VP of Technology & AI Infrastructure

Title: VP of Technology & AI Infrastructure Department: Information Technology Reports to: President Location: Remote About the Organization Upwardly Global is a national workforce development organization that connects work-authorized, college-educated immigrants to skill-aligned professional employment across the United States. We address one of the country’s most significant economic inefficiencies: more than 2 million highly educated, work-authorized immigrants are underemployed, representing over $40 billion in annual forgone wages and untapped productivity for the American economy. Our model works. Jobseekers enter our programs earning an average of $9,000 per year and are placed in roles averaging $67,000 per year. To date, we have supported an estimated 35,000 job placements, contributing billions in earnings to the U.S. economy. Upwardly Global is data-driven, economically accountable, and built for scale. We are committed to leveraging AI to its fullest potential, driving operational efficiency, jobseeker readiness, and national economic impact. We operate nationally, partnering with leading employers, workforce agencies, and policymakers to ensure that global talent becomes American advantage. About the Role The VP of Technology is responsible for building and leading Upwardly Global’s technology strategy and infrastructure to support both internal operations and externally facing digital products. This includes staff-facing technology as well as the technical infrastructure that enables jobseeker and partner experiences. This leader partners closely with the CEO, President and executive leadership to ensure technology is a strategic enabler of UpGlo’s mission, helping the organization transition towards an AI and product-first model while maintaining strong operational excellence, security, reliability, and scalable delivery practices. Upwardly Global will integrate AI into all aspects of the organization to drive operational excellence, improve jobseeker opportunities and outcomes, and this role will help lead these efforts. The VP of Technology is expected to be both strategic and execution-oriented: setting direction, making tradeoffs clear, and delivering consistently across teams. Key Responsibilities: 1. Technology Strategy & AI Infrastructure: • Own UpGlo’s technology strategy across staff infrastructure and jobseeker/partner-facing products, ensuring both are secure, scalable, cost-effective, and aligned to mission outcomes. • Build and maintain a multi-year technology roadmap covering staff infrastructure and IT operations, data systems and reporting, Salesforce/platform evolution, core digital products (jobseeker portal, online learning, partner tools), and integrations/interoperability across systems. • Translate organizational strategy into a sequenced plan with clear timelines, dependencies, resource needs, and success measures. • Provide clear tradeoffs and recommendations to Executive Leadership Team on what to prioritize, defer, or stop based on capacity and impact. • Support sprint planning, release planning, and other Agile ceremonies. 2. Product & Engineering Partnership (Jobseeker + Partner Products): Partner deeply with Product leadership to deliver a reliable, scalable technology foundation for UpGlo’s jobseeker and partner ecosystem. Ensure strong cross-functional delivery across product/tech/programs, including planning, prioritization, technical feasibility, timelines, and adoption/change management. Partnering with the Product Director, guide the technical approach to product delivery (architecture, build vs. buy, integration strategy, platform choices) and ensure consistent execution quality. 3. AI Enablement and Responsible Technology Innovation: Partner with the Executive team, Product and Program leadership to identify and deliver AI-enabled capabilities that improve jobseeker outcomes and staff productivity. With a cross-department steering committee, establish technical standards and governance for responsible AI use, including data privacy and consent, security controls and vendor risk assessment, quality assurance and bias considerations, and human oversight/escalation paths. Build the technical foundation required for AI-readiness: data quality, integration, and scalable infrastructure to support AI features and experimentation. 4. IT Operations, Service Delivery and Training (Staff & Product Infrastructure): Lead internal IT operations to ensure strong service delivery across the organization (helpdesk, devices, access control, onboarding/offboarding, troubleshooting). Establish service standards (response times, escalation, documentation, internal communications) and continuously improve the staff technology experience. Own vendor relationships and contracts across key systems and managed service providers. Ensure all staff are trained to use our infrastructure and tools, including AI, to maximum effect. Delivery includes accountability to staff usage, ensuring technology is utilized with maximum efficiency and effectiveness. 5. IT Operations, Service Delivery and Training (Staff & Product Infrastructure): Lead internal IT operations to ensure strong service delivery across the organization (helpdesk, devices, access control, onboarding/offboarding, troubleshooting). Establish service standards (response times, escalation, documentation, internal communications) and continuously improve the staff technology experience. Own vendor relationships and contracts across key systems and managed service providers. Ensure all staff are trained to use our infrastructure and tools, including AI, to maximum effect. Delivery includes accountability to staff usage, ensuring technology is utilized with maximum efficiency and effectiveness. 6. Systems, Data, and Platform Leadership (Salesforce + Reporting) Oversee Salesforce and related systems as the operational backbone for Programs, Development, and organizational reporting. Strengthen system usability, adoption, and reliability through clear requirements gathering, prioritization, and iterative improvements. Own data strategy in partnership with research and evaluation leadership: governance, quality, reporting, and dashboard reliability. Ensure the organization has trusted reporting that supports program improvement, fundraising narratives, and leadership decision-making. 7. Project Delivery, Execution Discipline & Cross-Functional Leadership: Implement and enforce a consistent project management framework across all technology work. Lead cross-functional execution so teams experience IT and technology as reliable, transparent, and partnership-driven. Build a culture of accountability and follow-through within the technology function and across stakeholders. 6. Security, Risk, and Compliance: Own cybersecurity strategy and operational risk management. Ensure appropriate controls for systems that handle sensitive data. Maintain risk register and communicate risks and mitigations clearly to Executive Leadership Team and the Board as needed. Ensure technology practices align with funder requirements, privacy expectations, and organizational policies. 7. Executive Partnership & Communication: Serve as a proactive, consultative partner to the CEO, President and Executive Leadership Team- bringing clear updates, risks, and decision-ready recommendations. Communicate in a structured way leadership can act on: what is on track, what is at risk, what decisions are needed, and what tradeoffs are recommended. Drive follow-through on Executive Leadership Team decisions by documenting commitments, assigning owners, and reporting progress. Success Measures: A clear, sequenced technology roadmap that covers staff infrastructure and digital products, aligned to strategic priorities. Strong Product-Tech partnership resulting in reliable delivery of jobseeker and partner-facing features and improvements. AI capabilities delivered responsibly with governance, safety standards, and measurable impact. Predictable project delivery with improved cross-functional satisfaction and fewer surprises. Improved reliability, security posture, and risk management across systems and products. Executive-level communication that is decision-oriented, clear, and consistent. Qualifications: 10+ years of technology leadership experience spanning IT operations, systems leadership, and product/engineering delivery. Experience building or leading technology strategy across both internal infrastructure and externally facing products/platforms with demonstrated experience in AI. Strong program/project delivery discipline; proven ability to manage multiple priorities with constrained resources. Experience with AI, data governance, enterprise systems, and CRM platforms (Salesforce preferred). Deep comfort partnering with Product leaders on strategy, roadmaps, prioritization, and delivery. Strong executive communication skills with the ability to translate complex technical issues into clear decisions. Commitment to our mission Salary Range: 200K- 225K annually Salary Disclaimer: The base salary range represents the low and high end of the Indeed salary range for this position. Actual salaries will vary depending on factors including but not limited to location, experience, and performance. The range listed is just one component of Upwardly Global's total compensation package for employees. Benefits include paid time off policy, hybrid or remote work schedule, medical/dental/vision insurance, paid parental leave, short term disability insurance, life insurance and retirement plan with employer match. ____________ Upwardly Global is deeply committed to building a workplace where inclusion is not only valued but prioritized. We’re proud to be an equal opportunity employer, seeking to create a welcoming and diverse environment.