Enterprise AI Transformation Intensive: Why 70% Fail and How to Fix It
About this Event
OVERVIEW
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.
WHAT YOU'LL LEARN
• 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
WHAT'S INCLUDED
✓ 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)
📚 EXCLUSIVE PRE-WORKSHOP PREPARATION ($497 VALUE):
✓ 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)
📖 EXCLUSIVE BOOK PACKAGE ($147 VALUE):
✓ "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.
WHO SHOULD ATTEND
• 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
VENUE
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
⚠️ IMPORTANT: WORKSHOP TERMS & CAPACITY
LIMITED CAPACITY: 25 seats total, allocated as follows:
- Early Early-Bird ($997): 5 seats
- Early-Bird ($1,497): 10 seats
- Final Call ($1,997): 5 seats
- Regular ($2,497): 5 seats
MINIMUM ENROLLMENT REQUIRED: This workshop requires a minimum of 15 confirmed
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
TEAM DISCOUNT ($1,997/person):
- 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.
CANCELLATION & DEFERRAL POLICY:
- 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/
PRICING
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)
CONTACT & REGISTRATION
Email: [email protected]
Website: www.hoba.tech/events/chicago-2026
Inside the Workshop
Real moments from a recent HOBA transformation intensive
Morning Session
🕑: 08:30 AM - 12:30 PM
MORNING (9:00 AM–12:30 PM)
Host: Heath Gascoigne
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)
Lunch & Networking
🕑: 12:30 PM - 01:30 PM
LUNCH & NETWORKING (12:30–1:30 PM)
Host: Heath Gascoigne
Info: Lunch provided | Meet peers from your industry
Afternoon Session
🕑: 01:30 PM - 04:30 PM
AFTERNOON (1:30–5:00 PM)
Host: Heath Gascoigne
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)
Where is it happening?
Event Location & Nearby Stays:
GBP 742.00 to GBP 1987.72
