Introduction to Becoming a Better B2B Tech Vendor in Sports and Media

This course exists because most of what is written about selling, delivering, and operating B2B technology in sports and media is written by people who have never had to pick up the phone at 21:47 on a Sunday evening, ten minutes before kickoff, with a client on the other end who is calm in a way that tells you something is very wrong.

It is written by someone who has. Repeatedly. Across twenty-something years, several cycles of the industry, and enough different types of client and deal to recognise the patterns when they repeat. The goal of the course is not to turn those experiences into war stories; it is to extract, from them, the small number of structural ideas that seem to hold up across organisations, seasons, and generations of technology.

Most vendor education focuses on the surface layer. The sales playbook. The demo script. The pricing grid. The migration guide. These things matter, but they are not what determines who lasts. What determines who lasts is a kind of quiet, accumulated judgment about how this industry actually behaves once contracts are signed, systems are live, and the person who championed the deal has moved on.

What the course is

Twelve lessons, organised into five movements — Foundations, The Transaction, Delivery, The Long Run, and Judgment. Each lesson is a tightly-edited video of roughly ten to twenty minutes, with the slide deck from the video and an audio-only track available alongside it. A separate companion book, 10 Things to Consider, serves as a shared reference across all twelve lessons — fifty-one working lists meant to be revisited at specific moments in a client engagement.

The lessons are arranged in sequence. You can read or watch them in any order once you have been through them; the first time through, the order matters. Foundations explains the structural reality of the market. The Transaction looks at what is actually being bought and sold, and how to design the deal to match. Delivery is about what happens when strong technology meets real environments. The Long Run covers service, scale, and the cycles clients move through over years. Judgment is about the one thing the rest of the course is ultimately in service of.

What the course is not

It is not a playbook. It does not contain a set of tactics to copy into Monday morning. It does not offer scripts for difficult conversations, templates for RFP responses, or frameworks with colour-coded quadrants. Those resources exist elsewhere and some of them are very good. This course is addressed to a different question: why do experienced vendors, with strong products and competent teams, so often end up in the same shape of difficulty across deals that look, on paper, completely different?

It is also not a course for beginners. It assumes you have lived through at least one full client cycle from pitch through delivery to renewal or loss, and that you are reading this because something in that experience did not fit the neat story you were told about how the work is supposed to go.

How to use the material

Each lesson is a tightly-edited video of roughly ten to twenty minutes. The slide deck from the video and an audio-only track are available alongside it. A few lessons include a short extra PDF — a checklist, a reference, a working list — where the material benefits from it. Watch the video, then treat the slides and any extra sheet as something to return to with a specific, current client in mind. The exercises in 10 Things to Consider are most useful when done with a real situation, not an abstract one.

The companion book, 10 Things to Consider: Becoming a Better B2B Tech Vendor in Sports and Media, sits alongside the course as a single reference across all twelve lessons. Fifty-one working lists across ten categories, built to be revisited at specific moments — before an RFP, during a difficult renewal, when a project is drifting and you cannot yet say why. The full annotated edition is included when you enroll.

A note on tone

The material is written in the first person and in plain language. There is no effort to make it sound like a business school case study, because the situations it describes do not behave like case studies. They behave like rooms full of tired people trying to make reasonable decisions with incomplete information and fixed deadlines.

What follows in the next four free chapters is the orientation you need before the paid course begins: why this course exists, who it is for, who I am, and what the course actually covers, lesson by lesson. If any of those chapters do not resonate — if the framing feels foreign to how you experience your work — the rest of the course is unlikely to be useful to you. That is a legitimate outcome, and I would rather you find that out here, for free, than three lessons in.