Executive AI Workshops
Maximize Value from Proven AI
Hands‑on, outcomes‑driven sessions designed for leadership teams that want to quickly identify high‑ROI AI opportunities, de‑risk adoption, and leave with a pragmatic 90‑day plan.
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Worked with Teams at:
Who These Workshops Are For?
Founders, executives, and department leaders ready to move from AI curiosity to measurable outcomes.
Ops, RevOps, Marketing, Product, Data/IT, and Customer Experience teams who need a shared language and a plan.
Organizations that want to validate use cases before making large platform or hiring decisions.
What You’ll Walk Away With
Prioritized Use‑Case Backlog: A ranked list of high‑impact AI opportunities aligned to business goals and constraints.
90‑Day Action Plan: Clear owners, milestones, and success metrics.
AI Policy Starter Pack: Governance, data privacy, security and acceptable‑use guardrails.
ROI & TCO Model: Simple calculators to estimate value, cost, and break‑even windows.
Tooling Shortlist: Recommended models, vendors, and build‑vs‑buy guidance for your stack.
Stakeholder & Skills Map: Who needs to be involved, capabilities required, and a lightweight enablement plan.
Interested in scheduling an AI workshop?
The Maximum AI Framework
Our proven three-pillar approach to AI transformation: Discover, Prove, and Scale
Discovering AI
Learn how to identify the top AI opportunities and tools that will transform your business operations and drive exponential growth.
Identify high-impact AI opportunities in your business
Evaluate and select the right AI tools for your needs
Understand the AI landscape and emerging trends
Build an AI opportunity assessment framework
Proving AI
Create a strategic roadmap with the right AI tools and technologies to prove AI can solve your challenges and improve operations.
Develop a custom AI implementation roadmap
Design pilot programs and proof of concepts
Measure ROI and demonstrate value quickly
Overcome common AI adoption challenges
Scaling AI
Operationalize AI tools and agents with proven people, processes, and technologies for sustainable long-term success.
Build scalable AI infrastructure and workflows
Implement AI governance and best practices
Manage change and drive adoption across teams
Create sustainable AI operations for the long term
Workshop options
Option 1: Half‑Day Executive AI Workshop (4 hours)
Outcome: A focused discovery sprint that aligns leadership on 3–5 priority use cases and a 90‑day plan.
Agenda Example (Can Customize To Your Goals)
00:00–00:15 | Welcome & Objectives
Roles in the room, success criteria, and constraints.
00:15–00:50 | AI Landscape & Possibilities (No‑Fluff Briefing)
What’s real vs. hype, common patterns (agents, automation, analytics, personalization), and risks.
00:50–01:35 | Use‑Case Ideation Lab
5x5 Impact vs. Effort matrix; map top 10 opportunities across Marketing, Sales, Ops, Product, and Support.
01:35–01:45 | Break
01:45–02:30 | Data Reality Check & Feasibility
Inventory relevant data sources, access, quality, and privacy; identify blockers and enablers.
02:30–03:15 | Build vs. Buy Rapid Assessment
Evaluate internal capabilities vs. vendor options; shortlist tools and integration paths.
03:15–03:55 | Pilot Design Sprint
Convert 3–5 use cases into Proof‑of‑Value (POV) briefs (scope, success metrics, timelines, owners).
03:55–04:00 | Commitments & Next Steps
Confirm owners, milestones, and reporting cadence.
Deliverables:
Prioritized backlog, POV briefs, 90‑day plan, policy starter pack, and tooling shortlist.
Workshop options
Option 2: Full‑Day AI Strategy & Roadmap Workshop (7 Hours + Breaks)
Outcome: A complete, board‑ready roadmap with pilots, governance, and change‑management plan.
Agenda Example (Can Customize To Your Goals)
09:00–09:20 | Kickoff & Desired Outcomes
Alignment on business objectives, constraints, and KPIs.
09:20–10:05 | State of AI for Business
Practical capabilities today (automation, copilots, agents, analytics), with sector‑specific examples.
10:05–10:45 | Value Stream Mapping
Trace a core workflow end‑to‑end (e.g., lead‑to‑cash, ticket‑to‑resolution) to surface automation, augmentation, and analytics opportunities.
10:45–11:00 | Break
11:00–11:50 | Use‑Case Prioritization Workshop
Rank opportunities by value, feasibility, risk, and time‑to‑impact. Select 5–8 candidates.
11:50–12:30 | Data, Privacy & Risk Lab
Map data sources; draft governance guardrails (privacy, IP, model risk, human‑in‑the‑loop, evaluation).
12:30–01:15 | Working Lunch: Tooling & Architecture Options
Compare SaaS APIs vs. platform vs. custom; integration approaches; cost considerations.
01:15–02:00 | Pilot Design: POV Charters
For top 3–4 use cases, define scope, datasets, dependencies, metrics, and success criteria.
02:00–02:15 | Break
02:15–03:00 | Change Management & Enablement
Roles, skills, training path, and communications plan. Mitigating “shadow AI.”
03:00–03:35 | ROI/TCO & Executive Read‑Out
Build the short financial case and risk register; align on decision gates.
03:35–04:00 | Roadmap & Commitments
Finalize 90‑day plan, ownership, and weekly/bi‑weekly cadence.
Deliverables:
Board‑ready one‑pager, full 90‑day roadmap, POV charters, risk & governance checklist, policy starter pack, tool/vendor shortlist, and enablement plan.
Sample Use‑Case Areas We Can Explore
Marketing & Growth: content workflows, campaign automation, lead scoring, personalization.
Sales & CX: call summarization, proposal assist, RFP/RFI support, knowledge assistant, next‑best‑action.
Operations: agentic process automation, document processing, forecasting, inventory & scheduling.
Product & Engineering: requirements assistant, QA & test generation, backlog grooming, support deflection.
Analytics & BI: natural‑language queries, anomaly detection, scenario modeling.
Custom: Have other things specific to your business you want to explore? Let's explore & prioritize it together!
Post‑Workshop Support: 30/60/90‑day check‑ins to unblock pilots, Rapid POV Sprint (2–4 weeks) to implement one pilot end‑to‑end, AI Policy & Governance Package tailored to your sector, Team enablement sessions (prompt patterns, evaluation, and model safety).
Meet Your Instructor
Who is the Instructor?
Jason Fleagle: Chief AI Officer & Growth Architect
Your workshop is led by Jason Fleagle, a global AI consultant and fractional Chief AI Officer who helps leadership teams turn AI from buzzword into measurable revenue, efficiency, and risk reduction.
Over many years, Jason has sat at the intersection of AI, revenue operations, and digital growth, designing and deploying real-world solutions for enterprises, high-growth companies, and values-driven brands.
He’s led AI strategy, architecture, and enablement AI workshops with brands such as:
• AT&T, Verizon, Cisco Systems, Presidio, Iron Bow, NTT Data, & More!
• Large channel partners, MSPs, universities, and non-profits
• Growth-stage companies that need AI to drive outcomes, not just headlines
As a real AI expert, Jason:
• Designs end-to-end AI architectures (agents, RAG, automation, analytics) that plug into existing CRMs, ERPs, contact centers, and data stacks.
• Leads executive workshops and board-level briefings that separate hype from reality and align the C-suite, Ops, IT, and frontline teams around a clear 90-day plan.
• Builds proof-of-value pilots that validate ROI quickly, then helps teams scale what works with governance, security, and change management baked in.
Unlike many AI “thought leaders,” Jason is a hands-on practitioner:
• He’s written the prompts, built the copilots, and shipped the agent workflows your teams are now being asked about.
• He’s worked inside enterprise complexity—procurement, InfoSec, compliance, vendor sprawl—and knows how to design AI initiatives that can actually get approved and adopted.
Most importantly, Jason’s workshops are tool-agnostic and outcome-obsessed.
You won’t get a vendor pitch or another generic AI keynote, you’ll get a working session that leaves your team with:
• A shared understanding of what AI can actually do for your business
• A prioritized use-case backlog and 90-day action plan
• Guardrails so you can move fast without creating AI chaos
If you want someone who can speak “AI” to your technical teams and “P&L” to your executives in the same conversation, you’re in the right place.
Real Results From Real Founders
"Thank you so much. I just tested this for a startup and wow, this is on point. Thank you so much!"
TParties – Business Owner, Entrepreneur
Frequently Asked Questions
Do we need technical expertise?
No. We design for cross‑functional teams. Technical stakeholders are welcome, but not required.
Will we use our data?
Yes—when available. We can also work with sample data or anonymized process docs.
Can you help us build the pilot?
Yes. Ask about the POV Sprint add‑on to implement a top use case in 2–4 weeks.
What’s the difference between half‑day and full‑day?
Half‑day is a fast alignment sprint with 3–5 prioritized use cases and a 90‑day plan. Full‑day adds deeper feasibility, governance, financials, and a board‑ready roadmap.
How do we book?
Email jason@thejasonfleagle.com with your goals, ideal timing, and whether you prefer virtual or on‑site.
What is the cost?
We do custom pricing for each event depending on number of attendees, half-day vs full-day, and other deliverables required.
Claim your spot at the next AI workshop, and if you're not satisfied we'll refund you 100% (YES, FOR REAL!)
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