Director of Digital Transformation & Innovation

<div class="content user-select-text"> <div class="ac-container ac-adaptiveCard has-image"> <div class="ac-textBlock"> <p>This role is an opportunity to help shape and lead a major transformation initiative within <strong>SISCO</strong>. The <strong>Director of Digital Transformation &amp; Innovation</strong> 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.</p> <p><strong>What you'll be doing</strong></p> <ul> <li><strong>Assess current-state operations, systems, and workflows</strong> to identify pain points, inefficiencies, and opportunities for modernization.</li> <li><strong>Develop and guide a multi-year transformation roadmap</strong> that aligns digital initiatives with business priorities and long-term organizational goals.</li> <li><strong>Identify opportunities for automation, AI, and process optimization</strong> that can improve efficiency, scalability, and overall service delivery.</li> <li><strong>Lead cross-functional implementation efforts</strong> by partnering with IT, Operations, and business leaders to move initiatives from strategy through execution.</li> <li><strong>Evaluate and recommend technology solutions and implementation approaches</strong> that support a more modern operating environment.</li> <li><strong>Drive change management and adoption</strong> to help teams transition successfully to new systems, tools, and ways of working.</li> <li><strong>Promote innovation and continuous improvement</strong> by staying current on industry trends, gathering feedback, and helping the organization adapt thoughtfully over time.</li> </ul> <p><strong>What we're looking for</strong></p> <ul> <li><strong>Strong digital transformation leadership experience</strong> in complex, evolving environments</li> <li>Background in <strong>healthcare, insurance, or TPA operations</strong> with understanding of modernization challenges</li> <li>Ability to <strong>communicate clearly and influence stakeholders</strong> at all levels</li> <li>Judgment to balance <strong>strategic vision with hands-on execution</strong>, especially in legacy transformation</li> <li>Comfort with <strong>ambiguity and cross-functional leadership</strong> while bringing structure to transformation</li> </ul> <p><strong>What you'll need</strong></p> <ul> <li><strong>7+ years</strong> in digital transformation, product management, or operations leadership roles</li> <li>Experience in <strong>healthcare claims processing, benefits administration, or TPA operations</strong></li> <li>Strong understanding of <strong>modern software platforms, APIs, data systems, and automation tools</strong></li> <li>Proven ability to <strong>operate independently, lead cross-functionally, and execute complex initiatives</strong></li> <li>Track record <strong>modernizing legacy systems and manual processes</strong></li> </ul> <p><strong>What we offer</strong></p> <ul> <li>The opportunity to join <strong>SISCO</strong> in a high-impact leadership role focused on shaping the organization's future.</li> <li>A chance to help define and build the <strong>"SISCO of the Future"</strong> through meaningful modernization and innovation work.</li> <li>Direct collaboration with leadership and key partners across <strong>IT, Operations, and the broader business</strong>.</li> <li>A position with visibility and the ability to influence <strong>how technology, processes, and workflows evolve over time</strong>.</li> <li>The chance to work on initiatives where your expertise can directly improve <strong>operational efficiency, organizational effectiveness, and long-term readiness</strong>.</li> <li>An environment where strong candidates can bring forward informed recommendations and help drive important transformation decisions.</li> </ul> </div> </div> </div> <p></p> <p><strong>About SISCO:</strong></p> <p>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.</p> <p>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.</p> <p>Learn more at <a class="fui-Link ___1rxvrpe f2hkw1w f3rmtva f1ewtqcl fyind8e f1k6fduh f1w7gpdv fk6fouc fjoy568 figsok6 f1hu3pq6 f11qmguv f19f4twv f1tyq0we f1g0x7ka fhxju0i f1qch9an f1cnd47f fqv5qza f1vmzxwi f1o700av f13mvf36 f1cmlufx f9n3di6 f1ids18y f1tx3yz7 f1deo86v f1eh06m1 f1iescvh fhgqx19 f1olyrje f1p93eir f1nev41a f1h8hb77 f1lqvz6u f10aw75t fsle3fq f17ae5zn" href="https://www.siscobenefits.com/" target="_blank">www.siscobenefits.com</a>&nbsp;| <a href="https://www.linkedin.com/company/siscobenefits/" target="_blank">LinkedIn</a>&nbsp;</p> <div id="ka-mon-j14ut0avmm"></div> <div id="ka-mon-kdystrir4w"></div> <div id="ka-mon-pwn5at7sxdj"></div> <div id="ka-mon-qlnm12is6wj"></div> <div id="ka-mon-9dl62x5i4ba"></div> <div id="ka-mon-u2ab1uw6dj"></div> <div id="ka_mon_xjvro7frel"></div> <div id="ka_mon_aeeilfwfpho"></div>