Jon Reily
Commercial AI Strategy & Commercialization | Operator-built. Revenue-focused. Results, not roadmaps.
I work with enterprises, platforms, and agencies when the gap between AI capability and AI revenue needs to close. My work is operator-led: diagnose the commercial constraint, build the GTM architecture, design the pricing model, and run the cadence until outcomes show up in the numbers.
Former Global President • ex-Amazon • RETHINK Retail Top Retail Expert (5×) • Fortune 500 + global transformation experience
The Reily Group is Led by Jon Reily — recognized retail expert and frequent industry commentator. Senior bench when needed.
What I do
- Commercial AI GTM architecture: go-to-market strategy, ICP definition, pricing model development, sales motion design
- Agentic AI platform commercialization: use case mapping, pilot-to-contract pathways, enterprise deal structure
- Partner & co-sell strategy: ISV co-sell, agency partnerships, channel motions designed to close
- AI operating model & governance: evaluation frameworks, KPI accountability, rollout sequencing
- Diagnose: commercial constraint mapping, GTM baseline, competitive position
- Execute: embedded operating leadership to build GTM infrastructure and sustain commercial momentum
- Measure: revenue-accountable scorecards, pipeline KPIs, learning loops, course-correction
How I work
No theater. Decision-ready clarity, owned roadmaps, and operating discipline.
- Diagnose: KPI baseline, constraints, decision-ready view of what to change and why
- Align: funded phased roadmap, owners, decision rights, governance cadence
- Execute: embedded leadership to ship outcomes and manage risk
- Measure: scorecards, experimentation, learning loops, course-correction
Selected outcomes
Selected examples; some anonymized by necessity.
AI-assisted B2B marketplace (anonymized)
- Enabled natural-language solution building across a multi-market, high-SKU catalog
- Applied AI/ML to interpret attributes and recommend assemblies/assortments
- Impact: 20%+ conversion lift and ~80% engagement lift
Cross-border track & trace (EU)
- Led and sponsored an AI + blockchain program to strengthen chain-of-custody and compliance outcomes
- Designed the operating approach and partner coordination to ship end-to-end execution
AI-enabled localization
- Used AI to accelerate multi-geo website localization workflows
- Reduced repeat effort and improved speed-to-market for launches
Growth outcomes (prior leadership roles)
- Built experimentation and conversion programs with measurable financial outcomes
- Established KPI frameworks and governance so progress is owned and improved quarter-over-quarter
Want the detailed case studies? Share your context and we’ll discuss what’s appropriate to disclose.
Boards & community leadership
Operator work, plus governance and community leadership where I can add leverage.
Board roles (selected)
- Vice Chairman (Incoming Chair), Corpus Christi Museum of Science and History
- President, Board of Trustees, Annapolis Christian Academy
- Committee Chair — Industry Partner Council; APAC Advisory Board Member, National Retail Federation
- Former Chairman, Corpus Christi International Airport (Board)
A bit personal
I’m based in Texas and work globally. Outside of consulting, I’m usually focused on family, community service, and aviation. I’m also an amateur radio operator (KU5I)—I like systems that work when it matters.
If you have read this far we really should have a coffee!
How I engage
Designed for enterprise pace: clarity fast, then disciplined execution.
Commercial AI GTM Sprint (2–3 weeks)
Commercial baseline, GTM architecture, pricing model framework, and revenue-accountable scorecard.
Agentic AI Platform Commercialization (8–16 weeks)
Embedded operating leadership across pricing architecture, sales motion development, and partner alignment.
Partner & Co-sell Architecture (4–6 weeks)
Deal architecture for co-sell, ISV, and alliance motions designed to close, not just generate activity.
Interim AI Operating Executive
Fractional leadership to stabilize AI commercial execution and drive the revenue cadence.
Contact The Reily Group
Brief context is enough. We’ll reply with next steps or a short call to scope the work.
Start a conversation
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Email: jon@reilygroup.com
Fastest way to start
- Your north-star metric and why it matters
- Where you feel stuck (commercial AI gap, GTM, pricing, partner strategy)
- The decision you need to make in the next 30–90 days
- Any constraints: timeline, risk, governance, stakeholders
If it’s urgent, email directly and put “urgent” in the subject.