In this episode of Tech Startup Stories, host Natalie Bins interviews Derry Holt, co-founder of One Up Sales, a platform that automates sales competitions and motivation tools, primarily for recruitment agencies. Derry shares his unique background as a video game developer and commentator, which inspired the product’s gamified approach. The company evolved from a simple competition tool to a comprehensive system including reporting, TV displays, and automation, born from Derry’s desire to simplify manual sales incentives he experienced in his own sales leadership.
Derry discusses shifts in the recruitment industry post-COVID, noting a move from fully office-based to hybrid work, with a recent push back toward in-office culture for energy and performance. Despite economic downturns in 2023-24 causing client downsizing, One Up Sales remains focused on efficiency, maintaining a team of 40 with a fully remote setup but regular in-person meetups to preserve culture. The company’s growth was not linear; early struggles included near-collapse in 2016-17 due to lack of revenue and mismatched hires, saved by a timely investor and later partnerships. Derry highlights the importance of learning from mistakes, such as not speaking to customers early and hiring friends, and the evolution of his co-founder relationship from conflict to clear role division. The conversation underscores the resilience needed in startup life, with Derry’s stubbornness and adaptability key to survival.
Welcome to Tech Startup Stories hosted by Natalie Bins. This is the podcast that takes you behind the scenes of the B2B startup world. Hi, I'm Natalie Bins and I'm the host of Tech Startup Stories. This podcast is really designed to share the unique and challenging journeys of all the people that are building small startups to scale-ups in the tech space. My background, initially I was in sales and then I moved into marketing and I've been lucky enough to work with some amazing tech companies. But my passion is really startups and that led me back to helping tech startups set up their marketing and go to market functions where the budgets are tight and the resources are few and far between. So let's get into this week's podcast. Hi everyone and welcome to this week's episode of Tech Startup Stories and super excited today because I've got Derry Holt from One Up Sales. I have to first talk about your LinkedIn profile picture because there you are and if you haven't seen it you do need to check it out. Derry is wearing a very snazzy jacket with what can only be described as almost Formula One headphones and microphones. So I'm not sure whether you're about to burst into song, do some kind of karaoke, Tom Jones rendition or what's going on there but please tell us what that photo is all about. Yeah I mean thankfully I'm not going to start singing anytime soon because I can't sing. So that's probably a good thing so that's possibilities been eliminated. That was actually a picture from South Paolo in Brazil in February last year so about 12 months ago. Basically in adjacent to the business I do video games commentary where I travel around the world talking about video games which sounds absolutely bonkers. Best way to think of it is you imagine like a football commentator. I do the same thing but put competitive video games at the highest level. I've been it for about 10 years or so and that was me and my co-caster working in the semifinals the day before the grand final. Loads of fun. It always means to get to dress up nice. There's some nice shirts and jackets and wear those very cool headsets that make us sound fabulous. So yeah here we are. That's my kind of light. My life by night and then during the day I run the business. Wow. I don't know how you actually have time to do both to be honest. I'm very glad to be fair but here we are. Well I mean obviously your background I mean tell us a little bit more. Yeah sure so my background I was a video games developer for a couple of years. Into university I was really really interested in computers as a young kid and went to university to go and do computer games programming and while I was there ended up getting a placement where the company called Exxient Down in Oxford and they were one of the developers on the Angry Birds series for Rovio. That's a game that no one remembers anymore because thought nights come along and very much off the top spot I feel these days. Get a pair of this everywhere now which kids love that game and just to take out the back of work in there me and my co-founder James will like it be really cool to combine what we know about making video games with the world of sales because he used to work in door to door sales and the company began life as being able to run sales competitions where whether you were the marketer, whether you were a cleaner, whether you were an admin didn't matter who you were. You could pick a squad of sales people and earn points for how they performed against their KPIs throughout the week and over time that then evolves into being a much more sprawling product that it is today with things like reporting, TV displays that go around the office, competition management still being a big part of it plus a lot of automation into tools that companies already use to try and keep their teams well motivated. A very long journey we don't know for about a decade or so, lots of lessons along the way. It's been a very, very fun ride. I want to know where you were when I was leading sales teams because I had to do everything manually and I used to love running those sales competitions and anyone that's listening to the hard cast will probably remember from the Blacks by the days of all sorts of competitions that we would run incentives. I think we even did like a well-built cup themed one at one point. So the fact that you're automating it is amazing. It's so incentive that for us everything is a spreadsheet in a whiteboard, right? There are times that speak to people and they say we love running and we always want to do them. But doing all the admins make sure it's up to date, communicating it out to people. It just adds so much burden unless you really invest in it, you don't get enough out of it. So that's what we're trying to solve. What has been the shift that you've seen within your customer base in the last five years? Yeah, we mainly sell to recruitment agencies. Although we do target sales teams and we have a few non-recruifters on our books, recruitment agencies is the niche that we fell into. We've tried to stay really, really focused on that area. We saw clients of COVID, say, basically most of our clients were office-based. There were very, very few that were remote. Host COVID, we ran a survey about a year on NAST, all the back clients. What are you doing these days? What she said up? 76% of them were hybrid. 4% were fully remote and the other 20% were fully back in the office. I think there's been a continual lean towards going back into the office more as many people are appreciating the energy that you get. They enjoy getting out of their home, for example. So I'd say these days it's probably more like 50/50 for those that are full-time versus those that have hybrid. But there's definitely more flexibility being afforded to recruiters that do want to say, on Friday I want to work from home, like I've got my customer kids, whatever else it might be, as long as the work is being done these days, it feels like there's more agency being afforded to people. That being combined over the down to means that expectations are still very high. So for those that can't deliver, that should kind of means people are asking you just the right job for you if you can't do the numbers even when you're at home. I want about for you guys what's your view on the setup for working from home? Or being in the office? Well back for COVID we had an office in Birmingham and Brindley Place, I think there's seven other soul in there together. And then COVID kicked in, the madness of furlough and all the rest of it broke out. And we kind of realised after about six months we actually like not commuting to three hours a day. That's a lot of time that you lose, we used to come public transport, 18 every second when you're packed onto a train like a sardine and it's not a good time. And I think because we were a very deaf heavy company early on and because we and my co-founder both technical by nature, we appreciate the fact that we're doing a good the time and the value that you get from being undisturbed to get things done without having to have someone more pastures start up a conversation for example. Like I think a lot of roles when it's not sales focused aren't very conversational. Things like death again is a great example. You being able to get locked into your work for like 15 minutes straight put you into that flow state where you can get a lot of done and time just flies. If you be in no's every five minutes have a conversation someone's checking to see how things are going, it just breaks you out the flow all the time. So we made the decision to go fully remote back then. One thing we've done really well that I'm very proud of and I've had some really interesting conversations with other founders about this is we put in place like a meet up, rota, schedule, whatever you want to call it that we employ across the company. So every three months the whole company comes together all four to almost a two days in a city in the UK. It could be leads, Manchester, Bristol, Birmingham, you know, we tried different place every single time and in between those big three month you get together. We also have six weekly department get togeters. So for example, it might just be the dev team getting together by themselves to have that day together and normally two days, sorry, and they'll focus on some topics that are quite relevant to their world. Sometimes we'll do a collaboration where a customer success team might get together with marketing or sales will get together with admin and finance like it can be a real mix bag. And we try and make sure that those very human connections still exist where it really then all comes to a peak or something, whatever you want to call it is once a year we do a big annual offsite where we take the whole company away to somewhere and Europe for a week. Done Portugal so far we've done Serbia, we've done Malta and then this year we're taking everyone to Barcelona in October. I think it is. So that's how we try and maintain that culture. So although we say it's one remote, we're all based in the UK. It's quite easy to do. We say that we're remote. I kind of you it's being hybrid, but not hybrid in the way that everyone else perceives it where you might have a day or two a week in the office. We just make it a very intense couple of days together or a whole week together in one burst rather than saying let's get together every week because naturally that is not going to be affordable or very friendly to the climate. And I'm guessing that Portugal is a little bit more glamorous than being in the centre of Birmingham. Is it just yet? Another bit of anything wrong with Birmingham. Birmingham is pretty much HQ but yeah I definitely go as far as saying it's not the most glamorous place to have a team get together. So with your target audience, how have you seen them shift in terms of the way that they work? The industry is blessed and cursed in many ways and one of the ways I'd say in which it's cursed is that it's one of the first to feel the effects of any kind of downturn or economic difficulty and one of the last to recover. So in 21 and 22 it was absolutely flying. Everyone was hiring. We were in that zero interest rate policy era. What it was called really everyone was hiring hundreds of people. So recruiters were absolutely loving life. It really was the gold nature recruitment. Then we get to 23 and 24 where Matt stops and the music is turned off and then everyone's like oh god we've over hired here. We haven't got enough jobs or requirements just to fill here. We're going to have to downsize our teams and truthfully even since like that's 24 months or so. That's been quite a constant trend like we have customers that come up to renewal that were on a contract for say 30 users and now they're down to 15 or down to 10. People are having to get really really tight on how efficient they're being as a business and frankly because it's quite a most recruiters make money by doing placements throughout each month as they go along. If they aren't making them they're costing the business money they have to move them on quite quick so we're still seeing a lot of companies downsize. The actual people themselves I think again there's a bit of a flood back towards working in more central locations London especially is very much a hot center for recruitment. I think people are realizing that when you've really got a hunk of down and deliver and put up good numbers. Having everyone together in the office and driving that culture not a toxic culture but I'd say an intense one is like you have to do it otherwise you're really going to struggle. They're going to be wrong some of stay more remote for those that have moved out to the countryside and they're making things work that's completely fine but I'd say by and large we're seeing a push back towards being in busy city centres now because of the culture that it creates. Sure sure absolutely.
So from your perspective, in terms of your own business growth, you've seen, you know, obviously you've talked about having a big team, you've got different departments, how big is the organisation now, and what does that kind of look like? Sure. We've got 40 people in total across the whole business. Think about a quarter of those are in sales, about a quarter in dev. I think our customer success function is five people, if you include our team lead, we've then got a delivery function that is support and implementation combined that is, Carly, can we forget the shrong? I want to say it's six people going up to eight weeks, and then a few of finance and that have been involved, like that support and get as well. So quite quite even, so to put, I say across the whole company and the key departments that we need. So you're growing quite quickly and guessing that that hasn't been a straight line in terms of your overall hiring process. Yeah, I'd say it's been, I wouldn't even call it so much lumpy. It has been kind of spread out as the one we've needed, the resource normally based on when we'd like raise a funding round, we'd go out there and say, right, here are the roles that we need right now. Let's go and pick up these people to make sure we've got the capacity in this department. And then as time rolls on, we'll say we expect that we're going to need a couple more developers, another customer success manager, two more in support at that point. And those have been planned, just not needed at that exact moment. And so this bill will do it to be about 40 heads now. I think we've set up 40 heads for about six months or so. I don't anticipate we'll grow much more beyond this point for now because in the same way our clients are focused on trying to become more efficient. We're now looking at the same and saying, cool, we've got to get revenue to this point to become profitable. So how can we do that with that increasing headcount? Where can we make efficiency gains here? And that's where a lot of our focus is at the moment. Indeed. And taking you back to sort of the early days of the organisation. So you set up with your co-founder and you're both coming from a slightly different perspective. You mentioned that he was sort of in door to door sales. You've come from that kind of gaming developer background. So was it a match made in heaven? How did you find those kind of early days? Well, we came together because I remember in the set. So we both did computer games programme at University. He'd done his time in door to door sales for 18 months. We've come a team leader and then thought, you know what? I really want to learn to code. It's where he really felt a passion existed. And it was sure in our second year at university where he said, you know, well, we were on a conversation as a big group of us, what do you want to do? And people all like, I'd love to go and work at this company and work on co-reduce you. I'd love to go and work at this company up in the North and work on the next Grand Deaths Auto. And me and him sort of said to each other and everyone else in the room, like we'd really love to do our own things, we'd be fair and give it a go independently. And that's when we sort of started the conversation about should we try our own thing one day? So we did come back from our placement years and settled down to the year we started things up. And I'd say in the early days, it was basically very, very scrappy. It was a, it was two guys who had zero clue about how the world of business really, really worked trying to build a company. And there were so many errors that we made around what we prioritized in terms of product development, not getting out there and speaking to customers enough, like very classically, often say, when I go and talk at events, I've got the presentation saying, uh, then ways not to build a startup because we did so many things wrong, like hiring your friends and investing money in the wrong place and not speaking to customers and all these different things that we've been bumped up along the way and probably lost five years of progress. It could have saved it a bit more clued up before the start of things. We always worked really well because we were both very ambitious. I think both very very stubborn. If you ask our first employee, you still with us today, you'll say, are these to shout and fight all the time and I was like, it wasn't that bad was it? I certainly don't recall it that way. But if you're saying it is probably true, I think there's two very, very passionate people with very, very strong ideas come in together and try and make things happen. Sometimes does mean that, you know, heads get butted together. But over time, we've set up very comfortably into a role where under CEO who deals with everything that's not tech and really he's the guy who worries about making sure things like the service of our online and the product actually works. We found out lanes now, we both operate inside of very, very comfortably, but definitely took a few years at the start to iron out exactly where those lines were drawn. But tell me about the kind of lows that you guys experienced during that time. Many lows along the journey when I look back at it. There's probably three or four cases where the business could have died, but we kept things going. Number one was back at the end of 2016. We'd been going out for about 12, 18 months, making about 300 pound a month through various sort of bits of contract work that we've done and our university had funded us through incubator program there running. He was having to sleep in my bedroom floor two nights a week, for example. It was, it was the real, got a classic scrap of the early startup stories, which was good fun. And we got to was in 2016. It was a bit like, man, we've been going for 12 to 18 months. We're not really making money here. We haven't got any customers. We don't really know what we want our problems to be yet. We should be packing in. And then I think it was the next week we had an email from an investor at the blue and I was like, yeah, I have a conversation and quite naturally that ended up in then funding us six months later, which is really cool. So we thought, yeah, cool. We're funded now. Everything's going to be absolutely great. Only we went out and hired the wrong people for what we needed. Truthfully, hard. A lot of people that we knew personally, like someone had done 20 years in sales, for example, and thought, oh, they'll be amazing at this. They weren't really could have a B2B sales and never really used LinkedIn, for example. It was just the wrong people at the wrong time. Greater what they do, just not for what we needed them to do. And so we got to the end of 2017, had to let everyone go down to me and my co-founder. We were making two K-month in revenue. Had no cash left. And of that two K, three quarters was going towards paying our service. A bill and five hundred pounds going to my co-founder to pay his mortgage. So we could have easily jacked it in then. So forget about it. Let's go into industry get jobs because we need to earn some money here. And over the next year or so, we managed to build it up to about 10 K-month. They're recurring revenue through a couple of key partnerships. They're going to be able to do that. And so we're going to be able to do that. Otherwise, it would have been an onwards struggle to really get nowhere. And also now we're dealing with the wine back of that. And we're trying to work through another problem. But I look back at now and just think we're only because we were so stubborn and probably a little bit stupid naive that we're still going today. Otherwise, it would have been bound up years ago. So I wonder on that when you define your positioning and your target audience and you guys have really honed in on the recruitment industry. And what is your view on expanding that? What was the real rationale behind narrowing in on that particular industry? Honestly, because we built the business back to front, it's another one of my like 10 ways not to build a startup. One of the things that we did very wrong was we came up with the idea for a product and then tried to find a market to buy it. We thought this whole like competition management thing would run like a fantasy sports style thing was really cool. The earlier one else was doing it. And when we found out that Microsoft had acquired a completely exact the same thing a week prior when we came up with the idea we were like, oh, no, someone else has done it. And our mentor actually was like, that's not a bad thing. If Microsoft wanted to buy a company that does this, like get out there and do it. And so we did. But the big problem was we didn't speak to enough customers. We came up with the idea on our own. We figured out this would be a really cool way to do it. Like it'd be nice if they could do it as well. And Zed and just started building these things. We were certainly lucky that some of the ideas we came up with were really light bar market things like the TV display system. We built in like a weekend thought that'd be really cool to give it a go. Like I'd like that if I was in an office just to happen that clients did. But it certainly wasn't a well thought out well research well under the problem area we were going into. And so we happened to just sort of stumble into the recruitment industry and we were presenting at I think it was our account at the time like a war did they look at an entrepreneur thing where they got a bunch of startups that were their clients and put them in a room and had them pitch to all their clients essentially. And we were one of the top three in that pitch on that day. I found out the next day on Twitter when I saw them post about it that a recruitment company called PSR Solutions were in the room. The end of them on Twitter got through to the intern who happened to be sat right next to the direct to was really into the whole sports fancy sports style idea. Me and for a coffee and they became our first customer paying us like 400 a pan a month or something like that. I can't say it went particularly well for six months because a bunch of their direct to so many of them are like we wouldn't use this even if it was free. Which is real sting in thing to hear when like you're the founder that's put all this blood sweat and tears into making this thing work. And they eventually turned out as a customer they're now back with us which is great to know all these years on that they're now back in using us again. But it really was by accident we fell into that industry and then we thought well if these guys have got this problem and others currently have got it as well. And then I just went crazy on LinkedIn thing back before it became an automated hellhole messaging people saying hey we're a tech star stuff doing it's why and Z would you mind having a coffee to talk through it and from that side about 10 customers and that was how we thought cool. That's our space now we're staying in recruitment so we never left it ever since. That's quite the story and I really like what you were sort of saying about the fact you're very vulnerable when you're
you hear negative feedback about your kind of baby. - That's horrible, yeah. - Yeah, it is. And it was one of our past podcast guests, Rodrigo Malakias, talked about the fact that you should really fall in love with the problem that you're solving. - 100%. - Fall in love with. - Absolutely, absolutely. And I think that is so key because when you've got this amazing idea and you put hours and hours into the thought process, before you think then written a line of code and before you've done any kind of marketing or anything and then somebody shoots it down. It's painful, but the fact you've been taking that embraced it, been vulnerable and kind of leaned into it, I think is amazing. There's lots of other use cases out there where there's competitive sales teams where it's tough, it's hard work being a salesperson. - Absolutely. - Really hard work. And sometimes having this incentive can be the difference between having fun in your work environment. - Totally. We've had this conversation every year for probably the last eight years, truthfully. Do we go into a new market? Do we go into a new territory? Do we take the product somewhere else? People have said all on the journey like, "Oh, you know, you shouldn't be in the recruit and you should go and serve into this one instead." And honestly, the conversation happens every few months like it's endless. We've largely, or at least I've said no, we're gonna sit by our guns here and stick to what we know. But for a few reasons, if we look at say B2B so that's the space that we know well, and the same way you do by the sounds of it too, is it's a more expectant market. The product that you offer to that market tends to be a little bit more mature and needs to be more developed. It needs to be pretty, got in get, just especially amongst the C of AI-led products that you have out there today and that are popping up all the time. It's a very mature market. There's also more competitors that serve that space already, whereas because we know that there's a bit of a barrier to entering the recruitment space, namely through integrations with the systems that you need to get data out of for this to be effective. We know that that's a good barrier to sort of protect the moat that we've now built in that space. It's not saying we'll never go outside at the recruitment market and try and serve a different one. We've done research into the real estate industry. We've spoken to utilities companies. We've done all this work before. We just haven't seen a big enough opportunity to say, yeah, there's a market of a similar size available here to recruitment that we should go into. If we're gonna go somewhere, it's gonna be opening up a market that is five to 10 times bigger than the recruitment one. And gives us the ability to really take this towards eight because of revenue rather than the seven that we're at now. Totally makes sense. And I think once you really hone in and find great product market fit, that's really where you want to stay. And for a lot of companies out there when they're starting out, they have to go on that journey, just like you did, of really finding which problem are we solving and who are we solving it for? We're almost the biggest thing. You know, when I speak with my clients and other founders and CEOs, it's forget what you think you're building. Who is this really gonna help? And why? And once you figure that out, then you can align everything to what they need and start to build the product around their needs and tailor it to their needs. And on that side, when it comes to tailoring for that specific market, what's your approach on development of the product? How are you gathering feedback or suggestions on features and things like that? - Largely, I push that away to my VP of products, being honest. Adam is very, very good at taking fit ideas from me, from customers, from prospects, from different stakeholders, and selling out a lot of the noise, whereas I was kind of pulled towards the one that I personally thought was really cool. And that's the way that we built the products in the early days. He's very, very good these days at knowing what it is that we need to do. A large part of our movements today have been, okay, how can we better support larger customers? Because we've built the product before, when I coded it all those years ago, it wasn't really built for scale, it was built for 10, 20, 30 users, maybe, whereas now that we've got a client that is, for example, that's 700 users, it's like, right, this has now got us a port 700 users' data on a page at once. That is a lot of data to be able to put in one place and get it to work efficiently. So a lot of what he's had to focus on in the last, say, year is, one or grading functionality we've got to be able to compete with incumbents in the market. And but also being able to better scale and support more users on a platform instance for those that are of a larger size, so we can try and close more of those out. That's been his move and the know already now what we're trying to do is talk about what's the next step. Because we had our leisure team in Teendale Wednesday, and one thing that our BP sales put out in the room was like, you know, we're at three and a half of users today and we've kind of worked through most of our market already. Of course, we can go back around it again, timing is a thing, but how could we take ourselves from 350 clients to 3,500? How could we 10X this genuinely? And a lot of it, we honestly think, comes down to product differentiation. Like, what we do is good, is it like, oh my God, once you see it, you have to buy it because it's that like groundbreaking. It isn't being completely candid with you. I don't mind being honest about that. And so one thing that we've actually put me and James from our co-founder task on his saying, right, let's go and spin up what we call nine incubator. Let's go and just take some random ideas. And it's written on them really quickly. It hasn't got to be pretty. It can be cowboy code. Like, it's taking me three hours to spin up an MVP of a proof of concept that we've got, for example, as one thing internally. But we're now going out there and saying, what can we do to really innovate here and do something beyond, you know, even be in 10 or 20 cents better than what I'll compete at. It might be, how can we be 10X better? How can we be completely different? So we're now really trying to innovate and say, let's come up with something completely new. Something that our team can't really do, because it's too high risk or because it would require too much time and resource. What can we as founders mutt together? And I was saying yesterday, I think that's something that we have lost along the way a little bit as a journey is. As I'm trying to kind of force myself into the CEO role to lead a business, to be focused on strategy, to hire the right people, to look after cash and things like that. We lose what really got us into this in the first place, which is building really cool things. Like, our whole reason for getting into business was, sure, we're a little bit stubborn. But the main reason was we were really wanting to build cool things that we wanted to build. Like, not just building them for someone else and doing it in the area, don't like. We wanted to build products we were interested in and solve really cool problems. And so we're trying to get back to our roots as founders a little bit now, where innovation really comes online inside the business. We'll see what that yields. It's only literally been two or three days since we started doing this. But while we've got the sort of stable side of the product running along with Adam Leed in that, me and James are over here trying to think about, right, cool. What's something that if we started again on day one, say today was day one, what would we go out there and solve, what would we go and do with all the knowledge we've got? So that's the interesting conversation we're going through in products at the moment. Love that. And I think everybody talks about innovation, particularly when you start an organization. But the fact that you guys are actively sort of saying, oh, you know, we kind of got a bit lost because life happens because your heads down-- To focus on trying to build this professional business that just does its thing without really being innovative and reminding ourselves of our startup origins, like that's what we lost it on the way, I think, a little bit. And I think a few guys has almost a Phoenix. You've gone through that journey in the time that you've been sort of growing the business. You've had those moments where you've almost got to the burning stage if you're a Harry Potter fan. I don't know whether you are. I have-- I'm not going to be. But you have those burning days and of things that just seem like they're awful. And then you guys have emerged beautifully out of each of those challenges. The recruitment market-- it's been a tough few years. It's been-- That's right. --heyes and lows. And I know quite a lot of recruiters in my network are starting to see the light at the end of the tunnel, so to speak. And I hope that that means great guns for you guys and a great opportunity for you to take that growth. From a go-to market strategy, you've mentioned you've got a VP of sales who's leading the charge. What's been your approach from a sales and marketing perspective to really drive into the market? Outbound sales has been our dominant thing. Like you led NESTDR teams to know exactly what I mean with this. Like marketing in our market has been a very interesting one where it's not always the strongest path. We've found a lot of success in having an NESTDR team who are outbound in that market. And I think very regular year on year, about 75% of our revenue comes from outbound sales. And even during those down markets where things got tough and Chair and kind of became negative, it took over and reduced our revenue size. Whereas in 2021 and '22, it always grew because clients for expanding so much. We've still seen the amount that cold outbound sales brings in year on year. Just much as there are people out there and social media see it a lot. Oh, cold calling is dead. Like trust me, it's not used looking in the wrong places. --Yeah, I think that's a really interesting topic. I see that too. Lots of people saying, oh, cold calling is dead. But in actual fact, we're so. I think that we're so overwhelmed with digital messages. We have so much content thrown at us that the old school approach should actually picking up the phone and speaking to somebody. I think there's so much value in that. And actually, again, a previous podcast guest really talked about that face-to-face interaction, networking and really having those personal conversations. That's what's really driving sales. And it breaks through that noise. So I'm really glad that you guys are being successful with that outbound sales model and practicing what you preach. I'm guessing that you guys run your own incentives using your own. We do. We do. But it's funny because we're remote rights. So we've had to make tweaks. The products we've gone along to be able to support those companies that are more remote.
But if nothing else, that's just better fuel for the product, which is always great to see. Yeah, you're a great test case for that, aren't you? Absolutely. Brilliant. So, I guess my final question is really having been through the journey that you guys have been through and wow, what a journey you've been through so far. And I can see that there's so much in your future and the next sort of 12 to 18 months are going to be really interesting. I think everything's going to start picking up already seeing lots of roles out there and lots of people saying they're hiring. What advice would you give to any kind of startup founders or co-founders that are out there in terms of just some tips and tricks, really? Ooh, always against such a broad question and many, many answers you can give to it as well. And there's lots of advice I could say I could give if I was to pick a specific one out. Try your very best to get out there and understand what a great team looks like because I think no matter what team you hire, you'll always be convinced it's a great team. But no one really has a true understanding of what a great team is unless you've been in one, I think. Like I look over the years as to how we built a part of business and I can think that's like day one being like, yeah, this team's amazing. Even when realistically six months later, we were moving some of those people on and that's been a trend throughout the years where you're like, yeah, team's great right now and it's like a catch. There's one or two names on there that we should move on and we've had to go and go and do that. If you don't know what it is, go and ask someone like another founder, can I just come and sit in your office for a day if you really believe they've got a great coach from a great team. And just speak to people and understand what really makes an A player as well. I think having a definition of that in your own mind is great. Get it written down and see if that marries up the sort of analysis understanding of an A player because I appreciate it more now than ever at 40 people. Having a team that you just trust and when I say, I say this is my leisure team all the time. I say trust is a trust that you think they'll lie to you but someone that you can give something to and you just know it's going to be handled. You haven't got to check in. They'll do a great job with it. That is worth its weight in gold. So it's not always the flashier sales person or the person with the greatest CV that's going to do a wonderful job for you is people that you can trust that are going to do a good job. Do it on time. Do it to a high quality. Find as many people like that as you can, put them in any role you can find for them in your organisation and you will do well. I love that. I think in this day and age with people using a lot of AI to filter through CVs and again, I've got another podcast who is going out in the next week or so. Who will be talking about that value of hiring people because of who they are and what they can bring to the organisation versus what boxes do they tick so to speak. You know what we do that's a really fun hiring thing that I've done for years. I've seen your hires, people who are at a junior level, it doesn't matter. We get the CVs through, if I like the CV, I always email the matter as I say, I've recorded an 10 minute video for you telling you about me, the company and the role, please watch it. I want one back from you that's three to four minutes long telling me a little bit about you so I think you're passionate about on why you think you're right for the role. That immediately cuts out about 70% of applicants who aren't serious about the job. The ones who do come back with the video, it sounds brutal but you can lean out the ones who aren't really going to be a bit fused straight away. The ones who catch your interest a little bit are say something cool, you just like, yeah, I want to have a conversation with you. Back in the early days we used to say, would you go for a beer with this person? It's not really the way we are these days when we're in the organisation now I'd say, but I still can't carry that. Does this person get me excited? Would I be keen to see what they can produce and what they can do? Is there generally a spark here? They do something remarkable, or have they said something cool they've done? It shows they've got that little something about them. Those are the things that we always try and look for. I just find that doing that video screening early on, not being a robot about it, I always record a video first to say, look, I've done one for you for you to watch here so you know what we're all about. I find that's a really cool way, one to build a really good candidate process, but two, to make sure that you're getting really interesting people inside the organisation as well. I love that, really, really excellent. Thank you so much for being on the show. Derry, it's been a pleasure to speak to you today. Your journey is super exciting and I can't wait to catch up with you again. In probably about 12 months time, to see how the company has grown and the things that you've experienced. I appreciate it. Thank you, LeFold's coming back on. That's it for this episode of Tech Startup Stories. Have a story you'd like us to share or a topic you'd want to cover. Reach out and we'd love to hear from you. Until next time, take care.
Podcast Summary
Key Points:
Derry Holt, co-founder of One Up Sales, combines a background in video game development and commentary with sales software, initially creating automated sales competitions that evolved into a broader motivation and reporting platform.
The company targets recruitment agencies, shifting from office-based to hybrid/remote work post-COVID, with a current trend back toward in-office culture for energy and performance.
One Up Sales operates fully remotely with periodic in-person meetups (quarterly company-wide, bi-monthly departmental, annual European offsite) to maintain culture without daily commuting.
The recruitment industry experienced a boom in 2021-22, followed by downsizing in 2023-24 due to economic downturns, leading One Up Sales to focus on efficiency and profitability with a stable team of 4
Early struggles included near-failure in 2016-17 due to lack of customers and cash, saved by an investor and later by letting go of mismatched hires, building revenue to 10K/month through partnerships.
Co-founder dynamics involved initial clashes over roles, but they now operate in distinct lanes (CEO vs. tech-focused), learning from early mistakes like hiring friends and not prioritizing customer feedback.
Summary:
In this episode of Tech Startup Stories, host Natalie Bins interviews Derry Holt, co-founder of One Up Sales, a platform that automates sales competitions and motivation tools, primarily for recruitment agencies. Derry shares his unique background as a video game developer and commentator, which inspired the product’s gamified approach. The company evolved from a simple competition tool to a comprehensive system including reporting, TV displays, and automation, born from Derry’s desire to simplify manual sales incentives he experienced in his own sales leadership.
Derry discusses shifts in the recruitment industry post-COVID, noting a move from fully office-based to hybrid work, with a recent push back toward in-office culture for energy and performance. Despite economic downturns in 2023-24 causing client downsizing, One Up Sales remains focused on efficiency, maintaining a team of 40 with a fully remote setup but regular in-person meetups to preserve culture. The company’s growth was not linear; early struggles included near-collapse in 2016-17 due to lack of revenue and mismatched hires, saved by a timely investor and later partnerships. Derry highlights the importance of learning from mistakes, such as not speaking to customers early and hiring friends, and the evolution of his co-founder relationship from conflict to clear role division. The conversation underscores the resilience needed in startup life, with Derry’s stubbornness and adaptability key to survival.
FAQs
It's a podcast hosted by Natalie Bins that shares the challenging journeys of people building B2B tech startups from small startups to scale-ups.
Derry Holt is the co-founder of One Up Sales. He started as a video games developer and also works as a video games commentator, traveling the world for esports events.
One Up Sales automates sales competitions and motivation for teams, replacing manual spreadsheets and whiteboards, with features like reporting, TV displays, and integration with existing tools.
Before COVID, most clients were office-based; now about 50/50 are full-time in the office versus hybrid, with more flexibility for remote work, especially in recruitment agencies.
They hold company-wide meetups every three months in different UK cities, six-weekly department gatherings, and an annual week-long offsite in Europe to build human connections.
They nearly shut down in 2016 due to low revenue and no customers, then got funded but hired the wrong people, forcing layoffs by 2017. They survived by being stubborn and building recurring revenue to £10k/month.
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