Director of Digital Transformation & Innovation

Director of Digital Transformation & Innovation

Cottingham & Butler/ SISCO

1 Positions

ID: 5164206008

Posted On 04/27/2026

Job Overview

This role is an opportunity to help shape and lead a major transformation initiative within

SISCO

. The

Director of Digital Transformation & Innovation

will play a critical role in helping the organization evolve from manual processes and legacy technology toward a more modern, efficient, and tech-enabled operating model. This position is suited for an experienced transformation leader who can bring both strategic vision and practical execution, helping the business define what the future should look like while building the path to get there. The person in this role will work closely with leadership and cross-functional partners across operations, technology, and the business, and will be expected to contribute not just to individual initiatives, but also to the broader direction of how the organization modernizes over time.

What you'll be doing

Assess current-state operations, systems, and workflows

to identify pain points, inefficiencies, and opportunities for modernization.

Develop and guide a multi-year transformation roadmap

that aligns digital initiatives with business priorities and long-term organizational goals.

Identify opportunities for automation, AI, and process optimization

that can improve efficiency, scalability, and overall service delivery.

Lead cross-functional implementation efforts

by partnering with IT, Operations, and business leaders to move initiatives from strategy through execution.

Evaluate and recommend technology solutions and implementation approaches

that support a more modern operating environment.

Drive change management and adoption

to help teams transition successfully to new systems, tools, and ways of working.

Promote innovation and continuous improvement

by staying current on industry trends, gathering feedback, and helping the organization adapt thoughtfully over time.

What we're looking for

Strong digital transformation leadership experience

in complex, evolving environments

Background in

healthcare, insurance, or TPA operations

with understanding of modernization challenges

Ability to

communicate clearly and influence stakeholders

at all levels

Judgment to balance

strategic vision with hands-on execution

, especially in legacy transformation

Comfort with

ambiguity and cross-functional leadership

while bringing structure to transformation

What you'll need

7+ years

in digital transformation, product management, or operations leadership roles

Experience in

healthcare claims processing, benefits administration, or TPA operations

Strong understanding of

modern software platforms, APIs, data systems, and automation tools

Proven ability to

operate independently, lead cross-functionally, and execute complex initiatives

Track record

modernizing legacy systems and manual processes

What we offer

The opportunity to join

SISCO

in a high-impact leadership role focused on shaping the organization's future.

A chance to help define and build the

"SISCO of the Future"

through meaningful modernization and innovation work.

Direct collaboration with leadership and key partners across

IT, Operations, and the broader business

.

A position with visibility and the ability to influence

how technology, processes, and workflows evolve over time

.

The chance to work on initiatives where your expertise can directly improve

operational efficiency, organizational effectiveness, and long-term readiness

.

An environment where strong candidates can bring forward informed recommendations and help drive important transformation decisions.

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

Primary Contact

12213

Human Resources

,

563-587-5104

Phone

Phone

Phone

563-587-5922

Fax

careers@cb-sisco.com

Email

True

False

True

Job Details

Categories

Delivery

Insurance

Management/Executive

Location

Dubuque, IA

Job Type

Employee

Full/Part

Company ID

943

Job REQ #

5164206008

# Positions

1

Start Date

20260427

End Date

20260615

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Cottingham & Butler/ SISCO

About the Company

ABOUT THE COTTINGHAM & BUTLER COMPANIES

Cottingham & Butler is one of the largest insurance brokers in the U.S. with over 1,200 employees dedicated to providing our clients with advice and insurance products to manage the risks they face. Better Every Day. That's our promise to our employees and our clients. We deliver better advice, better service, and better ideas than our competitors. Every Day. It's a commitment to challenging conventional wisdom, innovating, improving how we serve our clients and growing as industry professionals. This approach has produced superior results for our clients, endless opportunities for our employees, and a growth track record that continues to outperform the industry.