# Bounteous — VP, Digital Strategy (AI & Digital Change Management)

- Generated: 2026-09-15 10:48:11 PM EDT
- Original/canonical posting: https://wellfound.com/jobs/4710272-vp-digital-strategy-ai-amp-digital-change-management
- Provider: Wellfound
- Posted: Not disclosed
- Elapsed since posting: represented by the provider's relative posting label and approximate Eastern timestamp when available
- Applicants: Not disclosed
- Work model/location: Remote — United States
- Compensation: $230,000-$235,000 annually
- Travel: 50% or more; exceeds Keith's 5% maximum
- Positioning track: Executive leader
- Fit outcome: FAIL — 56%

## Direct-match strengths

Enterprise AI transformation, operating models, governance, AI enablement, executive communication, healthcare/life-sciences context, and measurable adoption.

## Hard or material gaps

Hard conflicts: 50%+ travel, $6M-$8M annual pre-sales responsibility, strategic-account expansion, business development, commercial growth strategy, and deep U.S. healthcare payer/provider transformation expertise are central requirements. These conflict with Keith's travel and no-GTM constraints and exceed his documented payer/change-consulting depth.

## Evidence map

1. AI-enabled enterprise transformation strategy (weight 3, evidence 3/3) — Direct enterprise AI, cloud, data, and operating transformation.
2. Organizational design and change management (weight 3, evidence 2/3) — Direct adoption and enablement leadership; dedicated change-management consulting depth is narrower.
3. Responsible AI rollout governance (weight 2, evidence 3/3) — Direct Responsible AI, privacy, model-governance, and control evidence.
4. Deep U.S. payer/provider consulting (weight 3, evidence 1/3) — Healthcare and regulated technology are direct; payer/provider transformation consulting is not.
5. $6M-$8M pre-sales and account expansion (weight 3, evidence 0/3) — Unsupported and conflicts with Keith's no-GTM preference.
6. Healthcare growth and commercialization strategy (weight 3, evidence 1/3) — Product commercialization exists; healthcare commercialization depth is unsupported.
7. Travel within 5% (weight 3, evidence 0/3) — Posting requires 50% or more.

## Keyword diagnostic

Strong transformation and governance adjacency, independently disqualified by travel, pre-sales/GTM ownership, and deep payer/provider change-consulting requirements.

## Full normalized job description

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Bounteous
Actively Hiring
We co‑innovate with the world's most ambitious brands to create digital experiences
B2B
Scale Stage
Rapidly increasing operations
4.8
Highly rated
Bounteous is highly rated on Glassdoor, with 4.8 out of 5 stars
+
2
B2B
Scale Stage
Rapidly increasing operations
4.8
Highly rated
Bounteous is highly rated on Glassdoor, with 4.8 out of 5 stars
+
2
Save
Apply Now
VP, Digital Strategy (AI & Digital Change Management)
$230k – $235k
|
Remote (
United States
)
|
15 years of exp
|
Full Time
Posted:
5 days ago
• Recruiter recently active
Hires remotely
in
United States
Remote Work Policy
Remote only
Company Location
Canada
•
India
•
Mexico
•
United States
•
Ukraine
Visa Sponsorship
Not Available
Relocation
Allowed
Skills
Business Development
Change Management
Mentorship
Organizational Design
Digital Strategy
Retention
Patient Engagement
Execution
Enterprise Technology
Communication Strategies
Commercial Strategies
Strategic Partnership Development
Stakeholder engagement
Technology Adoption
Client Service
Financial Acumen
Cross-functional Collaboration
Growth strategies
Member Engagement
Centers of Excellence
Roadmap Development
GDPR
Executive Presence
Solutioning
AI Strategy
Delivery Leadership
CCPA
Ai Adoption
Transformation Initiatives
Organizational Readiness
Target Operating Models
Operating Model Transformation
AI Literacy
Business Value
Role Redesign
Governance Frameworks
Ai Enablement
Change Controls
Resistance Management
Security Risks
Malware Protection
Data Protection Measures
Enterprise Change Management
Rollback Protocols
Strategic Pursuits
Payer Organizations
Provider Organizations
Escalation Paths
EBIT
Influence C-Suite Stakeholders
Lead Through Influence
Lead Through Ambiguity
Technology-Enabled Change
Life Sciences Organizations
Adoption Outcomes
Acceptable Use of Information Assets
Password Security Protocols
Navigate Complex Organizations
New Ways of Working
Matrixed, Global Organization
Operating Model Modernization
Responsible AI Rollout
Phased Adoption Plans
Member Engagement Transformation
Digital Front Door Redesign
AI-Enabled Commercialization
Health Portfolio Strategy
Bottom-Line Growth Modeling
ROI Impact
Adoption-Driven Change
Technology Transformation Consulting
U.S. Healthcare Ecosystem
Enterprise Digital Transformation Strategy
People, Process, Data, and Technology
Role Redesigns
Confidentiality, Integrity, and Availability of Information Assets
Data Privacy and Protection Standards
Safeguard Sensitive Information
About the job
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 transformation in 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.
$230,000 - $235,000 a year
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.
We invite you to stay connected with us by subscribing to our monthly job openings alert
here
.
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.
#BI-Remote
#LI-Remote
Apply Now
About the company
Bounteous
Actively Hiring
We co‑innovate with the world's most ambitious brands to create digital experiences
5000+
Employees
Canada
5000+
Information Technology
E-Commerce
Analytics
Information Services
Consulting
Web Design
E-Commerce Platforms
Software
Digital Marketing
B2B
Scale Stage
Rapidly increasing operations
4.8
Highly rated
Bounteous is highly rated on Glassdoor, with 4.8 out of 5 stars
4.6
Work / Life Balance
Employees rate Bounteous 4.6/5 on Glassdoor for work / life balance
4.7
Strong Leadership
Employees rate Bounteous 4.7/5 on Glassdoor for faith in leadership
Employees joined from
Accenture
Sapient Razorfish
Merkle
Hathway
The Archer Group
Learn more about
Bounteous
Founders
Julia Kowalik
Founder
Toronto
View the team
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## Artifact metadata

- Resume: Not generated because the fit gate returned FAIL.
- Cover letter: Not generated because the fit gate returned FAIL.
- LinkedIn note: Not generated for a FAIL role.
- Google Drive used: No