Chief Human Resources Officer

*This position will be based out of our Dubuque, Iowa Headquarters - candidates must be located in/open to relocation to Dubuque, IA*

We’re seeking a dynamic Chief Human Resources Officer (CHRO) to join our executive leadership team and drive transformative HR strategies across talent acquisition, development, culture, and organizational design. This is a high-impact role for a strategic leader who blends traditional HR expertise with modern, data-driven, and AI-enabled practices.

As CHRO, you’ll serve as a trusted partner to the CEO and senior leaders, helping shape a high-performance, values-driven culture that attracts and retains top-tier talent in a competitive market.

Strategic Talent Acquisition & Sales Recruiting

• Partner with leadership to attract top-performing producers and executives in key markets.

• Enhance & expand college recruiting program for emerging sales talent.

• Position the company as a premier destination for high-potential sales professionals.

• Align recruiting strategies with business priorities and long-term goals.

Learning & Development

• Prepare the workforce for success in an AI-driven, digital-first environment.

• Reinforce technical insurance education and service excellence training.

• Collaborate with practice leaders to build career progression and performance development frameworks.

Compensation & Retention Strategy

• Design innovative compensation models including various pay structures.

• Lead enterprise-wide succession planning.

• Develop tailored development programs for each practice area to drive measurable outcomes.

• Strengthen the employee value proposition for high-impact talent.

Succession Planning & Talent Development

• Build internal capabilities for talent development rather than relying solely on operational units.

• Ensure leadership continuity through structured succession planning.

• Implement scalable, high-impact development programs across the organization.

AI, Data & Analytics-Driven HR

• Use AI and analytics to enhance hiring quality, predict attrition risks, and monitor engagement.

• Deploy tools to understand employee motivators and feedback.

• Create systems for synthesizing employee and leadership insights to inform strategy.

Culture, Organizational Design & Change Leadership

• Act as a steward of a high-performance, values-driven culture.

• Shape and communicate a compelling employee value proposition.

• Lead change initiatives including AI adoption, digital transformation, and organizational redesign.

• Provide strategic guidance on workforce planning and infrastructure alignment.

• Design systems that reinforce engagement, recognition, accountability, and service excellence.

Qualifications

• Senior HR leadership experience (CHRO, VP of HR, or equivalent) within fast-growing, agile organizations where innovation and adaptability are critical.

• Deep understanding of the financial services sector, with an understanding of both service and sales environment, talent dynamics, and operational complexities.

• Experience leading HR functions in companies with 1,000+ employees, balancing scale with cultural cohesion and strategic agility.

• Proven success in sales recruiting and leadership talent acquisition.

• Expertise in compensation design and incentive programs.

• Strong background in learning and development strategy.

• Experience applying AI and data analytics in HR.

• Executive-level interpersonal and influence skills.

Ready to lead the future of HR? Apply now and help us build a culture of excellence, innovation, and impact.

About Cottingham & Butler:

At Cottingham & Butler, we sell a promise to help our clients through life’s toughest moments. To deliver on that promise, we aim to hire, train, and grow the best professionals in the industry. We look for people with an insatiable desire to succeed, are committed to growing, and thrive on challenges. Our culture is guided by the theme of “better every day” constantly pushing ourselves to be better than yesterday – that’s who we are and what we believe in.

As an organization, we are tremendously optimistic about the future and have incredibly high expectations for our people and our performance. Our ability to grow as a company, fuels investments in new resources to better serve our clients and provide the amazing career opportunities our employees want and deserve. This is why we are a growth company and why we are committed to being better every day.

Want to learn more? Follow us on www.CottinghamButler.com | LinkedIn | Facebook