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

1.      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

2.      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

3.      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

4.      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

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

Join Horace Mann: Empower Educators, Achieve Financial Success

Ready to Make a Difference?

Join Horace Mann today and take the first step toward achieving your career and financial goals while making a meaningful impact on the educators you serve. Together, we can help educators secure their future while empowering you to achieve your own.

As an Insurance Producer at Horace Mann, you’ll receive mentorship from an experienced agent while gaining hands-on experience in the industry. Our insurance products are tailored to meet the unique needs of educators, and we provide outstanding training, competitive rates, and flexible work options. With an unparalleled compensation structure, exciting incentives, and bonus opportunities, top performers have the chance to earn all-expenses-paid trips to amazing destinations.

Why Join Us?

• Performance-Based Compensation [1099] with a 36-month incentive plan and enhanced commissions
• Monthly incentives based on sales volume for the first 36 months
• Quarterly production bonuses for the first 36 months
• No external office requirement—work from anywhere
• Leverage established books of business while building your own practice
• Access to a niche market that increases your potential for success
• Value-added services to connect you with ideal clients
• Simple, streamlined products and sales processes for quick success
• Networking, community, and industry events to expand your connections
• A comprehensive, multi-line product portfolio in a ‘One-Stop Shop’ model

What You Will Do:

• Solve financial challenges faced by educators through tailored solutions
• Present with confidence—one-on-one or in large groups—to educate potential clients on products
• Engage in community and networking events, expanding your professional connections
• Stay current with industry trends and apply new knowledge to help clients
• Cultivate strong market relationships and build a solid client base
• Invest time and resources in ensuring the success and growth of your business

What We’re Looking For:

• A commitment to helping educators achieve financial prosperity
• Strong interpersonal and presentation skills
• Self-motivation and the ability to manage your own business
• The ability to obtain or currently hold state licenses in Life & Health and Property & Casualty

Compensation and Benefits:

• Sign-On Bonus
• Uncapped Earnings/Commission
• Structured Incentive & Bonus Pay to reward your hard work
• Work Environment—work in-person, in the field, and/or from an office setting

Support and Accountability:

As an Insurance Producer, you'll be guided by a mentor agent who will support you every step of the way to ensure your success.

We make a difference!

At Horace Mann, we are driven by our mission to support the educators who shape the future of our children. We believe that educators deserve someone who looks after their financial well-being just as they do for their students. Our passion lies in providing tailored solutions that protect what educators have today and help them achieve long-term financial security and happiness.

 #LI-MN1

#VIZI#

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

Cottingham & Butler Transportation Group provides first-class insurance solutions to over 2,500 trucking companies across the U.S. Our service extends beyond buying insurance to helping our clients with safety, claims, and compliance challenges. As the leading insurance broker in the transportation industry, we provide better solutions, better advice, and better results. 

We are currently adding experienced transportation producers. Joining our sales team will allow you access to the markets, tools, and expertise needed to write more business. You will also work with a top-notch service team that will ensure that you retain more business. A bigger book of business = more money in your pocket! This position requires 3 years of experience in Transportation Insurance.

Here are a few things that set us apart:

• Our Team. 300+ experienced professionals that specialize in the trucking industry and have the vision and expertise to help our clients clearly identify the risks they face and develop the necessary steps to mitigate or avoid them
• Market Access. Our experience and reputation in the transportation industry give us the ability to secure the most competitive terms from the top insurance markets.
• Our Solutions. We offer a full range of traditional and non-traditional insurance solutions, including in-house claims, safety management, and captive insurance services. We also offer an independent contractor platform and brokerage claims advocacy. The best part- the services aren’t charged back to the producer.
• Trucking Captives. We are the exclusive broker for 7 trucking captives, including the two largest in the world. There are over 245 captive members and a 99% retention rate in our captives.
• Clients love us. They choose us because they see value in the services we offer and stay with us because we exceed their expectations. The Transportation Division has an average annual organic growth rate of 12.5% and our client retention is over 95%. 

Ultimately, we like to win and have a track record of doing it year-over-year. Many of the best brokers in the nation have chosen to call Cottingham & Butler home and have built careers unlike anything in the industry. Here is a link to a highlight video from one of our National Sales Celebration Events: www.bit.ly/www.bit.ly/salesCB.

Pay & Benefits

• Full salary + bonus
• Most Benefits start Day 1
• Medical, Dental, Vision Insurance
• Flex Spending or HSA
• 401(k) with company match
• Profit-Sharing/ Defined Contribution (1-year waiting period)
• PTO/ Paid Holidays
• Company-paid ST and LT Disability
• Maternity Leave/ Parental Leave
• Company-paid Term Life/ Accidental Death Insurance

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