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.

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.

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.

Thank you very much.

I'm really pleased to be here.

Excellent.

We've also got co-host Dannii Mathers today, which is excellent.

Welcome Dannii.

Thank you.

Looking forward to this one?

I am, we've got Matt in the hot seat.

Excellent.

What are you looking forward to about most of today's conversation, Dannii?

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.

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.

Excellent.

Let's get stuck in.

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?

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.

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?

The current shirt choice?

No this is very much my choice.

Are you suggesting that people that Deliveroo aren't smartly dressed?

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.

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?

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.

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.

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.

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?

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.

T-shirt sizes as a framework.

I've heard that a few times.

Yeah.

It threw me the first time, let me just put it that way.

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.

Would the size of the t-shirt change depending on the, scale

of... so that would be an extra small?

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.

You gonna take that one away, aren't you?

It's, it is just, it is very simple principles, but

I think what that does encourages people to think differently.

Yeah.

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.

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.

Thanks for listening.

We'll see you in part two.

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