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

- Generated: 2026-09-21 08:32:55 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4467380699/
- Provider: LinkedIn
- Posted: approximately 2026-09-21 06:32 AM EDT (from '2 hours ago')
- Elapsed since posting: represented by the provider's relative posting label and approximate Eastern timestamp when available
- Applicants: Be among the first 25 applicants
- Work model/location: Remote — United States, with extensive client travel
- Compensation: $180,000-$220,000 annually
- Travel: 50% or more
- Positioning track: Executive leader
- Fit outcome: FAIL — 56%

## Direct-match strengths

AI adoption, digital transformation, change management, value realization, target operating models, executive advisory, financial acumen, roadmaps, and regulated healthcare technology.

## Hard or material gaps

Hard travel conflict: the role requires 50% or more travel, far above Keith's 8% maximum. The mandate also centers on pre-sales leadership, strategic account expansion, and business development—areas Keith explicitly does not prioritize—and requires deep U.S. payer/provider experience that is not supported.

## Evidence map

1. AI adoption and digital transformation (weight 3, evidence 3/3) — Direct AI strategy, adoption, operating model, and transformation leadership.
2. Change management and value realization (weight 3, evidence 3/3) — Direct adoption, metrics, business cases, and operating change.
3. C-suite advisory (weight 2, evidence 3/3) — Advised executives and 200+ AWS enterprises.
4. Pre-sales and account expansion (weight 3, evidence 1/3) — Consulting and customer work are direct; GTM ownership is not a target strength.
5. Healthcare payer and provider expertise (weight 3, evidence 1/3) — Healthcare technology is direct; deep payer/provider operating experience is not.
6. Travel within 8% (weight 3, evidence 0/3) — Posting requires 50% or more travel.
7. Compensation threshold (weight 2, evidence 3/3) — Maximum disclosed pay is $220,000.

## Keyword diagnostic

Strong transformation and executive-advisory overlap is outweighed by mandatory 50% travel, GTM/pre-sales ownership, and payer/provider depth.

## Full normalized job description

For our client, we are seeking a VP, Digital Strategy (AI & Digital Change Management) to join the team of a leader in the Technical Services space.
This executive will guide enterprise clients through AI adoption and broader digital transformation, with a strong emphasis on change management and value realization. The role partners closely with C-suite stakeholders to shape strategy, align execution to business goals, and support complex organizational change. It also combines strategic advisory, pre-sales leadership, and account expansion efforts across healthcare and B2B environments.
Location: Remote - US based candidates only, no visa sponsorship available
Compensation: $180,000 – $220,000 annually
Responsibilities
Serve as a trusted advisor to C-suite executives on digital strategy and AI enablement
Lead and define strategy for significant pre-sales activities and strategic account expansions
Ensure alignment between business goals and transformation execution
Integrate change management across all phases of transformation programs
Develop and implement AI-enabled transformation strategies for enterprise clients
Craft stakeholder engagement and communication strategies for diverse audiences
Build client-side capabilities to ensure sustainability of transformation initiatives
Qualifications
15+ years in digital strategy, change management, or technology transformation consulting
Deep understanding of the U.S. healthcare ecosystem, including payer and provider organizations
Proven success in enterprise digital transformation strategy and roadmap execution
Experience with AI/technology adoption governance frameworks and target operating models
Strong financial acumen linking initiatives to business value
Exceptional ability to influence C-suite stakeholders in complex organizations
Willingness to travel 50% or more for client engagement and business development
Benefits
Opportunity to work at the forefront of AI and digital transformation
Engagement with prestigious healthcare and B2B organizations
Chance to shape enterprise transformation agendas
Access to executive networking and mentorship
Flexibility to work remotely with required travel
Involvement in building sustainable change management frameworks
Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.

## 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