What happens when you drop an LLM on top of five ERPs and a decade of M&A? Aaron Sheehan and analyst Heather Hershey map the practical path: B2B use cases that work, risks that don’t, and why chunk-by-chunk modernization beats “robot, take the wheel.”

01:06 – Welcome back and introducing Heather Hershey

03:35 – Defining AI, LLMs, and RAG

09:30 – Why probabilistic AI makes ops teams nervous

11:58 – Is LLM an overkill compared to ‘boring’ machine learning and rule-based systems?

15:19 – The real blocker: fragmented data across ERPs and other systems

19:40 – The strangler pattern: modernize in chunks instead of ripping everything out

21:13 – Why commerce platforms become the orchestration layer for AI/NLP

24:37 – If you had $100K for AI: where to spend it

27:27 – Prisoner’s dilemma: agentic shopping and the disintermediation trap

34:53 – Agentic commerce predictions for B2B

40:30 – Are people replacing Google with LLMs?

This week, we met Kyle Gustafson, civil engineer by training, digital commerce expert by career. From scaling office supply giants to building businesses at Amazon, Kyle reflects on what digital transformation really takes and why WIFM – “What’s in it for me?” – is the key to adoption and growth.

00:00 – Introduction: Meet Kyle Gustafson & His Career Path

02:00 – Lessons from Office Depot, Staples, and OfficeMax

04:00 – Building Private Brands and Supply Chains at Amazon

06:35 – Transformation Mindset: Thinking 20 Years Ahead

11:35 – Why Companies Call for Help: Common Consulting Triggers

17:40 – Defining eCommerce: Where’s the line?

21:33 – Why Digital Transformation Never Really Ends

28:40 – Tech Adoption and the Power of WIFM

34:10 – The Alexa Microwave Story: When Customer Value Isn’t There

39:23 – Leadership Lessons from Mentor Ron Lala

45:10 – Book Recommendations & Closing Thoughts

Resources Mentioned

• Viktor Frankl – Man’s Search for Meaning
• Malcolm Gladwell – The Revenge of the Tipping Point
• Paul Leonardi and Tsedal Neeley – The Digital Mindset: What It Really Takes to Thrive in the Age of Data, Algorithms, and AI

Allie Copeland, Chief Transformation Officer at ADI Global, joins Aaron Sheehan to break down what transformation looks like in wholesale distribution. From merging companies and overhauling tech to building a customer-first culture, Allie shares how ADI keeps progress moving, even when change never ends.

Episode highlights:

00:00 – Introduction: Meet Allie Copeland & ADI

02:15 – What Does a Chief Transformation Officer Do?

04:50 – Why Transformation Never Really Ends

09:15 – Turning Strategy into Action

12:54 – Upgrading Tech: From Mainframe to Microservices

18:25 – Planning for Agility, Not Just Stability

21:45 – “Even Better Together”: Customer-First M&A

25:15 – Decision-Making: When Changes Help (or Hurt) Customers

27:24 – Real Feedback: NPS, Surveys, and Store Pilots

29:30 – How Distribution is Evolving Beyond Inventory

34:32 – Culture Change: Project Avengers & Rebel Alliance

40:13 – Radical Transparency & Leading Through Uncertainty

42:35 – Leadership Lessons & Advice for Transformation

46:25 – Book Recs & Closing Thoughts

Resources mentioned:

• The Singularity Is Nearer by Ray Kurzweil

• Apple in China by Patrick McGee