A Fireside Chat with the CEO and Co-Founder of TestBox

A Fireside Chat with the CEO and Co-Founder of TestBox
By Pedals | On Sep 29, 2021
10 min read
In this article:

Recently, TestBox CEO and Co-Founder, Sam Senior, had the chance to join Jim Coleman on the Fuse Show for a fireside chat. Jim is the co-founder of xFusion.io, a company that’s helping startups scale by growing and leading teams that provide top-tier customer support, back-office support, and customer success.

Read on to see what Sam and Jim discussed:

  • Why we’re building TestBox and how it all works
  • Future ideas and use cases for TestBox (such as for training or direct sales) 
  • Sam’s role at the company, as CEO and Co-Founder, and the biggest challenges he is tackling today
  • Why it’s so important to build a culture that puts wellness and DEIB at the forefront from day one here at TestBox 
  • How we’re thinking about TestBox’s brand and reputation
  • Sam’s role models and the importance of therapy for everyone 

Also stay tuned over the next few weeks, when we’ll be sharing a post that we co-authored with Jim and his team.  

Fireside Chat

Jim Coleman: Welcome back to the Fuse Show everybody. I'm joined today by my guest, my local guest Sam Senior of TestBox. Sam is from a small town in regional Australia, but always knew he wanted to build a tech company since he was eight years old. I'm looking forward to actually talking about that. Sam found his way to San Francisco by way of London, with Bain & Company, advising on software GTM and product strategy. Over time, he clearly identified a gap in the market and is now the CEO and co-founder of TestBox, which is a startup that's redesigning how software is bought, making it truly Customer-led. Nowadays he lives in Boulder and is always out there riding bikes, trail running and marveling at the beautiful incredible landscape. Hey, thanks for joining us on the show.

Sam Senior: Thanks so much, Jim. I really appreciate it.

Jim Coleman: All right. Let's get this kicked off. We met for drinks a few weeks ago and it was one of my first post COVID outings here locally. It was so awesome to meet you in person and actually get to enjoy that experience in real life.

Sam Senior: Yeah, it was fantastic for me. It was all similar. I hadn't yet met anyone out in Boulder physically to do anything like that. So it was nice to meet someone who's trying to do something similar in many ways.

Jim Coleman: Awesome. Obviously you and I spoke about TestBox and how it works, but if you wouldn't mind going into the details on what you guys do and the problem it solves.

Sam Senior: Yeah, absolutely. Buying enterprise software is a famously frustrating process. Often it is in the hands of the sales rep, takes a really long time and people find it challenging to do things using their own process or in a time period that works for them. What we identified over many years was actually that there needs to be a way to self-serve buying software in a way that enables you to have a hands-on experience, test and compare different options side-by-side, and collaborate with your team to make the right decision quickly and effectively. Essentially, what we’ve built is a way for people to come into our TestBox environment, be able to load in the various pieces of software that they're looking to compare, and do a side-by-side comparison of each of the use cases with AI generated data in there. It looks and feels like their environment, so they can make a decision around what truly is going to meet their company's needs rather than basing a decision on pitches, sales demos, slides or whatever it is from all the various vendors. It's all about the hands-on testing experience.

Jim Coleman: It's such a ridiculously good idea. It's one of those ideas that I'm just surprised hasn't come along years ago. I mean, it just absolutely makes sense. I mean, not that we don't all love sitting through an hour demo.

Sam Senior: Oh, my favorite. I'd love to do it every day of the week.

Jim Coleman: Five different companies. On that note, how does it work? I mean, so you have a client come on, they test several softwares shipped by several different companies. Do they then still go through that demo process or, I mean, is it possible for them to bypass that?

Sam Senior: Yeah. So you have the ability to bypass the whole thing. We enable you to go from discovery through to finalizing the deal. Our most recent user came onto TestBox, they started using it... It took them two and a half weeks to go from knowing really nothing about the various solutions to saying they wanted to buy Zendesk. They actually bought ten new licenses of Zendesk. Usually it takes quite a few months to go through the whole process to make the decision, but two and a half weeks! And then we just connected them with the account executive at Zendesk, they finalized pricing and were good to go. So super easy.

Jim Coleman: And there is no cost to your client?

Sam Senior: Totally free to the end user to use TestBox. The way we monetize is through vendor partnerships. There are a few other ways we're going to be monetizing in the future, but today our vendor partnerships pass roughly about the same, no matter which vendor you end up buying through. We have no reason to push you towards one vendor versus another, making us truly agnostic, which is fundamental to the platform we're building. We just want to help people have as little friction as possible to find the right platform for their company.

Jim Coleman: Yeah. As part of your sales material or process, do you tell them that they get to skip all of these demos?

Sam Senior: Yeah. The first line on our website is comparing, testing enterprise software, no more sales pitches and demos...something like that. So yes, it's very much all about that.

Jim Coleman: Oh, I see it right here. Comparing, testing customer support software, no more slides, sales pitches, demos, and unfulfilled promises. That is so solid.

Sam Senior: And so you mentioned that it's customer support software. That's very much our initial niche that we're focusing on. So I mentioned Zendesk just before. The goal is very much for this to be a broader marketplace for most of the major enterprise software that you're thinking about buying in really any company. But we are focused specifically on one so that we have a niche where we can build out our platform effectively and have a repeatable model when it comes to our go-to-market, before we think about expanding into other verticals. So if we don't have the software that you want right now on TestBox, it will come. Just give us a little bit of time.

Jim Coleman: That's awesome. So this recent user that ended up signing up for ten seats on Zendesk, did they actually go in and kind of simulate the Zendesk environment as if they had ten seats? I mean, I'm just curious if you could kind of walk me through what that looks like for that person.

Sam Senior: Basically when we create the instance for them in the TestBox app, you have the opportunity to test a few different options side-by-side. We ingest it with a bunch of AI generated data. In this case it was a B2B SaaS company. We had a bunch of data that resembles ticket data for a support platform. So it looks and feels like all the conversations have happened. There's hundreds of tickets over a period of time so you can see your reporting and that sort of thing. They come into the platform, that's all generated for them. All of the most important use cases are pre-configured. Think how ticket routing might work, ticket automations or live chat, service level agreements, those sorts of things, all totally pre-configured as well across each of the platforms. You can click for one use case in one platform, see how it works with that data.

We have a guided walkthrough for you to learn about that particular software. You can then flick to another piece of software and do exactly the same use case and see what you like and what you don't like. And as you're going, you actually input feedback on how directly did it meet our needs? How easy was it to use? Why was that? And just some free text and you start to build out what we call a notebook or report card potentially for people, where they can basically see all the scores and everything that they have for each of the use cases, across each of the vendors to really identify what is the right one for their needs. This particular user did all of those things, which was really fantastic. And they also invited a number of their team members. So we were originally talking to someone very senior in the organization, and then they invited a few of their direct reports and they started using the platform to do that testing back and forth. And they generated that report card together to make that decision.

Jim Coleman: That's amazing. I just had a thought and I wonder if the platform could work for this purpose. So we hire a lot of customer support people, and we have a very thorough vetting process, initial training process, etc. But still on occasion, there are situations where the agent goes and is working for a client and they just don't work out. So if we could simulate a test environment where there's data coming in, there's maybe even AI generated live chats where we can kind of evaluate the prospective agents in the wild, as part of the training sequence before they're client facing. I mean, we would absolutely pay for something like that. It'd be very, very useful. I don't know if you've thought through something like that.

Sam Senior: It's fascinating that you bring that up. It's not something that I had been thinking about up until a month ago, when we actually had two very large public tech companies reach out to us and say, "Could you help us with the learning and development platform essentially? We're onboarding so many new support agents right now, we don't want to put them in a production environment. Could you basically replicate our production environment, start seeding it with data, and then we could just add these people in and out of it?" And I think it's super interesting, very compelling. I love that you brought it up as well. We now have three fairly good data points on this but we haven't actively asked anyone about it yet, to be honest. I think this is something that we're thinking about. It's not a near term roadmap piece for us, but it's certainly an interesting avenue.

I think support is very particular in that you're training people to use it in a production environment. Something like cybersecurity is probably very similar, but your tools like marketing automation or maybe your HR ATS system, for instance, they probably don't need a learning and development platform. So I think it's going to be an interesting strategic decision for us as we go further down this road and we develop out our core platform more, as to whether this is an additional vertical for us, but we've had some interested parties. So it's one that I'm starting to think more about than I was ever expecting to, which is very cool.

Jim Coleman: It is cool. Sam, one of the fun things about startups is you just never know what's next. I'm curious, from a product perspective, if you suddenly want to do this next week, is the product ready for that? Would you just have to sort of make some minor tweaks to get it workable for that use case? Or would it be quite a big build?

Sam Senior: So one thing that we do today is we basically build out a full environment then we pull out the configuration of it, and then we replicate that using the API and all this sort of thing. Today that probably takes weeks, not months. So it's probably less than a month. So yes is the short answer. We're doing something like it. We probably have to do some other things. I think at most it probably would be a couple of months to build the most MVP version of this for someone... A couple of months with two engineers working on this. So not a big team. We could obviously ship that quickly. We would want a really nice onboarding portal and ways to monitor and all of these extra bits and pieces, but that very first version yeah, I think that’s a couple of months of work with a couple of engineers.

Jim Coleman: That could be a really big deal. I'm just telling you in our organization, that would be incredibly useful.

Sam Senior: I don't know if you want to get into this now, but how would you... This is a good user interview. When it comes to value, what is sort of the value of that to you? Because obviously there's the value of making someone more successful in the job, avoiding putting someone into a production environment where they maybe don't do well, avoiding a bad hire, all of these sorts of issues. Obviously there's a lot of risk mitigation here. How much is that worth to you on a per user basis?

Jim Coleman: A good amount. I would need to think through an actual number of that, but it's reputation management. From our perspective, we outsource customer support agencies and we provide a very high level of customer experience. It's a huge priority for us. Think like Chick-fil-A of the outsourcing world, Southwest Airlines, where we're providing this level of service and it hurts us reputationally when we do our very best to vet somebody, they go through our internal training and we put them on a client account and just sometimes it doesn't work out. That's a rare situation, but occasionally it just doesn't. So that can damage our reputation, which is something we have to be very careful with. And if we had an environment where we could provide more training to them and more evaluation, that would be very valuable for us.

Sam Senior: How perfectly replicated of your core environment would it need to be? Like what level of fidelity?

Jim Coleman: Not even. That's the thing – because we serve multiple different clients on different platforms and with different types of businesses, generally in the SaaS world, with different types of businesses, we just need something that would be, in fact, it could be the same each time. And I can imagine a situation like our use case may be a little bit different, but I mean TaskUs is one of the largest outsource companies, one of the larger ones and they're like 28,000 employees. I mean something just astronomical. But I can imagine if you had a contract with a fairly large tech company that maybe had 2000-3000 agents, it would be worth your while to build out an environment that was very, very similar to their actual real-world environment where there's... I don't know how this would work from a technical perspective, but where the questions are similar to the ones that are actually asked, but in our case, it can be quite generic. We're just monitoring for performance, quality of writing, tone, empathy, structure, etc., in a live environment or assimilation environment.

Sam Senior: So I think what we would do is basically in whether it be a large tech company or your situation, we would basically take a subsegment of what your most common types of questions are. And then we would run it through an AI engine that would then start to generate conversations on priority levels and this sort of thing. And that you could then have all that synthetic data set up and we could pump in whether it's fifteen tickets for this agent or whether it's 200 tickets and whether you need to simulate some of that thing, live chat or whatever it is, that would be relatively feasible.

Jim Coleman: Yeah. Yeah. And when I mentioned reputationally from our side, it would be reputation towards our clients, but imagine large companies, it's a matter of their reputation to their customers, right? If you send somebody out into the wild and they don't do a good job, that costs reputation points through each interaction...

Sam Senior: How long do you think you would want someone in this sort of environment for?

Jim Coleman: In our situation two weeks to a month. I mean, I think it depends on the complexity, but enough time to fairly evaluate them. I think we'd have to just kind of see how that goes, but enough time to build more trust and give them a fair evaluation.

Sam Senior: And then would you essentially want to have a manager or something associated with the account and then every day, every couple of days they basically go review the tickets to see how the conversation has gone?

Jim Coleman: Exactly. Yeah. Which is exactly what we do in a live sort of environment. But at the point that we're client-facing the stakes are higher.

Sam Senior: Yeah totally.

Jim Coleman: And we still do things like draft mode, etc. where they're not sending out live responses, but it's still in our client's actual inbox. You still have that potential for reputational damage. And like I said, this doesn't happen frequently, but when it does, it's just rather embarrassing. It's something that we would like to avoid if at all possible.

Sam Senior: Yeah, interesting. We should talk more about this.

Jim Coleman: Yeah it'd be pretty cool. You could look at it from an SDR perspective too. I mean, you could create a situation where they're crafting outbound personalized emails and then just actually having a back and forth conversation with AI generated content assuming it's good enough to replicate kind of a real world scenario.

Sam Senior: I think it's pretty good. So far from what we're seeing our results are pretty good on the AI stuff. I read it and I would say the first version of it, 85 to 90% of the time reads really, really well. And then you see some very rogue things coming to the AI, and you're like, this doesn't make any sense whatsoever, but honestly, 80 to 90% hit rate is pretty good for something that we can go through and vet.

Jim Coleman: Yeah, I agree. So certainly back to TestBox, what is your role at the company?

Sam Senior: So I'm the CEO and co-founder. We're still a relatively small company with 10 people at the moment and we're still hiring, we're looking to hire phenomenal engineers, product managers, basically really, really focused on the product. In terms of my day to day, for a while it's really been thinking about converting my product vision into day-to-day product results whether that be working with our product designer and helping her think through prioritizing based on user feedback and all that sort of thing, whatever we're trying to build which I do a lot of. I spend a lot of time with users. Every week we have user councils and do a lot of asking questions, listening, and getting feedback, just understanding how to make the product better. And then recently I've been doing a lot of work with thinking through two major things, one around just internally our culture, how we work effectively in a distributed team and what are the traditions that we want to put in place now so that they continue forward into the future? How do we make sure that we're building diversity, equity and inclusion into the way that we work? Those sorts of things are a really big focus for me. And then lately it's been a lot of building new partnerships with new vendors to come onto the TestBox platform.

Jim Coleman: And from a co-founder perspective, you have how many co-founders?

Sam Senior: Just myself and Peter, so two of us.

Jim Coleman: Okay, now you and Peter knew each other from the past right?

Sam Senior: Yeah. We've known each other for thirteen years. We actually met in our first year of our software engineering degrees when we were studying in Australia and within, I think it was like a few months after we met, he actually moved into my apartment. We were living together. We lived in multiple cities around Australia together. We worked together. I convinced him to move to San Francisco about three and a half four years ago. And I was like, "Hey," we both knew eventually we were going to start something together one day. It just depended on when and how. And so that was kind of prepping him for that. We were both like cool, come closer. It'll help us where we need to do this thing eventually. So yeah, we've known each other for a very long time.

Jim Coleman: So do you guys delineate your responsibility as your areas of responsibility? I mean, how do you handle the day-to-day-

Sam Senior: Yeah, absolutely. So he's the CTO. Despite us both having software engineering degrees, he's actually a very good software engineer. I kind of let that fall to the side relatively early on when I realized I really liked thinking about vision and strategy and all those sorts of things that really excite me. And he's really good at turning that into code and making it happen. And so he primarily thinks about engineering roadmap and working day-to-day with our engineering team, whereas I will tackle everything else.

Jim Coleman: That's great. Before you go too far, I want to circle back to culture and that was on my list of things to talk about. I read some press coverage on TestBox. And one of the things that you said is you want to build a company versus a startup and specifically talking about kind of the long game with developing culture. So would you speak to that?

Sam Senior: Yeah, the reason I said that is that so often people say whether it's friends, whether they're generalists, whoever it is will say, "Oh, you're building a startup. Great. Tell me about your startup." I think that has some connotations to it, of like this is something that's maybe potentially just going to run really hot and burn and crash and the whole thing falls apart. That is absolutely not my goal. The goal is to build a long lasting company so that in ten years time it's still running. We still have a team. We are still being successful and growing, but we've created stability for our employees and all of that sort of thing. And that is really important to me. 

And so to do that right now, we have to have this balance between things where we want to move really fast, areas where we feel comfortable having issues, knowing things will break and get fixed, and all that...having focus on where we just need to be fundamentally building right now. I think you can do all the getting-stuff-wrong with pieces of the product, and that's great. You can get things wrong with users, get feedback, fix it.

It's much harder to be doing that when it comes to culture and the values that you have. Because otherwise you put something out there, you'll try it, you pull it out, you try something else, you pull it out. And it actually starts to throw people from side to side all the time. It's better to have the perspective of here's the goal, we'll test things along the way to continue to improve culture and we'll continue to adapt to it. But having a clear perspective on how you want to be, how you want to act as a company is really important early on, because if you don't establish it today, even when you're at 20 people, suddenly the culture is out of your hands and is starting to disappear. Let alone when you're at 100 people, 500 people, whatever it is.

So we need to establish that now as early as possible, and a big part of that is thinking through how do we build DEIB into our company already? And that's frankly a really big challenge. It requires a lot of thought. It requires a lot of time and investment that most startups don't have. And so it's important to have that longterm game in mind to have the patience to focus on those sorts of things today.

Jim Coleman: Yeah, absolutely. Have you met Andrew Holliday? He's local in Boulder as well.

Sam Senior: I haven't.

Jim Coleman: Special Sauce Branding, great guy. He should definitely be on your list of people to meet. I had an in-person with him a little while back, which was awesome, but he works a lot on branding culture, etc. He talks about a company's brand being really just the reputation, the reputation of the company. And I kind of like, I don't know for whatever reason, it's pretty obvious... It resonated with me and thinking of how we build our reputation as individuals and how we can correlate that to the way we do so as a company and the way we treat people, etc. What's been really, really interesting to me...as I would say our number one focus at our business is to grow leaders ultimately, to build up leaders. And that just takes time and iterations. But I feel like I get proud dad when I see one of our up and coming leaders on a call that was recorded or whatever and I hear him or her talk about our values and missions. It just is automatic and I'm like, "Oh, I'm so proud. I just love that." It's like you start to see some of the fruits of your labor. But do you see it that way too, in terms of like your brand being really just your reputation?

Sam Senior: I'm not sure I entirely agree. I think about brand being how do you make people feel when they think of your company when it comes to, like for instance, is TestBox really easy to use? Does it make me successful? I think about functionality when it’s brand. And then when I think about reputation, it's, like, is this a company that cares about its employees, that cares about the world and wants to find ways to make the world successful? I personally think of them as different. Maybe that's not the right way. Maybe I should be merging them together. But I think of a brand as functional, features; reputation more as how we exist, how we treat people, our culture, who we are and if people respect that.

Jim Coleman: Yeah. I think the point is that it is subjective. And that's why I love asking founders about that because we view it differently. But I'm curious, what do you hope people think of when they think or hear about TestBox? When they think about TestBox, what do you hope that they're thinking about?

Sam Senior: I want it to mean different things to different people. So when I think about the functionality of the product for the CIO or the CTO, I want them to think there is no better way for me to have certainty that my team is buying the right software to make us successful in the most efficient and effective way and I have full confidence in that. That's kind of how I want our CIO and CTO to think. 

For the functional leader, so a support leader for instance, I want them to think "Well, I'm frustrated with the amount of time it's going to take me going through this process. I want to do it on my own terms, and I want to work with my team to make a decision that's collaborative, that we all feel confident in and this is the fastest and best way for me to do that, where I know that I can go to our company and say, this is the right decision and feel really confident about that."

For a prospective employee, I want them to think, "Hey, TestBox is doing something super innovative, that's very different to all the other options out there as to how you solve this problem. And it's a place where I feel like I'm going to grow successfully in my career. I feel like I will be included and belong there. And this will be a workplace that is a positive influence on my life."

Jim Coleman: That's good. I just had a totally off the wall thought, like, I can't get over how awful the whole demo process is to buy enterprise software. It's like what do you think it would take for Zendesk to refer their leads to you first? It's like, "Hey, before we set up this hour long stupid call where we're going to bore you to death, why don't you go over to Sam at TestBox and try out our software and see what you think." If they stand behind their product, I know you have other options for them, but I mean they can work.

Sam Senior: Yeah. So I think the broader premise is something that we're trying to tackle with the vendors. I don't think it's so much like go to TestBox and play with it. It would probably be like, "Hey, you've come to us, let's have a conversation. We'll do like 10, 15 minutes of discovery and then what I'm going to do on this call is set up sort of your persona, some of the things you just told me on this discovery call. I'm going to press a button and you're going to get this beautiful Zendesk TestBox. I'm going to show you real quickly how it works, then I'm going to hand it over to you." And the AI suddenly gives that personalized TestBox. So they can still do that direct sales motion where they kind of still get to tell that narrative and why they differentiate, etc., but still be able to hand over that customized TestBox environment. And then again, we would be involved in the process with them to make it more successful, but for the customer and then also for the vendor. So it's something I'm thinking about already.

Jim Coleman: Is there a potential licensing play there where Zendesk would pay you to utilize the software to give their prospects an opportunity to utilize it within their platforms?

Sam Senior: That's something like that, definitely yeah.

Jim Coleman: That could be very interesting as well. I like your outs. You have a lot of great choices.

Sam Senior: Yeah I feel very fortunate that we've landed on this idea where just the core platform of what we're building is so valuable that it is so extensible into all of these additional pods and mechanisms to make people successful. So I think that's the thing I'm most proud of – just the core platform and where it can go.

Jim Coleman: Yeah. I don't blame you. So what is the current biggest pain point for you guys right now? Or challenge if you want to look at it that way?

Sam Senior: Yeah, I think some of the biggest challenges right now, that people will tell me will last forever, is hiring incredible people that we think are going to be culture additions and not culture fits, and who will bring different perspectives. I think it's really hard, particularly right now, but the world is bonkers when it comes to hiring high quality talent. So yeah, that's a really big challenge and is going to continue being a challenge because we're likely going to grow really quickly, which I hope we do. And that means we just need to keep finding great people. So, that's going to be a really big challenge.

In terms of the actual company, in terms of the products specifically, I think we're at this point where we saw a lot of inbound excitement for what we're building, and now it's around turning that into broader awareness. Anytime we show someone TestBox and they're in that buying mode, they're like, "This is really fantastic. I'm absolutely going to use it". I just want that whole entire world to know that when they're going through the buying process.

Jim Coleman: Yeah, totally. You know Sam I've got to get to this before we run short on time. So you're eight years old and you had an interest in building a tech company. I mean, like never have I ever heard... We want to be firemen, or like a ballerina, or whatever...

Sam Senior: I was a weird kid, I guess. I was very much the kid that would come home from school, be watching the Microsoft events, the Apple events, that sort of thing. And yeah, I was just, it boggled my brain. I think some of the things I found most interesting were so quickly realizing that a line of code has such incredible reach in the world and can influence so many people's lives in really positive ways. Now TestBox isn't trying to solve human rights issues or anything like that necessarily, but I hope we reduce a lot of frustration out of people's lives. That's a pretty good thing that I'm excited about doing. And so when I was a child, I think I really realized that very little technical work can scale in a way that is beneficial for broader society and that really excited me. I just wanted to find ways to be able to do that.

Jim Coleman: So were you like a savant of sorts? I mean, did you go to college at 13-

Sam Senior: Absolutely not. I am a very normal person. That's absolutely not the right word to use. Very average person.

Jim Coleman: I don't know about that. I think what you're doing is incredible.

Sam Senior: So far it's still a promise we haven't fully delivered yet. We've got a long way to go, but no, I just knew very early on that this is something that I wanted to do, and it was very clear to me and I surrounded myself with that sort of thing growing up.

Jim Coleman: Who do you look up to in business? Whether that's somebody we would know or not. Who are your inspirations?

Sam Senior: There's a few people. One of them is actually someone that I worked with at my previous company, Bain. He was just one of these people who very early on just gave me a lot of rope to do things. And I was shocked anytime I reflected on it, I was shocked how much he sort of let me do and try and test. And he was always there to catch me if I was falling on something. But I think that really led me to have a lot of confidence in myself and know that I could kind of tackle things that felt very unknown to me. And that's kind of how I like to or endeavor to manage team members as well – be like, "Here's our broader goal, good luck and I'm going to help you along the way as you need it, but I suspect you're not going to need it when you get into this."

I just felt very fortunate to have someone who maybe put too much trust in me, but it worked out and that was incredibly valuable. And then more broadly, and it's not specific people, but that I was very fortunate. I have been very fortunate to have people in my life who have helped me go from being someone who's very problem solving focused and didn't really think about the human emotion behind things, that over time have led me to think about the feelings and the emotions associated with making decisions and how it affects people, how you make people successful and that sort of thing. It's a number of people who have contributed to that, but that has massively changed my leadership style and who I want to be as a human – from being black and white, let's make a decision to actually let's think through the effects of this on people and how it's going to make people successful or not successful if we do X.

I think that's been a big thing. And then probably the third thing kind of sitting over all of this is, honestly my therapist. So I've been doing therapy for a good number of years and I strongly encourage it to a lot of people. And I'm a huge advocate – at TestBox, as part of our benefits packages, we will pay for people's copay for any mental health therapy services that they're doing. On a weekly basis, I have this opportunity to work on myself with a therapist I've been working with for the last 18 months, who’s very good at just guiding me, helping me think through the challenges that I'm having, or just helping me reflect on my own decision making. So I think she's been really important to me.

Jim Coleman: I'm glad you brought that up. I would love to talk more about that. I am in therapy as well and I shared a little bit with you offline about my focus on weight loss and focusing on the emotional side of that. But it's been just so beneficial and as a kind of interesting aside, like I'm convinced that therapists would make the best salespeople ever. And we keep going back to the steam of awful sales presentations, but the ones that are the best, the best salespeople are the ones that just care, listen, and know who you are, do some research ahead of time and just listen. And maybe it's been five minutes out of an hour long conversation talking about their product. It's like, can you imagine therapists being just like amazing salespeople?

Sam Senior: I can. It's a real loyalty business as well. Once they've got you, there's no way I'm going to leaving my therapist at any time. So she knows that but we have a great relationship, but that's okay. But what, 18 months in, my churn rate is going to be real low. So I absolutely agree.

Jim Coleman: Well, I don't want to ask you about that because a lot of people have used therapy as specifically focused on one thing. So right now I'm working on the emotional side of weight loss, but it's like I got plenty of that I could work on, but I mean what are your thoughts on...and I think I know this based on what you're saying, but that ongoing, do you use your therapist just for focus on certain initiatives or is it more just like checking in?

Sam Senior: It can be a combination of both. It really depends where I'm at emotionally, week to week, month to month, whatever it is. I think what we've observed over time is there are periods of my life where there are acute things that I'm really having to focus on and think about. Whether that is how I'm relating to a friend, a loved one, something going on with my family or something at work that I'm just really bothered by in some way. Or we often talk about some of what I call chronic ongoing things, that maybe are things that have been going on for 20 years of my life and I have never really properly addressed or thought about. And so we tend to change in between acute issues to the more chronic ones. But what we observe is that almost all the acute things are really strongly tied to something chronic underlying.

And so we're always able to come back to those topics on an ongoing basis. I think my take on therapy when people start is that it can feel like you're not really getting anywhere from maybe five, six, seven sessions, but when you're getting up there, suddenly you start to have these revelation moments that are really meaningful. Not every session is going to change your life and you hope that it's not happening like that. But other times when you're like, "Hey, this is why I didn't last a month in therapy." You're like, "Wow, that's really changing my mindset and how I approach the next few months or whatever it is." So it's certainly a combination for me and I strongly, strongly encourage anyone who has the means and the time to be able to make this happen. I think you can always make the time to make this happen.

I do it in the middle of my week, no matter what. It does not matter how busy I am or whatever is going on. Even if I'm normally working 70 hours that week or something just insane, I will still have that hour of therapy because it's so incredibly beneficial to me. I think the biggest barrier for people is having the means to do it. Whether that is a health insurance thing or direct out of pocket. If you have the means, I would strongly encourage every single person to give it a go even if you don't think it's for you, because it will be for you even if you don't think it is.

Jim Coleman: You know, I've previously undervalued therapy and undervalued how important it is to be healthy emotionally and how much that impacts my business life. I can tell you that my wife and I, we get on very well. We've been married for 16 years, but occasionally we have disagreements and whenever we're in a bad place with each other, especially if that lingers, I perform poorly at work the next day. It's like I just can't get my mind in the game, you know? And it's deeply impactful.

Sam Senior: I notice it most when I'm exercising. If there's something that's just churning in my head, I won't be able to think about anything else really. And I will actively notice my performance drops significantly in that moment. And so having the opportunity, whether it’s by doing some meditation or journaling each day, or going to these therapy sessions to talk about it... If I don't do those things, I really notice it when I exercise. It certainly happens in my work life as well.

Jim Coleman: Yeah, I'm all about hiring a therapist full time on staff. If he or she would be willing to do that, I mean imagine a scenario where... And sadly the therapists don't make a lot of money. I'm sure software engineers make multiple times what a therapist makes and imagine a full-time therapist on staff that was able to work with employees that were interested in doing that. And at some point it could even be like a life coaching sort of situation, right? I mean, if you get to the place, which would be a great thing where we're not actively working on sort of acute or even chronic problems, but it's like how do I get to the next level? I think it could be very interesting to see how that would work out in terms of productivity and mental health improvements for staff.

Sam Senior: Yeah, there's a good amount of, relative, well, I guess in the last year, two years there's been significant growth in this area where there are some B2B therapy companies. I think Talkspace is a good example. They might be looking to go into that more. There are some other apps that are starting to do this where they will offer to enterprise companies the ability to have really easy to access mental health therapy services. One thing that we're looking at, at the moment, is executive coaching for our leadership team as well. That sort of thing is really important as an ongoing basis. So all of these, I just think we as a society focus so much on our physical training and physical health, and we don't think about our emotional and mental health enough. And so the more that you provide those opportunities for staff, the better we're all going to be as a result of it.

Jim Coleman: Yeah, absolutely. I'm curious what your thoughts are on the idea of founders upskilling themselves as the company grows as compared to hiring an external CEO for example. Let's just say TestBox does really well in the coming years, right now you have a relatively small team. Let's say you have a 100 or a 1,000 employees in the future. What are your thoughts on upskilling yourself via executive coaching versus a hired gun CEO?

Sam Senior: I think there are phases of growth in a company that require different skills. And so in phase zero, which we essentially are right now, which is very much the innovation, new idea, product market fit, kind of growing as quickly as we can phase, right? Then there's other phases around growth scaling and then optimization. You require different skills for each of those components. And I think it would be irresponsible of me to not try and upskill myself, otherwise we won't be as successful in each of these phases. And then even further irresponsible of me to realize, to not be willing to admit that I haven't been able to upskill myself to be successful in the next phase. And so when that starts to happen, it's either a situation of like, okay, I need to step away in some way, or I need to make sure that we have other executives on the team that are complementing those skills very specifically. And so I definitely think of that in phases and recognizing when that moment is to bring new people in if I haven't been able to upskill.

Jim Coleman: That makes sense. I want to ask you a question that you're one of very few people in the world that can answer. And I'm curious what your thoughts are on the cultural differences in business between Australia, you've been in London and then now in the United States.

Sam Senior: So thinking about Australia versus the U.K. versus the U.S., I think the culture in Australia is a very high performance culture, but it is absolutely not the same in the U.S. when it comes to just how much dedication people put to their work on a daily basis. I think the U.S. has an interesting perspective of really putting 100% of yourself into a job, which I understand. And I think it makes sense for some people, but probably not for the broader population at large. I think we've noticed issues in the U.S. where people will offer unlimited PTO and then team members will actually take significantly less than they used to as a result of that. I think there's this interesting pressure in the U.S. around turn up to work every day, put your best in every day.

Whereas somewhere like Australia, there's like people taking 20 to 30 days off a year. That's really very different, but I don't think it makes them any less productive. If anything, it probably makes them more productive. For ourselves, we've basically told our team yeah, you have unlimited PTO but you must take at least 15 days a year. If you do not, I will cancel your Slack account kind of thing. So I think that's like a very Australian mindset versus a more U.S. mindset on that one. But one thing I do think that is very positive about the U.S. is there is just this idea of untapped opportunity that anything that you might want to do is possible.

In Australia, there's this idea of tall poppy syndrome which basically is when people kind of get too big for their boots, society tries to pull you back down a little bit more and it's much more even. So I think there is that very big cultural difference. And part of the reason that I was like, if I'm going to start a company, I think the U.S. is the best place to do it, because people are just incredibly encouraging and believe in innovation and sort of kind of go anywhere. And that's really exciting.

Jim Coleman: That's awesome. We very much have adopted the same policy for our sales and leadership style. It's unlimited vacation policy, but you're required to take certain days. That was when David and I, my co-founder and I talked about it, it's like we were afraid of that because I've heard this negative side of it where there's this idea of, like I don't know, it's weird that they would take less. But I understand psychologically how that happens. Just on a call with one of our leaders in Kenya, Daniel, and he's been working so hard lately. One of our other leaders is on paternity leave. And I'm like "Daniel, when Martin comes back, you have to take some vacation time. You've got to take a break." Because he would just work 24/7 if we didn't force it. You need to take care of yourself, man. Do that. Yeah.

So we find that that's important. And it also to model that, it's important for David and I to model time off. And I made it really obvious when I was out of town and shared a couple of pictures and things. And I think it's important as leaders to make sure.

Sam Senior: Yeah. We’re actually putting on job descriptions that Sam typically takes 20 to 25 days a year because I hope that encourages people and that helps them realize the sort of place that we are. Like Peter, our CTO, is out entirely this week, not a problem. One of my team members actually posted in our Slack today, "Is there anywhere where I can track how many days I've taken this year before I get canceled on Slack?" I was like, "Yeah, there is. Don't worry." Which is great. He was very comfortable, openly asking about that in front of everyone that he wanted to make sure he was doing what we've talked about as a team of taking enough time off to rejuvenate and feel comfortable to come back to work and do a great job.

Jim Coleman: Yeah. That's great. Well Sam, this has been a lot of fun. You're so gracious with your time. I'm absolutely excited about TestBox and what you guys have in front of you.

Sam Senior: Thank you so much, Jim. I really appreciate you taking the time as well. It's always good to talk to you, the couple of times that we have so far and I look forward to working with you more.

Jim Coleman: Absolutely. So we'll have the full length recording on our landing page. We'll include your bio and also links, but what's the best way for someone to reach out if they just want to say hello or if they're interested in utilizing TestBox?

Sam Senior: You could go to onboarding.testbox.com and get started that way. Or if you just want to generally reach out – hello@testbox.com.

Sam's Face

Pedals is a beloved member of the TestBox team whose entire goal in life is to author amazingly helpful blog posts and to cameo on every piece of TestBox swag.

TestBox empowers you to have a self-serve, customer-led experience so you can buy new software and feel confident that you made the right choice. Currently focused on Customer Support, TestBox allows you to test out Zendesk, Freshdesk, HubSpot, Dixa, and other products side-by-side. It takes a matter of minutes to sign up and take these products for a test drive. Find out more at TestBox.com or follow on LinkedIn.