Reports To: VP Risk Management
About the Role
Cottingham & Butler is seeking a senior, client‑facing Sales Leader to play a pivotal role in driving new business growth and elevating producer performance in our Madison office. This is not a traditional producer role. Instead, you will operate as a strategic deal leader and coach, partnering with producers on complex opportunities, shaping sales strategy, and helping win high‑value accounts. At the same time, you will actively develop emerging producers, accelerating their growth and improving overall team performance. If you thrive in high‑stakes sales environments, enjoy influencing outcomes without sole ownership of a book, and want to have a measurable impact on both revenue and people development, this role offers a unique opportunity.
What You’ll Do1. Drive New Business Wins
- Partner with producers on qualified opportunities to shape strategy, messaging, and positioning
- Lead and participate in key prospect meetings, including discovery and proposal presentations
- Elevate the quality and effectiveness of the consultative sales process and deliverables
- Improve close ratios and win rates on complex, high‑value accounts
- Act as a senior advisor on large or sophisticated opportunities across industries
- Guide risk analysis, program design, and overall solution strategy
- Collaborate with marketing and service teams to develop competitive, differentiated proposals
- Mentor early‑ and mid‑career producers throughout the sales lifecycle
- Provide real‑time coaching before and after prospect meetings
- Refine prospecting strategies, meeting structure, and consultative selling skills
- Play a key role in accelerating producer ramp‑up and long‑term success
- Act as an extension of the Wisconsin leadership team in client‑facing situations
- Enable parallel pursuit of new business opportunities across the region
- Increase overall responsiveness and effectiveness of the sales organization
What Success Looks Like
- Improved close ratios on qualified new business opportunities
- Stronger, more consistent execution of the consultative sales process
- Faster development and increased confidence of emerging producers
- Increased team capacity to pursue and win complex accounts
What You Bring
- 7–12+ years of experience in commercial insurance, risk management, or a related advisory role
- Proven success in complex, consultative sales environments
- Experience influencing or leading high‑stakes new business opportunities
- Background as a Producer, Account Executive, Marketer, or similar client‑facing role
- Strong ability to coach, influence, and develop others
- Deep understanding of insurance program design and risk management strategies
- Executive presence with strong communication skills in client settings
- Strategic thinker with the ability to shape and win complex deals
- Collaborative, team‑first approach to sales
- Highly organized and adaptable in a fast‑paced environment
- Passion for developing talent while staying closely engaged in client work
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
Skills Required
- 7-12+ years of experience in commercial insurance, risk management, or a related advisory role
- Proven success in complex, consultative sales environments
- Experience influencing or leading high-stakes new business opportunities
- Background as a Producer, Account Executive, Marketer, or similar client-facing role
- Strong ability to coach, influence, and develop others
- Deep understanding of insurance program design and risk management strategies
What We Do
Cottingham & Butler is the 31st largest insurance broker in the U.S. and a recognized leader in offering innovative property & casualty and employee benefit insurance solutions. The company is headquartered in Dubuque, Iowa, and employs over 1,200 employees across the U.S. Better Every Day. That's our promise to our clients. We deliver better advice, better service, and better ideas than our competitors. Every Day. It's a commitment to challenging conventional wisdom, innovating, improving how we serve our clients and growing as industry professionals. This approach has produced superior results for our clients, and a growth track record that has propelled us forward since 1887
