Posted Apr 27, 2026
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. - that support a more modern operating environment. - to help teams transition successfully to new systems, tools, and ways of working. - by staying current on industry trends, gathering feedback, and helping the organization adapt thoughtfully over time.
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
What we offer
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
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