Sales Leader - New Business & Producer Development

Location: Madison, WI

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 Do

• 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
• Lead Complex Sales Strategy
• 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
• Develop and Coach Producers
• 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
• Expand Team Capacity
• 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

Key Attributes

• 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