Technology Executive · Royal Oak, MI

James
Anderson

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

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About

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.

Career Highlights

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.

Experience

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.

Expertise

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

Recognition & Leadership

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

Contact

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.