A new career in an old town: Josh Whitehead’s move from rider to sports director
Five years after winning the Lancaster Grand Prix, and with his riding career over sooner than expected, Josh Whitehead is back in the North West as sports director of 360cycling’s under-23 men’s team. In a Ramsbottom coffee shop, he explains how data is shaping his new career, and why it only takes you so far.
August 2026. It’s cracking the flags in Ramsbottom. I’m stood outside a coffee shop, somewhere between the bottom of the famous Rawson’s Rake (something of a landmark in the niche world of the hill climb) and the volunteer-run East Lancashire Railway (no steam trains on Mondays). I’m here to meet Josh Whitehead. At just 26, the winner of the 2021 Lancaster Grand Prix has recently transitioned from talented rider to neophyte team manager as sports director of 360cycling’s under-23 men’s team. A career that took him from the West Pennine Moors of Lancashire to the Midlands, and then on to three different regions of France, has now deposited him back somewhere close to where it all began.
This is a quintessentially northern town: it is home to the World Black Pudding Throwing Championships (the winner being the person who knocks the most Yorkshire puddings off a high platform). Any sense, though, of a cosy northern tale or a trip down memory lane fades the moment I spot Josh, laptop open, inside the hipsterish venue. “I’ve made some notes,” he says, and something tells me that the conversation is going to be more about now than then. But before that, we need to navigate the seemingly premature end of a highly promising riding career, and the events that led him to start work with 360cycling.
I didn’t even feel that sad from it. I thought, OK, on to the next thing
The 2025 season saw Josh, along with a host of other English-speaking riders, at Team Bricquebec Cotentin in Lower Normandy. This was his third French team in three years, and came after several disruptions to his career: the Covid years, injury, and then the demise of not one but three UCI teams. Perhaps, after all the disruption and upheaval, the fire to race had started to go out. It was therefore a disappointment but not necessarily a disaster when Bricquebec indicated that they wanted a younger age profile in 2026, and that someone in his mid-twenties was, well, a bit old. “I didn’t even feel that sad from it,” he says. “I thought, OK, on to the next thing.”
Whitehead (far right) with the 360cycling junior team. Image: supplied
In the autumn of 2025, Josh found himself back in the North West, working with a number of young riders. It was at this point that Simon Diggins and Joe Cadwallader, the founders and owners of 360cycling, a multifaceted cycling brand based in Bury, reached out to him. On the back of their own highly successful 2025, they were looking to expand the operation further, running more teams with more male and female riders. They needed a DS for the under-23 men’s team, and Josh did not need to be asked twice. Soon after, he was in at the deep end, learning many of the practical aspects of the job as he went. “All of a sudden,” he says, “everyone’s looking to me for answers.”
Josh had joined the team after the annual retention and recruitment process, and so he was meeting his riders (and their parents) for the first time at the team’s pre-season training camp in Majorca. During this immersive phase, it soon became clear that some things were not his forte. At a domestic camp in Lancashire, he realised that cooking the team’s evening meal might not be for him (more burnt rice, anyone?). But he quickly found his feet, and by the time the season came around he was forging a sense of how he would go about managing and motivating the young talent around him.
It’s like it’s interesting now, the stuff I found boring before
Back to the present, and Josh is keen to share how, even in his first year in the job, he is innovating. He has, for example, already developed a modern and relevant approach to data, drawing on both open and team-specific sources for a variety of purposes. Turning GPX routes into video for course reconnaissance, comparing the attributes of different riders quantitatively, and developing tailored race tactics are just some examples. This is far removed from the training regimen that brought him his first big domestic victory only five years ago: an unstinting fixation on 400 miles a week, every week, for many weeks. If that was steadfastly old school, Josh’s approach to his new job visibly reflects the fast times in which we all now live. “I just enjoy it. I like the data, I like the numbers,” he says, before adding: “It’s like it’s interesting now, the stuff I found boring before.”
Josh’s innate curiosity, and his willingness to learn about something by doing it, are very apparent. “I’ve learned a lot this year, a hell of a lot,” he says, as we whizz through a series of screens on his computer. Quite casually, he shows me a selection of his latest creations, some built as recently as the previous weekend. A data professional (me, in a not-too-distant previous life) would describe these as “data products” designed to provide actionable insights for the riders. A layperson would simply call them gold dust.
Image: supplied
For example, using publicly available information (the weather forecast, how often a particular race has ended in a bunch sprint, and so on), he is able to suggest if, when, and where the key break of the day is likely to go. And that is not all. Using metrics that he understandably prefers to keep up his sleeve for now, he can forecast the power that different riders in the team would have to produce, and for how long, to get into the move and then cement their advantage over the field. This wealth of material is pulled together in the detailed digital race briefs he produces for the team when they are competing at home or overseas, such as in May, when they took on a month-long period of racing in Europe culminating in the UCI Paris–Troyes one-day race, and more recently when they took part in the junior tours of Ireland and Wales.
I told them where it would break and it did break there, but they weren’t there
Are there any drawbacks to this approach? Well, says Josh, there was a race where “I told them where it would break and it did break there, but they weren’t there.” We ponder why this was the case. Firstly, we consider, not everyone is receptive to a message, however clearly it is communicated. Secondly, there are no radios at this level of racing, so there are limited opportunities to reinforce an idea on the go. Thirdly, the cognitive load of riding your bike this hard means that even the best of intentions can go awry. As many will attest, it’s just not so easy to think straight when you’re getting your head kicked in by an angry peloton. Lastly, some days you know what the right thing to do is, but you simply don’t have the legs. There is just a lot that can go wrong out on the road.
Such concerns could be filed under the heading of “the human factor”, and Josh is fast becoming aware that, for all the multifarious benefits of data, management is still essentially a people business. It is telling that some of the most receptive riders he has come across are from 360’s junior team. Could this be one explanation for professional teams signing riders at ever younger ages? Is this cycling’s version of the Premier League academies, where younger, more malleable talent is hoovered up and moulded to a team’s blueprint? The jury is still out, but I’m reminded of an old coach friend of mine, who used to say that it is easier to bend plywood than iron.
Image: supplied
The DS role has been an accelerated learning experience for Josh, but it is also just the latest area in which he has been able to display his keen ability to focus. Once that focus was on training; now it is off the bike. Alongside the management role and the associated data analysis, he is also eager to move into event management, and has well-advanced plans to reboot a well-known local event.
I was off work the other week, and he sent me this, almost like homework
The value of Josh’s proactive approach is not just to be seen in results, although these have continued to impress across all of 360’s teams in 2026 (notably Nicola Quaye’s solo victory at the Curlew Cup in August). It is also in the way the team is being built to evolve and grow in the years ahead. Both Simon and Joe are ambitious for the future, and in Josh they have someone who is also looking beyond the next race. Joe’s role as a mentor, and as someone who is constantly pushing at Josh’s sense of his own capabilities, came across particularly strongly as we spoke. “I was,” he says, “off work the other week, and he sent me this, almost like homework.”
As we ended our conversation, I was struck by what a positive story this was. Things hadn’t always gone according to plan for this talented young man. More often than not, in fact, they hadn’t. But with the support of 360cycling, coupled with his own resilience and an ability to commit to the latest challenge, Josh has moved quickly and healthily through a potentially tricky period in his life. So often, our elite sportspeople are left to fend for themselves once the dream is over, but Josh, it seems, has found a safe place from which he is already starting to take his next exciting steps. That can only be a good thing, and we should all be watching them closely.
August 2026. It’s cracking the flags in Ramsbottom. I’m stood outside a coffee shop, somewhere between the bottom of the famous Rawson’s Rake (something of a landmark in the niche world of the hill climb) and the volunteer-run East Lancashire Railway (no steam trains on Mondays). I’m here to meet Josh Whitehead. At just 26, the winner of the 2021 Lancaster Grand Prix has recently transitioned from talented rider to neophyte team manager as sports director of 360cycling’s under-23 men’s team. A career that took him from the West Pennine Moors of Lancashire to the Midlands, and then on to three different regions of France, has now deposited him back somewhere close to where it all began.
This is a quintessentially northern town: it is home to the World Black Pudding Throwing Championships (the winner being the person who knocks the most Yorkshire puddings off a high platform). Any sense, though, of a cosy northern tale or a trip down memory lane fades the moment I spot Josh, laptop open, inside the hipsterish venue. “I’ve made some notes,” he says, and something tells me that the conversation is going to be more about now than then. But before that, we need to navigate the seemingly premature end of a highly promising riding career, and the events that led him to start work with 360cycling.
The 2025 season saw Josh, along with a host of other English-speaking riders, at Team Bricquebec Cotentin in Lower Normandy. This was his third French team in three years, and came after several disruptions to his career: the Covid years, injury, and then the demise of not one but three UCI teams. Perhaps, after all the disruption and upheaval, the fire to race had started to go out. It was therefore a disappointment but not necessarily a disaster when Bricquebec indicated that they wanted a younger age profile in 2026, and that someone in his mid-twenties was, well, a bit old. “I didn’t even feel that sad from it,” he says. “I thought, OK, on to the next thing.”
In the autumn of 2025, Josh found himself back in the North West, working with a number of young riders. It was at this point that Simon Diggins and Joe Cadwallader, the founders and owners of 360cycling, a multifaceted cycling brand based in Bury, reached out to him. On the back of their own highly successful 2025, they were looking to expand the operation further, running more teams with more male and female riders. They needed a DS for the under-23 men’s team, and Josh did not need to be asked twice. Soon after, he was in at the deep end, learning many of the practical aspects of the job as he went. “All of a sudden,” he says, “everyone’s looking to me for answers.”
Josh had joined the team after the annual retention and recruitment process, and so he was meeting his riders (and their parents) for the first time at the team’s pre-season training camp in Majorca. During this immersive phase, it soon became clear that some things were not his forte. At a domestic camp in Lancashire, he realised that cooking the team’s evening meal might not be for him (more burnt rice, anyone?). But he quickly found his feet, and by the time the season came around he was forging a sense of how he would go about managing and motivating the young talent around him.
Back to the present, and Josh is keen to share how, even in his first year in the job, he is innovating. He has, for example, already developed a modern and relevant approach to data, drawing on both open and team-specific sources for a variety of purposes. Turning GPX routes into video for course reconnaissance, comparing the attributes of different riders quantitatively, and developing tailored race tactics are just some examples. This is far removed from the training regimen that brought him his first big domestic victory only five years ago: an unstinting fixation on 400 miles a week, every week, for many weeks. If that was steadfastly old school, Josh’s approach to his new job visibly reflects the fast times in which we all now live. “I just enjoy it. I like the data, I like the numbers,” he says, before adding: “It’s like it’s interesting now, the stuff I found boring before.”
Josh’s innate curiosity, and his willingness to learn about something by doing it, are very apparent. “I’ve learned a lot this year, a hell of a lot,” he says, as we whizz through a series of screens on his computer. Quite casually, he shows me a selection of his latest creations, some built as recently as the previous weekend. A data professional (me, in a not-too-distant previous life) would describe these as “data products” designed to provide actionable insights for the riders. A layperson would simply call them gold dust.
For example, using publicly available information (the weather forecast, how often a particular race has ended in a bunch sprint, and so on), he is able to suggest if, when, and where the key break of the day is likely to go. And that is not all. Using metrics that he understandably prefers to keep up his sleeve for now, he can forecast the power that different riders in the team would have to produce, and for how long, to get into the move and then cement their advantage over the field. This wealth of material is pulled together in the detailed digital race briefs he produces for the team when they are competing at home or overseas, such as in May, when they took on a month-long period of racing in Europe culminating in the UCI Paris–Troyes one-day race, and more recently when they took part in the junior tours of Ireland and Wales.
Are there any drawbacks to this approach? Well, says Josh, there was a race where “I told them where it would break and it did break there, but they weren’t there.” We ponder why this was the case. Firstly, we consider, not everyone is receptive to a message, however clearly it is communicated. Secondly, there are no radios at this level of racing, so there are limited opportunities to reinforce an idea on the go. Thirdly, the cognitive load of riding your bike this hard means that even the best of intentions can go awry. As many will attest, it’s just not so easy to think straight when you’re getting your head kicked in by an angry peloton. Lastly, some days you know what the right thing to do is, but you simply don’t have the legs. There is just a lot that can go wrong out on the road.
Such concerns could be filed under the heading of “the human factor”, and Josh is fast becoming aware that, for all the multifarious benefits of data, management is still essentially a people business. It is telling that some of the most receptive riders he has come across are from 360’s junior team. Could this be one explanation for professional teams signing riders at ever younger ages? Is this cycling’s version of the Premier League academies, where younger, more malleable talent is hoovered up and moulded to a team’s blueprint? The jury is still out, but I’m reminded of an old coach friend of mine, who used to say that it is easier to bend plywood than iron.
The DS role has been an accelerated learning experience for Josh, but it is also just the latest area in which he has been able to display his keen ability to focus. Once that focus was on training; now it is off the bike. Alongside the management role and the associated data analysis, he is also eager to move into event management, and has well-advanced plans to reboot a well-known local event.
The value of Josh’s proactive approach is not just to be seen in results, although these have continued to impress across all of 360’s teams in 2026 (notably Nicola Quaye’s solo victory at the Curlew Cup in August). It is also in the way the team is being built to evolve and grow in the years ahead. Both Simon and Joe are ambitious for the future, and in Josh they have someone who is also looking beyond the next race. Joe’s role as a mentor, and as someone who is constantly pushing at Josh’s sense of his own capabilities, came across particularly strongly as we spoke. “I was,” he says, “off work the other week, and he sent me this, almost like homework.”
As we ended our conversation, I was struck by what a positive story this was. Things hadn’t always gone according to plan for this talented young man. More often than not, in fact, they hadn’t. But with the support of 360cycling, coupled with his own resilience and an ability to commit to the latest challenge, Josh has moved quickly and healthily through a potentially tricky period in his life. So often, our elite sportspeople are left to fend for themselves once the dream is over, but Josh, it seems, has found a safe place from which he is already starting to take his next exciting steps. That can only be a good thing, and we should all be watching them closely.
Featured image: Simon Wilkinson/SWpix.com
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