Will Stevenson 0:02 One of the most important skill sets that anyone can have as a founder or an employee is self awareness and situational awareness. You know, I know what I’m really great at. I also know what I’m really terrible at.
Taylor Kenerson 0:15 Welcome to the Hyperengage podcast. We are so happy to have you along our journey. Here we uncover bits of knowledge from some of the greatest minds in tech. We unearth the hows, whys, and whats that drive the tech of today. Welcome to the movement
Adil Saleh 0:34 Hey, greetings everybody. This is Adil I have my co-host Taylor Kenerson on the stage of Hyperengage podcast, we have a special guest from YC. Since you all know that we have started a new segment where we are featuring YC stories, all our- all the startups that are growing in a very quick succession, which is previously we had June now we have
onboard.io, the founder of
onboard.io is sitting right next to us. Thank you very much for taking the time.
Will Stevenson 1:03 Yeah. Thanks so much for having me, excited to chat today.
Adil Saleh 1:05 Cool. Cool. So just like we always begin, like we, we wanted to know, like, we’ve seen your team, we’ve seen the product, we’ve seen a touch of some of the on the on the funding side, like how you made your decision on the funding side post YC. We just wanted to see like, there’s so much. I would say Productboard is there. There’s so many SaaS in the industry, it’s getting quite saturated right now. So what what what made you, you know, basically start off with all this idea, and what was the initial thought process? And, of course, it is it is a big part of the conversation that we always have in startups.
Will Stevenson 1:47 Yeah, for sure. So, I think I’ve always been an entrepreneur. So I think it starts back when I was like a little kid, right? I think in fifth grade, I started my first business. By the time I was 12, I was working weekends and summers. And by the time I was 19, I had my real estate license and enjoy my first tech startup. So it kind of goes back a long ways for me. But really what spurred the idea of onboard is for the last 12 years or so I’ve either managed or helped build, CS and onboarding teams. And I just saw onboarding teams struggling you look around the organization and sales teams have Salesforce and Salesloft, and product teams have Productboard and marketing teams have marketing automation. And your onboarding team is usually stuck with Excel files, Google Sheets, generic project management software, something that some other department purchased and passed down to them. So that was really kind of the the first sight that I had that I was like, you know, this should change. And then after my my last acquisition, I went out and consulted for about 18 months with about a half a dozen customers. And really, I realized that everyone’s onboarding process was struggling. This wasn’t just a problem that I had experienced over the previous 10 years it was it was something everyone else was having. So that’s where that was the straw that broke the camel’s back, per se. So got the got the crew back together from the last company and started Onboard. And here we are a few years later.
Taylor Kenerson 3:33 Love it. That’s an incredible journey. It’s- So you know, you you see, even though when you were younger, you might look back and you had so many similar values to what you carry through today. Like that passion that grittiness. You know, your perspective might have changed, and you see things in a different light, but you still have these core things that you’re like, wow, like, I’m still a little kid just building like you were building Legos and such. But can you dive a little bit into like your team, I know you have a co founder. So what goes into like choosing a co founder? How do you even decide that? I need a co founder? What can you walk us through that and then building a team and expanding that getting your buy in all that stuff?
Will Stevenson 4:12 For sure. So for me, it wasn’t really a question of who the who the co founder is going to be. So Jeff is the other the other founder here at onboard Jeff was actually the previous founder of Ambassador, which was my last company that that I was at, and we we helped scale the acquisition. So Jeff and I had always kept in contact prior or after the acquisition. So it really it really wasn’t a question and I even remember it was after the acquisition Ambassador is probably the last conversation that we all had sitting around the table after work and someone said- I forget, there are a few people there, but someone said, if you were going to build another software, what what space would you build a software and, and I immediately said onboarding. And Jeff immediately said, onboarding. So it was kind of like the synergy was aligned from the, from the very beginning. So really no question on that. On the founder side. What’s not typical about our relationship as founders is neither of us are technical founders. So usually, what you see is you’ll see a non technical founder pair up with a technical founder, Jeff and I, we kind of knew that we’d both been through acquisitions in the past, we knew how to scale companies. So for us, it was it was more dividing and conquering. So what side was he going to take? What side was I going to take? And then who do we who do we rope in from there? So we brought in Matt, who was our previous director of engineering at Ambassador as our CTO here, and a co founder as well. And Matt was kind of our first technical lead, hire. And then outside of that, we scaled primarily through people we knew. So a bunch of people at Onboard have worked with us in the past. And there are some that haven’t, but most of the people that’s kind of where we started is, we started with the people that we knew. And I think it was really a huge competitive advantage. By doing that. You don’t have questions about how each other works or what their values are, you kind of know that going in. Which is, which is a huge, huge benefit when you’re when you’re talking to new company and new hires, and really trying to move fast.
Taylor Kenerson 6:48 Absolutely. And it’s also really unique to when you build a team off of friendship first, and then you know, everything else is a byproduct of that cohesive friendship. And when we talk about friendship, it’s not also like all like flowers and like lovey stuff, there are friction points. Di- dive into that a little bit on like, maybe some of the challenges or like frictions you face within your team scaling, growing, just throwing out ideas, how that whole dynamic works.
Will Stevenson 7:18 So what’s interesting is, is and I think we all agree with this year of Onboard, like, we had this concept at Ambassador, that was radical candor, you know, you have to be able to give each other real feedback in real time. And he can’t sugarcoat that, right? It doesn’t help. It doesn’t help to, you know, wrap everything up, and butterflies and rainbows, you have to, you have to give real feedback to get real results. And I think we all do a great job of that today. Now, that doesn’t mean like, go out and be a jerk, right? It means it means that you have to get feedback, but you also have to take people other people’s feelings into consideration. So I think everyone does that. Really well. And I also think one of the most important skill sets that anyone can have as a founder or an employee is self awareness, and situational awareness. You know, I know what I’m really great at, I also know what I’m really terrible at. And hiring people that are better than you at those things that you you’re, you have a shortfall on really makes a big difference. So I think all those things kind of play into it. But I really think self awareness, situational awareness is crucial for anyone in a startup.
Adil Saleh 8:45 I love that. I love that you mentioned because, you know, knowing your instincts, knowing that you can, you can really suck at this, knowing that inside core, and then you can even build systems or processes or maybe team members, you can inspire people to do the job that you’re not so good at. But you got to be very much self aware of that thing that you’re not so good at usually might suck at it. But this is something that you can really good do and ready, you can kill it. So that’s very important. And it started in a team and with a bunch of folks doing one idea
Will Stevenson 9:20 And stacking that talent up that’s really great at things that you’re you’re not great at does a few things like one it’s going to be done right? And you don’t have to do it right. But to it’s also going to teach you like you’re learning by immersing yourself in the situation like, you know, I was my background and largely what I focused on over the last 10 or 12 years is operations right? So like enterprise systems like CRM, marketing, automation, and stringing all those things together to make them work well together, while overseeing CS and onboarding, and that kind of that kind of went well. gave me a unique perspective, because it’s not a normal job title, right are not normal job functions. But I was really good at that stuff. And I would say secondarily to systems, I was good at CS and onboarding. But I really learned that by immersing myself around people that were absolute crushers in that area, and absolutely dominated that area, and I learned a ton of things from them. And that’s what’s ultimately blossomed me to the career that I’m in and the company that I’ve started.
Adil Saleh 10:33 It’s, it’s all about learning from experts, and, you know, hanging around people that can that can move better than you, you cannot live long enough to do and learn all of them yourself. So that’s the part. So learning the CSR questions, of course, onboarding is very, very critical, then adoption and all, we talk about it a lot in stages, like this. And your product is some somewhat related to custom, you know, customer data platforms like CDPs. Is that right? So you got to deal with a lot of CRMs, like Salesforce, and then product uses Segment, Amplitude, all of these, you got to integrate all of that data and build experiences on top? Can you touch a bit on your product?
Will Stevenson 11:15 Yeah for sure. So really, the hole that I saw in the Customer Success lifecycle, or the customer lifecycle for that matter, was sales, the sales teams and marketing team sales teams have really great systems to manage everything from lead to close, right. And then on the CS side, we have some pretty good systems on the CS side, that have been around for a while to manage, post onboarding, really, when a customer is up and running, and quarterly business reviews, and all that good stuff that goes into managing a customer long term. But there really was nothing on the onboarding side. So we wanted to build as we wanted to build a platform that helped you first and foremost, organize your onboarding process, get everything related to onboarding into one platform. And then we wanted to help you automate it. So rather than manually creating templates in Excel and saying, This is what this is the task that needs to happen first, second, third, fourth, fifth, we we do that dynamically through what we call variables. So ultimately, rather than having templates, you have customer attributes that tell you how that customer should be onboarding. And then automating everything from follow ups to escalations. So all of that can be automated and onboarded. But the third piece, and one of the most important pieces here is providing visibility to everyone. Very, very often, I see companies that are operating on the sense that they have visibility into that onboarding process, and the customer never sees it right? When the customer sees it, it’s through a slow drip through email of, hey, I need you to make sure that you go and do this. But it’s without giving that holistic picture to the customer upfront, the customer is not going to be able to accurately plan. So many times our customers when they come to us are coming to us and they’re saying, yeah, the slowdowns are never on our side, it’s always on the customer side, they always delay. Well, the issue may be that you’re not giving them the information upfront that they need to properly plan out the implementation. So those are kind of the three big places that we highlight and really solve problems is organization automation, and then visibility.
Adil Saleh 13:37 Yes, great. So we have, we’ve proven a lot of customer success teams, product teams, you know, and a lot of them are very, very technical. Let’s say you talk about cybersecurity, you talk about platforms that are indicating risk on your websites on the security side. So they have what they want the onboarding, while the onboarding journeys. They have solution engineers, you know, technical people, and it is not so much to do with the data like the you know, the experiences like exceptional experiences inside the platform. But it’s more to do with people that are very, very much technical, they know the problems. They know all the integrations, all that configuration part. So how in those cases, were those specific segments? It’s big enough segment, how does
Onboard.io helps to automate?
Will Stevenson 14:26 So the beautiful part about Onboard is it can work with very simple implementations, where it’s one person involved from from our customer side. And one person on their customer side to massive organizations that have year long implementations where there’s 20 people working internally on the project and 50 people working on the customer side. The beautiful thing about Onboard it’s it’s a shared it’s a shared list basically writers shared project where everyone has visibility into that project. act, and they all have assigned tasks that they need to get done. Or they may have visibility just from the, from the top side and just want to see what’s happening in the project. But everyone, every task is individually assigned. So when you look at a project at Onboard or a launch plan, what you’re gonna see is, you’re gonna see what needs to happen, how it needs to happen, when it needs to happen, and who needs to do it. So it’s a completely different dynamic, or there’s almost a little psychology behind it. If you send an email to one person and say, Hey, I need you to go do this, this and this, it’s really easy for that person to start that email and say, I’ll come back to it later and get it done. When you have a full project that everyone has visibility to, and there’s a face next to a date next to a task, they’re more likely to get it done. And that’s what we’ve seen with Onboard is we’ve seen faster time to value faster time to launch.
Adil Saleh 15:57 Great, great. So you talked about, you know, of course, working with the tech team, getting the technical founder getting from the people that you have previously worked with that, of course, it’s a trust development part that is that is pretty critical in the in the startup teams. So you got that taken care of. So once you you know, move from the stealth, good launch, like MVP mode, what was that process? How soon did you do that? And how did you decide that we should go to, you know, Y Combinator instead of TechStars? Cam? Is there loads in Austin, Texas, they’re both in New York City. So what was why YC? And how soon did you do that? What was that?
Will Stevenson 16:38 Yeah, so really, we were pretty fortunate in the way that that we rolled the product out. So we raise money pre product, and that was just purely based off of our previous exits, if we went to previous investors and said, Hey, this is what we’re doing. We didn’t have a product, I don’t even know if we had a domain at the time when we when we went to him. So it was early. But they invested. And so at that point we had capital to work with, we went out hired, the tech team spent about six months or so building out the product and really a large part of that time. We were when I say building out the product, I mean 100% focused on the product like Jeff and I were both working with our technical co founder as well as is his team every single day, like really honing in the product and making it as perfect as we could get it. So we spent the time to do it, right. We launched in early access program that lasted about six months, probably 30 customers or so and that. And then we rolled out and went live. And we were actually live for probably about a year before we joined yc. So we joined YC, relatively late compared to most people, most most companies that were in our batch, they were brand new companies pre revenue or just getting started, we had real revenue on the box we had already taken taken investment dollars. So it was it was a little bit of a different experience that what most YC companies have. But nonetheless, the experience was was without fail. One of our best decisions that we’ve made, just from the sheer fact of you’re immersed in yc. And YC has become really, really good at identifying the right companies. And identifying even beyond that the right founding team. So, you know, I think a big bet that they’ve made isn’t necessarily on the company itself. It’s on the team that’s, that’s behind the company. You’ll see a lot of people that are in YC, and they pivot and they change directions. And some of the best success stories have been those that have come out and pivoted. Like I think you know, Airbnb and those guys have all gone through. Yeah, they all went through yc. But I think Airbnb then pivoted while they were in YC and Brax as well. So you get some really great stories out of that. But just immersing yourself in YC was was a really great decision from potential customers, which we gained a lot of YC customers to investors, right, the investor network that they have is, is wild. So it was really a great decision. It was an amazing experience. And I’m super glad that that we went through that.
Taylor Kenerson 19:43 Can you tell us a little bit about your stories of pivoting if there was any from the end? Yeah, so like how it came to be.
Will Stevenson 19:50 I wish I had some because those are the best ones right? Like the best ones are, hey, we started off and we were going to be like a b b to c operate, we were going to be a consumer app. And then we decided to pivot the business, b2b. And we really don’t have that. What’s crazy about this, and I think, what call it locker, call it experience or call it, whatever you want to call it. But one, what’s funny is the first slide that we ever created an investor pitch was the niche that we fill in the customer lifecycle. And we still use that slide to this day, like, it’s, the idea hasn’t changed. The idea is the same idea that we had, at the very beginning. And I think it was, I really think it was me suffering 10 years of not having a solution. And I really, I think, by the time we got here to let’s create onboard, the idea was like, halfway flush it out, you know, like, it was like, almost there. So I really don’t have any pivot stories, but we, you know, we really narrowed in and focus from an early, early time, and it’s kind of proven to work at this point, which is, which is an awesome feeling.
Taylor Kenerson 21:15 That’s amazing. It’s sometimes you know, it’s mostly, it’s about the journey, you know, and if you’re, if something doesn’t pivot, but there’s, you know, your perspective on the solution, how you might position it and your messaging, that’s what pivots you know,
Will Stevenson 21:30 that, well, that’s a great point. And now that’s definitely changed. So that’s, that’s absolutely changed when we first started, we 100% focused on b2b software. And because that’s what we knew. And that’s where all of our connections and contacts were. So that’s absolutely what we focused on. And it’s really cool to see some of the use cases that have popped out of onboard, like, now we have, you know, full scale agencies using it marketing agencies, sales agencies, we have all kinds of different service companies that are using it. And then I even tell the, there’s a funny story of a customer. It’s one person, and they came to us, and they said, Hey, I sell OEM auto parts. And I needed a system to train all the service teams of all these different dealerships. And we set up a proof of concept, and it was really early on. And we set up a proof of concept. And this is exactly what I needed. And it was like, you know, just crazy use cases that you would never, never expect came out of it. And that’s, that’s a really, that was a really good point. Like, I think that vision of ideal customer profile has really pivoted quite a bit. So now we have customers that are all over in all different industries, which is, which is really cool thing to see.
Adil Saleh 22:55 Yeah, great. So I was super glad while I found
onboard.io that is serving in the post sales journey. I was just thinking that what kind of segment you have started off with, like startups, like a team of a couple customer success managers that are serving the post sales journey they have made may have customers in the mid market or maybe slightly in the medium scale enterprise. So how did you penetrate in the in the in the beginning into the tech, like tech teams that are more geared toward like data driven onboarding, data driven adoption, all of them.
Will Stevenson 23:29 I wish there was a magic bullet there really wasn’t like, it was, it was all groundwork, there was 100%. Like, when we were when we were building the product, and we hadn’t even opened it up to early access users. It was myself, my other founder, we were calling people that we knew, right? And saying, Hey, this is what we’re doing. Like, you know, do you want to try it? Like, we won’t charge you, you know, and it was like, if I had to say there was one mistake early on, charge earlier and charge more like, for sure. Like whatever you Whatever you know about your product, you’re being over critical on yourself or what you think it should be. But probably what you have is something that people will pay for, right? So we didn’t charge people really early on. But you know, we’re trying to knock down those barriers early of like, I don’t want price to be an issue I just want I just want to say hey, here’s the software, go use it and give us feedback. And what what I found was when no one has skin in the game, and they’re getting something for free, they probably won’t use it. They probably don’t value it enough to think that they should use it. So once we started charging and it was super cheap early on, I mean I’m talking like 100 bucks a month or 99 bucks a month. Even that $99 A month price tag, got people to start using it and using it across their team. though, you know, it was a big learning, learning lesson for us for sure. But yeah, it was all it was a lot of manual work. It was called emails, cadences reaching out on LinkedIn, asking people for intros. That’s, that’s all it was for the first six months probably. And then we kind of, we’ve kind of hit market penetration at this point to where a lot of what we have a lot of our customers come from inbound, the majority of them do so we’re in a fortunate place there. And that’s with very little paid efforts behind it at this point, which also a great problem to have.
Adil Saleh 25:44 Oh, great. Great. So of course, as a product model, of course, you initially had a freemium model. So did you build anything on top of it like to expand those customers? You know, make sure that they use the platform, potentially, you had a product stickiness? Of course, they integrate their data, they do all the integration of the customers data and all of that. So how did you utilize in the person how you’re thinking of doing moving forward, because that’s a bigger part, like increasing the lifetime value of the customer, how you guys are working on that?
Will Stevenson 26:18 Yeah, there’s really two different avenues to increase. And both of them are kind of organic growth with the customer. So really, we’re taking the don’t want to say force expansions out of the equation. But that’s how a lot of companies do it. And it’s and believe me, we’ve done it right in the past that past companies, and it’s the wrong way to do it right is now that I have them in and they’re using, we should try and figure out a way to get them to pay more. And it’s kind of forced, right? The way that we set up pricing or pricing model and onboard is we really grow with the company. So the only two levers you can pull to increase or decrease price or the plan that you’re on, which contains different features that are needed by small companies need the starter plan or scale plan, right? It’s it’s they don’t need every feature under the enterprise plan. And enterprise doesn’t need everything they need under the custom plan. So we really set it up to where they’re naturally going to expand over time as the company gets bigger. And the second lever that you can pull is users. So and that’s internal users. So with any plan, you can have unlimited external users. But we charge for internal users. And the idea there is if we sell into a company that has two people that are onboarding today, internally, my bet is in a year, they’re gonna have five people onboarding internally, right? So we naturally scale up with with those teams. So it’s a little bit easier to digest rather than saying, Hey, it’s $10,000 for the first year, and the second year is $20,000. Right. So that’s, that’s been the logic behind the pricing plan.
Adil Saleh 28:09 I love the way notion domain notion builders, you know, we’ve been adding notion for about two years now. And they, of course, they recently charged you for additional users from the team, if you want to add more user like as we grow as a team like they charge is more similar to on the stack on the usage model. Like as we grow as an entire organization, they’ll charges more in the second year. This is, you know, the product lead growth at strategically, that’s how you build your GTM. So you haven’t found product market fit now. Like, if you do if you have a division of your customers, so what percentage of customers fall in the small to mid market? And what kind of customers they are like they’re fully product? Yeah, please like tech companies or the agencies work?
Will Stevenson 28:55 Yeah. So you know, I think the majority of our customers are still software, there’s still there’s, I would say it’s probably a 60-40 split, right. 60% software, 40% other companies, including a large majority in that 40% are agencies of some kind, right? I think, as we expand here, and, and really just to define the ICP, really, the ICP in traditional terms is small to medium sized businesses, right? What’s a big business to us is, you know, 500 600 700 employees, that’s a that’s a big business to us. That’s what we would consider enterprise and in our world, and I know a lot of people like true enterprise companies gonna laugh at that right there like, No, we need 10,000 employees to be considered an enterprise solution. So traditional under traditional terms small to medium sized businesses, really when I’m defining the ICP it’s it’s one or two people solely focused on onboarding, customer onboarding. And that’s at the smaller side. And then on the larger side, I don’t think we’ve hit that that upper limit yet, you know, we have people that are creating 1000s of launch plans and still growing. So for us, you know, I don’t know, we’ve hit that upper limit yet. But really the value and onboard is anyone that has any sort of onboarding process, where they’re bringing their customers on to the product can use onboard, and it doesn’t really matter if it’s doesn’t really matter if it’s like a human lead, right, you have an onboarding person leading them, or you have someone sign up and you want to have them self serve, onboarding, both can work. I think we’re, we’re kind of focused on that team. Team growth, though. So the people that have people that are dedicated to or employees that are dedicated to onboarding, but it kind of works kind of works across industry and, and across segments.
Adil Saleh 31:08 Yeah, up to our experience, like with 60, around 60 CS teams that we spoke with, most of them, 90% of them, they had onboarding process pretty much nailed, pretty much, you know, systematic, like, you know, probably they’re using software’s like
customer.io, intercom, all these sort of FreshWorks, they came into market in the past six years, pretty cool. They scaled pretty big, too. So now, but what I was thinking that they don’t, we never experienced that they had a dedicated onboarding team, the onboarding manager takes care of the entire customer journey, like, it serves their, like automation on the adoption side, and to make sure that customers retain and expanded at one point and, you know, monitoring the 360 view of the entire customer journey. So how does that play, like, if I project myself being a CSM for a tech company, having the book of business about 20 customers, and onboarding all those customers using onboard, and then I’ll help be used or have to use another platform to make sure that I, they are well adapted, and then they’re continuously using the platform to be able to retain them, and then increasing in value and growing those customers. How does that? Sure.
Will Stevenson 32:21 So I think there’s different models, right? There’s, we all kind of do it. When we’re starting a company where you have one person that does like five different things, right? And then as you get bigger, you start specializing in, Alright, now we’re going to split out CS into two, CS and support, or CS and onboarding. And so as companies naturally grow, I think they become more specialized. And we we have companies that have CS teams that focus on onboarding, CS and support, they do it all. And we we work well with that. What I’ll say is, and I won’t give away too much is in 2023, maybe they won’t have to go to another platform. That’s all I can say.
Adil Saleh 33:13 Great. So there’s there’s something you’re cooking.
Will Stevenson 33:16 Yeah. We have we have something up our sleeves here for 2023.
Adil Saleh 33:21 Great, great, I wish you good luck with that. So it was really nice, meeting you and having to listen to the entire story that you shared. And I love the journey. Love the energy and motion that you you begin with the beginning and you trusted your friends, their instincts and their their skills. I love that.
Will Stevenson 33:39 Awesome. Well, thank you so much for having me. It was awesome. Love these chats.
Taylor Kenerson 33:43 Thank you so much now beautiful.
Adil Saleh 33:45 We’ll talk soon. Have a good rest of your day.
Will Stevenson 33:47 All right, thanks. See ya.
Adil Saleh 33:53 Thank you so very much for staying with us on the episode. Please share your feedback at
adil@hyperengage.io, we definitely need it. We will see you next time and another guest on the stage with some concrete tips on how to operate better as a Customer Success leader and how you can empower engagements with some building some meaningful relationships. We qualify people for the episode just to make sure we bring the value to the listeners. Do reach us out if you want to refer any CS leader. Until next time, goodbye and have a good rest of your day.
