Director of Digital Transformation & Innovation

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.

Who We Are

and what we believe in.