Jessie Stauffacher

Career transition

Career Break

Sep 2025 - Current (1 year)

After a fulfilling 28-year career in the insurance industry, including 21 years of impact and leadership at American Family Insurance, I made the bold choice to retire early and take a career pause. This time is dedicated to rebalancing life, focusing on family and health, continuing to contribute through nonprofit board service, and exploring opportunities that align with my values. Energized by the freedom to design my next chapter, I’m excited for the growth and possibilities ahead.

Chief People Officer

American Family Insurance

Dec 2022 - Sep 2025 (2 years 10 months)

As Chief People Officer, I led the organization’s people strategy and oversaw enterprise functions including talent management, leadership development, employee experience, compensation and benefits, talent acquisition, inclusive excellence, HR business partners, business and workplace services, corporate security, and aviation. I partnered with executive leadership to align people and operational strategies with business goals, driving a high-performing, inclusive, and values-driven culture. I also championed organizational change and operational excellence across all functions, helping to create a workplace that thrives on collaboration, innovation, and accountability.

President, Exclusive and Independent Agency

American Family Insurance

Jul 2021 - Dec 2022 (1 year 6 months)

President of American Family Enterprise agency distribution channels. This includes the American Family Insurance brand sold and serviced through the American Family exclusive agencies and the Main Street America brand, sold and serviced through independent agencies.

President and CEO, CONNECT

American Family Insurance

Oct 2019 - Jun 2021 (1 year 9 months)

President and CEO of CONNECT during the company's acquisition and post-acquisition transition into the American Family Insurance Group. Led a team of highly skilled leaders and team members to improve operating performance and achieve improved levels of growth.

Chief Operating Officer, American Family Agency

American Family Insurance

Jun 2017 - Oct 2019 (2 years 5 months)

Responsible for the profit and loss of all P&C and Life products sold through American Family Insurance's exclusive agency sales force. Provide strategic leadership for sales, product management, claims, underwriting, pricing and operations for Personal Lines, Commercial, Farm/Ranch, Life and Brokerage & Alliances teams.

Chief Administration Officer

American Family Insurance

May 2016 - Jun 2017 (1 year 2 months)

Provided strategic leadership to the following areas at American Family Insurance: human resources & talent management, talent and leadership development, communications, business & workplace services, strategic data and analytics and corporate flight operations

Vice President, Chief of Staff

American Family Insurance

Oct 2014 - May 2016 (1 year 8 months)

-Chief of Staff to Chair and CEO -Responsible for executive leadership development -Responsible for oversight of corporate flight operations

Internal Audit Director

American Family Insurance

Jun 2013 - Oct 2014 (1 year 5 months)

-Led enterprise internal audit function consisting of four departments across three business units -Directed the development of a comprehensive risk assessment and annual audit plan -Oversaw the execution of the internal audit plan consisting of risk-based financial, operational, and IT audits, fraud investigations, Model Audit Rule controls testing, external audit assistance and continuous assurance programs -Prepared materials and presented audit plans and results to the Audit Committee on a quarterly basis -Reported administratively to the Chief Financial Officer and functionally to the Chair of the Audit Committee

Executive Administrative Director

American Family Insurance

Feb 2010 - Jun 2013 (3 years 5 months)

-Provide leadership, coordination and oversight in the development of strategic and operational initiatives -Act as a liaison to senior leadership team members and external parties on behalf of the Chair and CEO -Develop research, conduct analyses, and create communication materials

Planning and Metrics Manager

American Family Insurance

May 2009 - Feb 2010 (10 months)

Senior Modeling and Risk Management Analyst

American Family Insurance

May 2008 - Apr 2009 (1 year)

Project Manager

American Family Insurance

Jun 2006 - May 2008 (2 years)

Senior Financial Analyst

American Family Insurance

Apr 2004 - Jun 2006 (2 years 3 months)

Senior Accounting Analyst

Humana

Jun 2000 - Apr 2004 (3 years 11 months)

Pricing Specialist

Ameriprise Auto Home Insurance

Jun 1997 - Jun 2000 (3 years 1 month)

Jessie Stauffacher

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