Digital Transformation — Step 0

Paul Mabray
4 min readApr 11, 2024


As you may have read, I am working with multiple wineries of various sizes to help them with a Digital Transformation process and documenting it to share with everyone. This first step, Step 0, is the prelude to the journey.

The first step for digital transformation starts with “priming the pump.” To ensure you have the best way to ensure people from so many backgrounds and disciplines speak the same language, you need to help align and inspire them with a shared understanding of thinking and operational frameworks.

For my part, I like to start a book club with every company I run. It’s a way to start building a common language. I found it works best if the leaders set reading goals as team objectives but, most importantly, participate in the conversation. And if you are the leader, YOU need to participate (even if you’ve already read the books). I once made the mistake of not joining; my leadership team didn’t take it seriously, and the book club became a nuisance and, candidly, a useless exercise.

I like to make Danny Meyer’s book the first primer to ensure that we inject customer-centric thinking and service into the culture of the organization.

Then I have a series of books that either speak to the challenges of startups, about user experience or inspire new ways of thinking about companies/products.

  • The Cold Start Problem — Too many people underestimate the difficulty of getting past the initial product market fit, but how hard it is to build a customer flywheel. This book is an excellent primer to understand how other companies kickstarted their audiences/customers.
  • The Hard Thing About Hard Things — A startup is a different animal. Most don’t understand the challenges and turmoil that always come with a new business, especially digital ones. This book is a guide for some of those tough business lessons.
  • The Experience When Business Meets Design — Customer experience should always be at the center of your business — no matter what product or service you sell. Brian Solis understands this like very few people on the planet and provides principles and examples on how to make CX central to your company.
  • Blue Ocean Strategy — When they zag, you zig. This is a great read to demonstrate to your team how you look for opportunities with high rewards and limited or no competition.
  • Free — First, you can go on Amazon and get the audiobook for FREE. Second, the concept of free is something that widens a team’s aperture about conjunctive marketing.

A few Seth Godin Books — His style of provocatively using real company stories to articulate the changing nature of business always makes for a great read.

  • Purple Cow — How do you stand out in a world of endless choices? This is a good way to help your team rethink what makes your company or product different. Similar to Blue Ocean Strategy.
  • Marketing — certain corners of the wine industry have besmirched Marketing. I think it’s essential for all departments to understand the importance of this crucial business skill — engineering, finance, sales, public relations, and customer service. This is a great book that helps everyone understand marketing similarly.

Also, I am a giant fan of these two thinking frameworks with principles of creating, building, operating, and selling services or products. They are incredibly valuable for organizing teams around strategic goals, aligning on purpose and activities, helping reduce noise, and setting priorities.

  • JTBD (Jobs to Be Done) — This framework helps eliminate wasted energy. It helps every department look for the ultimate purpose of any activity. Understanding purpose helps everyone align with the final customer’s actual use case (internal or external).
  • Wardley Maps — This is an incredibly useful framework to understand what you need to buy, build, or rent and where you should focus, putting your resources and attention to best compete by understanding the key factors impacting your business. It requires a bit of practice or a professional to use it effectively.
  • This video, in which swardley speaks, is a great and entertaining explanation of the framework.

Because I work in the wine business, here are a few content sources that we ask everyone to read so they get comprehensive understanding of the industry -

  • The Annual SVB Report — This is the easily one of the most important reports in the industry.
  • Rabobank Reports — The guys at Rabobank do a good job looking at all of alc-bev and have a penchant for examining some of the lessor-covered parts of the industry.
  • Annual Sovos DTC Report — A decent benchmark of the DTC side of the business.
  • Ciatti Grape Reports — There is no better reports to get a view into the current and future state of the industry by understanding the prices and demand of grapes.
  • Joe Fattorini — His writing is absolutely brilliant and almost always on the mark.



Paul Mabray

Firestarter. Former CEO of I also create content about the intersection of wine and tech at