TSPPB: Dave interviews Sandi Lin, CEO and co-founder of Skilljar

Speaker A: Good morning, you're listening to the SaaS product power breakfast with Thomas Otter, my co host and I'm Dave Kellogg. We're here with our guest this morning, Sandy Lin, co founder and CEO of Skilljar. Um, and with Sandy we'll be talking about how and why product managers make great founder CEOs and what are some of the things they should look out for along the way. Good morning, Sandy.

Speaker B: Good morning. Very happy to be here.

Speaker A: Awesome. We're thrilled to have you. Um, before we jump into the meat of this, I'd love to just ask you to do a quick self introduction so people can get to know you.

Speaker B: Sure. So, ah, I am the founder of Skilljar, which uh, I'll talk about shortly. But before starting this company I was a product manager@Amazon.com between 2009 and 2013 and a couple different teams, B2B and B2C. Um, before that I got my MBA from Stanford and um, was a civil engineering major from mit.

Speaker A: So did you want to build bridges? My dad was a civil engineer. He worked on bridges and infrastructure. Was that where you were headed?

Speaker B: You know I actually had a transportation focus, although I did love my um, uh, bridges and uh, infrastructure classes as well. So. But I, and actually my, I worked part time and then for two years after graduation in a transportation planning company so really doing like systems level modeling, you know, 2050 year population and employment forecasts and you know, where do you build, you know, incremental highway capacity and how do you charge, you know, dynamic tolling in various areas and that sort of thing.

Speaker A: Cool. Well, just uh, I always felt, not to talk too much about me, but, but I was like, got into computers in like kind of the 80s and 90s. My dad had got into the interstate highway system in the 1950s and I felt like both of us managed to catch a wave at the right time in our respective careers.

Speaker B: Yeah, yeah. Well my dad was actually a very early computer science person as well. So we were also the family that was building, you know, computers in the 80s at home.

Speaker A: Ah, cool. I did a little bit of that. Um, could you tell us a bit about Skilljar?

Speaker B: Yeah. So we are a customer education platform which means companies use us to launch online academies for their external constituents. So typically, customers, partners in the community. Um, some of our tech customers include Tableau and LinkedIn and DocuSign. And so you know, these companies use Skilljar to improve the product adoption and also ultimately customer satisfaction, customer retention through learning. Um, we are about 150 people growing very quickly. Um, hiring A lot, uh, uh, fully distributed. Although historically we are based in Seattle, Washington, where I live. Um, and we have raised, uh, just over $50 million from, um, Insight Partners Letter Series B last year and, uh, Mayfield Letter Series a couple years before that.

Speaker A: Super. Yeah, I know. Rajeev Batra, uh, on your board, uh.

Speaker B: Ah, yes, yes. Love, Rajeev. We talk weekly.

Speaker A: Awesome. Awesome. Um, so before we jump in, so you're working at Amazon in product, uh, and then you decide to start a startup. What was the story like? Because you strike me as a passionate person. What kind of triggered you and said, I gotta go start this company? What was the founding story, if you will?

Speaker B: Yeah, so, you know, my dad actually started his own company back, you know, in the 80s and it was an IT consulting firm. I grew up in D.C. so, um, they ultimately did a lot of work for the federal government. And it was a, uh, really hard slog for him and his co founders. But I've, um, kind of always had had that entrepreneurial tech bug and in my mind, and, you know, but I graduated, uh, from Stanford in 2009, which, um, you may recall was, uh, the global financial meltdown. And so I ended up going, and I thought I, uh, went to business school with intention of either starting a company or joining a startup right after that, but the circumstances were such that I decided I would go, you know, to Amazon instead. And that was an amazing experience and I'm actually very, very happy that it worked out that way. Uh, in the end, it's where I met my co founder. It's where I learned a lot of skills that are actually very relevant to where Skilljar is today. Maybe not the first, you know, product market fit stage, but it's very relevant today. Um, uh, and so I was there at two different teams. I was there about four years and my second team, it was time for me to do something different. Right. And I accomplished. You know, I'd worked in B2B, I'd worked in B2C, I'd been promoted, I'd launched an international business. I, you know, grown a team. I had, you know, manager of managers. And so there's a lot that I had felt like I'd accomplished. And, um, so when I was kind of considering my next opportunity, you know, I looked at, I looked internally, of course, and, you know, the company was actually very, very supportive and accommodating for, you know, whatever I might want to do. I looked externally, but I kind of just had this little voice in my head saying, you know, if not, if not now, when, like, if you're actually going to start a company, uh, is there going to be a better time than, than, than now? And I think I was. Gosh. So I just turned 40, so 20, 2013, I was like 32ish, 33. And, uh, I was out of debt. I'd saved enough money from my Amazon stock to go a year without a salary. Um, I had no dependence. And so it was just a moment when you look yourself in the mirror and say, am I going to try this or not? And so it was more based, I think, around my personal timing than anything else, because I do believe that there's always opportunity out there and there's never a perfect time for anyone. If you wait for the perfect team or the perfect idea, you're going to be waiting forever.

Speaker A: That's awesome. So for you. So first I have to commend you on your LinkedIn. You're the only person I've ever seen on, um, LinkedIn write, same job, different title, after getting a promotion. Congratulations on that. Um, so for you, it was really, I love the if not now, when? Um, and so because oftentimes you hear, oh, I saw this opportunity that had to go after it. It was a terrible time, and I quit. You're in some sense the opposite. You said, wow, this is the time, if not now, when? Which implies you had to go look for an idea. Is that what happened? And how did you find the idea?

Speaker B: Yes, um, that is what happened. And, uh, it's funny. I'll give you the full story. Uh, so I knew nothing about startups, nothing. Steve Blank was very popular at that time, but, uh, that was about all I knew. Steve Blank and Y Combinator. And so, you know, they say you should work on a problem that you really care about. And at the time, the thing I really loved was, uh, mobile and social again, 2013. And so, um, you know, designed this whole game. It was similar to Words with Friends, except with math. I'm a huge nerd, in case you haven't figured that out yet. Um, and coming from a product management background, I could figure that all out. I could spec it out. And then I decided to look at Zynga's financials. They're a public company. I was like, I'm not doing this business. It's completely dependent on Facebook. Um, the financials were not strong and I was like, wow, I don't think I want to do a mobile game anymore. So then they say that if it's a success that you're going to be doing it. For 10 or 15 years and you should do something that you really, really care about. And I also kind of went into this very pragmatically thinking. Most of the time founders ideas and product visions change over time, just very practically speaking. And so I didn't want to fall in love with a specific product idea. So I made a list of different industries that I really cared about. What could I do for the rest of my life and you know, wake up every day being excited about. And for me that is learning. Like I said already, I'm a huge nerd. I'm the kind of person that reads, you know, three books a week. I was taking a lot of online classes at the time. Um, I could do that forever and know that, you know, this is a problem that I really. Problem space that I really love. Now on the flip side, I also knew that I was never going to sell to any nonprofits and I didn't want to do anything that required. Like I'm also, you know, a greedy capitalist founder and I, for various structural reasons, I didn't want to sell into nonprofits or to school. So, um, the first iteration actually of what I was building was kind of like a yelp for online classes. You know, I was taking a lot of online classes and myself. And that product is actually fairly easy to build, um, for those, uh, any CS people. I actually built that first product in Ruby on Rails. And so my joke is there's a gem for anything, right? There's a gem for search, there's a gem for browse, there's a gem for calling. And so it's a bit of like almost a precursor of today's no code movement. You can actually assemble product pretty easily in um, Ruby on Rails if it's a pretty simple product like that one. And so, uh, you know, so I kind of built that and that was a little bit of a fun like you know, product manager, hacker project. Great. Product managers can typically pack their own things too, I think. Um, but you know, again, like, you know, I actually met Rand Fishkin from Moz around that time and you know, the, the SEO business for traffic generation is very, very hard and it's very dependent on um, you know, Google algorithms and then Seattle. Right. There's actually a lot of very successful lead gen businesses. So there's a place for mom. Um, there's a lot actually in the education space, you know, all star directories being one and kind of just like talking to those CEOs through the startup community. I quickly realized also that, you know, the business Model doesn't work unless you have like a very, very high priced item on the other side, like a senior home placement or a college, uh, online college degree. And you know, and then you run into the, the ethics of how do you, how do you do the results based on, um, kind of what the algorithm says versus who's paying you. And so, you know, net net, I was like, this business is not for me either.

Speaker A: Cindy, was this kind of while you were still on Amazon on nights and weekends, or had you left Amazon and said, I'm going to start a company, let's do this. Yelp for education. Um, and like, was Skill Jar created as an entity? Where were you in the evolution?

Speaker B: Oh, I'd already left. I gave myself, I left cold turkey, right. Because I sort of had to manage my exit. I had a team, I wanted to get them through the review cycle. Um, and that actually took a long time. I did want to exit very gracefully and I'm very glad because, you know, many of my VPs and above are we're early investors now in the company and you know, they're people I still keep in touch with today. So I feel very fortunate that kind of, I left on very, you know, satisfactory timelines for everyone involved. But Amazon is an all consuming job, at least at the time. You know, ten plus years ago, um, I worked probably as hard at Amazon as I did in the first, you know, four or five years of this company, like easily.

Speaker A: So, uh, the Onion story that uh, did you see this one? Jeff Bezos, uh, assures workers that HR is working 100 hours a week to address their concerns.

Speaker B: That sounds about right. That sounds about right. Um, so yeah, there's no time for like, ah, ideation or doing anything else. Ah, it's an all consuming job.

Speaker A: So you could, you're doing this, you're, um, working on this app, uh, and basically you pivot, quote, unquote. It sounds like you decide, no, I don't want to do this. And when was Skilljar next? Or was there another one in between?

Speaker B: There's another one in between.

Speaker C: Um,

Speaker B: so at that point I'd gotten into a accelerator called techstars and my co founder Jason, at that point was um, able to leave Amazon and join me. And so it's in the middle of this accelerator. We're like, we're not doing this anymore, but what are we going to do? And we're six weeks from demo day and so we're kind of stuck in a hard place. And so one of the things we did have out of this was this database of, you know, thousands of instructors that were teaching online. And um, these are typically like, you know, business book authors that want to like have. They wanted to launch a video course online. Um, you know, honestly, people like you, Dave, a little bit. And uh, so we just did, you know, deep customer discovery with about 100 of these folks just like no idea in mind, almost desperation. And one of the things that you know, kept coming up was they wanted to be able to, you know, deliver their own video courses themselves. And so. And um, the only way they could do that the times, like put it on YouTube, which is not exactly what they wanted to do, or kind of try to build a WordPress site and put it five WordPress plugins together. And you know, no normal person is going to do that either, right? So we're like, okay, well we can do that. And we were super scrappy about validating that concept. Like very, very scrappy, which is not necessarily the, the um, topic of this podcast, but it's an interesting, you know, evolution. And uh, and that was actually working pretty well for like you know, a year. And it's interesting there's been a lot of successful um, companies that came just after us in this space. So you know, Thinkific, which is one which is in British ah, Columbia, pretty close to us, like teachable, kind of addressing that. So a solopreneur extra small business market. But it was not the right business for us I think from a temperament standpoint. But it was going okay, right? What they say is like ramen profitable. Um, and then really around 2015 was the tipping point where we just started getting approached by a lot of. I called them real companies at the time because my background was Amazon and civil engineering. I didn't really understand the difference between Little B and Big B when it comes to B2B. And so uh, you know, companies like you know, Spotify and Autodesk and um, you know, Tableau. And then we started, you know, winning these deals. And the common thread here was these companies really needed a video based, modern, you know, commerce enabled training platform for, you know, external consumption, which, you know, their HR internal platforms were entirely unequipped to do for variety of product reasons. And we were just the closest thing in the market to it. And so this, you know, group of, you know, five or six people in Seattle, um, you know, barely any product like angel funded. We just, you know, started seeing this steady stream of, you know, real enterprise requests and winning those. And I look back on that now, I was like, that really shouldn't happen. But, so, but it was. And uh, so we're like, we're not going to do this kind of self service, what's today known as, I guess PLG anymore. We're going to go to the sales driven model. And so that's when um, you know, that's when kind of skill jar became what it is today.

Speaker A: That's awesome. Amazing story, um, unusual story in my experience. So, so I loved it. Um, let me, let me now flip over here. Uh, let me just ask Thomas before we jump into the, to the first of the five questions. Did you have any uh, questions there, Thomas?

Speaker D: Hey, I've got a whole load of uh, edtech HR tech questions but, but I'm going to save those till we get a bit uh, further along in the show. So Dave, I don't want to, I don't want to ding your flow here,

Speaker A: but I get so interested in the story of the founder that this, this is how it takes an hour. Sandy. Sandy was like, is this really going to take an hour? And I was like yeah, I haven't even started started yet. And we're 20 minutes. Um, so uh, the first of the five questions, uh, that I promised everyone I would ask. Why do you think, uh, having been a product manager and a founder, that product managers make great founders?

Speaker B: You know, I think, and I see it especially now in the enterprise world that product managers just have a natural focus on solving customer problems and uh, really understanding the customer customer and building a product to fulfill those needs. And ultimately isn't that what business success is about? Right? You've got to create long term revenue and solve real problems. So I think especially in the founder era, that's key to that kind of survival, embryonic phase. Uh, I mean I know probably sales driven founders can sell and then try to build it later and that's probably just as valid. But I think product managers just have really natural customer empathy. And I think the, the other thing is product managers can be, you know, Jill of all trades, Jack of all trades, where you know, I like to say I'm, I'm excellent at nothing, but I'm good enough at everything where, whether it's talking to customers, you know, hacking a little bit on a product, you know, uh, writing out specs, you know, actually qaing and getting things, things at the door. Um, PMs are just Swiss army knives that can fill so many holes in the early stage of a company, no matter, you know, what the gap is. And when you have very few people and very few resources Being able to plug whatever hole may emerge I think is a, is a real superpower. Um, there were many years where Jason and I were fortunate enough where we had a lot of kind, uh, of burned out Amazon engineers that just wanted to join our startup for minimum M wage. And so there's long times when we had four or five excellent senior engineers from Amazon and me. And so I was everything else, right, the webmistress, marketeer, sales, uh, onboarding support, fundraising, not to mention all the back office payroll, HR stuff. Um, it was on me

Speaker A: to activelisten and launch. Another question. The argument is hey, product managers make great founders because they're great at listening to customers and wanting to solve problems with which I agree. They're also great because they're Swiss army knives that you can do typically a broad range of things. Agree. What, I don't want to say blind spots because that's our last question, but what do you think are some of the liabilities they bring? Like for example, a friend of mine, um, was a sales oriented founder. He started a company, got to a certain size, he called me up one day and said dave, I never really understood what marketing is. Now I'm running it. It terrifies me. You know, hey, I've got the finance, I've got the hr. But, but, but, or it might be product for some people. So when you're a product founder, what is there a thing that you were afraid of? Like oh gosh, I've never run that and, and I don't have a tool in my Swiss army knife for that.

Speaker B: Oh 1000%. But at least I understand half the business. So I would say, and yeah, I don't want to like short shortchange that question later as well. But um, I do think uh, I was terrified of sales and now many years later I actually realize product management and sales are the same thing in many ways. Um, especially in the enterprise. But, but I just had this kind of visceral fear, sales as a concept. Um, also I think under um, weighted the difficulty and importance of building the go to market function. And this may be, I mean everything is situational. But I came from Amazon where essentially the go to market was completely established, right? And the saying, I've heard this joke in Seattle where Seattle in terms of startups is really good at building product and cramming it down existing distribution channels, whether that's Amazon's consumer channel, Microsoft's B2B channel. Um, I think product oriented founders can obsess about the product a bit too much and underweight the go to market aspects of what it takes to build an early stage business and then m. Similarly like, you know, the success rate on B2B is much higher than B2C for startups. And you know, my, my guess, I don't have any data I'd be interested to for somebody to do this analysis is that, you know, product founders might lean towards B2C uh, and that has a higher failure rate as well.

Speaker A: So what was inherently scary about sales? Uh, because we. That that was the most interesting thread to pull out in that answer. I love that answer. But what was scary about sales?

Speaker B: I think the um, sales from a consumer standpoint because we're all consumers, it conjures up images. There's kind of two images it conjures up for me. One is the used car salesman and the other is the person that keeps calling you at dinner and interrupting family time. And there's a, or you know, Wolf of Wall street just like, you know, a bit of a, just like a pushy, aggressive, um, that, that was my like completely unfounded and I would even say completely untrue basis of kind of the sales ethos. And that was just really scary. And then there's also something about just putting yourself out there constantly to be judged and rejected. And um, I mean I think it's hard for founders and especially female founders in general. And so like whether that's fundraising or sales. But I very quickly learned that sales, uh, is a lot more fun and rewarding than investors. But that's a whole nother story. Um, uh, and so, and then I think the, yeah, the cold calling aspects of it, the asking for things constantly, uh, it just was scary.

Speaker A: Makes sense. Makes sense.

Speaker B: I love sales now though, out of

Speaker A: curiosity, what was your views on marketing? Were you afraid of marketing? Not interested. Somewhere in the middle. What was your view?

Speaker B: In the early days, I didn't really know what marketing was. I kind of was a bit more of a blue pens marketer and uh, social media thing. And I didn't really understand what it was for two reasons. One is, you know, Amazon at the time was not really into marketing. I think like Jeff had said specifically, you know, why would we buy a TV ad, uh, when we could give, you know, a million customers more free shipping or something like this is pre Kindle. Pre, you know, pre. All the wonderful things they do with marketing now. And at uh, Stanford, I remember my marketing class, it was when the project was, you know, the kind of CPG packaging for like a roach killer. Right. It was very like brand, um cpg, consumer packaged goods pricing oriented type stuff. So I really did not even understand what marketing was. Although HubSpot, which we still use as our marketing automation platform, has a very excellent startups program which has like a 90% discount so it's basically free. So we got on HubSpot very, very. But I didn't. But one thing I did do which was actually excellent because Skilljar then and now still gets a lot of great inbound, um, leads is I made a commitment to myself to blog once a week. And so those early years of the company, like every week there'd be a blog post that went up.

Speaker A: Awesome, awesome. Okay, one day you can mail me a PDF of your roach, uh, packaging. I'd love to see what you came up with. Um, do you keep that stuff?

Speaker B: Gosh, it's probably on a old laptop in the back of my closet somewhere.

Speaker A: I still have the first four financial, uh, statement, ah, integrated spreadsheet I made in class one day. Thomas, I could dig it up for you if you want.

Speaker D: That was actually during Dave.

Speaker B: You can keep that sidetracked. That's an era which I actually have very little easy access to my own documentation because it was like computer centric but pre cloud. So I'm like, why do I have no photos from like the late 2000s? They're like on some hard drive somewhere,

Speaker A: you know, funny, funny. Uh, yeah, that's true actually. Um, okay, um, next question. Um, how has your planning process evolved through kind of three phases from the founder phase early on to let's just call it kind of the early stage startup phase to more of the scale up phase. How has things changed in terms of how you approach product planning and skill turn?

Speaker B: Yeah, so I would say in the early days it was as pretty much a lightweight process as you can get. So we just had a simple trello board, it was you know, uh, on deck, doing, done. Um, and we would just do a weekly kanban where it was just a very rapid iteration and reprioritization just based on what I was hearing from potential customers that week. And actually that's a great superpower for product founders as well is when you're talking to a customer you have this instinctive knowledge of okay, that's easy, I know we can build that in two weeks. That's hard. That's never going to happen in the time frame that the customer wants. Right. And so um, and so if we had a customer that we, I remember a customer really wanted a marketo integration and I kind of looked into it and it's more or less a JavaScript based um, very little dev uh, work required because we already built the platform in a way that allowed for JavaScript based um, tools. So I was like, okay, I know we can do this relatively quickly and so we just need to you know, make a few changes and get it done. So um, it's a very like rapid iteration cycle to you know, meet the needs of the market on a weekly monthly basis. I would say after crossing you know, a million ish ARR. At this point we've got, I don't know, a couple dozen customers, right, that are real and live and driving, you know, real usage. Then we'd hired our first product manager at that point. And so um, at that point we started to you know, get on, I would say like loose sprints. And uh, this was actually a huge, huge, huge change. Like probably one of the hardest changes from a culture mindset to go through because um, you know, we had essentially two feature squads. And so how do you actually plan, work and deliver and start to make timeline commitments? Because when you have customers and they're pushing the product in certain ways, you sort of have to be able to give them an expectation of when something's going to be done or not and maintain the service and scale. Um, and so that was a more difficult I think transition but still, still relatively, I think agile. And then now we've just brought in our first um, product executive a uh, couple months ago, which people are like whoa, you guys have been around 6 years in market, just hired your first product leader. Um, and so our next phase up is how do we plan across? We've got three different go to market segments now, like competing business goals. Right. Like new market versus something to close a large customer versus retention versus you know, customer delight versus technical scaling, um, you know, more resource trade offs and then the communication around that internally and externally gets a lot more complex too. So um, so this. Yes.

Speaker A: So you're about 150 people. You've only recently hired your first product executive. So it sounds like really for the first 0 to 150ish people, while you had some PMs you were the de facto head of PM. Is that a fair statement or no?

Speaker B: It's actually I would say my co founder more than me. And um, this may be unique to skilljar, but for a long time it was fairly obvious what to do and because we were playing catch up in the enterprise space. Right. So there are a few things that made our product really unique which was the commerce aspect, being video Native and um, our Salesforce app. Uh, but there are a lot of things, especially in the early years we did not have, for a long time we did not have any live training capabilities which is absolutely essential to kind of any scaled training, uh, program. Um, uh, we didn't have APIs, multiple single sign up protocols, security sock two. So uh, localization, um, uh, our back end tools were always like super hacky compared to our learning experience. And so that took a long time to get to a real sort of sellable state. So for a long time, especially in enterprise software, it was pretty obvious what to do, especially when you're arguably underfunded and can only take a few big bets every year. So now that we're more about scaling and acceleration, the it becomes a much more difficult question of how do we actually deploy our resources in a way that drives outcomes for our customers and ultimately the business. But my co founder was the one that actually has been more involved just because for me I've had to really focus on go to market and the fundraising and all that stuff.

Speaker A: Got it. Yeah, I'd forgotten that you had a co founder to do that. Because the question I was going to ask is would you do it any differently? On the theory that there was a high opportunity cost of you de facto running it, but the reality is you had a co founder who could do that, so you weren't excessively drawn into product, it sounds like.

Speaker B: Yeah, I mean I think there was a cost like in hindsight. Well, in hindsight I wish Skilljar had been more distributed and fully remote from day one, but that's easy to say now where everybody's distributed and so it's not really a fair comparison. But you know, we've always struggled a lot with go to market compared to, compared to product. And I think part of that has been location. So um, I wish like, you know, there had been a way or been more like normalized to hire um, to be distributed, uh, in the past.

Speaker A: So, um, would you say you've always struggled with go to market and that relates to location? Is this back to the kind of what Seattle is good at versus what Silicon Valley is good at? Or is there another dimension mentioned there

Speaker B: that that is it? And um, you know, with my entire like the. One of the most important jobs of the CEO is to build their executive team, like at every stage of the company. And you know, Seattle, despite you, everybody's like, oh, I didn't know Seattle was so underinvested. Or like why, why this or that. And um, you know the real success stories out of here have largely been, you know, bootstrapped or, or paid by customers to a point where they can raise Bay Area capital. And we're the same way. And, um, and because that early stage capital and go to market expertise is just really, really, really hard to get. And so for, for my entire executive team, you know, in the past, like, having to hire somebody that was willing to commute or relocate or be in Seattle is just a very, very small pool compared to the talent that's actually out there.

Speaker A: Interesting. Wow. Um, uh, okay, so, uh, let me reset the room real quickly. Hi, this is Dave Kellogg. You're listening to the SAS product Power Breakfast with my co host, Thomas Otter, and our special guest, Sandy Lynn, uh, co founder and CEO of Skill Jar. Um, the room is being recorded per the red ball in the room title. And uh, while we don't often get any, everyone in the room is free to ask questions. So if you, you are interested, just raise your hand and we'll get to you, uh, when we think it's an appropriate time.

Speaker D: So Dave, I'm gonna, I'm gonna derail things for a quick second and ask a, ask a question, if I may. So, Sandy, one of the things that Dave and I, we spend quite a lot of time talking about is the ideal customer. You know, this idea of when you're building a product, um, it's pretty hard to build it if you don't have an idea who you're building it for. And uh, because otherwise you end up promising things to a whole bunch of people and you end up building something that's not very clear. When you were building, when you were starting out, did you have, uh, a, did you kind of have an ideal customer profile in mind? And how do you think about, how do you think about the concept of an ideal customer in your work?

Speaker B: Yeah. So as it relates to Skilljar, right. We had that kind of inbound flow from real companies. And one of the people that was most instrumental in shaping, um, what Skilleder is today is a woman named Suzanne Ferry, who, um, was the VP of education at a company called Matbar. She was formerly leading education at Marketo, um, still a customer after acquisition by hp. And she saw Skilljar. Matbar was in a very difficult learning situation for various reasons, and she got it immediately and really spent a lot of time educating me on sort of the market and the gaps. And you know, there's a few other people like her, like Dino Nishi, uh, at Procore is another one that, you know, became a customer in 2015, still a customer today, that you know the nice thing about enterprise is when you have your first, you know, 10, 20 customers, you really get to know them and they become huge advocates. Um, Mike Zinni who is at Zendesk and um, is now at uh, uh, Outreach also two time skilledra customer was very instrumental in kind of shaping my views um, on the market. And you know I'm sure there's a lot more, more people that I'm, I'm forgetting right now.

Speaker D: Yeah, I think it's really important to find those. Um, and I, I think it's mistake that some PMs make is they think it's the company. You know, this is the ideal company, but it actually it's the, it's the person so often that, that, that has the, has the belief in you when you, sometimes when you don't have the belief in yourself yet they have a belief in your, your ideas and the vision and then, and you really, you really can learn from those people. So when you find those, you know, it's really important that you treasure them and that, that and that you uh, always uh, joke, half joke to my PMs. You should have at least, at least two customers where you know the names of their kids. Yeah.

Speaker B: Or their cats in my case.

Speaker D: They're cats.

Speaker A: Yeah.

Speaker B: Yeah. I feel uh, or in Dean's case his dogs. But um, I do feel uh, very, very, very fortunate because um, there's not that many Personas in the enterprise that had nothing and were on the upswing in um, terms of their prominence. And so this education leader in the services and success organization is one of them. Where education and success were back in 2015 it was still this kind of somewhat foreign concept. Right. Gainsight was just getting under underway and like this customer success thing. Uh, and then the existing tool set, which Thomas you know quite well was just not designed for this at all. Right. And so we just happened, we had a product that was close enough for the SMBs that kind of hit upon this nerve that um, a uh, lot of these very like great uh, education leaders were like we need this and we're going to help kind of shape your vision around it. And I'll give one example. Right. So in external training, uh, you know many uh, companies sell this, whether that's through direct sales or through um, online. And so revenue recognition is an important thing. And so for most traditional learning products, right. When they mark attendance, they actually mark it based on completion. Because if you're like you know, completing a normal college class or even an HR required, you know, harassment training or whatnot. It doesn't count until you're done. But, you know, Suzanne was like, actually, this is like, for rev rec. We actually just need to know whether somebody attended. Like, yes, I want to know how far somebody got through the content because, like, from a learning standpoint, from a business standpoint, I actually want them to be, you know, counted as there if they show up for like five seconds. Right. Because of the revreck things. And so, um, so those are like the many small. Just one example of, like, how those early customers shaped our product to be really uniquely suited for the use case that we have today.

Speaker D: So I'm going to. I've got a lot of product questions for you, but we'll do that. We'll, Sandy, we'll try and find those in the end. Or maybe we'll catch up. We'll catch them that day. But I don't want to. I don't want to hijack anymore. But Sandy and I can go down deep. Deep, uh, uh, learn tech. Learn tech hole here. So, Dave, so back to you.

Speaker A: The educational tech bonding session can begin at nine. Hey, Simon, we have an audience question. Simon, great to have you here again. And, uh, what's your question?

Speaker C: Yeah, hi, uh, this is Simon. I'm, uh, in South Africa. Um, Sandy, earlier on you talked about the fact that you did the blog for, um, Skilljar. And I was looking up and I see that there's kind of almost one every day these days. Um, so my question is, my questions are, first of all, uh, who should be responsible for that? Is it product management? Who should be responsible for that? And second of all, how important actually is it? Do you think blogs are? And by the way, uh, Thomas will know I have a vested interest in asking this question.

Speaker B: So if I understand the question, it's who should be responsible for blogging and how important is it? So I'll kind of separate this by stage of company. So, you know, in the startup phase, like, it's kind of weird because I felt like whatever deficiencies I had in marketing, for some reason, I got it in my head that they would all be solved if I at least blogged every week. So, um, and the blogs at that time, I mean, if you rewind, I mean, it may even go back to 2013, like, depending on whether somebody was kind enough to remove them from our blog yet. But the, uh, they were very product oriented because the way I thought about it was. Okay, what's this one question I'm hearing from our customers this week and I'm just gonna blog about it or like I'm just gonna blog about this new feature because I came at it from a very product standpoint. But you know, I think I just, I had it in my head and I don't even know whether it's true that you know, to you know, show up properly in Google, you needed to have a regular, you need to create content and like blog regularly. So maybe I just, you know, was influenced by HubSpot and what was going on at the time. Um, I mean these days, you know, we have um, a marketing team and um, we've got, you know, a content marketer and you know, a couple interns. And so um, especially we are having our conference in about two months and so we have a steady stream of content. Um, uh, that's kind of being deployed because of that. I think for Skill Jar it's important because we serve, you know, educators and so they really like our content. And anecdotally, um, we haven't done a lot of performance based um, analysis or maybe Michael has, but it hasn't been a core focus of yet of what um, we've been doing. But you know, part of our mission and part of who we serve is uh, best practices and content and um, we have a unique vantage point having you know, hundreds of deployments in external education. So it's, it's quite important to me. And I would also say coming from an Amazon background, I, which has a very strong writing culture which I'm very aligned with. I like things to be documented and put on the web so that they can be reused.

Speaker A: Awesome. Thanks Sandy. Thanks Simon for that question. Um, I got 15 minutes and three more to hit so I'm going to ah, defer a follow up. Simon, if you have them, we'll leave you up here on the stage. But let me plow through two of these before we open it back up. Sandy, question number three. Uh, as a CEO of the product background, how do you interact with your product team now? Um, it must be hard to pull back. If we had your product executive, what, what might they say? Uh, what's it been like?

Speaker B: Yeah, you know, if anything I think that, you know, when Nero and our new product executive, he joined in July, so it's, you know, we're less than three months in. Um, I had actually been pulled back too much and like, which is not a good thing. Um, I had to be really, uh, because then go to market and recruiting and fundraising and all those things. And so like I knew Roughly what the product team was working on. But I was not involved in like scoping in sort of the artifacts like whatsoever. And um, and actually I do need to be and just start like aligning the go to market with the product. Right. So um, I see my role as just making sure the business priorities are clear, but really Neuron should be owning the kind of product strategy and execution beneath that. And um, it actually hasn't been hard for me to pull away just because there's other areas of the business that need my, my intention much more. Now the interesting thing is like I kind of like we he and I also joke that like you can't really pull a fast one on me because normal, normal um, things that product leaders or product managers do to get their thing like prioritized. It's like I know all the tricks right, um, because there is no right answer. There's an art and a science to product management. It's a portfolio, um, strategy at the company level. And so it's hard at any one feature to say whether this is important or not. And that's actually not from a company standpoint. It's this collection of things going to accomplish our goals. So um, I also find that I don't have to spend much time on it because I can tell with very little effort like whether the function is um, how it's doing. Right. Because uh, unlike things like marketing or sales that are not my domain expertise, I really have to dig deep into my, sometimes even then I don't understand and really have to rely on my management team to, you know, to deliver what they say they're going to.

Speaker A: When you made the hire, how much of the process was about. You do know you're working for a product oriented founder? Uh, like was that, what did you, was that something you put on the table during the process or was that something you kind of just left silent and you figured they'd figured out?

Speaker B: Uh, I talked about it with different candidates, but I think it was more from. I focus a lot now when hiring my team about how their expectations of how they interact with the CEO. Um, because I found that that is a very key. It's one of the most important things. How do they like to influence and be influenced and what are their expectations of me as their quote unquote boss? And there's a problem if they actually expect me to be their boss. Like so actually one of the, one of the worst failings of I think product managers as founders is that I'm very, very bad at being directive like Product managers cannot tell engineers what to do. They can't tell support what to do. They certainly can't tell like legal attacks what to do. Right. So it's a very kind of high context, high communication, not consensus, but like you know, full transparency type of leadership style, which is my kind of natural inclination. And so um, with all my executives, but especially in more like high task oriented functions, it is very, very difficult for me to be directive and to be um, kind of employ what might be like a more say actually I'm not going to like judge any other functions but to be a very detail like task oriented CEO. And so that is something which I really try to vet out with um, not just my product leader, but all of my leaders about like what's, you know, how do they interact with um, their kind of CEO and leadership today? And especially for people that have not replaced to CEO for the first time. Because I've just kind of found over and over that it's a difficult transition, especially with my, with my style, which is extremely hands off.

Speaker A: Yeah, it's a super interesting point. Right. Because PM is all about collaboration, influence, kind of getting people to do what you want because they want to do it. Um, and that is not the way the entire company runs. I once did a blog post called, I think it was something like sales is from Mars, engineering is from Venus. And that like, like engineering wants to be reasoned with. Sales actually in my opinion wants to be told what to do and you can frustrate them by reasoning with them. Like they just like take Bruce Hill. Um, so it is interesting. So it must have been interesting for you to try and run sales because if they're waiting for you to say take this Hill and you're trying to explain something, you know, they're sitting there going confused. Like why is she explaining this to me? And uh, they're not confused.

Speaker B: It's an opportunity for negotiation is what I found.

Speaker A: That's a good point.

Speaker B: It's. I am the world's worst sales manager. I'm actually a pretty good salesperson, but I think I'm a pretty poor sales manager. And this is just one of the reasons, reasons why it's just a very different um, management, uh, and I know we're speaking of generalizations, but um, yeah, so it's been very, very hard like to you know, manage sales teams and sales leaders over the years. But um, I think we're at a scale now fortunately. And I love our Chief Revenue Officer Kathy Lord. Um, uh, so interestingly, managing product managers is also Very similar I think to managing executives in some ways once you're at scale, like people are fairly independent, you know, high degree of ownership, high degree of execute, but kind of during the startup period it was definitely difficult.

Speaker A: Interesting, super interesting. Uh, I just tweeted that blog post for anyone interested. Um, okay, number four here. You used to work at Amazon, which I'm told, as we discussed earlier, is a pretty hard place to work. Um, what are the key similarities, differences in PM from a large company or particularly Amazon, uh, to a startup?

Speaker B: Yeah, I think similarity side, you know, Amazon is a PMs are the GMs and at the time, you know, 10 years ago they would only hire post MBAs. Um, and maybe this is similar to like consumer PLG type companies today, but your product manager is responsible for growth and responsible for the performance of the business. And so um, the you know, similarities, you know, super high accountability, super high ownership, you know, buck stops here,

Speaker A: a

Speaker B: ah, lot of customer focus. You know, Amazon of course was highly data, I would just say data informed because they were not data driven but highly data informed. And then you know, stakeholder management. We touched on this, you know, just now where you know, product management, especially at a big company is about kind of herding the cats. Um, especially when you have any major initiative, you've got to not only coordinate amongst the, you know, five feature squads in your team, but the other 10 future squads and other teams that you need work too and influence them. So um, differences. I feel like every year my ability to write a coherent six pager disintegrates more and more. And I see this every year around now because we start to kick off annual planning and I look at all my previous documents and I just see the slow slide into the nonsense that comes out of my fingertips today. I look at my Amazon documents and I'm like, wow, I used to be smart, um, but actually no, I used to be really good at like you know, structure and internal communication and that the return on that in a startup is just much less versus getting results. Right. And so um, and then there's just much less like negotiation and like I used to remember like having to stack like how do I get to these four Sprint plannings, like within the same two hours to make sure my like two points here, my five points here all get done. Um, so that you know, complexity, you know, doesn't exist yet here thankfully. I'm sure it's coming. Um, and yeah, we just be a lot more agile because the cycles are faster and uh, there's Fewer dependencies.

Speaker A: Cool. Thomas. Been a while.

Speaker D: Yeah. You know, I think the one thing I'm kind of curious to go back to is um, a little bit back towards the Edtech HR tech space. I think you know what's really super interesting about, about your business is you, you found an underserved niche that you know, at first sight seemed served. You know, um, it's, you know, how did you, you know, when you go back to thinking about that, what would you do? You know, would somebody else who was like thinking about a startup, you know, how do you, how do you think about finding that niche?

Speaker B: Oh, that's such a big question Thomas, because I feel like I got really lucky. Um, but in hindsight, right, Like I think to be a really successful um, business and I mean like a venture scale unicorn decacorn, you've got to be the everything to somebody. And so I would like if I were starting a new enterprise business I would probably list out all the different Personas in the enterprise and figure out like who is massively underserved and why and then what are the structural reasons like um, and, and I would particularly look in non sales and marketing because I feel like those uh, those parts have been highly invested in and there's also like you know, arguably a uh, a you know, winner already. Like marketing automation platforms are in, you know, Salesforce or your CRM of choice are in all. Although there's plenty of startups attacking that space and various reasons. But who's serving the DevOps? There's plenty of people serving DevOps but what I'd probably do is go through the different Personas and see who's on the upswing and who's massively underserved and why. Um, I do think especially for product people, the more you can actually understand the problem emotionally and viscerally the better. Like one of the challenges for me and why we had such a slow start is because this is not a problem that I understood at all. Um, and it took a while to get there. Like when I first heard, I was at I think the second Gainsight Pulse conference ever. And um, when I first heard the concept of customer success I was like, I don't get this, like why is this a thing? Like because you turn out of Amazon every time you leave your browser, you turn out of Nordstrom every time you walk out the door. Of course customers matter when it comes to consumer or small businesses. And so this idea of there having to be like a movement to promote customer success in the enterprise, in some ways I've still a little bit smack my head and don't really get it. Um, and so that learning curve for me was pretty steep. Um, for sure.

Speaker D: Thanks.

Speaker A: I actually think we covered Most of question 5 in the other questions. But is there anything we missed there, Sandy, on the blind spots, um, that you'd have as a CEO coming from a product management background?

Speaker B: Yeah, well, I think especially now, having been out of the discipline for a long time, like I, I fully recognize that I am not a modern product management person. Right. And so for example. Right. We actually just made our hire for Director of Product Operations. And like that is not a function that even existed when m. I was in product management or maybe it did, but it was not like a thing. And so that concept of what this person is and what this role is, which is, you know, a fairly common one in product orgs these days, it's just not something I had real intuition on. Um, and uh, so yeah, I fully recognize that I'm not the modern product marketer today and neither should I be. But it is a blind spot, I think, for any CEO to feel like they're too knowledgeable about any given area because, you know, times change.

Speaker A: Yeah. I was a marketing background and CEO and I've been out of it at some point for over 15 years. And I can tell you, you know, there's a discipline that's changed. I mean a lot of things have changed, but marketing has changed dramatically between, you know, 2004 when I stopped being a CMO, uh, uh, full time to today. So it's something that's important to try to stay current as best you can and also just be aware that these things have really moved greatly out from underneath you. Um, well, we're coming up here on time. I don't know if Simon, if you had a follow up question, you're still up here. If you do that one's still on mute. So this, uh. Go ahead, you got one.

Speaker C: No, no, I was just going to say uh, it's interesting to hear someone talking about B2B because here in Africa we're not very strong on B2B. It's much more B2C and I think the um, product management in B2C and the kind of stuff that the startups are coming out here is very different. Uh, it's much more of a kind of a customer focus, um, area. But yeah, no, that was my comment. Thanks.

Speaker B: Yeah, actually that's a. I have just said maybe a closing thought too. I thought a lot about B2C versus B2B product management having done. I'm a consumer, I've done small business, and I'm doing enterprise. Right. And my relationship to my customer is so different. Like the, the B2C world is very. I call it like being a godlike view of being the product manager. You're thinking about the customer experience, but it's a bit of the law of averages and like, I'm God, so I'm going to design this product experience for you. Right? And then. But I think with enterprise, it's very different because you've really got to understand the business problems. And then your sample set is much smaller. But also every customer's is more important in that sense. And you're not God anymore, although you still kind of have to be across the entire customer base. But it's a very different customer relationship. Um, uh, and I think in some ways a more authentic one too, in B2B.

Speaker A: Awesome. Okay, well, thanks for that question, Simon. Thanks for your answer, Sandy. Did you have any closing thoughts, Sandy, before we wrap up?

Speaker B: No. This is so fun. Um, and thank you very much for having me on the show, Sandy.

Speaker D: It's awesome having you on the show. And we will. We will talk HR tech and edtech another day. I look forward to it. I should close things out with our usual, um, usual round of applause.

Speaker A: Thanks so much.