VP, Digital Strategy

We are seeking a Vice President, Digital Strategy (AI & Digital Change Management) to lead Bounteous’ most complex transformation engagements across Health Systems, Life Sciences, and B2B organizations. This role sits at the intersection of AI strategy, organizational design, and enterprise change - responsible for ensuring that technology investments translate into sustained adoption, new operating models, and measurable business outcomes. The VP will serve as a senior client-facing leader and internal capability builder, working alongside strategy, delivery, and technology practices to embed change management discipline into the full lifecycle of AI-enabled transformation. This leader brings a deep understanding of how organizations must evolve (in structure, culture, and capability) to realize the value of AI and digital transformation in regulated healthcare and B2B environments. Role & Responsibilities •Serve as a trusted advisor to C-suite executives, shaping enterprise transformation agendas that span digital strategy, AI enablement, organizational change, and operating model modernization. •Lead and contribute to $6M–$8M in annual pre-sales activity, defining solution strategy for complex change-led pursuits and expanding strategic accounts. •Act as executive strategist across key engagements, ensuring alignment between business goals, solution approach, delivery e [... source excerpt omitted ...] d Delivery leadership to ensure change management is integrated across all phases of transformation programs. •Define and lead AI-enabled transformation strategies for enterprise clients, connecting technology capability to organizational readiness, role redesign, and new ways of working. •Develop and evolve target operating models that reflect how AI changes workflows, decision rights, and organizational structure across growth, marketing, operations, and technology organizations. •Design stakeholder engagement, communication, and resistance management strategies tailored to C-suite, operational, and frontline audiences. •Build client-side change capability through trainin [... source excerpt omitted ...] evelopment aligned to digital strategy, enterprise technology, AI, and operating model transformation. •Connect bottom-line growth modeling to transformation initiatives, helping clients and internal teams articulate the EBIT and ROI impact of adoption-driven change. Preferred Qualifications •15+ years of experience in digital strategy, change management, or technology transformation consulting, with significant focus on technology-enabled change. •Deep expertise within the U.S. healthcare ecosystem, including payer, provider, and/or life sciences organizations at enterprise scale. •Proven track record of leading enterprise digital transformation strategy, including roadma