Jenna Sullivan

I help organizations turn bold strategies into meaningful outcomes by aligning people, processes, and products. I specialize in orchestrating cross-functional teams in legacy financial services companies to design customer-centered products and scalable systems that improve both user satisfaction and business performance. What I offer is a rare blend of service design, product strategy, and operational expertise. I can build the vision, craft the roadmap, and operationalize the work to get there, whether you need to evolve your design system, mature your product operating model, or align stakeholders around a shared outcome. At USAA, I’ve led teams through transformative design and product initiatives, growing a native design system, improving servicing experiences, and contributing to a 1.8% YoY increase in digital MSAT. I built scalable frameworks for prioritization and sequencing, implemented portfolio management practices, and drove continuous improvement rituals that improved team clarity and cohesion. In previous roles, I’ve shaped financial wellness and personalization strategies, introduced discovery frameworks, and facilitated co-creation workshops with 30+ stakeholders to align vision across business, design, and technology. I’ve also launched fraud remediation and digital self-service experiences, contributing directly to growth, efficiency, and member trust. I bring curiosity, systems thinking, and a bias toward action. I thrive in ambiguity and excel at creating structure where there is none—through storytelling, artifacts, rituals, and collaboration. I’m not just a strategic thinker, I’m an orchestrator of progress. If you're looking for someone to drive clarity, cohesion, and measurable outcomes across complex initiatives, I can help you get there through better systems, smarter processes, and experiences people trust.