VP, Digital Strategy (AI & Digital Change Management)

Bounteous; Northern (KY); Hybrid; USD 200,000 - 300,000; Full time

Job summary

Bounteous seeks a Vice President, Digital Strategy (AI & Digital Change Management) to lead 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 - ensuring 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,

Qualifications

• 15+ years of digital strategy, change management, or technology transformation consulting.
• Deep expertise in the U.S. healthcare ecosystem (payer/provider/life sciences).
• Proven enterprise digital transformation strategy experience across people, process, data and technology.
• Experience developing target operating models, governance, and AI adoption frameworks.
• Strong financial acumen linking transformation initiatives to business value.
• Willingness to travel 50% or more to support engagements and business development.
• Bachelor’s degree required; advanced degree preferred.

Responsibilities

• Serve as a trusted advisor to C-suite executives, shaping enterprise transformation agendas across digital strategy and AI enablement.
• Lead and contribute to $6M–$8M in annual pre-sales activity, expanding strategic accounts.
• Ensure change management is integrated across all phases of transformation programs.
• Define AI-enabled transformation strategies linking technology to organizational readiness and new operating models.
• Develop governance frameworks for responsible AI rollout and phased adoption plans.
• Build client-side change capability through training, AI literacy initiatives, and Centers of Excellence.
• Lead industry-specific strategy development in health and life sciences offerings.

Skills

Executive presence

Stakeholder management

Financial acumen

Healthcare domain knowledge

Business development

Travel 50%+

Education

Bachelor’s degree

Job description

Bounteous is a global AI Services firm where agentic engineering and human experience converge to deliver transformative business outcomes for the enterprise. We help organizations design, build, and scale AI-driven products, platforms, and processes. With more than 5,000 team members worldwide, Bounteous delivers AI that sticks, powering adoption and outcomes that move organizations from experimentation to true transformation. Bounteous is backed by New Mountain Capital, a New York-based growth-oriented investment firm that emphasizes business building.

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 transformationin regulated healthcare and B2B environments.

Information Security Responsibilities

• Promote and enforce awareness of key information security practices, including acceptable use of information assets, malware protection, and password security protocols
• Identify, assess, and report security risks, focusing on how these risks impact the confidentiality, integrity, and availability of information assets
• Understand and evaluate how data is stored, processed, or transmitted, ensuring compliance with data privacy and protection standards (GDPR, CCPA, etc.)
• Ensure data protection measures are integrated throughout the information lifecycle to safeguard sensitive information

Role and 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.

Bounteous is proud to be an equal opportunity employer. Bounteous does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, national origin, veteran status, or any other status protected under federal, state, or local law.Bounteous is willing to sponsor eligible candidates for employment visas.

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.

Bounteous has always encouraged us to be honest with what we can or cannot do. This is not seen as a negative, but as a vessel for support in every way possible. For example, when I went through a number of life-changing events, my team supported me through every step of it. Be honest with your boundaries, availability, capability, and how you’re doing personally and Bounteous will always have your back.