Matthew Hill
Product & Technology Leader · Software Solution Architecture · AI Strategy & Governance
Building solutions people actually adopt.
15+ years bridging business intent and technical execution across franchise and retail networks, from enterprise platform architecture to AI governance and software solution design.
Matthew Hill
Product & Technology Leader · Software Solution Architecture · AI Strategy & Governance
Building solutions people actually adopt.
15+ years bridging business intent and technical execution across franchise and retail networks, from enterprise platform architecture to AI governance and software solution design.
About
My perspective on technology was shaped early on. As an apprentice machinist on a tool & die shop floor, I experienced the inefficiencies present when the needs of the material handlers, operators, and machinists got ignored. That instinct carried forward when I was consulting on P&Ls for a 75-store franchise territory, sitting with owners to move locations from break-even to profitability by fixing the systems underneath them. I call it Operational Empathy, and it is the lens I bring to every platform decision.
Over the last 15+ years, I have applied that lens across networks of 1,900+ locations. At Primrose Schools, I built the product management function from scratch and grew it into a cross-functional organization of 9+ spanning product, engineering, helpdesk, and data. I directed enterprise platform migrations across 550+ schools, established an AI governance framework with legal counsel, and launched a classroom application that hit 95%+ voluntary adoption before it was ever mandated. At Edible Brands, I spent nine years as the client-side product owner for retail technology across 1,300+ stores — owning POS, ecommerce, delivery, and mobile solutions — and architected a delivery driver application that integrated real-time GPS routing with the store-level POS.
I sit between business teams and technology teams and make sure what gets built solves the real problem. That's the job, regardless of the platform or the industry.
Key Achievements
$250K+
AI Cost Savings
Direct cost avoidance from AI-enabled content workflow in 6 months
95%+
Voluntary Adoption
New product adopted across all locations during early access
$750K+/yr
Platform & Vendor Savings
Combined savings from migrations, negotiations, and platform consolidation
150+
Employees AI-Enabled
Organization-wide Copilot deployment across two tiers
1,900+
Brand Locations Served
Technology portfolio spanning early childhood education and retail
1,500+
Locations Migrated
Two enterprise platform transformations from legacy to modern systems
~70%
Monthly AI Engagement
Sustained org-wide adoption after 6-9 months
9+
Team Built
Cross-functional organization spanning product, engineering, helpdesk, and data
Domain Expertise
Multi-Location Operations & Store Technology
- POS systems and store management platforms
- Ecommerce, delivery technology, and consumer mobile apps
- Loyalty and rewards programs
- Enterprise rollouts and adoption strategy (100 to 1,300+ locations)
- Multi-brand platform management
Digital Product Strategy & Lifecycle Management
- Product function built from scratch and scaled
- Agile practices, OKR-aligned roadmaps, stakeholder engagement
- Discovery process: translating operational pain points into technical requirements
- User research driving real adoption outcomes
- Cross-functional platform management: corporate, franchise operators, consumers, and B2B development
AI Governance & Enterprise Enablement
- Enterprise AI policy and governance frameworks
- Microsoft Copilot deployment and individual-level adoption tracking
- Stewardship program design for sustained adoption
- Responsible AI in regulated environments (child PII, healthcare data)
Software Solution Architecture & Platform Strategy
- Acting as technical liaison between business stakeholders and engineering teams
- CRM platforms (HubSpot, FranConnect)
- Service management (Zendesk, Freshservice, Freshdesk)
- Vendor evaluation, contract negotiation, SLA enforcement
- Data infrastructure and analytics (Databricks, Tableau, Power BI)
Building AI Programs That Actually Work
- $250K+ in direct cost avoidance from AI-enabled content workflow
- 150+ users enabled, ~70% monthly engagement after 6 months
- Ahead of 60%+ of companies in establishing enterprise AI governance
Most companies are still figuring out where to start with AI. I built and deployed a governance and enablement framework that was delivering results before 60% of organizations had established any baseline AI policies (IBM, IAPP, AuditBoard data).
Starting with an AI Acceptable Use Policy driving data protection and copyright compliance before anyone got access. Copilot deployed in two phases: base-level access for 150+ employees, then a targeted M365 pilot for power users and senior leaders with high engagement. Adoption tracked at the individual level with talent and performance teams closing gaps. That data drove the creation of a stewardship program — executive-nominated champions driving workflow standardization and sustained adoption.
The outcome: $250K+ in direct cost avoidance from a single AI-enabled content workflow in six months. Not an efficiency estimate. A specific, documented result.
Career Timeline
February 2024 – February 2026
Director of Technology Product & Operations
Primrose School Franchising Company
Led technology strategy, solution architecture, and a cross-functional team of 9+ across product, engineering, helpdesk, and data for a national early childhood education franchise. Acted as the primary bridge between business leadership and engineering to deliver high-adoption platforms, enterprise AI governance, and vendor strategy that generated $750K+ in combined annual savings.
550+ franchise locations · 9+ team members · $750K+ combined savings · 95%+ voluntary product adoption
April 2019 – February 2024
Senior Manager of Product Management
Primrose School Franchising Company
Built the product management function from the ground up as sole contributor, then led the enterprise-wide migration of 500+ schools from a legacy platform to modern SaaS. Led organization-wide process discovery for the franchise CRM, diagnosed the root cause as implementation and data quality rather than platform capability, and directed the remediation that restored trust and adoption — saving the cost of a full platform replacement.
500+ school migration · Product function built from scratch · CRM relaunch with restored adoption and trust
June 2015 – February 2019
Senior Product Manager, Retail Technology
Edible Brands
Owned product management for ecommerce and store technology across 1,300+ retail locations. Served as client-side product owner and technical liaison between corporate operations, UX design, and third-party engineering providers. Architected a delivery driver mobile application integrating automated routing, real-time GPS tracking, and back-of-house POS messaging — and designed the mobile-first cloud replacement for the legacy POS through discovery, scoping, and roadmap phases.
1,300+ retail locations · $200K annual savings (work order system) · 9-year POS lifecycle through next-gen design
2010 – 2015
Franchise Business Consultant
Edible Brands
Led 30+ new franchise store openings across North America while managing a 75+ store home territory, personally configuring systems, training operators, and translating field-level friction into platform improvements. This hands-on work with franchise owners — driving locations from break-even to profitability through operational system improvements — built the foundation for everything that followed.
30+ store openings · 75+ store home territory · North America scope
2006–2009
Earlier Experience
Lyons Tool & Die Company · Verizon Wireless · Tweeter Home Entertainment
Foundation in systems implementation, technical training, and consultative solution design. Managed the material inventory platform for a tool & die manufacturing facility; promoted to training lead at Verizon within six months.
Case Studies
Enterprise AI Governance & Enablement Program
$250K+ cost avoidance · ~70% monthly engagement · 150+ employees enabled
Enterprise AI Governance & Enablement Program
$250K+ cost avoidance · ~70% monthly engagement · 150+ employees enabled
Challenge
The organization needed to deploy AI tools across 150+ employees with no governance framework, no deployment strategy, and no way to measure whether people were using them.
Approach
Treated AI adoption as a product problem, not an IT rollout. Drafted acceptable use policy with legal before any tools were deployed. Rolled out base Copilot org-wide, then ran a targeted M365 Copilot pilot for power users and senior leaders. Tracked engagement at the individual user level and partnered with talent and performance teams to close gaps. Designed a stewardship program with executive-nominated champions for sustained adoption.
Outcome
$250K+ in direct cost avoidance within 6 months. ~70% monthly engagement org-wide. Near-universal engagement in pilot cohort. Stewardship program fully designed and leadership-aligned.
Role: Program owner and solution architect — drafted policy, designed phased strategy, acted as technical liaison with Microsoft, managed deployment, built measurement framework, designed stewardship model.
Software Solution Architecture, Delivery Operations
Proprietary mobile app deployed across 1,300+ locations · Real-time POS integration · Fulfillment visibility at scale
Software Solution Architecture, Delivery Operations
Proprietary mobile app deployed across 1,300+ locations · Real-time POS integration · Fulfillment visibility at scale
Challenge
A 1,300+ location retail brand had no real-time visibility into active deliveries. Store managers could not track drivers after dispatch, customers had no visibility into order status, and the POS had no connection to what was happening in the field. Fulfillment errors were frequent, and no off-the-shelf solution matched the operational model.
Approach
Acted as the client-side solution architect and technical liaison between corporate operations, UX design, and the third-party engineering team. Defined the integration architecture: automated route optimization, real-time GPS tracking, and two-way store messaging — all surfaced in the existing POS for back-of-house visibility without requiring store managers to operate a separate system. Managed the discovery, scoping, and requirements phases before handing a structured technical roadmap to engineering.
Outcome
Proprietary delivery driver mobile application deployed across 1,300+ locations. Store managers gained full real-time visibility into active deliveries via the existing POS interface. Fulfillment error rates and coordination delays reduced. Platform remained in active use throughout the product lifecycle.
Role: Solution architect, client-side product owner, technical liaison between operations and third-party engineering. Discovery to delivery oversight.
Franchise CRM: Discovery, Diagnosis & Strategic Redesign
CRM relaunched with high adoption · Dual-CRM environment established · Full migration cost avoided
Franchise CRM: Discovery, Diagnosis & Strategic Redesign
CRM relaunched with high adoption · Dual-CRM environment established · Full migration cost avoided
Challenge
The franchise CRM had years of adoption failure and leadership wanted to replace it entirely with a new platform. The organization also had no CRM solution for franchise development and sales. Both problems needed a solution on a budget that could not absorb a rip-and-replace.
Approach
Ran a structured discovery process across every department to map how the platform was being used and where it was breaking down. The diagnosis: FranConnect was the right tool for the job. The problem was implementation quality and data integrity, not the platform itself. Advocated for a strategic redesign over a platform replacement — directing data cleanup, workflow reconfiguration, and stakeholder re-engagement. Simultaneously evaluated and implemented HubSpot for the franchise development pipeline, creating a dual-CRM architecture serving two distinct audiences.
Outcome
Successful platform relaunch with restored franchise trust and strong adoption. HubSpot delivered a functioning sales pipeline. Both outcomes achieved without the cost, timeline, or disruption of a full migration.
Role: Discovery lead, strategic solution designer, executive recommendation owner, data remediation director, parallel HubSpot implementation lead.
New Product Launch Across a Franchise Network
95%+ voluntary adoption · 550+ locations · Adoption earned before mandate
New Product Launch Across a Franchise Network
95%+ voluntary adoption · 550+ locations · Adoption earned before mandate
Challenge
550+ franchise locations needed the organization's first fully custom classroom application, designed to reduce teacher administrative burden and maximize time with students. Mandating adoption is standard in franchising, but getting it right meant validating the product with real users first.
Approach
Structured the rollout as an early-access program, treating the initial phase as a live proving ground for the product vision. The design philosophy was Operational Empathy: the product had to be demonstrably easier than the paper-based processes it was replacing. Cross-functional alignment with operations, field teams, and franchise leadership ensured the product reflected how teachers actually work, not how corporate assumed they work. Oversaw full lifecycle at the Director level with product and engineering teams driving execution.
Outcome
95%+ voluntary early-access adoption across all classrooms before the mandate ever took effect. The speed and scale of organic adoption was unprecedented for the organization, validating both the product vision and the team's understanding of end-user needs.
Role: Oversaw product lifecycle at Director level. Product and engineering teams engaged in design and delivery execution.
What I'm Looking For
Multi-Location Operations & Technology Leadership
- Retail and convenience
- QSR and fast casual
- Specialty retail and grocery
- Education and childcare
- Field and Multi-location Services
Looking for a technology leadership role where I own the full platform lifecycle for a distributed network, not just vendor selection and rollout. The ideal role partners closely with operations, has clear roadmap ownership, and values adoption as much as delivery.
Product Leadership & B2B SaaS Solutions
- B2B SaaS serving retail, franchise, or operations verticals
- B2B SaaS serving education, healthcare, or services verticals
- Internal product leadership at multi-location operators
- Platform companies with multi-sided ecosystems
Looking for a product role where client-side operational experience is an asset, not a gap. I've been the buyer, the implementer, and the person living with the platform daily. The ideal role values that perspective in shaping product direction and customer outcomes.
AI Strategy & Digital Transformation
- Mid-to-large enterprise with active AI programs
- Financial services, healthcare, and insurance
- Technology companies and platforms
- Organizations building AI governance infrastructure
Looking for a strategic role focused on how AI actually gets deployed and sustained inside an organization, not just enabled. I have built governance frameworks, designed stewardship programs, and measured adoption at the individual level. The ideal role combines policy ownership, deployment strategy, and organizational change management in a mandate-driven environment.
Fractional & Agency Partnerships
- Boutique and mid-size software agencies
- Digital transformation consultancies
- Enterprise brands managing high-stakes custom builds
- Organizations needing a discovery or scoping engagement before committing to a build
Open to fractional and project-based engagements where client-side enterprise experience creates immediate value. I specialize in discovery, solution scoping, and technical liaison work for organizations standing up new platforms or navigating legacy-to-modern transitions. If your team builds it and your client needs someone who has lived on the other side of that relationship, I can help.