supervision What You’ll Bring to Baird: • Bachelor's degree or equivalent work experience in the financial industry • FINRA SIE, Series 7, Series 63 or 66, Series 24 or 9 & 10 and Life & Health Insurance license required • Certified Annuity Specialist designation preferred or obtain within 12 months • Knowledge of Microsoft Excel, Word and Adobe Acrobat • Superior oral and written communication skills • Experience resolving highly sensitive and complex issues with composure and a partnership mindset • Expert on the laws, regulations, products and ethical standards of the insurance and annuity industry • Ability to identify potential areas of concern while prioritizing work assignments and take ownership of issues through to completion • Strong organizational and analytical skills with exceptional attention to detail • Change driver • Positive attitude, enthusiastic about working in a compliance and regulated environment #LI-PWM2 Baird is committed to diversity and provides employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, pregnancy, citizenship, national origin, age, disability, military service, veteran status, sexual orientation, gender identity or expression, genetic information, or any other status protected by law.