Technology Executive · Royal Oak, MI

James
Anderson

A designer's instincts. An operator's discipline.
Decades of solution delivery.

Download Career Summary
Get in touch →

Technology built on a foundation of design

Based Royal Oak, Michigan
Available Full-time & Fractional
Industries Healthcare · Workforce · Financial Services
LinkedIn andersonjamesm

I've been writing code since high school. I've also spent years as a graphic designer, photographer, and creative professional, working in publishing, advertising, and even the comic book industry.

Most technology executives come from a single direction. My career journey has been both technical and creative. That dual foundation of systems and aesthetics, shaped how I think about every platform, workflow, and team problem I've encountered since.

Across three decades and six industries, one pattern has defined my career: When things are broken, understaffed, ungoverned, or stalled, I fix them. An integrations team with no inventory and runaway costs. The platform collapsing under its own weight. The project with no owner and no requirements. I've built the structure, assembled the team, and delivered.

I've presented technology strategy to boards of directors from my first VP role onward. I've negotiated vendor contracts that saved millions. I've built AI programs from zero to production. And I still believe the best technology is the kind people barely notice. Because it just works.

A few moments that define the arc.

$7M
Progress Software Negotiation
Converted a ~$14M licensing liability into $7M in savings through strategic timing, VP-level negotiation, and a deep understanding of how the vendor's billing model misaligned with actual usage.
190+
Global Engineering Team
Led a 190+ person global engineering organization at Cross Country Healthcare spanning AI, cloud platforms, integrations, SaaS, mobile, RPA, and architecture. Promoted from VP to Group VP in 18 months.
US Patent
Hybrid CV Sensing Solution
When AI computer vision couldn't resolve refrigerated unit edge cases, designed a novel infrared laser-based secondary input stream. The resulting solution was submitted for US patent.
$550K
Boomi Cost Prevention
Inherited an ungoverned integration environment on a trajectory toward $550K/year in licensing costs. Introduced a dual-architecture framework pairing AWS event-driven integrations with right-sized Boomi licensing.
600+
Credit Union Platform
Recognized a gap across 600+ Symitar credit unions with no modern online banking upgrade path. Proposed and co-developed a new platform with Michigan First serving as the vendor's integration lab and adopted by many credit unions nation-wide.
Dreamforce
Industry Presenter, 2016
Selected to present at Dreamforce on Kelly Services' innovative use of Salesforce as a talent platform API for mobile and other delivery channels, representing the company as an industry thought leader on using Salesforce for enterprise application modernization.
2022 — 2026

Group Vice President, Solution Delivery

Cross Country Healthcare
Led enterprise AI strategy, platform modernization, and a 150+ person global engineering organization. Promoted VP → Group VP in 18 months after absorbing two additional VP-level functions in year one. Delivered production AI capabilities, recovered $250K+ in vendor penalties in the first 30 days, and drove $2M+ in offshore cost reduction.
2021 — 2022

Vice President, Software Engineering

365 Retail Markets
Led engineering for a PE-owned unattended retail automation platform spanning AI computer vision, SaaS, POS, and kiosk systems globally. Resolved critical platform reliability gaps and architected a patent-pending hybrid CV solution for refrigerated retail environments.
2015 — 2021

Senior Director, Global Applications

Kelly Services
Six-year tenure leading enterprise application delivery across a 50+ person team in the US and Kuala Lumpur. Built Kelly's first RPA practice, assumed ownership of a 60+ application Salesforce platform, secured 4M+ users with Auth0, and presented at Dreamforce 2016. Promoted Senior Manager → Senior Director.
2013 — 2015

Senior Manager, Application Development

Meridian Health Plan
Directed software development for Medicaid and Medicare business units. Reorganized delivery into domain-aligned teams, negotiated a $7M software contract savings, and designed a mobile data collection platform with direct revenue impact.
2010 — 2013

IT Manager, Web & Application Development

Beaumont Health System (now Corewell)
Led web, portal, and mobile initiatives across a major Michigan health system. Consolidated 136 ungoverned SharePoint instances, rescued a long-stalled surgical onboarding application, and presented mobile strategy directly to the board of directors.
Earlier

Vice President, Electronic Services

Michigan First Credit Union
Senior leadership team member reporting to the CEO with monthly board participation. Co-developed an online banking platform adopted across 600+ credit unions and negotiated contracts generating $200K+ in annual financial impact.

A resume lists roles. This is the fuller picture — what I inherited, what I built and fixed, and the results, role by role.

Group Vice President, Solution Delivery

Cross Country Healthcare · June 2022 – January 2026 · Boca Raton, FL (Remote)

Promoted from VP to Group VP in January 2024, within 18 months of joining, after absorbing two additional VP-level functions in the first year. At peak I was responsible for 190+ people across software engineering, cloud platforms, enterprise integrations, SaaS, mobile, RPA, architecture, and corporate applications.

What I Inherited

  • Nine applicant tracking systems with fragmented support, no unified governance, and a vendor who had been overcharging the company by $250K+ in the first six months alone
  • An integrations team with no license inventory, no governance, and no accountability — a vendor true-up had forced $150K+ in immediate unplanned spend, with projected costs heading toward ~$550K/year as the roadmap expanded
  • A product and development organization frustrated by slow release cycles, poor roadmap governance, and inadequate QA processes
  • Several major business divisions with no product representation and no technology roadmap

What I Built and Fixed

  • Recovered $250K+ in vendor penalties within 30 days of discovering the overcharge; restructured all vendor contracts with financial SLAs and introduced systematic monitoring against contractual terms
  • Conducted a full inventory of all Boomi integrations and introduced a dual-architecture evaluation framework — pairing event-driven AWS integrations (SNS, DynamoDB, EventBridge, Aurora, Lambda) with right-sized Boomi licensing, bringing projected costs down from ~$550K/year to a controlled, sustainable level
  • Designed the enterprise data tier (MTDB, MFDB, MMDB), creating a single source of truth that enabled automation at scale across all business units
  • Built and executed the enterprise AI strategy end-to-end — recruited dedicated AI teams, designed automation workflows, wrote requirements, tracked ROI, and reported outcomes to the board via a Power BI performance dashboard. Delivered production capabilities including semantic search, AI-assisted recruiting and credentialing, job matching, voice AI, and automated submission workflows
  • Restored development velocity across the Intellify, Web, Portal, and Mobile teams through QA leadership hires, a formal QA process, test automation (Katalon), roadmap governance, and a structured technical debt program
  • Scaled offshore engineering operations across multiple time zones, reducing annual delivery costs by $3M+ while maintaining output quality
  • Presented AI roadmap and technology strategy directly to the board of directors; served as primary technology voice to the C-suite on growth, profitability, and platform direction
  • Vendor penalty recovery: $250K+ recovered in year one
  • Boomi cost prevention: Projected ~$550K/year brought to a right-sized, controlled cost
  • Offshore cost reduction: $3M+ annual savings
  • Vendor spend managed: $10M+ annually
  • AI capabilities delivered: Semantic search, job matching, voice AI, credentialing assist, automated submissions — all in production
  • Team at peak: 190+ total, 12 direct reports
  • Promotion: VP → Group VP in 18 months

Vice President, Software Engineering

365 Retail Markets · June 2021 – June 2022 · Troy, MI

PE-owned proprietary retail automation platform spanning AI computer vision, customer SaaS, POS, and kiosk systems across global unattended retail deployments.

What I Inherited

  • A platform architected for a fraction of its current scale — reliability and scalability gaps were compounding as the customer base grew, while leadership pressure to add features continued unabated
  • Significant friction between legacy engineering leadership (who came via acquisition) and the PMO — release velocity had stalled and the conflict was unresolved
  • The Stockwell computer vision platform facing an expanding set of edge cases it could not resolve as customers began deploying in refrigerated environments — condensation and camera fogging were defeating the CV model entirely

What I Built and Fixed

  • Implemented a fault-tolerant, self-healing AWS integration architecture — messaging failures between platform components were automatically detected and resynced, addressing the most critical reliability threats
  • Assumed direct ownership of the offshore development team, restructured design governance, and inserted myself as the operational bridge between engineering and the PMO — restored on-schedule delivery and resolved the organizational friction
  • Designed a hybrid computer vision solution for the Stockwell cold-unit problem. An early approach using photo resistors similar to assembly-line sensors was ruled out due to the cost of physical shelf customization. The final solution used infrared lasers aligned with each shelf pusher row, measuring distance to calculate products removed and detect items returned to the wrong position — resolving the full set of refrigerated-unit edge cases. Submitted for US patent
  • Delivered payment integrations supporting millions of daily transactions globally
  • Platform reliability: Fault-tolerant, self-healing AWS integration architecture implemented
  • Delivery: Release schedule restored; PMO friction resolved
  • CV innovation: Hybrid infrared laser solution eliminated all cold-unit CV failures
  • Patent: US patent submitted for hybrid CV/infrared sensing solution
  • Payments: Integrations supporting millions of daily transactions globally

Senior Director, Global Applications

Kelly Services · June 2015 – June 2021 · Troy, MI

Six-year tenure leading enterprise application delivery across a 50+ person team in the US and Kuala Lumpur, Malaysia, with full operational cost ownership of the offshore team — office rental, salaries, hardware, and equipment. Promoted from Senior Manager to Senior Director during tenure. Navigated zero-based budgeting cycles, building full annual justifications where production support budgets covered only ~40% of onshore team compensation.

What I Inherited

  • A development organization still destabilized from the KSN 2.0 launch — weekly software churn, panic bug fixes, and no regular release cadence despite the project being declared a success
  • The eRegistration application — the sole entry point for all candidate registration — collapsing under outdated business rules and poor system design that was multiplying data complexity to an unsustainable level
  • A Salesforce platform placed on autopilot after the CIO who introduced it departed — no ownership, no license governance, no vendor relationship
  • A candidate portal with no security controls serving 4M+ users, and release management processes that couldn't handle both admin-built and developer-built applications

What I Built and Fixed

  • Stabilized KSN 2.0 through structured problem triage and prioritization, restoring regular release cadence and roadmap discipline
  • Rearchitected the eRegistration application with a cross-functional team (QA, software dev, DBA) — reduced document processing steps, eliminated redundant session versioning, and redesigned data management to separate operational and archive data, restoring throughput and availability
  • Built Kelly's first RPA practice from zero — led vendor evaluation (Blue Prism vs. UiPath bake-off), assembled the team from existing staff, operationalized platform support, and successfully transitioned the practice to business ownership
  • Assumed full Salesforce platform ownership — re-established vendor governance, right-sized licensing, rebuilt development and admin teams, and managed 60+ custom applications at a scale that required Kelly's Apex code limit to be expanded from the standard 1M to 12M characters
  • Partnered with Auth0 to implement social login, multifactor authentication, and modern identity management for the candidate portal — securing 4M+ users
  • Built an API layer enabling a single codebase to serve both the candidate portal and a new native mobile app — later extended for direct Bullhorn ATS integration. Presented this solution at Dreamforce 2016
  • Served as sole IT representative on the corporate Digital Innovation Team and IT lead for M&A activities across acquisitions and divestitures
  • Worked directly with Google Cloud to build a proof of concept for machine learning-based candidate matching
  • Team: 50+ people across BA, QA, RPA, Web, Support, Portal, Front Office, Mobile, and Salesforce — US and Kuala Lumpur
  • Salesforce platform: 60+ applications; Apex code limit expanded from 1M to 12M characters
  • Portal security: 4M+ users secured via Auth0 identity management
  • RPA practice: Built from zero; successfully transitioned to business ownership
  • Dreamforce 2016: Selected to present on enterprise platform modernization
  • Promotion: Senior Manager → Senior Director during tenure

Senior Manager, Application Development

Meridian Health Plan · March 2013 – June 2015 · Detroit, MI

Directed all software development for Medicaid and Medicare business units at a nonprofit managed care organization.

What I Inherited

  • A generalist development team with no domain alignment — delivery was inconsistent because no one had sufficient depth in any single area to meet business demands reliably
  • A ~$14M Progress Software true-up exposure — the result of a licensing model mismatch that had been informally managed through personal CIO relationships that had since dissolved
  • Uncompetitive IT salaries in a market complicated by a boutique technology stack (Progress/OpenEdge), creating persistent recruiting and retention challenges

What I Built and Fixed

  • Designed a full organizational restructure before being asked — reorganized delivery into domain-aligned scrum teams (Mobile & Web, Enrollment, HEDIS, Medical Management, Claims), elevated PMs to product owner roles, and assigned business liaisons to each team, improving delivery velocity across the entire organization
  • Strategically timed the Progress true-up to coincide with the contract renewal, converting a standalone $14M liability into a negotiation. Worked directly with VP-level Progress representatives to rationalize licensing against actual distributed system usage — saved $7M from the anticipated exposure
  • Designed and delivered an iOS mobile app and backend workflow for HEDIS data collection — routing incomplete member records to field representatives with route mapping, data capture, and direct HEDIS dataset integration, directly supporting the state-measured quality metrics that determined new member assignments to the plan
  • Launched a college recruitment program and internal technology academy — including a retired senior developer brought back to teach the curriculum and architect mentors assigned to each new hire — building a sustainable talent pipeline for a niche technology environment
  • Worked with HR to re-band all IT salaries from helpdesk through CIO level, addressing retention risk across the department
  • Progress negotiation: $7M saved from a ~$14M true-up exposure
  • Org restructure: Domain-aligned teams; improved delivery velocity organization-wide
  • HEDIS platform: iOS app and backend workflow with direct impact on state quality metrics and revenue
  • Talent pipeline: College recruitment + internal academy for a boutique tech stack

IT Manager, Web & Application Development

Beaumont Health System (now Corewell) · April 2010 – March 2013 · Royal Oak, MI

Led enterprise web, portal, and mobile initiatives across a major Michigan nonprofit health system. Operated in a player-coach capacity — small team, large scope — stepping into admin, BA, PM, UI design, and testing roles as needed.

What I Inherited

  • 136 separate SharePoint instances across multiple outdated versions (WSS 2.0 and 3.0) — no IT support, no governance, and most users having access to patient data with no PHI controls in place
  • A surgical onboarding application that had been stalled indefinitely — no requirements, no architecture, no owner
  • No physician engagement portal despite the organization's private practice model creating a real need for one
  • The Nursing Dashboard — a 24x7 critical care alerting tool for nursing staff — with no dedicated technical depth supporting it

What I Built and Fixed

  • Recruited clinical and business leaders at the Director and VP level to form and chair the first enterprise SharePoint governance committee — defined IT engagement standards, prioritization process, and business unit guidelines, and led the full migration of 136 instances to a single governed, upgraded on-prem environment with PHI content controls implemented across the platform
  • Rescued the surgical onboarding application — authored requirements, designed the architecture, and led delivery. In the process, uncovered a systemic security vulnerability: private practice physicians had been signing blank system access forms for staff with no tracking or monitoring. Worked directly with the HIPAA committee, privacy, and security teams to design a new access management framework that satisfied all stakeholders
  • Reframed a CIO request to survey admitted patients — which would have violated Beaumont's Press Ganey agreement and created institutional risk — into a Nurse Rounding application that routed real-time patient experience issues to responsible department leadership, with layered Epic integration security and full HIPAA compliance
  • Presented mobile technology strategy to the Board of Directors; personally onboarded board members on their first Epic MyChart experience
  • Built Epic integration capability by hiring former Epic/Caché engineers; led all system integrations with Epic across administrative and clinical teams and assumed support ownership of the Nursing Dashboard
  • Launched a physician portal (custom SharePoint + Citrix integration with mobile version) and a consumer mobile app for doctor and service search — predating Epic's MyChart
  • SharePoint: 136 ungoverned instances → single governed, upgraded environment
  • Surgical onboarding: Delivered a stalled project end-to-end; resolved an enterprise security vulnerability
  • Nurse Rounding: Reframed a flawed CIO request into a patient satisfaction tool with HIPAA compliance
  • Board engagement: Mobile strategy presentation; MyChart onboarding for board members
  • Epic integration: Built from scratch using former Epic/Caché engineers

Vice President, Electronic Services

Michigan First Credit Union · Lathrup Village, MI

Member of the senior leadership team of a not-for-profit, member-owned credit union, reporting directly to the CEO. Participated in monthly board of directors meetings as a standing member of the executive team — not as a guest presenter, but as a consistent voice at the leadership table. Served on the CO-OP Network national technology committee.

Selected Contributions

  • Recognized that 600+ Symitar credit unions nationwide had no upgrade path to a modern online banking platform. Proposed a partnership to an online banking vendor — offering Michigan First as an integration lab and development partner. The resulting platform was adopted by many credit unions nationwide, delivering a significant feature and design upgrade at far lower cost than a commercial alternative
  • Inherited an outdated multi-function ATM platform increasingly difficult to maintain and source parts for. Reached out directly to the North American VP of Wincor-Nixdorf and negotiated a permanent resolution covering both software and hardware, personally leading the project with a distributed vendor team
  • Replaced the ATM service vendor (~$100K/year savings) and negotiated a new debit switch network contract generating ~$100K/year in additional interchange income
  • Partnered with the VP of Audit and Security on all card fraud investigations

Manager & AVP-Level Leadership Roles

Flagstar Bank · Troy, MI

Progressed through Manager and AVP-level roles spanning project management, software development leadership, UX/creative services, and enterprise governance. Led technology work through Flagstar's transition from a private, family-owned savings and loan to a publicly traded company.

Selected Contributions

  • Co-authored the company SDLC and trained departments across IT on its adoption — foundational governance work that standardized how software was built and delivered
  • Ran the IT Banking PMO with SOW approval authority for all banking-related IT projects; maintained the full project portfolio and managed all incoming requests
  • Led development of the retail lending portal in direct partnership with the EVP and VP of Retail Lending; presented the platform at the retail lending staff conference
  • Founded the organization's first IS Creative Services Team — establishing formal UX and usability leadership within IT ahead of when most financial institutions were treating it as a discipline
  • Managed software development through all regulatory and application changes required by Flagstar's conversion from a private to a publicly traded company

Where I do my best work.

Enterprise AI

Strategy to production: team assembly, workflow design, ROI tracking, and board-level reporting

Platform Modernization

Legacy-to-modern migrations, composable architecture, and event-driven platform design

Global Engineering Leadership

On and offshore teams across the US, Malaysia, Philippines, and India

Vendor & Financial Management

Contract negotiation, SLA enforcement, zero-based budgeting, and $10M+ spend oversight

Healthcare Technology

Payer, provider, and staffing. Epic, HIPAA, HEDIS, Medicaid/Medicare regulatory environments

Integration Architecture

AWS-native event-driven systems, Boomi, Salesforce, and enterprise middleware at scale
Dreamforce 2016 — Industry Presenter
Enterprise Platform Modernization · Selected by Salesforce
US Patent Submission
Hybrid CV / Infrared Retail Sensing Solution · 365 Retail Markets
Usability Testing Workshop Presenter
Banking Industry Conferences · Multiple engagements
CO-OP Network National Technology Committee
National industry committee membership
President — Royal Oak Arts Council
Current · Community arts leadership
Royal Oak Board of Education
Former President, VP & Treasurer

Let's start a conversation.

I'm open to full-time VP and C-Level roles as well as fractional engagements. If you're building something that needs experienced technology leadership, or fixing something that's broken, I'd like to hear about it.

Availability
Open to full-time and fractional VP or C-Level roles.
Based in Royal Oak, Michigan. Open to remote and hybrid arrangements. Available for both retained search and direct conversations.