# VP of Technology & AI Infrastructure — Swooped ## Posting metadata - Canonical source: https://www.linkedin.com/jobs/view/4461033554/ - Provider: LinkedIn - LinkedIn job ID: 4461033554 - Posting company: Swooped - Hiring organization described by the posting: An unnamed national workforce-development organization - Title: VP of Technology & AI Infrastructure - Primary LinkedIn location: United States - Verified work model: Hybrid or remote schedule (role-specific language in the canonical JD) - Employment type: Full-time - LinkedIn seniority classification: Director - Compensation: $200,000-$225,000 base salary annually - Travel: Not disclosed - Applicants: 65 applicants at capture, below Keith’s 90-applicant ceiling - Posting age: 23 hours ago as displayed at 6:30 PM EDT on August 31, 2026; exact posting time unavailable - Generated: August 31, 2026 at 6:45 PM EDT - Duplicate/repost note: This is substantively the same Swooped posting previously captured as LinkedIn job 4459047812. ## Eligibility verification Eligible for optimizer review. The canonical posting explicitly says the position’s benefits include a “hybrid or remote work schedule.” LinkedIn lists the role’s primary location as United States. That role-specific remote option satisfies Keith’s work-model gate; a remote label was not inferred from generic employer language. ## Positioning track Executive leader. The mandate owns organization-wide technology strategy, AI infrastructure, internal IT operations, externally facing products, data and CRM platforms, security, governance, vendor relationships, and executive/board communication. ## Fit outcome **BORDERLINE — 78% weighted requirement coverage.** Keith has strong, direct evidence for the AI strategy, product/platform delivery, data governance, technology roadmaps, cross-functional execution, team leadership, and executive communication portions of the role. The material gap is the JD’s core internal-IT service-delivery scope: helpdesk, employee devices, access control, onboarding/offboarding, troubleshooting, and staff technology training/accountability. Keith’s sources document cloud/platform operations, IAM/security architecture, data operations, and engineering leadership, but not direct ownership of an enterprise staff IT function. The preferred Salesforce element also has only limited source support without an outcome-backed Salesforce ownership example. Per the optimizer gate, no resume or cover letter was generated automatically for this BORDERLINE role. ## Weighted evidence map | Requirement | Weight | Evidence score | Source-supported evidence | Assessment | |---|---:|---:|---|---| | Own technology strategy across internal infrastructure and external products | 3 | 2/3 | Defined IDW’s AI/product strategy and architecture; led external SaaS products; led TriMark data operations and MassMutual cloud governance platforms | Direct product/platform strategy; only partial evidence for broad internal enterprise IT ownership | | Build AI capabilities and responsible-AI governance | 3 | 3/3 | Built AssistX with 70+ AI automations across 20+ workflows; led five MassMutual privacy/AI-governance initiatives; advised on bias, drift, transparency, and MLOps | Strong direct match | | Partner with Product on roadmaps, architecture, prioritization, and delivery | 3 | 3/3 | Translated Product requirements into architecture and work breakdown at SuccessKPI; owned roadmaps and delivery at IDW; prioritized 50+ analytics use cases at TriMark | Strong direct match | | Lead staff IT operations, helpdesk, devices, access, onboarding/offboarding, and troubleshooting | 3 | 1/3 | Cloud infrastructure, IAM/security profiles, CI/CD, platform operations, and organizational leadership are documented | Material gap: no direct evidence of owning enterprise helpdesk/device lifecycle or staff IT service delivery | | Lead systems, data, reporting, and CRM/Salesforce evolution | 2 | 2/3 | Built TriMark’s enterprise data lake and reduced reporting from two months to one day; led MassMutual data-governance systems; CRM/Salesforce appears in source skills | Strong data/reporting match; limited outcome-backed Salesforce ownership evidence | | Deliver multiple initiatives with constrained resources using Agile discipline | 2 | 3/3 | Built IDW’s production platform in eight months with an 11-engineer Agile team; delivered SuccessKPI’s initial platform in six months; delivered TriMark’s data lake in seven months | Strong direct match | | Own security, privacy, compliance, and operational risk | 2 | 2/3 | Led privacy-rights and AI-governance systems addressing CCPA, CPRA, and GDPR; established AWS IAM and security patterns | Direct privacy/security architecture evidence; less evidence of enterprise-wide cybersecurity-operations ownership | | Advise executives and translate complexity into decisions and tradeoffs | 2 | 3/3 | Advised 200+ AWS customers, including senior leaders; regularly communicated with executives; secured executive support and funding for enterprise roadmaps | Strong direct match | Weighted calculation: 47 earned points out of 60 maximum points = 78.3%, rounded to 78%. ## Direct-match strengths - AI strategy and execution: built a production GenAI platform supporting 70+ automations across 20+ workflows and delivered the first production release in eight months. - Responsible AI and data governance: led architecture across five MassMutual data privacy and AI-governance initiatives, including bias, drift, transparency, security, and auditability considerations. - Product/engineering partnership: repeatedly translated business and product requirements into roadmaps, architecture, work breakdown, Agile delivery, and measurable production outcomes. - Data and reporting transformation: delivered TriMark’s first AWS data lake and reduced cross-ERP reporting from roughly two months to one day. - Organization and executive leadership: recruited and led an 11-engineer IDW team, led a 24-person NorthBay team, managed managers in prior roles, and advised 200+ AWS enterprise customers. ## Material gaps and caveats 1. The role explicitly owns staff IT service delivery, including helpdesk, devices, access control, onboarding/offboarding, and troubleshooting. Keith’s source materials do not establish direct ownership of those functions. 2. Salesforce is preferred. The source materials list Salesforce/CRM exposure but do not provide a clear, outcome-backed Salesforce platform-ownership example. 3. Enterprise-wide cybersecurity operations and risk-register ownership are broader than the documented privacy, cloud-security architecture, IAM, and AI-governance evidence. 4. Travel is not disclosed. Under the fit-gate rules, undisclosed travel is a caveat rather than an automatic failure. 5. This appears to be a repost of LinkedIn job 4459047812. The requirements and fit outcome are unchanged; the current canonical job ID and applicant count are recorded above. ## Normalized job description ### About the opportunity The company is a national workforce development organization that connects work-authorized, college-educated immigrants to skill-aligned professional employment across the United States. It addresses a significant economic inefficiency: millions of highly educated, work-authorized immigrants are underemployed, representing substantial forgone wages and untapped productivity. The organization reports that jobseekers enter its programs earning an average of $9,000 per year and are placed in roles averaging $67,000 per year. It has supported an estimated 35,000 job placements and operates nationally with employers, workforce agencies, and policymakers. The VP is responsible for building and leading technology strategy and infrastructure for internal operations and externally facing digital products. The leader partners with the CEO, President, and executive leadership to move the organization toward an AI- and product-first model while maintaining operational excellence, security, reliability, and scalable delivery. The role is both strategic and execution-oriented. ### Key responsibilities #### Technology strategy and AI infrastructure - Own technology strategy across staff infrastructure and jobseeker/partner-facing products, ensuring security, scalability, cost-effectiveness, and alignment to mission outcomes. - Build and maintain a multi-year roadmap spanning staff infrastructure and IT operations, data systems and reporting, Salesforce/platform evolution, core digital products, and systems integration/interoperability. - Translate organizational strategy into a sequenced plan with timelines, dependencies, resources, and success measures. - Give the Executive Leadership Team clear priority, deferral, and stop recommendations based on capacity and impact. - Support sprint planning, release planning, and Agile ceremonies. #### Product and engineering partnership - Partner with Product leadership to deliver a reliable, scalable foundation for jobseeker and partner products. - Ensure cross-functional delivery across product, technology, and programs, including planning, prioritization, feasibility, timelines, adoption, and change management. - With the Product Director, guide architecture, build-versus-buy decisions, integration strategy, platform choices, and execution quality. #### AI enablement and responsible technology innovation - Partner with executives, Product, and Program leadership to deliver AI-enabled capabilities that improve jobseeker outcomes and staff productivity. - With a cross-department steering committee, establish standards and governance for responsible AI, including privacy and consent, security controls, vendor risk, quality assurance, bias considerations, and human oversight/escalation. - Build AI-readiness foundations in data quality, integration, and scalable infrastructure. #### IT operations, service delivery, and training - Lead internal IT operations across helpdesk, devices, access control, onboarding/offboarding, and troubleshooting. - Establish service standards for response times, escalation, documentation, and internal communications. - Own vendor relationships and contracts across systems and managed-service providers. - Ensure staff are trained to use infrastructure, tools, and AI effectively and are accountable for adoption. #### Systems, data, and platform leadership - Oversee Salesforce and related systems as the operational backbone for Programs, Development, and reporting. - Improve system usability, adoption, and reliability through requirements, prioritization, and iteration. - Own data strategy with research and evaluation leadership, including governance, quality, reporting, and dashboard reliability. - Deliver trusted reporting for program improvement, fundraising narratives, and leadership decisions. #### Project delivery and cross-functional leadership - Implement a consistent project-management framework across technology work. - Lead reliable, transparent, partnership-driven execution. - Build accountability and follow-through within technology and across stakeholders. #### Security, risk, and compliance - Own cybersecurity strategy and operational risk management. - Ensure controls for sensitive-data systems. - Maintain a risk register and communicate risks and mitigations to executives and the board. - Align technology practices with funder requirements, privacy expectations, and organizational policies. #### Executive partnership and communication - Serve as a proactive, consultative partner to the CEO, President, and Executive Leadership Team. - Communicate decision-ready status, risk, needs, and tradeoffs. - Document commitments, assign owners, and report progress on executive decisions. ### Success measures - A clear, sequenced technology roadmap spanning staff infrastructure and digital products. - Reliable Product-Technology delivery for jobseeker and partner-facing capabilities. - Responsibly governed AI capabilities with measurable impact. - Predictable delivery, stronger cross-functional satisfaction, and fewer surprises. - Improved reliability, security posture, and risk management. - Clear, decision-oriented executive communication. ### Qualifications - 10+ years of technology leadership spanning IT operations, systems leadership, and product/engineering delivery. - Experience leading technology strategy across internal infrastructure and external products/platforms, with demonstrated AI experience. - Strong program/project-delivery discipline and 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 and ability to translate complex issues into clear decisions. - Commitment to the organization’s mission. ### Compensation and benefits - Base salary: $200,000-$225,000 annually. - Benefits described in the posting include paid time off, hybrid or remote work schedule, medical/dental/vision insurance, paid parental leave, short-term disability insurance, life insurance, and retirement plan with employer match. ## Artifact metadata - JD capture: Generated and validated for publication. - Resume: Not generated because the fit outcome is BORDERLINE and no override was provided. - Cover letter: Not generated because the fit outcome is BORDERLINE and no override was provided. - Google Drive: Not used.