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 | Facebook
Skills Required
- 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
Cottingham & Butler Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Cottingham & Butler and has not been reviewed or approved by Cottingham & Butler.
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Strong & Reliable Incentives — Variable pay elements—such as commissions, bonuses, and profit sharing—create meaningful earning upside in certain roles. Feedback suggests these incentives contribute to stronger satisfaction where performance pay is prominent.
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Retirement Support — A 401(k) with company match and profit sharing strengthens long‑term savings potential. Feedback suggests tax‑advantaged accounts and, in some roles, day‑one eligibility add tangible value.
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Parental & Family Support — Priority access and discounted rates at the Dubuque HQ onsite childcare center directly support working parents. Family‑oriented perks complement the broader health and time‑off offerings.
Cottingham & Butler Insights
What We Do
Cottingham & Butler is the 31st largest insurance broker in the U.S. and a recognized leader in offering innovative property & casualty and employee benefit insurance solutions. The company is headquartered in Dubuque, Iowa, and employs over 1,200 employees across the U.S. Better Every Day. That's our promise to 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, and a growth track record that has propelled us forward since 1887
