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

We are seeking an experienced Risk Management Insurance Broker with at least 3 years' experience of B2B sales in the P&C space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of insurance and connected programs. Individuals who apply should possess:

• Proven experience and success as an insurance broker, with a focus on property & casualty sales.
• A strong understanding of insurance and risk management products to evaluate complex policies and identify cost-saving opportunities. 
• Ability to work with C-Suite Executives to develop the best risk management solution for their insurance program.
• Excellent communication and interpersonal skills and the ability to build rapport and trust with clients.

Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the insurance industry. We have a high concentration of clients in Construction, Manufacturing, and Food & Agriculture industries. Over the years, our team has experienced double digit growth year-over-year (driven organically) and a client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results. A few highlights about our team:

Unmatched Sales Support: We surround our sales team with everything they need to be successful, including:

• Experienced Account Management Teams – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible.
• In-House Specialists- Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology. 
• Tools & Resources- You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc.

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 or hear from one of our Risk Management Sales Executives: 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
  • Subsidized Parking
  • 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

We are seeking an experienced Risk Management Insurance Broker with at least 3 years' experience of B2B sales in the P&C space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of insurance and connected programs. Individuals who apply should possess:

• Proven experience and success as an insurance broker, with a focus on property & casualty sales.
• A strong understanding of insurance and risk management products to evaluate complex policies and identify cost-saving opportunities. 
• Ability to work with C-Suite Executives to develop the best risk management solution for their insurance program.
• Excellent communication and interpersonal skills and the ability to build rapport and trust with clients.

Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the insurance industry. We have a high concentration of clients in Construction, Manufacturing, and Food & Agriculture industries. Over the years, our team has experienced double digit growth year-over-year (driven organically) and a client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results. A few highlights about our team:

Unmatched Sales Support: We surround our sales team with everything they need to be successful, including:

• Experienced Account Management Teams – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible.
• In-House Specialists- Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology. 
• Tools & Resources- You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc.

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 or hear from one of our Risk Management Sales Executives: 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
  • Subsidized Parking
  • 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

We are seeking an experienced Risk Management Insurance Broker with at least 3 years' experience of B2B sales in the P&C space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of insurance and connected programs. Individuals who apply should possess:

• Proven experience and success as an insurance broker, with a focus on property & casualty sales.
• A strong understanding of insurance and risk management products to evaluate complex policies and identify cost-saving opportunities. 
• Ability to work with C-Suite Executives to develop the best risk management solution for their insurance program.
• Excellent communication and interpersonal skills and the ability to build rapport and trust with clients.

Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the insurance industry. We have a high concentration of clients in Construction, Manufacturing, and Food & Agriculture industries. Over the years, our team has experienced double digit growth year-over-year (driven organically) and a client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results. A few highlights about our team:

Unmatched Sales Support: We surround our sales team with everything they need to be successful, including:

• Experienced Account Management Teams – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible.
• In-House Specialists- Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology. 
• Tools & Resources- You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc.

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 or hear from one of our Risk Management Sales Executives: 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
  • Subsidized Parking
  • 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

We are seeking an experienced Risk Management Insurance Broker with at least 3 years' experience of B2B sales in the P&C space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of insurance and connected programs. Individuals who apply should possess:

• Proven experience and success as an insurance broker, with a focus on property & casualty sales.
• A strong understanding of insurance and risk management products to evaluate complex policies and identify cost-saving opportunities. 
• Ability to work with C-Suite Executives to develop the best risk management solution for their insurance program.
• Excellent communication and interpersonal skills and the ability to build rapport and trust with clients.

Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the insurance industry. We have a high concentration of clients in Construction, Manufacturing, and Food & Agriculture industries. Over the years, our team has experienced double digit growth year-over-year (driven organically) and a client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results. A few highlights about our team:

Unmatched Sales Support: We surround our sales team with everything they need to be successful, including:

• Experienced Account Management Teams – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible.
• In-House Specialists- Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology. 
• Tools & Resources- You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc.

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 or hear from one of our Risk Management Sales Executives: 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
  • Subsidized Parking
  • 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

We are seeking an experienced Risk Management Insurance Broker with at least 3 years' experience of B2B sales in the P&C space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of insurance and connected programs. Individuals who apply should possess:

• Proven experience and success as an insurance broker, with a focus on property & casualty sales.
• A strong understanding of insurance and risk management products to evaluate complex policies and identify cost-saving opportunities. 
• Ability to work with C-Suite Executives to develop the best risk management solution for their insurance program.
• Excellent communication and interpersonal skills and the ability to build rapport and trust with clients.

Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the insurance industry. We have a high concentration of clients in Construction, Manufacturing, and Food & Agriculture industries. Over the years, our team has experienced double digit growth year-over-year (driven organically) and a client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results. A few highlights about our team:

Unmatched Sales Support: We surround our sales team with everything they need to be successful, including:

• Experienced Account Management Teams – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible.
• In-House Specialists- Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology. 
• Tools & Resources- You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc.

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 or hear from one of our Risk Management Sales Executives: 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
  • Subsidized Parking
  • 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

We are seeking an experienced Risk Management Insurance Broker with at least 3 years' experience of B2B sales in the P&C space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of insurance and connected programs. Individuals who apply should possess:

• Proven experience and success as an insurance broker, with a focus on property & casualty sales.
• A strong understanding of insurance and risk management products to evaluate complex policies and identify cost-saving opportunities. 
• Ability to work with C-Suite Executives to develop the best risk management solution for their insurance program.
• Excellent communication and interpersonal skills and the ability to build rapport and trust with clients.

Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the insurance industry. We have a high concentration of clients in Construction, Manufacturing, and Food & Agriculture industries. Over the years, our team has experienced double digit growth year-over-year (driven organically) and a client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results. A few highlights about our team:

Unmatched Sales Support: We surround our sales team with everything they need to be successful, including:

• Experienced Account Management Teams – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible.
• In-House Specialists- Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology. 
• Tools & Resources- You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc.

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 or hear from one of our Risk Management Sales Executives: 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
  • Subsidized Parking
  • 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