VP, Digital Strategy

Bounteous; Northern (KY); Hybrid; USD 230,000 - 360,000; Full time

Job summary

Bounteous seeks a Vice President of Digital Strategy (AI & Digital Change Management) to lead its most complex transformation engagements across Health Systems, Life Sciences, and B2B sectors. You will fuse AI strategy, organizational design, and change management to drive adoption, new operating models, and measurable outcomes.

You will work with senior clients and internal teams to embed change, design governance, and scale AI-enabled transformations that deliver sustained value across

Qualifications

• 15+ years of experience in digital strategy, change management, or technology transformation consulting.
• Deep expertise in the U.S. healthcare ecosystem (payer, provider, life sciences) at enterprise scale.
• Proven track record leading enterprise digital transformation strategy with roadmap development and execution.
• Experience developing target operating models, governance frameworks, and AI adoption.
• Strong financial acumen; ability to tie transformations to business value.
• Willingness to travel 50%+ to support executive client engagement and business development.

Responsibilities

• Serve as a trusted advisor to C-suite executives across health systems, life sciences, and B2B.
• Lead and contribute to multi-million pre-sales activity, shaping solution strategy and expanding strategic accounts.
• Ensure alignment between business goals, solution approach, delivery, and change outcomes.
• Partner with leadership to embed change management across all phases of AI-enabled transformation programs.
• Define AI-enabled transformation strategies and operating models reflecting evolving workflows and decision rights.

Skills

Executive presence

Stakeholder management

Strategic thinking

Client relationship management

Travel willingness

Education

Bachelor’s degree

Advanced degree preferred

Job description

We are seeking a Vice President, Digital Strategy (AI & Digital Change Management) to lead Bounteous’ most complex transformation engagementsacross 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 transformationin 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 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.

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 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.
• Individual pay is determined by many factors, including experience, relevant education or training, and organizational needs. The mid-range to maximum of the salary range is generally reserved for individuals who are highly experienced in the role.

Why do I get up every morning excited to start my day at Bounteous? I am able to have an impact - to my teams, clients, and Bounteous. To me, that means I am able to contribute to something bigger than myself. I can ask questions, challenge the status quo, and contribute to new ways of doing things. Working with teams of energetic, fun, and innovative people collaborating to solve some of the most challenging problems that our clients and Bounteous face is truly rewarding! My roles here have allowed me the opportunity to challenge myself, grow, and contribute to a better Bounteous.

Let's discuss how Bounteous can help your organization turn AI into business outcomes

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