---
title: 'Regional Sales Leader - Employee Benefits at Cottingham & Butler'
canonical: 'https://feeny.ai/job/regional-sales-leader-employee-benefits-cottingham-butler-madison-wisconsin-y2sp37je8wa5'
type: 'job'
last_seen: '2026-09-09'
---

# Regional Sales Leader - Employee Benefits at Cottingham & Butler

- **Company:** Cottingham & Butler
- **Location:** Madison Wisconsin, United States
- **Posted:** 2025-04-24
- **Last confirmed live:** 2026-09-09
- **Apply:** https://boards.greenhouse.io/cottinghambutlerinsuranceservicesinc/jobs/4646885008?gh_jid=4646885008

## Job description

Regional Sales Leader, Employee Benefits Location: Madison, WI

Cottingham & Butler is seeking an Employee Benefits sales leader for our Madison, WI office. As the Sales Manager of our regional office, you will drive profitable growth in employee benefits, spearhead sales initiatives, and deliver exceptional value to our clients. Your leadership will be pivotal in developing a high-performing team that achieves sustained success. Don’t miss your chance to be part of one of the largest and fastest growing insurance brokerages in the nation.

Key Responsibilities:

- Sales Leadership: Take charge of the regional employee benefits sales efforts, combining marketing, sales, and analytical strategies to cultivate and close business with target customers. Drive new business through hiring, managing, and developing sales executives. Attend sales calls to assist in closing deals and build strong personal relationships with sales producers.
- Strategic Vision: Execute and implement the employee benefits vision and strategy for the regional office. Translate this vision into actionable annual operational plans. Promote the identification and evaluation of new products, services, and processes to enhance practice performance.
- Client Service & Partnerships: Ensure our Employee Benefits service model exceeds client expectations and revenue retention targets. Review work products to meet service standards. Develop strong relationships with insurance carriers and partners to offer unique benefits and differentiate from competitors.
- Financial Management: Achieve growth and profitability targets for the regional office. Drive initiatives to improve overall financial performance, including cross-selling.

Qualifications:

- 5+ years of proven experience in sales leadership within the employee benefits insurance industry.
- Strong track record of achieving sales targets and driving business growth.
- Ability to develop and mentor a high-performing sales team.
- Excellent interpersonal and communication skills.
- Strategic thinker with the ability to translate vision into action.
- Strong relationship-building skills with clients, carriers and vendors.

If you are a proven leader with a passion for sales and employee benefits, and a knack for driving team success, we want to hear from you! Apply now to join our team and lead the Madison Regional Office to new heights.

Pay & Benefits:

- Full annual salary and bonus opportunities
- Most Benefits starting day one
- Medical, Dental, Vision Insurance
- Flex Spending or Health Savings Account
- 401(k) with company match
- Profit-sharing/Defined contribution (1-year waiting period)
- PTO/Paid Holidays
- Maternity Leave & Parental Leave
- and so much more!

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](http://www.cottinghambutler.com/) | [LinkedIn](https://www.linkedin.com/company/cottingham-&-butler/) | [Facebook](http://www.facebook.com/cottinghambutler)

## About Cottingham & Butler

## Company Overview
- **One-liner**: Cottingham & Butler is a privately-held national insurance broker providing risk management, property & casualty, and employee benefits insurance and consulting services.
- **Entity Type**: Private (privately held, bootstrapped – no external funding rounds reported)
- **Headquarters**: Dubuque, Iowa, United States
- **Founded**: 1887
- **Founders**: Not publicly named (family-led; current leadership includes David Becker – CEO, Andrew Butler – Executive Chairperson, John E. Butler – Chairperson, Mike Hessling – President)

## Core Business
- **Primary industry**: Insurance brokerage and risk management
- **Target customers**: B2B – mid-market to large enterprises across various industries
- **Mission**: “To partner with our clients, to protect their most valuable assets, and to build an exceptional company of passionate insurance professionals.” [cottinghambutler.com](https://www.cottinghambutler.com/about/leadership)

## Products & Services
- **Property & Casualty Insurance**: Coverage for commercial property, liability, workers’ compensation, and more.
- **Employee Benefits Solutions**: Health, dental, vision, life, disability, and voluntary benefits consulting.
- **Captives & Programs**: Alternative risk financing and captive management for sophisticated clients.
- **Claims Management**: Full-service claims administration and advocacy.
- **Safety Management Services**: Risk control, loss prevention, and safety consulting.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (privately held)
- **Key Metric**: Annual revenue of approximately **$779.8M** (LinkedIn estimate) [linkedin.com](https://www.linkedin.com/company/cottingham-&-butler)
- **Notable Investors/Partners**: Privately held; no external investors disclosed. Key partners include New Horizon Academy (on-site childcare provider).
- **Growth Signals**: 
  - 3rd largest privately and independently held insurance broker in the U.S. [cottinghambutler.com](https://www.cottinghambutler.com/about/leadership)
  - Over 1,300 employees (company states) [cottinghambutler.com](https://www.cottinghambutler.com/about/leadership); LinkedIn reports ~715 employees with +6.9% YoY growth [linkedin.com](https://www.linkedin.com/company/cottingham-&-butler)
  - Active job postings increased +36.9% quarterly and +43.8% yearly [linkedin.com](https://www.linkedin.com/company/cottingham-&-butler)
  - National presence with offices across the U.S. and in Canada.

## Competitive Advantages
- **Scale & Independence**: As the 3rd largest privately held broker in the U.S., they combine national resources with independent ownership, enabling long-term client focus without shareholder pressure.
- **Longevity & Trust**: Operating since 1887 – 135+ years of stability and client relationships.
- **Culture of Continuous Improvement**: “Better Every Day” mantra drives innovation and service excellence.
- **Integrated Services**: Full suite from insurance placement to claims and safety, offering a seamless client experience.

## Strategic Focus
- **National Expansion**: Growing geographic footprint and service capabilities to reach more clients.
- **Talent Development**: Heavy investment in employee growth, with a scholarship program that has awarded over $1M to students and strong internal promotion paths.
- **Innovation in Risk Management**: Developing new captive and program structures to meet evolving client needs.

## Why Work Here
- **Culture**: Emphasizes “Better Every Day” – a commitment to personal and professional growth, integrity, transparency, and respect. [cottinghambutler.com](https://www.cottinghambutler.com/ourculture-people)
- **Benefits**: Comprehensive medical, dental, vision, prescription, free telehealth, paid disability, brain health resources, 401K with profit sharing, tax-advantaged accounts, dependent scholarship program. [cottinghambutler.com](https://www.cottinghambutler.com/careers-culture)
- **Family Support**: On-site childcare center at Dubuque headquarters with preferred rates for employees (powered by New Horizon Academy). [cottinghambutler.com](https://www.cottinghambutler.com/careers-culture)
- **Work Environment**: Headquarters in Dubuque, Iowa, with onsite dining and fitness; hybrid/remote options not explicitly stated but likely role-dependent. Offers both sales and corporate/service career tracks.
- **Growth Opportunities**: Strong internal mobility, mentorship for new grads, and a track record of promoting from within.

## Sources
1. [cottinghambutler.com](https://www.cottinghambutler.com/) – Company homepage, services, mission
2. [cottinghambutler.com/careers-culture](https://www.cottinghambutler.com/careers-culture) – Careers page with benefits and culture details
3. [cottinghambutler.com/about/leadership](https://www.cottinghambutler.com/about/leadership) – Leadership, history, and company facts
4. [cottinghambutler.com/ourculture-people](https://www.cottinghambutler.com/ourculture-people) – Culture and values page
5. [linkedin.com](https://www.linkedin.com/company/cottingham-&-butler) – LinkedIn company profile with employee count, revenue, and growth trends

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