# Ladders — Vice President, Software Engineering & AI Transformation

## Posting metadata

- Generated: 2026-09-02 01:32:57 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4458883803/
- Provider: LinkedIn
- Job ID: 4458883803
- Listed employer: Ladders, recruiting for an undisclosed client in Aerospace & Defense
- Primary location: United States
- Work model: Remote — U.S.-based candidates only
- Employment type: Full-time
- Seniority: Executive
- Posted: LinkedIn displayed “1 day ago” when fetched on 2026-09-02 at 01:32 AM EDT; the page did not expose a reliable absolute timestamp
- Elapsed since posting: Approximately one day according to LinkedIn; exact elapsed time is unavailable
- Applicants: 34
- Compensation: $175,000-$250,000 annual base salary
- Travel: Not disclosed
- Visa sponsorship: Not available
- Positioning track: Executive leader
- Fit outcome: FAIL — 80% raw weighted coverage, overridden by two hard conflicts

## Direct-match strengths

Keith has strong direct evidence in executive AI and engineering leadership, enterprise architecture, modern software engineering, AI/ML implementation, Generative AI, governance, cloud platforms, product delivery, and translating strategy into operating priorities. He built and directly led an 11-engineer AI organization, led software teams of approximately 23-25 people, founded AWS technical communities of 80-100 specialists, delivered production AI and SaaS platforms, advised 200+ enterprises, and shipped AssistX with 70+ automations across 20+ workflows.

## Hard or material gaps

1. The role is explicitly for an Aerospace & Defense client. Defense is a standing no-go constraint and therefore a hard fit conflict.
2. The job requires 3-5+ years in EHR and healthcare software environments. Keith has source-supported life-science, regulated dental-health software, HIPAA, FDA-cleared software, healthcare-customer advisory, and ontology experience, but his source files do not document 3-5 years of EHR implementation or ownership. The requirement is mandatory, not preferred.
3. The posting calls for 8+ years leading large software engineering organizations. Keith has extensive leadership and has led software organizations of roughly 11-25 people plus larger 80-100-person technical communities, but the source evidence does not establish eight years leading large software-engineering organizations at the scale implied by this mandate.
4. The listed bachelor’s degree is in Computer Science, Software Engineering, Information Technology, or a related field. Keith’s Ph.D. is in Molecular Biology / Microbiology & Immunology; his decades of software experience are strong but do not change the degree field.

## Evidence map

1. **Lead and scale a high-performing, large software engineering organization** — weight 3, score 2/3: Direct leadership of engineering teams up to approximately 25 people and broader technical communities up to 100, but the duration and software-organization scale specified by the JD are not fully demonstrated.
2. **Improve delivery predictability and software quality** — weight 3, score 3/3: Direct evidence establishing Agile delivery, testing, CI/CD, engineering practices, and rapid production delivery across SuccessKPI, Intelligent DataWorks, MassMutual, and earlier software roles.
3. **Translate business strategy into technology priorities and operating standards** — weight 3, score 3/3: Direct executive-roadmap, investment-prioritization, architecture, governance, and cross-functional delivery evidence.
4. **Establish metrics for engineering effectiveness and AI adoption** — weight 2, score 2/3: Direct KPI prioritization and measurable delivery/adoption outcomes, though no explicit enterprise-wide engineering-effectiveness measurement program is documented.
5. **Evaluate emerging technologies and drive AI-powered customer-facing products** — weight 3, score 3/3: Direct evaluation and implementation of LLMs, AI agents, GenAI frameworks, RAG, ML, and production customer-facing products.
6. **Govern technology standards and investment priorities** — weight 2, score 3/3: Direct architecture standards, AI governance, responsible-AI, platform-roadmap, and executive investment-prioritization evidence.
7. **15+ years of progressive technology experience and 8+ years leading large software organizations** — weight 3, score 2/3: The progressive-technology requirement is exceeded, but the exact eight-year large-software-organization scope is not fully evidenced.
8. **3-5+ years in EHR and healthcare software environments** — weight 3, score 1/3: Adjacent regulated healthcare, dental software, life-science, HIPAA, FDA, ontology, and healthcare-customer evidence; no direct EHR record or required duration.
9. **Modern software engineering practices and enterprise architecture** — weight 3, score 3/3: Deep direct evidence across cloud-native architecture, distributed systems, APIs, CI/CD, testing, SaaS, data platforms, and production operations.
10. **AI/ML implementation and Generative AI / ML frameworks** — weight 3, score 3/3: Direct production AI, ML, GenAI, RAG, agents, MLOps, SageMaker, TensorFlow, LangChain, and LangGraph experience.
11. **Bachelor’s degree in CS, software engineering, IT, or related field** — weight 2, score 1/3: Keith holds a Ph.D. in a scientific discipline and has decades of software experience, but not the listed computing degree.

Weighted evidence score: 72/90 = 80%. Outcome remains FAIL because the defense-industry conflict and mandatory EHR requirement are hard gaps.

## Full normalized job description

Ladders is recruiting, for an undisclosed client described as a leader in Aerospace & Defense, a Vice President of Software Engineering & AI Transformation. This remote, U.S.-based executive role will oversee a large-scale software engineering organization and shape the technology direction behind critical solutions in a highly regulated, mission-driven environment. The mandate centers on improving engineering execution, strengthening software quality, accelerating AI adoption in customer-facing products and internal capabilities, translating business strategy into technology investment priorities and operating standards, and measuring outcomes.

The employer seeks a leader with experience managing complex engineering organizations and modernizing enterprise technology practices. The role also calls for evaluating emerging technologies, establishing effective governance, and driving innovation for competitive advantage and long-term scalability.

### Responsibilities

- Lead and scale a high-performing software engineering organization.
- Improve delivery predictability and software quality.
- Translate business strategy into technology priorities.
- Establish metrics to measure engineering effectiveness and AI adoption.
- Evaluate emerging technologies for competitive advantage.
- Drive AI-powered experiences into customer-facing products.
- Govern technology standards and investment priorities.

### Qualifications

- Bachelor’s degree in Computer Science, Software Engineering, Information Technology, or a related field.
- 15+ years of progressive technology experience.
- 8+ years leading large software engineering organizations.
- 3-5+ years in EHR and healthcare software environments.
- Expertise in modern software engineering practices and enterprise architecture.
- Experience implementing AI and machine learning capabilities.
- Strong understanding of Generative AI and machine learning frameworks.

### Benefits

- Career-growth opportunities.
- Medical, dental, vision, short-term disability, long-term disability, and FSA benefits.
- Three weeks of vacation plus five personal days.
- Employee stock ownership and RRSP program.
- 401(k) and life-insurance benefits.
- Flexible work arrangements.

## Artifact metadata

- Resume: Not generated under the FAIL fit gate.
- Cover letter: Not generated under the FAIL fit gate.
- LinkedIn connection note: Not generated for a FAIL role.
- Google Drive used: No
- Optimizer validation: Fit gate completed against the canonical role and Keith’s source files; no unsupported evidence was added; publication is limited to this JD capture.