# Swooped — VP of Technology & AI Infrastructure

- Generated: 2026-09-14 08:13:57 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4467037395/
- Provider: LinkedIn
- Posted: approximately 2026-09-14 02:13 AM EDT (from '6 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
- Compensation: $200,000-$225,000 annually
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 72%

## Direct-match strengths

Technology and AI strategy, external digital products, product partnership, data platforms, AI governance, privacy, integrations, roadmaps, Agile delivery, vendors, CRM exposure, executive communication, and resource-constrained execution.

## Hard or material gaps

Hard functional-ownership gaps: the mandate centrally owns enterprise IT service delivery, help desk, hardware lifecycle, access provisioning, staff onboarding/offboarding, cybersecurity strategy, operational risk, and Board-level mitigation reporting. Keith has strong adjacent cloud security, IAM, governance, platform, and vendor experience, but not this full corporate-IT/cybersecurity operating remit. The end employer is also unidentified.

## Evidence map

1. Technology strategy across internal and external products (weight 3, evidence 3/3) — Direct enterprise platform, SaaS, data, AI, and product strategy.
2. AI implementation and data governance (weight 3, evidence 3/3) — Direct production AI, governance, privacy, data architecture, and Responsible AI.
3. Product partnership and platform delivery (weight 2, evidence 3/3) — Direct product/engineering alignment, build-versus-buy judgment, and delivery.
4. Internal IT operations and service delivery (weight 3, evidence 1/3) — Cloud operations and IAM are direct; help desk, endpoints, and hardware lifecycle are not.
5. Cybersecurity strategy and Board risk reporting (weight 3, evidence 1/3) — Security controls and executive advising are direct; enterprise CISO/Board ownership is unsupported.
6. CRM and enterprise-data oversight (weight 2, evidence 2/3) — SuiteCRM integration and enterprise data-platform leadership are direct; organization-wide CRM ownership is less direct.
7. Program management and executive communication (weight 2, evidence 3/3) — Extensive planning, prioritization, risk, metrics, and executive communication.
8. Workforce-development mission commitment (weight 1, evidence 1/3) — HR/workforce technology is relevant, but mission-sector commitment is not established.

## Keyword diagnostic

Strong AI, product, data, governance, roadmap, and executive alignment; full corporate IT operations and cybersecurity ownership are decisive gaps.

## Full normalized job description

VP of Technology & AI Infrastructure
About the Opportunity
A national workforce development organization dedicated to connecting skilled, work-authorized professionals to career-aligned employment across the United States is seeking a VP of Technology & AI Infrastructure. The organization focuses on creating economic opportunity, scaling programmatic impact, and leveraging modern technology and artificial intelligence to drive operational efficiency and positive participant outcomes.
Role Overview
The VP of Technology & AI Infrastructure is responsible for defining and executing the organization’s technology strategy and infrastructure across internal operations and externally facing digital products. Reporting to the President and working closely with the CEO and executive leadership, this leader guides the organization toward an AI- and product-first model while upholding operational excellence, security, reliability, and scalable delivery practices. This role operates in a full-time, remote capacity within the United States.
Key Responsibilities
Own the overarching technology strategy across staff infrastructure and external user- and partner-facing products, ensuring systems are secure, scalable, cost-effective, and mission-aligned.
Build and maintain a multi-year technology roadmap encompassing staff infrastructure, IT operations, data systems and reporting, platform evolution, core digital products, and system integrations.
Translate organizational strategy into sequenced roadmaps with defined timelines, dependencies, resource requirements, and metrics.
Provide executive leadership with clear tradeoff analyses and recommendations on priorities based on organizational capacity and impact.
Support Agile ceremonies, including sprint planning and release planning.
Partner with product leadership to guide technical architecture, build-versus-buy evaluations, platform selection, integration strategy, and delivery for participant and partner platforms.
Establish technical standards and governance for responsible AI adoption in collaboration with cross-functional committees, covering data privacy, security controls, vendor risk management, quality assurance, bias mitigation, and human oversight.
Build the technical foundation for AI readiness, focusing on data quality, system integrations, and scalable infrastructure for feature deployment and experimentation.
Oversee internal IT operations and service delivery, including help desk support, hardware lifecycle management, access controls, onboarding, offboarding, and technical troubleshooting.
Define IT service standards, manage vendor relationships and managed service provider contracts, and lead staff training initiatives to maximize adoption of organizational infrastructure and AI tools.
Oversee the customer relationship management (CRM) platform and associated systems as the operational backbone for programs, development, and reporting.
Direct enterprise data strategy in collaboration with research and evaluation leadership to maintain reliable governance, dashboards, and reporting for program improvement, funding requirements, and executive decision-making.
Implement a consistent project management framework across technology initiatives to maintain accountability, predictability, and cross-functional transparency.
Lead cybersecurity strategy, data protection controls, and operational risk management, maintaining a risk register and presenting mitigations to executive leadership and the Board.
Required Qualifications
10+ years of technology leadership experience spanning IT operations, systems leadership, and product/engineering delivery.
Proven experience building or leading technology strategy across both internal infrastructure and externally facing digital products or platforms, including demonstrated experience with artificial intelligence.
Strong program and project delivery discipline with the ability to manage competing priorities in a resource-constrained environment.
Experience with AI implementation, data governance, and enterprise systems.
Demonstrated experience partnering with product leaders on strategy, roadmaps, prioritization, and technical execution.
Strong executive communication skills with the ability to translate complex technical topics into actionable decisions for leadership.
Demonstrated commitment to the organization's workforce development mission.
Preferred Qualifications
Experience with Salesforce CRM platforms.
Compensation and Benefits
Base Salary Range: $200,000 – $225,000 annually. Actual salaries vary based on factors including location, experience, and performance.
Benefits include medical, dental, and vision insurance; short-term disability and life insurance; paid parental leave; paid time off; a retirement plan with an employer match; and a remote work schedule.
Equal Opportunity Employer
The organization is committed to building an inclusive workplace where diversity is prioritized and is proud to be an equal opportunity employer.

## 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