The enduring and evolving ‘craft’ of customer support - Interview with Nick Francis

0:00So welcome to the next edition of the Punk CX podcast. We have today a returnee and we were just talking before we press record and it was back in September 2017 that Nick Francis was back on the podcast. So Nick, welcome back to the podcast I reckon. Thank you very much. You haven't aged a day Adrian. Oh, you're too kind. Too kind. And so Nick, can I actually just introduce yourself? Tell me a little bit about you and your background. And so just to fill people in that's listening to this, tell them about you and what you're about. Yeah, I've been an entrepreneur pretty much for as long as I can remember.

0:41And I've always had this fascination and curiosity around the customer experience. And so I was coding from a young age and really learned the craft and was enthralled by the early internet and started building things with my friends. And the first sort of big substantial entrepreneurial effort I ever had was HelpScout. So it's a customer support platform for small businesses. It's been around for 15 years now, and we have more than 12 ,000 customers all over the world. Still a booming company doing really great work. I'm really proud of what we built there. And at the end of 2025, so about five months ago, I stepped down as CEO, and I'm still chairman of the board.

1:27But yeah, it's, it's been an extraordinary journey and I'm, I'm excited to see what comes next. Awesome. Now you just basically stole my thunder a little bit. Cause I was about to kind of like say that, you know, according to my research that yourself, Jared and Danny started HelpSkite way back in 2011, which was actually coincidentally the same year I started this podcast, although it was under a different kind of like name. And it was on the same wavelength. Yeah. And so, as you say, 15 years on, you recently decided to step back from the position of CEO. Now, so I wanted to dive into a couple of things.

2:03First of all, your time as CEO. And secondly, about the whole customer service and support space. So if I may, let's kind of start with your time as CEO and also the stepping down. I mean, what's behind the change? You know, HelpScout's a big company now, at least by my standards. Okay. I think the next phase of growth for the business is less aligned with what I do best. I love zero to one and I love one to 10. And, you know, help scout is beyond those phases of the business. And so I think we came to that realization collectively as a board and said, look, I think the next person in this role or if we were to hire fresh for this role, we'd hire a different skill set.

2:47We would hire someone who spikes in different areas than I do. It's nothing personal. It's just like the way that things work as companies mature. And so over time, I came to that realization. I think it was hard because I still love the heck out of the company. And so that was just the right thing for me to do. I'm still involved. I'm leading the hiring process for a new CEO. We've been working on that for a few months. And at the same time, it's clear to me that I have unfinished business as an entrepreneur. and in my career more broadly. My career is not meant to be only about Help Scout. I'm really excited to kind of pursue.

3:27I've probably got one more company in me, and so I'm really excited to kind of think about what that looks like. Awesome. I mean, I must say I tip my hat to you for recognizing that it's the right time to step down because I know that many entrepreneurs struggle with that step that step because it's almost like it feels like letting go of the of the of the day-to-day and so making that transition i think is you know as you say it's it's possibly painful and a little bit uncomfortable and and takes a little bit of time but still had 15 solid years in the you know in the chair and so i wanted to think about or ask you about what are some of the biggest lessons that you learned along the way?

4:14And what are some of the biggest challenges that you faced in your tenure and how did you navigate them? Because, you know, there's a lot of people that listen in, I think, that are in that sort of space are either running kind of teams or running their own sort of like startups or scale-ups and things. And they'll probably benefit from some of the things that you've learned. Yeah, we could sit down and have a few pints over this one, couldn't we? I think we probably could, yeah. There's been a lot of learnings. I think, you know, one of the big sort of things that I've realized over the last several years is that, you know, that instinct, that gut that an entrepreneur possesses is really what, you know, what makes us do crazy things and start companies.

4:58But at the same time, those instincts can work against us. Sometimes, you know, as an entrepreneur, at least myself, speaking from my own experience, I was, you know, at different points, just too confident in my own instincts because you're so used to fighting against the status quo and kind of moving against the grain, so to speak, that, you know, it's hard to parse without just having more reps. It's hard to parse when you should go against the grain and use your instincts and when you should really rely on the data. Right. Even when it conflicts, particularly when it conflicts with your instinct.

5:36And so a good example of this is hiring. Right. Generally, every founder CEO thinks they are way better at hiring than they are. It's kind of like people in driving, right? Like every man particularly thinks they're a way better driver than they really are. Right. Right. And and I think it's really important as a CEO and as a as an entrepreneur to sort of come to that realization and learn to rely on the data. So I've become incredibly rigorous in the way that I run a hiring process because I actually I've trained myself not to trust my instincts for the most part. OK. Or at least, you know, that's one data point, my instinct.

6:16Right. There's a lot of other data points that that have to be considered. And so you learn some of those things the hard way over time. And given all of that sort of stuff, you talked about being very instinctual, trusting your gut and things. Has your perspective on leadership changed and evolved over the last 15 years? You know, I think that's an interesting thing to reflect upon because in many ways, I'd say like at a DNA level, my perspective on leadership hasn't changed. What I value has not changed whatsoever, but I've put in my 10 ,000 hours into the craft. I've put in the time to really work at being a leader.

7:03And now I can look back on 15 years of learning and say that I'm an entirely different person, even though my values haven't really changed. even though in some ways my leadership style hasn't devolved at all. And in some ways I'm a completely different person. I've just put in the time to really understand. And typically someone who's put 10 ,000 hours into a craft of some sort will tell you they feel like they know less about that craft than ever. It's like the more you progress as a leader, the more you realize that you don't know. Right. And I think that that probably makes sense. And it makes me think about it's almost like a sporting analogy where there are you know the sporting world is probably littered with examples of people that have have quote-unquote natural talent but actually the it's the as you say you use the word often but the craft is actually the training and the practice about how do you take that talent and think about how do you execute it the most appropriately in kind of any given kind of context.

8:15Is that fair? Yeah, absolutely. I think it's very similar to being an athlete. And so as a leader, I'm just a different and I bring different skills to a company now, given all that I've seen and experienced. Like, you know, I was a way better coder 15 years ago. What was Claude and all and vibe coding and stuff, you could probably get back to kind of like - Right. I am getting back, but I was spiking in different areas at that point. Now that I've put the time in really as a leader and I've worked with so many people, I've hired so many people, I've just had all the privilege of those experiences.

8:56I'm also energized by different things. Now, if you were able to, so let's say kind of like bill and ted's telephone box kind of like landed on your front loan and you were able to you're you would be able to teleport yourself kind of back to back 15 years to when you and jaron and denny were setting the company up and you were to be able to speak to your younger self what advice yeah would you give yourself you know i don't want to oversimplify this, but I would tell myself not to raise money. Okay. You know, I, I, uh, and it's, it's really not a, nothing against like, we, we've actually had great investors that help scout.

9:37I think it's just a path. I've, I've always been, you know, similar to you, Adrian, like sort of counterculture, sort of punk, right? Like sort of, uh, I, I really enjoy like the, like I was in the music business before this, right? Like I really enjoy like a great indie artist and what that, what that really like how that elevates the art. And I build software and products because of the, the, the craft and like the, the, the ability to be close to the customer. And like, I love small businesses. I, I just don't have it in my DNA to get excited about building a hundred million dollar plus business or a billion dollar plus business or whatever that might look like.

10:22Like if it happened by accident, then maybe. But, you know, I think threading the needle between building a company according to my values and raising money and sort of aligning those two goals and trying to like thread the needle between them and find the common ground. It's virtually impossible. And I think I did a pretty good job for 15 years of trying to thread that needle. But if I were to do it again, I would just simplify it. Right. And say, look, like maybe we raise that initial capital just so we can pay our bills and kind of get the product launched. But we didn't need, you know, every time we raised institutional capital, we were actually, we were profitable.

11:06We didn't actually have to do it. Okay. And if I were to look back and just give myself some really simple advice, it'd be just don't take the money. The incentives are not always going to be aligned. And it's not really worth it. the trade-off, the growth trade-off is not worth it. Right. Yeah, I think that's sound advice. I mean, as you say, it's very counter to some of the path that many startups in this space are on right now. And I think it's probably further complicated with the advent of this AI era that we're in where the cost of infrastructure and computing and everything else is just kind of like ramped up and expectations are ramped up.

11:48So that makes it kind of, I guess, possibly more complicated. This hype cycle is really interesting to me because it's just from a startup lens, because companies are raising unbelievable amounts of money at this time. But I think that we're at a point in the hype cycle where that's actually pretty normal. If you look at previous hype cycles before, what I actually think we're going to see on the other side of this is a renaissance in bootstrap companies. Okay. Right. Right. I think bootstrapping is going to become much more the norm and VC much more the exception, which is really what it was intended to be.

12:27VC was not meant to be what every startup founder does. That's just step one is raise a bunch of money. That's not actually meant to be the default. It's meant to be for the people who are, who are, who are laying like groundbreaking technology before consumers, you know, like it's meant for those foundation model creators. It's not necessarily meant for people that are building on top of those models. And the truth is when you've got these incredible tools now available to you, it just doesn't make sense to hire tens of, or to raise tens of millions of dollars when you can just go build with a couple of teammates and get really far on your own.

13:06so let's move away from your time as kind of CEO and actually because because this is the the bread and butter of the of the podcast and and talk about the whole customer service and support and experience sort of like space and you've used the word a number of times because when you first on the kind of podcast you talked about the craft of customer support and and it's a word you've often i mean do you still think great support is a craft a hundred percent and that's you know when i said that i i don't i wouldn't say my values have changed as a leader i think that's a good example you know whether no matter what it is like i as a leader am energized by the craft by excellence right and most definitely people in that that do customer support on a daily basis are being asked more of themselves than they ever have been.

14:05And I think in a world where, let's say, there is tooling that really helps with the Tier 1 and even the Tier 2 customer support, then we're going to be asking our people to really elevate their craft in, I think, extraordinary and valuable ways. And I genuinely think talking to customers is always going to be important. I don't care what AI does. Talking with customers, spending time with them, being able to kind of feel what they're feeling, to sense the ocean, that can't be bottled up by an AI. You really have to be able to sense that for yourself. And so the craft of working with customers is still incredibly important and I think will continue to be for the foreseeable future.

14:54I think I remember talking to you about that back in 2017, and I really liked the idea. I mean, just because, I guess, linguistically and philosophically, the idea of the job you're doing being craftful, as it were, is that there's levels to it. and it embodies more than just you know time and experience and the kind of tools that you use because it's i think about it with great craftspeople there or like or great chefs or great artists can probably produce exceptional things with minimal amounts of ingredients so no amount of extra stuff isn't necessarily going to make you a great artist or a great chef or a great support person because actually it's how you bring them all those things together that's the craft right and includes how do you develop yourself and so i really liked that sort of idea i also like the idea that because you really lent into the idea of highlighting salaries and growth and salaries and career paths and all these different things back and kind of helps go and And I think it was championing kind of that, championing that sort of topic was very fresh and very welcome because it's essential work as far as I'm concerned.

16:18You know, I think that transition is still pretty similar, meaning, you know, we're continuing to elevate the value that customer support folks can have in an organization. Because, yeah, some of the stuff that actually customer support people don't even like doing, some of the, you know, the repetitive sort of work is going to be taken off our plate so we can really focus on the highest value. I mean, this is a slightly off script sort of question, because let's get your view on this. There's two perspectives. One is that we're talking about automating a lot of the simple stuff with some of this new technology.

16:59And that, in principle, is great. But there's a reality that many support agents used to go to simple support queries as a way of almost reducing the intensity between kind of like high kind of say calls or interactions that required a high cognitive kind of like load so if you remove all that simple stuff then it creates possibly other sort of problems that you're almost expecting people to perform at a high level all of the time rather than kind of like dipping in dipping out do you see that as an emerging kind of problem or how are companies responding to that or should they be responding to that yeah there are a couple of things that are really that we're going to have to that customer support leaders are going to have to be paying attention to so for instance if you have a chatbot that's basically let's just say it's resolving all of your tier one level customer support well that tier one support is going to be is that is actually needed in order for you to build a better product Like in that tier one bucket are going to be bugs that you should probably fix, you know, typos that are just little like little niggles throughout the experience that need to be smoothed over.

18:21Right. And so you want to ensure that one of the words that I find most detestable in this realm is deflection. Yeah. In a world of true deflection of the tier one customer support, that is going to be incredibly harmful to the business in the long term. No doubt. But being able to, what I like to do is center around, which is the same thing we've always done, which is center around what's the best customer experience here? What's the highest quality customer experience that we can bring to bear to get the customer unblocked? And in a lot of cases, in the tier one case, like if I can unblock a customer and they can get moving in my product without having to wait for a 24 hour response or whatever, I would love to do that.

19:13But behind the scenes, there needs to be a feedback loop that, hey, so-and-so ran into this challenge and it needs to be resolved. Now, there will actually be agents, because this isn't just happening in customer support. There will be an agent that will pick that up, go log a bug in Lanier, and go create a PR to fix that bug without any human intervention whatsoever. Right. But there needs to be a feedback loop in the organization to take all of that in. It's not actually meant to be deflected. Yes. It's meant to be instructive in terms of how your product can be better. And so how do you kind of like see, I mean, as you say, we're in this hype cycle, but it's undoubted that the technology around us is, particularly the AI power technology around us is evolving rapidly and its capabilities are incredible in many respects and the potential is huge.

20:09So how do you see sort of support evolving in the coming years? I mean, yes, there's people will elevate to deal with more complex, more complicated sort of things. But how do you also see it evolving as particularly in that sort of craft realm? In a few ways. You know, one, I think that the initial wave, which was scary for everybody in customer support, which was this like customer facing chatbot that can answer all the questions that it's going to eliminate all these jobs. I think most people in customer support now know that I haven't seen many jobs eliminated as a result of these tools. And they will get better, but there's this whole feedback loop to manage.

20:49And so there's still a lot of work to be done. But I think those tools are going to continue to get better, and they're going to unlock new kind of roles and responsibilities within the customer support team that are just higher value. But I think that's one piece of it. Another thing that I've noticed that I find the same in coding, for instance, is the time to onboard somebody to the team is radically faster. Right. Right. Because I can actually open up a conversation or like having the whole company do support, which we still do at HelpScout. Like, man, people were getting lost in our queue, but now they show up in the queue and they're like, hey, can you draft a response for me?

21:35and AI will draft a response. And that really gives them a way to add value, learn more about the product, determine if that drafted response is factually correct. You know, there's a lot of additional steps that they can take and they're learning about the product as they go. And so onboarding new employees has been so fun or just being able to like dip into the queue and be helpful. The barrier to entry there is much lower. And I find that to be really exciting. You know, the whole concept of whole company support and getting everybody into the queue is actually more approachable now than it was thanks to these tools.

22:14But just generally, I love the framing and it's probably not a surprise to you, but I love the framing. Like we're sort of preoccupied in this initial phase of AI tools. We're preoccupied with like how it just like improves productivity. The framing of like, oh, you can do more in less time. Yeah, to some extent you can, but I don't think that's actually the promise of these tools. The promise of these tools is that you can actually craft better. Yes. You can actually create better output, whether you're creating a slide deck or whether you're writing a post for LinkedIn or whether you're sending a response to a customer or whether you're processing feedback from a user test.

22:59AI is meant to help you do better work at the end of the day. That's certainly how it's impacted me. I'm much more excited about that framing because that framing creates value. It doesn't take away jobs. It actually creates value for the business that everybody can see and feel on a daily basis, which is really exciting. Yeah, no, absolutely. And I think the thing is that you have to make it make sense for you as well. and so you you know it's that that's the thing i don't i know that i've been a do i use it yes i use it in in particular bits but i'm very conscious about where i use it and how i use it because there's certain things around i feel like my craft i'm like i'm not giving that up i'm not giving that up i'm not giving that up because these are things i value but there's things here that i'll accelerate through the use of these tools because it just helps in that that productivity bit that But without a doubt, what we've seen over the last two, three years is this explosion of tools and options and things.

24:02And what I also find is that I find that many service and experience leaders almost get lost in the fog because there's so much choice. choice and so there's somebody who is recently a ceo but now chairman of the board and founder of the of of a support technology firm what sort of advice would you give to leaders in this space when it comes to sort of choosing and technology navigating that sort of technological sort of space because there's like a lot of promise and a lot of fireworks yeah and then there's but there's this incredible amount of choice and sometimes working your way through that sort of uh And that landscape can be challenging.

24:45The fog can be very challenging and add to it that leaders in these companies are facing top-down mandates to use more AI, do more with less. You know, we want to cut costs, but we don't want to actually cut the experience at all. And that's a virtually impossible task, at least at the moment, as far as I can tell. And so, you know, what I think is really important in terms of, you know, managing this fog and finding the signal is going back to first principles and saying, like, what do we really, truly want to be about here? Like, what are we, what's the, what's the problem that we're trying to solve?

25:27Has the problem we're trying to solve changed or evolved in some way? I don't think that it has. I think the problem we're trying to solve is actually the same. It's just the tools that we use to solve that problem are different and they're evolving at a very fast pace. You know, for instance, at Help Scout, we would say, look, we want, you know, our first principle focus is we want to deliver the best possible customer experience that we can. When somebody has to engage with support, we are optimizing for what we believe is the highest quality experience, not the cheapest, not the fastest, the highest quality.

26:05And so at some cases, that means a chatbot facing thing that will get you unlocked and get you like the percentage of customers who now use our chatbot tool in the onboarding process to get through just the basics of learning the tool is astounding. And that's a win for everybody. That's a better experience for the customer. And it's great that our customer support team doesn't have to answer the same onboarding questions 52 times a day. Yes, yes. So really, and I would encourage folks to write those down and say, look, do we agree that this is the problem that we solve? And these are the principles with which we want to adhere to in order to solve that problem.

26:46Everything else is fog. Like, let's, if we have agreement in the organization, this is how we want to operate. then you can really start to evaluate tools and changes to your process and all of those things through a very opinionated lens yeah i mean i think i i completely agree with that it's that old kind of idea sort of start with the end in mind that's right you know because i see people falling into the trap of like they buy something and it's a bit like buying a tool or a spanner or a screwdriver and then trying to find something to to tighten you know rather than going okay rather than actually kind of like embracing the idea like what game are we in the game are we that we're in is to deliver great service or deliver a great experience to our customers and therefore what does that look like let's describe what that looks like and then figure out where we are and then where we need to be and work a path towards that and that will inform your your tool sort of selection well and keep in mind a big piece of the fog it's it's worth just being honest with yourself.

27:48A big piece of the fog is your own fear, uncertainty, and doubt. Right? And so you have to be able to acknowledge and name the fact that, hey, this stuff scares the shit out of me. And I have no idea what anybody's talking about. Right. I'm really worried about what this means for my team and what this means for me and my livelihood. And it's really important to name that those feelings are real, but they can't cloud your judgment unless they're part of sort of the problem statement that you're trying to solve and the first principles with which you're going to adhere to. And so I think a lot of that fog is, believe it or not, just self-manifested.

28:30And we have to be really careful about that and be open to new and better ways of doing our job. That is actually the job. Yeah, it's like, what is it? There's an old thing that says, fear stands for false expectations appearing real. There you go. Like we live in an ever-changing world and we got to, these tools can do some really beautiful things. But we got to be open to learning from them. Yeah, I think we have to kind of put ourselves into it and then, and, and realize that, well, they are, but tools that help us achieve things. And then we have to, but we have to, we have to take ownership of what it is that we want to achieve.

29:15And then all the things that, that, that, that, that are the right sort of inputs in that and the right sort of like, um, kind of like things to be considered in that kind of that, in that journey. But what I was going to say, I was going to ask you on, as we're kind of starting to wrap up, I mean, you're deeply, still deeply immersed in this sort of like space. What are some of the trends or things you're expecting to see emerge in the next sort of 12 months in this sort of space that we should be looking out for? Yeah. So I think phase one was, you know, a, a, a, cause remember like there was a world of chatbots when we first met in 2017, there were chatbots.

29:52They were just God awful, terrible. Nobody trusted them. They were really bad experience for everybody. It was just too early. The technology wasn't there. I think we're, you know, whether conscious or unconscious, I think that we're, you know, in this first phase entering a world where people can actually use these chatbots, get a great experience, get answers to their questions. And as consumers start to trust that these tools are there to help us and they can actually be helpful. Like I personally am much more willing and eager to engage with a chatbot today than I was many years ago, just because the tooling is so much better now.

30:31And so that's sort of phase one. I think phase two is these tools, same sort of tooling on the backend, but maybe it's not a chatbot. Like maybe the tooling is, is, is helping or even leading in terms of some of the tier two support. So, you know, people use the word agent a lot, but this concept is real that there's going to be an AI agent that will evaluate every incoming support ticket and triage it for you. And so I think that sort of phase two is letting these tools do their magic at the tier two level and seeing the impact of that, which can also be like much better for the customer at the end of the day.