# Ladders — Lead Director - Engineering

- Generated: 2026-09-14 08:13:57 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4464787264/
- Provider: LinkedIn
- Posted: approximately 2026-09-14 07:13 AM EDT (from '1 hour 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; no visa sponsorship
- Compensation: $144,200-$288,400 annually
- Travel: Not disclosed
- Positioning track: Technical manager
- Fit outcome: PASS — 91%

## Direct-match strengths

Technology-program and software-engineering leadership, modernization roadmaps, matrix-team leadership, architecture/product partnership, cross-workstream dependency management, risk resolution, executive reporting, KPIs, and AI-enabled transformation.

## Hard or material gaps

The end employer is not identified by Ladders and remains a material caveat. Keith has healthcare and regulated-technology experience, but no direct retail-front-store operating background; that domain is contextual rather than listed as a qualification.

## Evidence map

1. 10+ years technology program or software-engineering leadership (weight 3, evidence 3/3) — More than 20 years of technical leadership across software, data, cloud, and AI.
2. 8+ years managing teams in matrix organizations (weight 3, evidence 3/3) — Led teams at multiple matrixed enterprises and organizations up to 25 people.
3. Architecture, product, and PMO collaboration (weight 3, evidence 2/3) — Direct architecture and product partnership is extensive; formal PMO partnership is less explicit.
4. Cross-functional software-team leadership (weight 2, evidence 3/3) — Led cross-functional engineering, data, security, platform, quality, and product delivery.
5. Modernization and transformation roadmaps (weight 3, evidence 3/3) — Direct cloud, data, AI, platform, and operating-model modernization.
6. Risk, dependencies, plans, reporting, and KPIs (weight 2, evidence 3/3) — Direct planning, risk, dependency, budget, executive reporting, and KPI accountability.
7. Retail front-store value streams (weight 1, evidence 1/3) — Transferable enterprise transformation; no direct retail-front-store claim.

## Keyword diagnostic

Strong coverage of engineering transformation, modernization, matrix delivery, program planning, architecture/product alignment, risk, metrics, and AI-enabled execution; no unsupported retail claim added.

## Full normalized job description

For our client, we are seeking a Lead Director - Engineering to join the team of a leader in the Healthcare space.
This leader will guide engineering transformation efforts that modernize core value streams and strengthen execution across a complex, matrixed environment. The role will partner closely with architecture, product, and PMO teams to align technical delivery, manage dependencies, and keep large-scale programs moving forward. This person will also help shape AI-enabled initiatives, improve visibility into progress and risk, and ensure outcomes are measured against business KPIs.
Location: Remote - US based candidates only, no visa sponsorship available
Compensation: $144,200 – $288,400 annually
Responsibilities
Lead transformation and modernization roadmaps for retail front store value streams
Drive AI-enabled transformations and execution strategies
Identify and manage risks, engaging teams for resolution
Manage cross-workstream technical dependencies
Create end-to-end program plans with tracking and reporting
Communicate program status to stakeholders
Define and track metrics and KPIs for business outcomes
Qualifications
10+ years in technology program delivery or software engineering leadership
8+ years managing teams within a matrix organization
4+ years collaborating with architecture, product, and PMO teams
2+ years leading cross-functional software teams
Bachelor's degree or equivalent experience
Benefits
Medical, dental, and vision coverage
Paid time off
Retirement savings options
Wellness programs
Additional resources for physical, emotional, and financial well-being
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: https://bit.ly/4itbyuK
- Cover letter: https://bit.ly/4hpqGIq
- Validation: PASS — 2-page resume (934 words), 1-page cover letter (218 words); PDF geometry, bounds, annotations, links, and visual pages verified.
- Google Drive used: No