---
title: 'Operations Leader at Cottingham & Butler'
canonical: 'https://feeny.ai/job/operations-leader-cottingham-butler-dubuque-iowa-9a8y67dt0kyk'
type: 'job'
last_seen: '2026-09-09'
---

# Operations Leader at Cottingham & Butler

- **Company:** Cottingham & Butler
- **Location:** Dubuque Iowa, United States
- **Posted:** 2026-07-27
- **Last confirmed live:** 2026-09-09
- **Apply:** https://boards.greenhouse.io/cottinghambutlerinsuranceservicesinc/jobs/5368685008?gh_jid=5368685008

## Job description

Lead Operations. Develop People. Drive Results.

SISCO is seeking an experienced and strategic Operations Leader to help shape the future of our organization. This role serves as a key partner to leadership and provides oversight across operational functions to ensure exceptional service, operational excellence, employee engagement, and business performance.

The ideal candidate is a collaborative, results-driven leader who thrives in a fast-paced environment and has a passion for developing teams, improving processes, and delivering outstanding customer experiences. If you enjoy building alignment across departments, leading change, and creating scalable operational solutions, we'd love to connect with you.

## What You'll Do

As Operations Leader, you will:

- Provide leadership and strategic direction across multiple operational teams and functions.
- Partner with organizational leaders to align people, processes, and priorities with business objectives.
- Drive operational excellence through continuous improvement initiatives, process optimization, and performance management.
- Develop, coach, and mentor leaders while fostering a culture of accountability, collaboration, and engagement.
- Monitor key performance indicators and implement strategies that improve efficiency, quality, and service outcomes.
- Lead cross-functional initiatives that support organizational growth and scalability.
- Collaborate with internal stakeholders to resolve complex operational challenges and maintain high levels of client satisfaction.
- Assist with workforce planning, budgeting, resource allocation, and operational forecasting.
- Support implementation of new programs, technologies, and organizational initiatives.
- Ensure compliance with company policies, client requirements, and applicable regulatory standards.

## What We're Looking For

Required Qualifications

- Bachelor's degree in Business, Healthcare Administration, Management, Insurance, or a related field; equivalent experience may be considered.
- 7+ years of progressive leadership experience in operations, service delivery, insurance, healthcare administration, employee benefits, claims administration, or a related industry.
- Demonstrated success leading leaders and managing multiple teams.
- Strong business acumen with the ability to analyze performance metrics and drive meaningful improvements.
- Proven ability to build relationships, influence stakeholders, and lead organizational change.
- Excellent communication, problem-solving, and decision-making skills.
- Track record of developing high-performing teams and delivering business results.

## Preferred Qualifications

- Experience within employee benefits administration, healthcare, insurance, claims administration, or a third-party administrator (TPA) environment.
- Experience leading enterprise or large-scale operational improvement initiatives.
- Lean, Six Sigma, or other operational excellence certifications.

Why SISCO?

At SISCO, we are focused on delivering exceptional service and innovative solutions for our clients and partners. We believe our people are our greatest asset and are committed to creating an environment where leaders can make an impact, drive change, and help others succeed.

As our Operations Leader, you will:

- Play a critical role in shaping organizational strategy and performance.
- Partner with senior leadership on high-impact business initiatives.
- Lead talented teams and develop future leaders.
- Drive operational improvements that create meaningful results.
- Join a collaborative, values-driven organization committed to service excellence.

Ready to Make an Impact?

If you're a strategic operations professional who excels at developing people, improving performance, and leading through influence, we encourage you to apply and become part of the SISCO leadership team.

## 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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