Jon Reily
Strategy, commercial AI and enterprise growth.
I work with CEOs, investors and leadership teams as a senior strategy partner: where to compete, how to grow, and how to make acquired firms work as one company. I also help enterprises, platforms and agencies make the commercial decisions around AI: what to sell, how to price it, what it costs to deliver and how to bring it to market. My work draws on years of building and running commerce businesses and agencies, as well as recent enterprise AI pricing and commercialization work.
Former President and Global Chief Strategy Officer, Dentsu Commerce • Global President, McFadyen Digital • VP, Global Head of Commerce, Sapient • ex-Amazon • RETHINK Retail Top Retail Expert (5×) • Fortune 500 + global transformation experience
Independent advisory, with senior specialists brought in when the work calls for them.
What I do
- Company strategy: where to compete, what to stop doing and how the plan shows up in the numbers
- Integration after acquisitions: one offer, one story and services turned into priced offers
- Pricing and packaging: subscriptions, usage charges, bundles and implementation
- Commercial economics: customer value, cost to serve and margin
- Enterprise offers: pilots, contracts and delivery responsibilities
- Go-to-market: customer focus, sales approach and partner roles
- Operating leadership: helping the team put decisions into practice and measure results
How I work
Start with the business question and agree on the scope before work begins.
- Understand the product, customers and economics
- Agree on the decisions, owners and budget
- Work alongside the team where execution is needed
- Review results and adjust the approach
Selected work and outcomes
Examples from prior roles and recent engagements. Some client details are kept confidential.
Case study: making acquired products sell as one company
A marketing data and software business with more than $100M in annual recurring revenue had grown, partly through acquisitions, into about 16 products sold separately. The products were strong, but organic growth had slowed. The diagnosis was a sales architecture problem, not a product problem.
I built the scaled sales plan the business's CEO presented to the parent company's CEO:
- One suite to buy: about 16 products regrouped into three capability pillars, each with an anchor product and attach products.
- Three sales motions: enterprise, mid-market and self-serve, phased so the team funds itself as it grows.
- Cross-sell mechanics: deal registration, shared credit in sales compensation, and a recurring pipeline review where product groups hand off opportunities. Every renewal became a bundle conversation.
- Pricing and the numbers: pillar bundles priced below the sum of the parts, progressive discounts across pillars, sales compensation design and a revenue model kept deliberately conservative.
Recent work, anonymized. Client names, pipeline and internal figures are not disclosed.
Enterprise AI pricing and packaging
Developed the commercial model for an enterprise AI portfolio, covering an anchor platform, add-on licenses, standalone pricing, enterprise bundles and scoped implementation.
The model extended to attach pricing for brand research and media intelligence products, with bundle tiers leading to a multi-year, full-stack enterprise agreement.
The work also addressed variable data and infrastructure costs through a separate consumption charge rather than burying those costs in a flat subscription.
Recent work, anonymized. Client rates and confidential product details are not disclosed.
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
Strategy and agency leadership (prior roles)
- Global Chief Commerce Strategy Officer at Dentsu, then Global Chief Strategy Officer of Dentsu Commerce
- President of Dentsu Commerce: about $200M in revenue over its first two years, with full P&L
- Global President of McFadyen Digital
- Built Bounteous's Commerce & Loyalty practice to $30M
- VP, Global Head of Commerce at Sapient, including enterprise commerce for one of the world's largest retailers
AI-assisted agency delivery (McFadyen Digital)
- Introduced AI-assisted development across delivery teams, reaching 30% of code
- Impact: EBITDA up 9% and more than $1M saved
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)
- Board 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
Focused projects or a longer operating role, depending on the decision and the work required.
Commercial AI GTM Sprint (2–3 weeks)
A focused review of pricing, packaging, customer economics and the sales approach, with clear recommendations.
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.
Agency Integration Review (3–4 weeks)
After a run of acquisitions: where offers overlap, where cross-selling is stuck and what to fix first.
Fractional Chief Strategy Officer (3–12 months)
Senior strategy leadership for agency and services CEOs and their investors: company strategy, integration, and offer and pricing decisions.
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
This form opens your email client (no data stored on the site).
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.