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

This episode tackles the real reasons manufacturers and distributors stay stuck: old systems, patchwork processes, and business habits that don’t change overnight. Jason Greenwood and Aaron Sheehan dig into what goes wrong in B2B projects, how leaders can spot roadblocks early, and why honest internal conversations matter more than buying the latest software.

Key Highlights

5:00 Why B2B companies still run on spreadsheets and ancient ERPs

9:00 Shadow IT in B2B operations

11:03 Field reps aging out, digital-native buyers moving in – how it’s reshaping expectations

13:05 The real question companies ask: Should we replace the ERP or launch eCommerce first?

15:23 Customers force the issue: “We’ll switch suppliers if you don’t make it easier”

17:05 How Jason breaks the customer base into three digital adoption buckets

19:16 Manual ordering habits (screenshots, PDFs)

23:20 When eCommerce is dismissed as ‘just for small customers’ and why that’s wrong

32:00 How eCommerce automation solves pain points beyond the transactional workflow

Resources Mentioned

• Digital Services Layer (DSL): Jason’s concept for all the non-transactional digital capabilities customers expect.
• OroCommerce's AI SmartOrder: An AI-powered tool for processing unstructured purchase orders and enabling digital self-service.
• Upcoming Movie: A Big Bold Beautiful Journey
• Top Gun: Maverick
• B2B eCommerce World 2025 in Scottsdale, AZ