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.

•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 execution, and change outcomes.

•Partner with Solutioning, Client Service, and 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 training programs, AI literacy initiatives, and Centers of Excellence that ensure transformations are self-sustaining after engagement close.

•Develop governance frameworks for responsible AI rollout, including change controls, phased adoption plans, rollback protocols, and escalation paths.

•Lead industry-specific strategy development, including member/patient engagement transformation, digital front door redesign, and AI-enabled commercialization of health and life sciences offerings.

•Contribute to the Health portfolio strategy and support strategic partnership development 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.

•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 roadmap development and execution across people, process, data, and technology.

•Experience developing target operating models, role redesigns, and governance frameworks in the context of AI/technology adoption.

•Strong financial acumen, with experience connecting transformation initiatives and adoption outcomes to business value.

•Experience developing commercial and growth strategies within healthcare, including patient/member engagement and retention.

•Exceptional executive presence with the ability to influence C-suite stakeholders, navigate complex organizations, and lead through ambiguity.

•Proven success in business development and strategic pursuits.

•Ability to lead through influence, mentorship, and cross-functional collaboration in a matrixed, global organization.

•Willingness to travel 50% or more to support executive client engagement, strategic workshops, and business development activities.

•Bachelor’s degree in business, technology, or related field; advanced degree preferred.