Director of Digital Transformation & Innovation

SISCO; Dubuque (IA); On-site; USD 120,000 - 150,000; Full time

Benefits offered by this job

High-impact leadership role

Collaboration with key partners

Opportunities for meaningful modernization

Job summary

SISCO is seeking a Director of Digital Transformation & Innovation in Dubuque, Iowa. This role will be critical in driving modernization efforts, transforming manual processes into efficient, tech-enabled operations.

The ideal candidate has strong experience leading digital transformations, particularly in healthcare or insurance sectors, and is skilled in communicating with stakeholders across all levels. Join SISCO and play a pivotal role in shaping its future through meaningful innovation.

Qualifications

• 7+ years in digital transformation, product management, or operations leadership roles.
• Experience in healthcare claims processing or TPA operations.
• Proven ability to operate independently and lead complex initiatives.

Responsibilities

• Assess current-state operations and identify areas for improvement.
• Develop a multi-year transformation roadmap aligned with business goals.
• Lead cross-functional implementation efforts and change management.

Skills

Digital transformation leadership experience

Communication and stakeholder influence

Judgment in balancing strategic vision and execution

Comfort with ambiguity and structure

Education

7+ years in relevant roles

Tools

Modern software platforms

APIs and data systems

Automation tools

Job description

Director of Digital Transformation & Innovation

Dubuque, Iowa, United States

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 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.