# Upwardly Global — VP of Technology & AI Infrastructure

- Generated: 2026-09-11 07:44:21 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4465871961/
- Provider: LinkedIn
- Posted: approximately 2026-09-10 08:44 PM EDT (from '11 hours ago')
- Elapsed since posting: represented by the provider's relative posting label and approximate Eastern timestamp
- Applicants: Be among the first 25 applicants
- Work model/location: Fully remote — United States
- Compensation: $200,000-$225,000 base
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: PASS — 83%

## Direct-match strengths

Enterprise technology and AI strategy, internal and customer-facing platforms, multi-year roadmaps, build/buy decisions, data architecture, governance, security, responsible AI, AWS operations, access controls, systems integration, Agile delivery, executive communication, budgets, and workforce technology.

## Hard or material gaps

Keith's strongest infrastructure background is AWS and software/data platforms rather than enterprise help-desk and hardware-lifecycle operations. Salesforce is preferred; Keith has CRM experience including SuiteCRM, while direct Salesforce implementation depth is limited. Vendor/MSP contract negotiation is less strongly documented than architecture, budgets, delivery, and operations.

## Evidence map

1. Technology strategy across internal and external platforms (weight 3, evidence 3/3) — Direct strategy, architecture, delivery, and operations across AI, SaaS, data, and cloud platforms.
2. Multi-year roadmaps, priorities, resources, and metrics (weight 3, evidence 3/3) — Direct roadmap, budget, staffing, delivery, KPI, and executive reporting experience.
3. AI implementation, data governance, and enterprise systems (weight 3, evidence 3/3) — Direct production AI plus MassMutual governance and enterprise-data platforms.
4. Product partnership, architecture, build/buy, and integration (weight 3, evidence 3/3) — Direct product/engineering alignment, architecture, vendor evaluation, APIs, and integrations.
5. Internal IT operations, access, service delivery, and support (weight 3, evidence 2/3) — Direct system administration, accounts, security, cloud operations, and user support; hardware/help-desk scale is less direct.
6. CRM platform stewardship (weight 2, evidence 1/3) — Direct SuiteCRM and CRM integration; Salesforce is preferred and not claimed as deep implementation experience.
7. Enterprise data, reporting, and dashboards (weight 2, evidence 3/3) — Direct data strategy, data lakes, analytics, KPIs, and executive reporting.
8. Cybersecurity, privacy, risk, and Board communication (weight 3, evidence 2/3) — Strong security/privacy/risk and executive communication; formal Board risk-register ownership is less explicit.
9. Vendor and managed-service contracts (weight 2, evidence 1/3) — Budget and vendor evaluation are supported; contract-negotiation depth is limited.
10. Project and program delivery discipline (weight 2, evidence 3/3) — Twenty-nine years of project leadership, Agile delivery, prioritization, and risk management.
11. Commitment to workforce opportunity (weight 2, evidence 3/3) — Built workforce-management and HR technology and designed AI to improve workforce operations.

## Keyword diagnostic

Strong direct alignment across AI transformation, enterprise architecture, data, governance, security, product delivery, internal operations, and mission-adjacent workforce technology.

## 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: https://bit.ly/4r8s0CS
- Cover letter: https://bit.ly/46ehujT
- Validation: PASS — 2-page resume (909 words), 1-page cover letter (247 words); PDF geometry, bounds, annotations, links, and visual pages verified.
- Google Drive used: No