Enterprise AI Transformation Intensive: Why 70% Fail and How to Fix It

AI transformation is failing in most enterprises—not because of technology,

but because of architecture, governance, and execution. This one-day intensive

teaches the framework that separates success from failure. Perfect for enterprise

leaders attending Chicago AI Week.

• Why 70% of AI initiatives stall (and what to do instead)

• The three-layer architecture: Strategy, Execution, Governance

• Building a 90-day delivery roadmap from scratch

• Securing C-suite alignment and budget

• Real case study: UK Government transformation (10k+ users, 6-month delivery)

• HOBA Pro: The software layer that makes transformation stick

• Leading a distributed transformation team

• Measuring ROI and business impact

✓ 8-hour intensive workshop (includes 1-hour lunch break)

✓ Breakfast, lunch, snacks, and beverages

✓ Transformation planning workbook and fully editable templates

✓ Case studies and implementation guides

✓ 6-month HOBA Academy access (includes 24 self-paced courses)

✓ 3-Week "Introduction to Business Transformation" Pre-Workshop Course

- Week 1: Focus Step 1 (goal-setting, business architecture, VSOM, strategy mapping)

- Week 2: Control Steps 2–3 (governance framework, design principles)

- Week 3: Analyze (organization, stakeholder, user journey, process, capability mapping)

- Business Transformation Delivery Scorecard (baseline assessment)

- Fully editable templates

- Biweekly live Q&A calls + access to past recordings

- 12-month community access

- Support: Knowledge base, forum, email, chatbot

✓ HOBA Pro 30-day free trial ($500 value)

✓ Certificate of completion

✓ 30-minute post-workshop consultation (1-on-1 with HOBA strategist)

✓ Private Slack community access (12 months)

✓ Networking with 20–25 transformation leaders from Fortune 500 companies

✓ Invitation to HOBA Partner Community

✓ Biweekly live Q&A calls (ask questions, view past recordings)

✓ "The Business Transformation Playbook" – Signed hardcover by Heath Gascoigne ($100 value)

✓ "The Business Transformation Playbook E-Book”" – Digital guide ($47 value)

[Hardcover shipped 1–2 weeks post-workshop / E-Book emailed upon registration]

BONUS: If you need to transfer to the HOBA Agile Transformation Accelerator

(in case workshop doesn't run), you'll receive an additional signed hardcover

accelerator guide. You won't receive a duplicate of The Business Transformation Playbook.

• Enterprise executives (CEO, COO, CIO, CFO, CMO)

• Chief Digital Officers and transformation leaders

• Enterprise architects and technology strategists

• Government and public sector digital leaders

• Consulting partners expanding transformation practice

• Internal change management teams

WeWork Chicago Downtown

500 W Madison Street, 8th Floor

Chicago, IL 60661

Parking: $20/day discounted rate available | WIFI: Fiber included |

Accessibility: Full ADA compliance | Public Transit: Blocks from CTA stations

- Early Early-Bird ($997): 5 seats

- Early-Bird ($1,497): 10 seats

- Final Call ($1,997): 5 seats

- Regular ($2,497): 5 seats

registrations to proceed. If we don't reach this threshold, we will notify you

21 days before the event date with your options:

1. Auto-enroll in HOBA Agile Transformation Accelerator (no additional cost)

2. Defer to another 2026 HOBA workshop city

3. Receive a full refund

- Requires 5 or more people registering simultaneously

- Cannot be offered if it would exceed 25-seat capacity

- Example: If 20 seats are confirmed and you want a team discount for 5 people,

that would be 25 total (acceptable). If 22 seats are confirmed, you'd need

4 colleagues to reach 5 people, but that would exceed capacity.

- Cancel 30+ days before: 20% cancellation fee (80% refund)

- Cancel 14–29 days before: 50% cancellation fee (50% refund)

- Cancel <14 days: Non-refundable; transfer to Accelerator or defer options

- One free deferral per registration; subsequent deferrals require Accelerator

enrollment or refund

- If your workshop doesn't reach minimum enrollment, we offer Accelerator

enrollment, deferral, or full refund

For full details, see our Refund & Cancellation Policy: https://hoba.tech/refund-policy/

Early Early-Bird: $997 (First 5 seats or 30 days)

Early-Bird: $1,497 (Next 10 seats or Days 31–60)

Final Call: $1,997 (Last 28 days – 5 seats)

Regular: $2,497 (Final 27 days + day-of)

Team Discount: $1,997/person (5+ team members, any tier)

Email: [email protected]

Website: www.hoba.tech/events/chicago-2026

Info: - Welcome & Objectives (9:00–9:15)
- The 70% Problem: Why Transformations Fail (9:15–10:00)
- The Three-Layer Architecture Framework (10:00–11:15)
- Break (11:15–11:30)
- Case Study: UK Government Visa Modernization (11:30–12:30)

Info: Lunch provided | Meet peers from your industry

Info: - Designing Your Transformation: Step-by-Step (1:30–2:45)
- Building Your 90–180 Day Roadmap (2:45–3:45)
- HOBA Pro Demo & Live Implementation (3:45–4:30)
- Q&A, Peer Discussion, Next Steps (4:30–5:00)

Event Venue & Nearby Stays

500 W Madison St, 500 West Madison Street, Chicago, United States

Concerts, fests, parties, meetups - all the happenings, one place.

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