The Growth Workshop Podcast · 2026-03-30 · 12 min
Key moments - from our scoring
Substance score
56 / 100
Five dimensions, 20 points each
Matt Ring brings nine years of experience from Facebook and previous roles at Sky and The Guardian to Deliveroo, where he identified a critical gap in how the company launches products and processes. Despite significant investment in building tools, CRMs, and features for restaurant partners and riders, adoption was failing because teams worked in silos with no coordinated communication or change preparation. Ring introduced a T-shirt sizing framework - borrowed from engineering and program management - that evaluates launches across two dimensions: the magnitude of change required and the number of people impacted. This simple model transformed internal alignment by forcing cross-functional teams to think collectively about communication strategy, capability requirements, collateral needs, and timeline. An extra-large T-shirt launch affecting both riders and restaurants now triggers comprehensive preparation across the organization, whereas smaller, policy-level changes affecting only restaurant decision-makers require less intensive rollout. The episode covers how this framework evolved through organizational feedback and iteration to become the foundation of Deliveroo's modern go-to-market engine.
Products weren't being adopted because nobody knew about them and nobody was prepared for the change they required - neither the internal account teams nor the restaurant customers. The organization was building in silos without coordinated communication or change management.
They size launches by two dimensions: how much change the launch requires and how many people it will impact. For example, a change affecting all riders and restaurants is an extra-large requiring extensive preparation, while a policy affecting only restaurant decision-makers might be smaller.
A critical moment when a highly-requested product feature that teams had been asking for over a year finally launched but nobody used it, prompting the realization that without proper communication and change preparation, even well-built solutions fail.
His experience selling partnerships at Sky Media, scaling new products at Facebook, and bringing together cross-functional alignment at Deliveroo taught him that effective go-to-market requires moving from siloed execution to coordinated communication, capability building, and change management across all affected audiences.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains a solid core insight about go-to-market maturity - the T-shirt sizing framework for assessing change impact - but much of the runtime is spent on career biography, pleasantries, and repetition of the same framework concept. The insight about misalignment between product development and adoption (tools built but unused) is valuable but not densely packed with additional novel claims; most of the substance concentrates in the final third of the transcript.
something which the account teams had been crying out for, well over a year when it finally launched. Nobody used it
we created a simple framework using T-shirt sizes to say, how much change does this require and how many people is it gonna impact?
The T-shirt sizing framework for change management is borrowed from engineering and program management teams (the guest explicitly disclaims invention), and the underlying insight about change management maturity is relatively standard organizational wisdom. The application to go-to-market is sensible but not contrarian or first-principles thinking; this would be recognizable to most ops and enablement practitioners already familiar with change management frameworks.
I don't think we invented that. I know we didn't.
it's used in some kind of engineering teams. And program management teams
Matt Ring holds genuine practitioner credentials as a global commercial director at a high-scale platform (Deliveroo) and has operated at scale across multiple large organizations (Facebook, Sky, The Guardian). However, the caliber is somewhat diluted by the fact that this is a short Part 1 segment and he functions more as a peer enablement expert than as a cutting-edge operator pushing new frontiers; he's solid but not exceptional for a B2B podcast guest.
global commercial director of Deliveroo
I did a number of different roles selling directly to advertisers, running relationships with media agencies
The episode lacks specific metrics, timelines, or named examples of products or outcomes. The T-shirt sizing framework is explained in broad strokes but without concrete case studies showing before/after results, adoption rates, or business impact. The reference to launching a product around rider-restaurant interaction is mentioned but not detailed; no dollar figures, customer counts, or measurable success metrics are provided.
something which the account teams had been crying out for, well over a year when it finally launched. Nobody used it
a group of people who are focused on launching a product around, the interaction between a rider and a restaurant
The hosts (Jonny and Dannii) ask reasonably structured questions that follow a logical arc, but follow-ups are soft and rarely push for deeper detail or challenge claims. There is minimal productive disagreement or skeptical probing. The hosts occasionally deflect into off-topic banter (shirt colors), and questions tend to accept the guest's framing rather than interrogate assumptions or ask for evidence of impact. One follow-up (on policy vs. rider impact) shows promise but is quickly resolved without drilling deeper.
I have to ask the, shirt choice, is that Deliveroo based?
We're not gonna continue talking about your wardrobe
Computed from the transcript - who did the talking, and the words that came up most.
In Part 1 of this episode, global commercial leader Matt Ring charts his journey from selling TV ads at Sky to building enablement and go‑to‑market at Deliveroo. He shares the painful moment when a long‑awaited product launch flopped because no one was prepared for the change - not sales, not restaurants. Matt explains how this led to a deceptively simple “T‑shirt sizing” framework that helped Deliveroo finally coordinate product, ops, and frontline teams around change.
Transcribed and scored by The B2B Podcast Index.
Matt Best: Hello and welcome to the Growth Workshop Podcast. In this podcast, we'll be sharing insights and hearing from other industry leaders to get their thoughts and perspectives on what growth looks like in modern business. We'll cover all aspects of leadership, sales, account development, and customer success alongside other critical elements required to build an effective growth engine for your business. We're kicking off with part one.
Jonny Adams: Brilliant. Welcome to the Growth Workshop podcast. Today we've got Matt Ring, a global commercial leader who has held some fantastic positions at Deliveroo, amongst other organizations, and we're gonna have a great opportunity to unpack some insights, a little bit about Matt's career around how he's supported Deliveroo grow over a number of years. So welcome Matt.
Matt Ring: Thank you very much. I'm really pleased to be here. Jonny Adams: Excellent. We've also got co-host Dannii Mathers today, which is excellent.
Welcome Dannii. Dannii Mathers: Thank you. Jonny Adams: Looking forward to this one? Dannii Mathers: I am, we've got Matt in the hot seat.
Jonny Adams: Excellent. What are you looking forward to about most of today's conversation, Dannii? Dannii Mathers: I am looking forward to hearing how Matt really changed some of the go to market principles with such a large organization where I imagine there would've been a fair bit of challenge and pushback. So yeah, I'm looking forward to uncovering more of that.
Jonny Adams: Yeah, and, as someone that I've spoken to many times, got a wealth experience and understanding of account development, and so forth. So we'll be able to unpack that. I'm just gonna shape the session, I'm gonna shape the episode for the audience. So we're gonna understand a little bit about you, Matt, the journey that you've been on, some of the successes you've had within commercial roles.
And then we're really gonna look at what does the go to market approach and engine look like and, then start to use some of those examples of what you've been doing in industry and hopefully support some of the audience members moving forward as well. So really looking forward to that. Matt Ring: Excellent. Let's get stuck in.
Jonny Adams: So let's start with you, let's a little bit of a background. Where have you come from? How did you get to where you got to as a global commercial director of Deliveroo and so forth? Matt Ring: Yeah, so I started my career at Sky, in Sky Media, selling TV advertising back in the day when, that was, that was a big thing before the internet.
And that was a really good opportunity for me to start to understand how to build partnerships and drive value with existing clients that, that I was looking after at the time. An opportunity came up then to move into the digital side of Sky, and that was the newly launched Sky sports.com. which now kinda seems crazy to say, that was a thing that I went for.
And then I moved to a number of different places. The Guardian and then found myself at Facebook. And at that time Facebook was just 80 people in the London office. We were selling very small classified ads and all of my friends told me I was mad because Yahoo and MSN were the place to be on the internet.
And so I was very fortunate to spend nine years there and, I did a number of different roles selling directly to advertisers, running relationships with media agencies. And then I moved into our enterprise product, which was called Workplace, unfortunately no longer exists, but that was a great kind of BD role where I had to actually bring new business into what was a very nascent product. I managed to sell that to the likes of BT and Virgin Media. And then, I was asked to join Deliveroo.
For those of you who don't know, Deliveroo is a food delivery platform and now deliver a lot more things and maybe we can talk about that later. But I was asked to join Deliveroo, to help optimize and grow their account team and then three and a half years ago I moved to use all of my commercial frontline experience to basically build out our enablement function, which, I think we're gonna talk a lot about today. Jonny Adams: Fantastic. There's some nice, alignment there, right?
What you've done at Deliveroo, what we do on a day-to-day basis from enablement. I have to ask the, shirt choice, is that Deliveroo based? Matt Ring: The current shirt choice? No this is very much my choice.
Are you suggesting that people that Deliveroo aren't smartly dressed? Jonny Adams: No, just the color. Me and Dannii spoke today, Matt, about, what you're wearing and, you're in the southwest of England and I'm wearing green. I'm like, oh no, I'm too.
So we should have checked in before. But welcome and, yeah, looking forward to today. Dannii Mathers: We're not gonna continue talking about your wardrobe. You'll be pleased to know Matt we'll be talking about things that the audience will probably want to hear more about today.
And, just before you explained some of the different markets that, delivery went into, and I am really interested to understand more about, so the previous go to market model that you had, what was that kind of pinnacle moment or that linchpin moment that you decided, okay, we need to look at this cross market engine, we need to do something different. What was that kind of critical point? Matt Ring: I think like in, in many large organizations, you've got, that, that are trying to grow quickly and develop new products and processes.
You've got loads of people building loads of really cool stuff, right? whether that is, something that can make a restaurant partner optimize their, service on the platform better. Whether it's like a new CRM system for your salespeople to use. Lots and lots of things happening, and that was very typical at Deliveroo.
We were growing quickly, we were making a lot of progress, but what was happening was those things were happening very much in isolation. So we would find, for example, that something which the account teams had been crying out for, well over a year when it finally launched. Nobody used it. And that was probably the key moment when we realized, actually the reason that no one's using it is because firstly, no one knew about it and secondly, no one was prepared for the change that it required, and no one being both the account teams and then also our end customers, which in this case was the restaurants.
And so I think it was that one moment that we'd, observed this over a number of years and it really came to fruition when so much effort had been put into that thing that was being built, for it to effectively fall, and not be used. Dannii Mathers: It's almost that maturity part, isn't it? You get to, you're at a stage where, okay, we're we, can't keep on going the way we are. We need to put something more in process to become more mature as a, commercial organization.
Matt Ring: Yeah, absolutely. Absolutely. And, there were pockets like there are in any organization where you've got, a group of people who are, perhaps more interested in understanding, or not interested in the wrong word, but they're, really keen to understand how do we really land this effectively? And so we identified a small group, who are focused on launching a product around, the interaction between a rider and a restaurant.
So when the rider goes into the restaurant, they have to do certain things and the restaurant has to do certain things, and that group of people spent much more time thinking about, okay, how do we better plan, and prepare all of the audience for change? What are the assets and the materials that we need to provide those two audiences or multiple audience with? How much time do we need to give them? And that was actually like the formation of what is now the go-to market engine of Deliveroo.
Dannii Mathers: And it is great to hear you talk about that, that change piece. And I'm interested to hear how there's always lessons learned from change. Change management doesn't always run according to plan. What were your kind of big lessons because it's quite a significant change internally.
So what were the main lessons that came out of that change rollout? Matt Ring: So the way that we thought about this was, we can't, we need to try and organize everybody in the same way, which is quite a boring thing to try and do really and so we've faced kind of significant internal pushback for that change, if that makes sense. What we did was we said, okay, what's been going on today? We've really been looking at what are these products and these processes and these tools, and how big are they rather than how much change they require.
So we created a simple framework using T-shirt sizes to say, how much change does this require and how many people is it gonna impact? And so those were the kind of two initial elements that we took, put them together. And then what started to happen was you'd see that an extra large T-shirt size was actually something which previously we might have not even communicated at all. And so that was the real moment when, in internally everyone started to realize that the thing that we needed to do was prepare.
And so that's probably the, key, I think, insight that we found, which helps us then to unlock all of the other pieces, the process that we put in place. Dannii Mathers: T-shirt sizes as a framework. Jonny Adams: I've heard that a few times. Matt Ring: Yeah.
Jonny Adams: It threw me the first time, let me just put it that way. Matt Ring: I'm just gonna say, so I think it's a, to be clear, I don't think we invented that. I know we didn't. Yeah but I, believe it's, used in some kind of engineering teams.
And program management teams. And so really, like I said, what we looked at was how much change is this going to require, and how many people will that impact? To have a, to make an example of that, if you need every rider and every person in every restaurant to do something, that's a really big change. Yeah.
So you have to tell lots of people about that big change. If there is a new policy which Deliveroo is rolling out, and it's going to impact all restaurants, you only need to tell a smaller group of people who are the ones who are making the decisions about operating on the platform. Jonny Adams: Would the size of the t-shirt change depending on the, scale of... so that would be an extra small?
Matt Ring: No, that wouldn't be an extra small. That wouldn't be an extra small, yeah because of the the size of the change. So if the policy was a big change, that kind of adds extra weight to the, the t-shirt sizing, because you only have to tell a smaller number of people. Jonny Adams: You gonna take that one away, aren't you?
Dannii Mathers: It's, it is just, it is very simple principles, but I think what that does encourages people to think differently. Matt Ring: Yeah. Dannii Mathers: As opposed to, I guess what I often see in organizations is especially when you have, operations in silo, which is often the case. A function would do something and not really understand how that will affect people outside of that function.
Yeah. So I think just having that almost, that view on how many people does this affect? How large is this? Yeah.
I think just encourages different thinking. Matt Ring: Yeah. And, like to be clear, it wasn't perfect to start with. In that example that, you just asked there, Jonny, many people said, why isn't this an extra small?
Why isn't this an extra large? Actually that process across the organization was really powerful because we collectively worked that through, and we made some iterations over time, but we made sure that we set our stall out early on and said, okay, if it requires this much change with these people, this is what we're gonna do. And that includes how long are we gonna take to prepare, what collateral and assets are we gonna do? What are the capability requirements?
And how are we gonna communicate that to which audience? And so all of those things, then fed in and we continue to evolve that over time because as you get more change coming in, you can't, you have to evolve it. Matt Best: Thanks for listening. We'll see you in part two.
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