Strategy.
Commercial AI.
Growth you can measure.
The Reily Group works with CEOs, investors and leadership teams on where to compete, how to grow and how to make AI pay off. It is led by a former global chief strategy officer and agency president who has also run the businesses he advises on.
The work starts with the decisions that matter. Where should the company compete, and what should it stop doing? How do acquired firms become one company? What should the AI offer cost, and how does a successful pilot become an enterprise contract?
When to call
Questions that bring clients to TRG:
- The strategy is unclear, or the plan isn't showing up in the numbers
- Several acquisitions in, the firms still sell and deliver separately
- The CEO needs a senior strategy partner without adding a full-time executive
- The product is working, but the pricing is still a judgment call
- Pilots are not turning into ongoing contracts
- Partnerships generate meetings but little business
What the work can cover
A focused engagement, scoped to the decision:
- Company strategy: where to compete and what to stop doing
- Integration after acquisitions: one offer, one story, one plan
- Pricing and packaging, including AI offers
- Enterprise pilot and contract structure
- Clear decisions, owners and measures of progress
What we do
Three practices, all grounded in operating experience and sized to the problem.
Strategy, Integration & Growth
For CEOs and investors who need a clear strategy and the follow-through to deliver it, including companies built through acquisitions that need to sell and deliver as one. Senior strategy leadership, fractional or embedded, from a former global chief strategy officer who has built and run commerce agencies.
Fractional Chief Strategy Officer
A senior partner to the CEO and the investor. Decide where the company competes, what it stops doing, and how the plan shows up in the numbers.
- Where to compete and what to stop doing
- Positioning and the story clients hear
- An annual plan tied to the investment thesis
- Clear reporting for the CEO, board and investor
Making Acquisitions Work Together
Turn a group of acquired firms into one go-to-market. Sort out where offers overlap, who owns each client, and how the teams sell each other's work.
- One offer structure across acquired practices
- Cross-sell plays into the existing client base
- Shared account leadership and delivery standards
- Keeping founders and key people engaged
From Services to Priced Offers
Package what the firm does, especially new AI services, into offers that sales can sell and finance can forecast. Shift revenue from one-off projects toward ongoing work.
- AI service packaging and pricing
- Project work converted to recurring retainers
- Rate cards and margin guardrails
- AI in delivery to protect margin
B2B & D2C Commerce Growth
Experience on both sides of commerce: enterprise B2B platforms for manufacturers and distributors, and growth programs for consumer brands. Bring them together where each makes the other stronger.
- B2B digital commerce strategy
- D2C acquisition, retention and conversion
- Platform partners: Adobe, Salesforce Commerce Cloud and Marketing Cloud, Sitecore, Shopify, SAP Commerce Cloud, Mirakl, VTEX
- Measures tied to revenue and margin
Commercial AI Strategy & Commercialization
For teams with an AI product or platform that need to decide how to price it, sell it and support enterprise customers.
Pricing & Go-to-Market
Define the offer, the right customers and the economics of serving them. Connect pricing and packaging to the way the product is used, then build a sales approach the team can put into practice.
- Customer segments and sales approach
- Pricing, packaging and usage economics
- Sales materials and deal guidance
- Measures tied to revenue and margin
Agentic AI Platform Commercialization
Shape an enterprise offer that can be sold and delivered. Define the use case, the pilot, the ongoing license and the implementation work so that a promising deal does not become an open-ended delivery commitment.
- Use cases matched to buyer priorities
- Pilot terms and the path to an ongoing contract
- Platform and add-on licenses
- Implementation and forward-deployed engineering scope
Partner & Co-sell Strategy
Make partnerships useful to the people closing business. Agree who brings the opportunity, who owns the client, how the work is priced and how revenue is shared.
- Co-sell motion design + field enablement
- ISV + platform alliance architecture
- Partner economics + deal split structure
- Joint pipeline governance + cadence
AI Operating Model & Governance
Set clear responsibilities for AI delivery, risk and results. Put the review process and measures in place so the team can see what is working, make decisions and keep improving after the engagement ends.
- Governance + risk evaluation frameworks
- KPI accountability systems + scorecards
- Rollout sequencing + change management
- Operating cadence design + decision rights
Practical AI for Businesses That Want to Win
Most businesses know AI matters. Very few know where to start. The ones that figure it out first build a real competitive advantage — and it compounds. This practice is built to get you there fast, without the vendor hype or the wasted pilots.
AI Opportunity Assessment
A focused audit of your business that identifies exactly where AI can save time, reduce cost, and drive growth — ranked by impact and how fast you can act on it. No vendor pitches. No generic frameworks. A prioritized roadmap built for your specific operations.
- Operations + workflow audit
- AI opportunity mapping by function
- Prioritized roadmap: impact vs. effort
- Tool + vendor recommendations
2–3 weeks
AI Implementation Sprint
From roadmap to running. We configure the right AI tools for your specific workflows, build the automations that connect AI to your actual business processes, and train your team so adoption actually happens. Not installed — running. With your people using it and your operations measurably improved.
- Tool selection + configuration
- Workflow automation + integration
- Team training + adoption support
- Measurement: time saved, output improved
4–8 weeks
Ongoing AI Advisory
First-mover advantage in AI compounds quickly. Monthly advisory keeps your tools current, expands to new use cases as the technology evolves, and ensures your business keeps pulling ahead as competitors start catching on. Access to a senior operator who tracks what's actually working across industries — not what's being marketed.
- Monthly strategy + implementation review
- New use case identification + rollout
- Tool evaluation + vendor management
- Competitive AI landscape monitoring
Monthly retainer
When growing businesses call
You know AI is important but don't know where to start — and you're tired of generic advice
You've tried ChatGPT but it hasn't connected to your actual business workflows
Your competitors are talking about AI and you want to move before they figure it out
You want to do more with the team you have — not hire more people to do manual work
You need someone to cut through the vendor hype and tell you what's actually worth doing
You're growing fast and AI is the leverage that lets you scale without proportional headcount
How we work
Start with a clear question. Agree on the scope, make the decisions and stay involved where execution is needed.
2–3 weeks
Review the product, customers, pricing and costs. Identify the decisions that will make the biggest difference and the evidence needed to make them.
1–2 weeks
Agree on the changes, the budget and who owns the work. Set priorities and a practical sequence for putting the decisions into use.
6–16+ weeks
Work alongside the team on pricing, sales, partners and delivery. Resolve issues as they arise and keep the work connected to the original business goal.
Continuous
Track the measures that matter to the engagement, such as conversion, contract value, cost to serve and margin. Use the results to decide what changes next.
Proof
Selected work from strategy and operating roles and recent engagements. Client details are withheld where confidentiality requires it.
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.
Jon 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.
Strategy and agency leadership
- Rose from Global Chief Commerce Strategy Officer at Dentsu to Global Chief Strategy Officer and then President of Dentsu Commerce: about $200M in revenue over its first two years, with full P&L responsibility.
- Global President of McFadyen Digital, a digital commerce agency.
- Built Bounteous's Commerce & Loyalty practice to $30M.
- VP, Global Head of Commerce at Sapient, including enterprise commerce work for one of the world's largest retailers.
AI in agency delivery
- Introduced AI-assisted delivery at McFadyen Digital: 30% of code produced with AI assistance.
- EBITDA up 9% and more than $1M saved.
- Delivery standards and measures that held up as adoption grew.
Enterprise AI pricing and packaging
Developed the commercial model for an enterprise AI portfolio, including platform and 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 absorbing those costs into a fixed subscription.
Recent work, anonymized. No client rates or confidential product details are disclosed.
Commercial outcomes
- $550M+ incremental revenue delivered in a prior operating leadership role via experimentation, conversion architecture, and platform optimization at scale.
- 20%+ conversion lift and ~80% engagement lift from an AI-assisted B2B marketplace initiative — anonymized. Use cases tied to KPIs, not demonstrations.
- Recent enterprise AI work: pricing, go-to-market planning and partner co-selling for a major agentic AI platform serving Fortune 100 organizations.
- Global operating cadence across 51 countries in prior executive roles, including founding and scaling a 6,000-person global commerce organization.
Want to discuss a relevant example?
We can share a redacted example after an intro call.
About
Led by Jon Reily. Advisory grounded in operating experience, with senior specialists brought in when needed.
The Reily Group is an independent advisory firm focused on strategy, commercial AI and enterprise growth. Engagements range from a single pricing decision to ongoing strategy leadership alongside the CEO.
Jon Reily has been Global Chief Strategy Officer and then President of Dentsu Commerce, Global President of McFadyen Digital, VP and Global Head of Commerce at Sapient, and an Amazon executive. He brings 25 years of strategy and operating experience across agencies and client-side businesses, and works with CEOs and investors as a senior strategy partner. His recent enterprise AI work covered pricing and packaging, go-to-market planning and partner co-selling for a major agentic AI platform. That experience informs advice grounded in what a business can sell, deliver and support profitably.
Jon also serves in select governance and community leadership roles.
Focus areas
Small by design. Senior by default.
Contact
Share the decision or problem at hand, whether it involves strategy, integration, pricing, enterprise growth or putting AI to work. Jon will respond personally.
Start a conversation
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Email: jon@reilygroup.com
Engagements (typical)
Platforms · Agencies · Enterprises
Commercial AI GTM Sprint (2–3 weeks): a focused review of pricing, packaging, customer economics and the sales approach, with clear recommendations.
Agentic AI Commercialization Leadership (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 pipeline activity.
Interim AI Operating Executive — fractional leadership to stabilize AI execution and drive the commercial cadence.
PE Sponsors · Agency & Services CEOs
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 the CEO and investor, covering company strategy, integration, and offer and pricing decisions.
Growing Businesses · $5M–$100M
AI Opportunity Assessment (2–3 weeks) — operations audit, AI opportunity map, prioritized roadmap, tool recommendations.
AI Implementation Sprint (4–8 weeks) — tool configuration, workflow automation, team training, measurable outcomes.
Ongoing AI Advisory (Monthly) — keep current, expand use cases, maintain competitive advantage as the tools evolve.