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 doingAssess 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 forStrong digital transformation leadership experience in complex, evolving environmentsBackground in healthcare, insurance, or TPA operations with understanding of modernization challengesAbility to communicate clearly and influence stakeholders at all levelsJudgment to balance strategic vision with hands-on execution, especially in legacy transformationComfort with ambiguity and cross-functional leadership while bringing structure to transformationWhat you'll need7+ years in digital transformation, product management, or operations leadership rolesExperience in healthcare claims processing, benefits administration, or TPA operationsStrong understanding of modern software platforms, APIs, data systems, and automation toolsProven ability to operate independently, lead cross-functionally, and execute complex initiativesTrack record modernizing legacy systems and manual processesWhat we offerThe 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 SISCO:SISCO was established in 1980 as a boutique third-party administrator dedicated to the administration of unique, complex plan designs. Today, SISCO is recognized as a premier third-party administrator for employee benefits, serving 600+ employers and 1,000,000+ members from our headquarters in Dubuque, IA.For the past decade, many Health Insurance Carriers and Payers have been quietly driving industry trends in the wrong direction. The result is a lower standard of prudent review and ever-increasing costs. Our strategy is to simply administer employer plans with the same care, diligence, and expertise we apply to our own benefit program.Learn more at www.siscobenefits.com | LinkedIn