Sandi Lin

Successfully Pivoting a SaaS Business – with Sandi Lin [245]

Successfully Pivoting a SaaS Business

In this episode, I talk to Sandi Lin, the co-founder, and CEO of Skilljar, a customer training platform that helps enterprises improve product adoption and customer retention.

Sandi left her job at Amazon in 2013 to work on her startup. She had enough savings to give her a 1-year runway. Her idea was to build a Yelp for online learning. But within a few months, she realized that there wasn't a need for a product like that.

So she and her co-founder decided to pivot and build an online learning platform for course creators. Their runway was quickly getting shorter and so they had to be ruthless about prioritizing the features and building a minimum viable product (MVP) that did the job but wasn't particularly easy to use.

They were able to attract customers who paid $49 a month. But they still hadn't found product-market fit. According to Sandi, they had enough customers to be ramen profitable' and pay themselves a minimum wage.

And then something interesting happened. They started getting approached by larger companies who wanted a product to help them create training content for their customers.

Eventually, the founders realized that these were the customers they needed to focus on. So they pivoted again to an online learning platform for larger companies.

In this interview, you'll hear Sandi's story in more detail.

We also talk about how she had a really hard time raising a seed round because no one wanted to talk to her. We also discuss the multiple times she failed at hiring and building a sales team.

And how she finally realized that as a founder, she was the best person to lead sales in the early days – even though she didn't believe that she could sell.

Today, Skilljar has raised over $20 million in funding, has a team of around 100 people and is closing in on $10 million in annual recurring revenue (ARR).

It's a great story that I think you'll really enjoy.

Skilljar Team


Click to view transcript

Omer Khan 0:09
Welcome to another episode of the SaaS podcast. I'm your host, Omer Khan. And this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business. In this episode, I talked to Sandy Lin, the co-founder and CEO of Skilljar, a customer training platform that helps enterprises improve product adoption, and customer retention. Sandy left her job at Amazon in 2013 to work on her startup, she had enough savings to give her a one-year runway. Her idea was to build a Yelp for online learning. But within a few months, she realized there wasn't a need for a product like that. So she had her co-founder decide to pivot and build an online learning platform for course creators, their runway was quickly getting shorter. So they had to be ruthless about prioritizing the features and building a minimum viable product that did the job. Even though it wasn't particularly easy to use. They were able to attract customers who paid them $49 a month, but they still hadn't found product-market fit. According to Sandy, they had enough customers to be Robin profitable, and pay themselves a minimum wage. And then something interesting happens, they started getting approached by larger companies who wanted a product to help them create training content for their customers. Eventually, the founders realized that these were exactly the customers they needed to focus on. So they pivoted again to an online learning platform for these larger companies. In this interview, you'll hear Sandy's story in more detail. We'll also talk about how she had a really hard time raising a seed round because no one wanted to talk to her. We also discussed the multiple times she failed at hiring and building a sales team. And how she finally realized that as a founder, she was the best person to lead sales in the early days, even though she didn't believe that she could sell. Today skill jar has raised over $20 million in funding, has a team of around 100 people and is closing in on almost $10 million in annual recurring revenue. It's a great story, I think you'll really enjoy it. Real quick before we get started. Firstly, don't forget to grab a free copy of the SaaS Toolkit, which will tell you about the 21 essential tools that every SaaS business needs. You can download your copy by going to Secondly, if you're a new early-stage SaaS founder who needs help launching, building or growing your SaaS business, then check out SaaS Club Plus our online membership and community. Instead of wasting cycles figuring out what you need to do at each stage, you can get step by step guidance to help you take the right next steps with confidence. And you'll connect with a community of like-minded people who can support you through challenging times, and help you find solutions to your tough problems. If you want to learn more, or are ready to join, just go to Okay, let's get on with the interview. Sandy, welcome to the show.

Sandi Lin 3:32
Thanks, excited to be here.

Omer Khan 3:34
So do you have an inspiring or motivational quote to to help us get started here?

Sandi Lin 3:40
I do. My favorite quote is from Vincent van Gogh. And it is “What would life be if we had no courage to attempt anything”. And this was actually written on a card that my officemate gave me the day I was leaving Amazon to start my company. So it's a beautiful beginning of a startup journey. And I love it because it reminds me that there's no guarantees in life or startups, but let's find meaning in the journey and that attempt and be brave and have courage to attempt things.

Omer Khan 4:17
I love that. I've done close to 250 interviews, and I've never heard that one before. So that's great. Awesome. So let's talk about Skilljar. For people who aren't familiar. Can you just kind of give us the overview? What is the product do? Who is it for? And what's the big problem that you're helping to solve?

Sandi Lin 4:39
Yeah, Skilljar. We are a customer education platform, and we help companies deliver online training and certifications to their end-users. And some of you might be familiar with learning platforms from either an academic context or employee and HR context. What makes skill jar and our product different is that we are designed for the external customer and partner context. So our champions, our customer education teams, and they typically report into a professional services client solutions, customer success function. We're about 100 people based in Seattle, Washington. We're approaching about 300 customers and we primarily serve mid-sized software companies like Zora, Tableau, Slack, Asana. And, you know, prior to working with Skilljar, these companies have really struggled with bridging the gap between sales and support, you know, as much as we'd like to think so not every product is self-service for every single user, especially in the enterprise. And yet companies are still struggling with with, you know, approaches other than just hiring more customer success managers or support reps to essentially deliver one on one training.

Omer Khan 6:08
So Skilljar would be used by somebody like Asana to help train and educate their customers?

Sandi Lin 6:16
Correct. So Asana, for example, they actually it's open to the public. So anyone can go to Asana Academy, which I believe is that Academy dot Asana calm and take courses about project management and how to use Asana product more successfully, and that's actually delivered through skill jar under the covers.

Omer Khan 6:36
Got it. So how did you come up with the idea for this business?

Sandi Lin 6:40
Well, it's a bit of a long story, but I hear this as a longer podcast, but I was pretty aware in starting a company that my first idea would almost certainly be wrong. And so I did go into the process with a lot of humility, and even so I was humbled even further. I call actually call the first two years of Skilljar are my two failed startups. I wish I could have been, you know, sitting in around Amazon dreaming up of this vision and executing exactly towards it. But that's not what actually happened. So, you know, initially, I think, especially in 2013, when I started this company, a lot of the advice around lean startup, it was to solve a problem that you have for yourself. And at the time, I was taking a lot of online classes myself to brush up on my own programming skills, I have an engineering background, and I was having a lot of difficulty finding the appropriate quality and skill level of content. So came up with the idea of a Yelp for online learning, built a prototype and that type of product is actually pretty easy to build, you know, got traffic and did what I thought was quote, unquote, customer discovery and even generated a tiny bit of affiliate revenue from conversions. But I soon realized that, you know, doing an SEO driven business was not for me. And in this market, in the online learning market, there's just not enough value being generated on the other side as opposed to businesses like mortgages or senior living facilities. And fortunately, in Seattle, there's a lot of demand gen entrepreneurs. And, you know, I quickly realized that that was not the business that we that I wanted to do. And at that point, I thought it would be a hard reset. Like something I've had to go out of online learning into something else entirely, but I decided to at least, you know, do some interviewing of the instructors on that Yelp platform to see if I could salvage something. And I did not have any hypothesis, nor idea, just purely open-ended discovery, digging for pain. And, you know, there are a couple things that emerge. And I think actually did a research survey of you know about the 50 interviews I did to see, you know whether there was a clear pattern. And what I did learn was that many of these instructors that had been part of our kind of Yelp concept, they also needed a learning platform to deliver their training without having to sell it to, you know, or Udemy. And so I thought, well, how can I prove this in say, 30 to 60 days, that's a ton of product and my co-founder, and I decided we would just manually do everything on the back end, and we had to believe the market had enough pain that people would just jump through all kinds of hoops to use the product, and I'm happy to talk about that more if it's of interest, but

Omer Khan 9:49
Yeah, no, totally. I would say a few questions like so when you left Amazon was that in 2013? Yes. And so this was this product. This this kind of Yelp for online learning was that also called Skilljar, or was it called something else?

Sandi Lin 10:05
It was called Everpath.

Omer Khan 10:07
Okay. And then so for how long? Did you work on that idea? Before you decided that you needed to, I guess, pivot? And also did you and your co-founder raise money at that time? Or were you sort of self-funding sort of bootstrapping the business at that time?

Sandi Lin 10:26
Yes, we were self-funding. And my co-founder actually hadn't joined at that point. So I probably spent about three months building that first product. In some ways, it was actually really good because it was a way to exercise my very rusty programming skills and get back into that game. And actually, in deciding to shut that down at that point, my co-founder, was able to come on, but we had no idea so we really went through it. new customer discovery process together. We hadn't raised any money at this point.

Omer Khan 11:04
Okay, cool. And then did you say like, how long did you work on that business before you pivoted

Sandi Lin 11:08
about three months? And in hindsight, I should probably never have started. But I didn't know what I didn't know those days.

Omer Khan 11:15
Okay. And then when you went out and you said, I thought I had done the customer discovery stuff, but it sounds like maybe you felt you hadn't. Then when you went out and you started talking to these instructors? Did you do anything differently this time?

Sandi Lin 11:35
Yes. So I would say the first time I suffered from, you know, it's called like the free ice cream problem or the social network for pet owners problem, where the idea is if you ask someone, hey, do you want free ice cream? Everybody's going to say yes. And so or if you ask pet owners, Hey, would you be interested in joining a social network where you can meet other pet owners, like every usually everybody says yes, but it doesn't mean that they would actually do it or that there's enough pain in their lives. Or even the third step, which is, you know, a pivot, I haven't even got to yet but monetization. So in the beginning, it's like, can I just build a product that people actually use and adopt? And so, you know, the second round, because, you know, I've given myself actually a year to go without a salary. And I'm something like six months in at this point. So the second round, you know, I, we honestly did not have an idea. And it was like, we were starting over from scratch. All we had was this essentially database that I built of people teaching classes online. So almost out of last ditch attempt, were like, hey, let's do a call down and see what pain people have. And we literally had no idea going into that process. And so after, you know, roughly 50 conversations, you know, there were three pain points that are more And I still remember what they were like one of them was video editing, video editing is very difficult. People would say for, you know, one hour video, it probably takes me 40 hours of editing, you probably have some sympathy being in the podcasting space. Another one was, you know, marketing, of course, everybody wants to figure out how to get more customers to their door in an efficient way. And then the third was this, hey, you know, I have a mailing list of 40,000 people already and I'm releasing this book, and I really want to do this video course. But I don't have a way to actually distribute that and kind of own the intellectual property as well as the revenue from this. And so there were three, those three pain points emerged after all these interviews. And so the survey that you know, I talked about was, Jason, my co-founder and I were like, well, at the time actually, I've after the interviews, it's still wasn't clear. We probably heard a third, a third, a third from a pain point perspective, so we decided, let's actually survey everyone, we talked to you again, and design that survey to fail, in a sense, and I can't remember exactly what was on that survey, but it was, you know, rank order, which of these problems is most significant from you? And, you know, how much would you be willing to pay theoretically for a product that does X, Y, and Z. And I thought this is going to be like, I'm gonna end up with a third, a third, a third, again, I and you know, I'm kind of in not the best mental state at this point, because I've just developed an emotional attachment to the ideas that you're working on. And it's been hard to shelve that first product. And also, like, I was feeling desperate to get some kind of idea. So I was like, Oh, it's wasn't clear. Any of these is actually a huge opportunity with enough pain, and we're just going to get a third, a third, a third, but actually, it was extremely clear that people were moving Interested In This learning platform concept and that they were willing to pay for it. So that's where that gave us the call. And I was honestly shocked. And that's what gave us the confidence to start building our MVP there.

Omer Khan 15:11
So you first reached out to these people, and did kind of like what, like a phone interview, and then you use the survey as a follow up to try and sort of, I guess, validate or clarify, where to go? Is that kind of what you did?

Sandi Lin 15:28
That's correct. That's correct. Yeah,

Omer Khan 15:29
I think that's really interesting. And it's it, there's an art to putting together surveys, which, you know, I always find out like the hard way, like, you know, part of what we do here is like, I have a private membership community called SaaS Club Plus. And so it's made up of like an early-stage SaaS founders, and once they're in the membership, you know, they get access to content, you know, community forum. We do like live events, you know, like webinar type stuff and One, I totally get the video editing piece because creating like a 10-minute video lesson. Oh my god, it's like the amount of time it takes to do that, to create it to record it to edit it to public, it's like it really is like, Did I really spend that much time to create a piece of content, which is 10 minutes. And then the other thing I've also personally experienced is like, doing surveys where I go out to the community and I say, Okay, what do you like? And you know, the whole idea being like, can I learn from what people find the most valuable? And do it, you know, double down and do better there. And I had the exact same experience where, you know, the sort of three sections are on content community and sort of live events. It came back like a third, a third, a third. And it was like, Okay, well, what what do you do here? Right, it's like so basically, it's not telling me anything?

Sandi Lin 16:53

Omer Khan 16:54
So so I'm kind of curious like when you said like designed to fail, even if you can't remember the specifics, like How are you trying to get it to fail? And, and sort of like, what's the lesson that you know, someone like me or anybody listening who's thinking about surveys could learn from that?

Sandi Lin 17:08
Yeah. So, you know, going into that survey, I will say that I had a strong bias towards hoping that the learning platform for win because I did not see a you can identify a problem, but it doesn't mean that there's going to be a solution. And even if there is that it's something that is a founder, solution fit founder market fit. And so and also, it wasn't clear that there was a clear signal that the learning platform would win. And so you know, randomized questions, randomized answers, stack rank, and even people in who in the interviews had told us didn't even mention that this was a problem. We're ranking this as their top problem. So that's the part where, I guess it was designed to fail and that we had no real indication that the learning platform would win. And then we set up the survey in a randomized way. And there were enough people responding to it that didn't even mention it in the interview that I was shocked, were raking this as their number one problem that they were willing to pay for a solution for. So even more than a video editing or the, you know, the marketing problems. So, yeah, I think it's easy to design a survey to tell you what you want to hear.

Omer Khan 18:28
That's interesting. And and I would add to that and say, I think it's, it's also easy to go into customer interviews and ask questions that helps you validate your idea. If you want it to be validated. Yes, it's a lot harder to you know, I think someone once said to me, like, Don't, don't kind of validate your idea and see if you can, you know, invalidate it or actually talk them out of the idea that that you want to go and build and if you can't do that, then it means you're onto something really worthwhile.

Sandi Lin 18:56
Yes. And then even that, I would say like our customer despite customer discovery, just gave us enough confidence to continue investing in the idea. But it's a good question to ask at each milestone, whatever that is on the product-market fit side or on the monetization side, because nothing is real until your customer, your target customer either uses or pays for your product, depending on the business model. And my first job was in transportation planning. And so this is a very understood concept in transportation because for example, when you're trying to figure out where to put a new subway station, you'll typically go and stand in that area and ask people walking by like, you know, if there were a subway station here, would you use it and that kind of thing. And there's actually statistical models that correct for what people will say versus what they do. It's called stated versus revealed preference. And so even in this survey, you know, I always knew that people are saying this, it doesn't mean people will do it, but it was enough to say let's go try building something minimal that will prove that people will use it. And then after people will use it, the question is, will they pay for it? If that's part of the business model?

Omer Khan 20:10

Sandi Lin 20:10
And then after that happens, you have to figure out well, is that scalable? Or will enough people use it and pay for it? And so there's many versions of, I think, always throughout a company, and we're still, in some ways doing many versions of that with, you know, various customer segments.

Omer Khan 20:25
Yeah. Yeah, I bet. So you've given yourself a one-year runway after Amazon. And it sounds like I think you said, by the time you were done with these interviews and survey you had about, what, six months left.

Sandi Lin 20:40
I think by the time we were done with these surveys, I had about four months left.

Omer Khan 20:47
Nothing like a little bit of added pressure here. Okay. And so what did the second iteration or the second version of your startup look like?

Sandi Lin 20:57
Yeah, so, so this was like, you know, Jason and I are like, wow, that's a lot of product to build a learning platform. So what is the absolute minimum we can do to prove whether it will work in 30 to 60 days, because we had a belief that if we're going to work on something that's going to become huge, that the market must have enough pain that people will jump through all kinds of hoops to use it. And so, on the sort of learning platform side, we decided okay, to prove this, all we need to show is that if this is a video with user book author, video course example, if this video course exists, that the author will be able to launch it to their audience, and people will buy it and consume the content. And it doesn't matter that the author actually sent us his files on the thumb drive, or that we're cutting them checks every two weeks to pay them the money like all kinds of hoops. There's no administrative tools to manage the course or the content. You can only have one course not two courses. You can only have videos not PDFs or quizzes, or any of that stuff. So we really stripped that down. And because of that, we were able to launch, you know, a proof of concept with a handful of, you know, those early survey respondents. That's the other advantage of a survey, you get to understand who your alpha group is going to be. And they were able to watch something, you know, within 60 days. And so, so that was the second product concept that that I was working on. And, you know, for the next year, we continue to get more signals from the market more people signing up slowly, we began building self-service tools, we began building content management and more and more instructors were, you know, signing up and launching, launching courses of scale jar. So that next year was, you know, very organic in terms of how we continue building on the product.

Omer Khan 22:50
Yeah, so I was gonna say one, like, it sounds like you guys were very ruthless about what you were going to build in the future. product that in the next 30, 60 days, we need to prove this concept. And there's a whole bunch of stuff that we know we should have. Because that's how we're gonna make our product easy to use. But we're not gonna put that in there. And as you said, you know, people are gonna have to jump through a whole bunch of hoops to, to use it. And in many ways, that's a great way of again, validating whether there is a real need for this in terms of are people willing to go through some level of pain to solve this problem that they have? But I'm also curious, it's kind of a hypothetical question. But I also wonder if this was the product that you were building from day one, when you left Amazon and you still had a year's runway, would you have maybe spent more time trying to build in more features and make it easier to use like what was the time constraint, a big factor in forcing you guys to really kind of think much harder about what absolutely needed to go in the product?

Sandi Lin 24:12
I think time constraints are critical when you're first starting a company, and my backgrounds in product management, so you might, so parts of me see all the holes and I want to lay out a three-year roadmap and make this amazing thing. But the other part of the product management hat is exactly what you said. Absolutely ruthless prioritization. And the reality is most like good products will die in darkness. It's easier to build a product than to market and distribute it and finding the and tapping into the market demand is usually the key for any startup, like consumer businesses. You know, what I hear is a lot of people, the key to scaling consumer businesses is apparently Facebook ads and this is not my domain expertise. So, you know, please if you're listening, don't just assume what I'm saying is true, but I hear a lot of people actually just test all their consumer business ideas just on Facebook testing. And you know, there's an example actually a waiter from Skilljar when we pivoted to the enterprise or to sales-driven motions, you know, we heard a lot about the need for a Salesforce integration, but we didn't really know exactly what that meant or how many people use it. So you know, I just put up a landing page on our website that said, Skilljar for Salesforce and you know, made an educated guess at you know, three or four bullet points to describe what my men and said, for more information, you know, sign up here, and then people started signing up. And so then I called them and understood more so there's there's various ways to test things without actually building it. building things is the most costly because it takes time and usually it's not necessary to prove whether an idea will work or not.

Omer Khan 26:02
Okay, so you've sort of come up with the next idea. And you sort of built that and I guess, got some level of validation because you continue to run with that idea into sort of year two of the business. Were you generating enough revenue to keep going or was was sort of raising money at that point, something that you started to do?

Sandi Lin 26:28
We were what I would call ramen profitable. I think that comes from Y Combinator. So, you know, we're like three or four people, I think we're paying ourselves minimum wage or contractor wage or something. So we were generating a little bit of revenue, but not enough to say, you know, scale the business or spend any money on marketing or hire sales reps, and that's when we went to what we've so we had raised our Angel round during that first pivot and that's a whole another story, I probably didn't, you know, deserve it based on our traction at the time. And so partly because we were, this actually ties into kind of a second pivot of, you know, in 2015. So kind of towards the end of that second year, you know, we just started, we knew that this, you know, our initial target customer, which was that kind of solo instructor and book author, that there was product pain there, and that we were sort of breakeven to profitable as a small business. But at the same time, we started getting a lot of inbound interest from much larger companies like even fortune 500 companies that wanted to use the platform to educate their external customers and partners. I mean, same product, you know, video-based training, often with a commerce component, you know, very brandable scalable technology. And, you know, we just started winning Fortune 500 deals and we were tiny company, Angel funded. And so we're like, we should start doing more of that, and not this, you know, $49 a month thing. And, and so partly knowing we were shifting into a sales-driven model, which is really that second pivot of going up market was when I went out to raise the seed round, knowing that we'd have to invest in a sales team.

Omer Khan 28:23
Okay, so I want to talk about the seed round, because I know there was some challenges there. Yeah. But before we we get into that, I'm curious as you started getting these larger companies reaching out to you, I mean, you weren't the only, you know, online learning platform around at the time. So when you talk to these companies, Was this something you were hearing from them that why they were coming to you, you know, versus like trying some other product or maybe working with a company that was kind of more established or had a bigger team like what was it that was attracting them to you when you talk to some of these customers?

Sandi Lin 29:05
So at the time 2015. And I would say it's still the case today that from a learning platform perspective, and when you're talking about like a white-labeled for corporate purposes, the best option other than Skilljar is typically, like an HR learning platform. And on a feature basis, there's a ton of limitations like one of them just being does this person have to be in your HR system sometimes. And so those first say like 10, no big customers we've had, they all were in severe technical pain. They had done things like launched a $50 million free training initiative and their system had died like the first day and they were looking for a learning platform that was designed for an external audience and that was built with strong tactical foundations and, and suitable for an enterprise business model. And the fact that we were video-based and that we had commerce builtin because a lot of companies do charge for customer education and training in some way. We're also sometimes necessary. So there are a lot of learning platforms out there, but not really for companies or that are geared towards external audiences. And so I think we just had enough of the right words on our website and our blog that these companies found us

Omer Khan 30:38
And you weren't like in terms of your positioning or messaging. on your website, you weren't kind of deliberately targeting those companies at that point, right?

Sandi Lin 30:50
No, our website, I was the web-mistress. It was not good.

Omer Khan 30:56
Okay, so let's talk about so so next. Okay, you see this opportunity. Okay, so this is like the second pivot moving from, as you said, focusing on sort of instructors who you're paying like 49 bucks a month to these larger companies. And then you, you decided you were going to go and raise a seed round. So, like, how did that go?

Sandi Lin 31:20
Gosh, that was probably, oh, there's so many hard times in the first three years of a startup, or let's face it anytime in the startup, but that was probably one of the hardest. So, you know, at this point, we're, you know, we're still paying ourselves minimum wage, you know, building our own furniture, but we're starting to sign fortune 500 companies and there's an increasing number of interesting companies just finding us and talking to us and so I decided that the time was right, that we needed to raise a little bit of money so that we could, you know, hire some what I thought were real sales-people at the time and, you know, take business sitting next level invest in more sort of enterprise-ready features, like API's and single sign-on and that kind of thing. And so, you know, being in Seattle, Seattle is a tough there's not a lot of early-stage capital here. And I had an amazing angel investor community. And, you know, did all the right things made a list of target seed funds, you know, largely in the Bay Area, some in Seattle, the probably five Seattle in the 50 in the Bay Area, and you know, got warm introductions and it was just so hard to even get meetings and this is yeah, 2015 so seed investing is hot. And it was like being like, even with the most of the warmest introduction and just people not even wanting to take a meeting with me over and over. was just really, really hard because I know at this point that we are we are onto something, the deals we were winning and the deals the interest we were getting from the market. And our ability to meet that demand without Like I said, I was not the world's best salesperson at this point. But when you start signing six-figure deals per year, you know, you know you're onto something and and inbound demand as well, but then to, you know, go out to the seed investor market and not get meetings or if I did get meetings, I would ask questions like, why is this different from YouTube or like questions that were totally, like not understanding what you're doing? That was really, really hard. And, you know, our first employees and my co-founder just happened to be people with families with children, and I knew that they were taking, you know, huge salary cuts versus what they could be earning at Amazon, to be working on this. And so, you know, I did feel a lot of pressure because we had something to lose. You know, we had amazing customers that had taken huge risks within their own companies to bet on sculptor I had, you know, a team that was making temporary sent their market salary probably, and, you know, some angel investors, but I think they had come into it, knowing the risk and, and then most importantly, the opportunity to make a big impact on the world. And then here I am needing to raise money and not even able to get meetings with people that I have very warm connections to. So, that was a real struggle for, you know, 90 days, 180 days. And this is all in the lens of also still continuing to, like, do all the business functions for this company, because, you know, it was only engineers and myself and so, payroll, responding to sales, people signing up for demos, customer onboarding ourselves, you know, customer support. I was doing all of that at the same time. It's trying to raise money, so it was a lot.

Omer Khan 34:50
And were you able to eventually raise a seed round?

Sandi Lin 34:53
Yes. So we raised a 2.6 million seed round from a local investor. Stir here in Seattle, Trilogy Equity Partners, they're amazing. And probably they were actually not on my radar initially, because I was under the mistaken impression that they only invested in mobile solutions. But it actually all worked out for the best, which usually is what happens on startups

Omer Khan 35:21
Awesome. And then so you've got this money. And I think sort of part of the plan was, they're going to use this and you're going to start hiring salespeople, and they're going to go out and start selling to all these companies. And then everything is going to be great.

Sandi Lin 35:35
That's exactly what I thought.

Omer Khan 35:37
Yeah. And it didn't quite work out like that. So tell me a little bit of like, what was the sort of the, your experience with trying to build a sales team?

Sandi Lin 35:47
I have failed so many times at building a sales team. So as context, my background is in engineering and product management. I like working in code, not people. All the time. And I sort of had this fear. I mean, I still do, to some extent this fear of sales. And so I thought that hiring a sales rep and I did not understand all the different flavors of sales out there. But if I hire salespeople, I teach them the product, they would be able to sell it, and everything would be magic. And that is not the case. I think, for any founder, you're just gonna have to sell all of your first deals for at least in SaaS, like a million dollars of era, or nobody can do it except for the founders. And then after that, like you're still will still have to be heavily involved in sales, probably 5 million of ARR. Because it's just impossible to replicate the knowledge of the customer and a market and with a product doesn't, doesn't does not do and matching that to the customer's problem.

Omer Khan 36:55
Yeah, and then you're no one is going to be as passionate or as big advocate for the product as you as the founder. Yes. And I think that's that's kind of can be sort of the challenging piece as well. So how many sales-people did you initially hire? And I think also you you spent some time trying to kind of get sales leadership in place as well. Right.

Sandi Lin 37:16
Yeah, I mean, you know, we went from one to three or a handful at various times. And I think the tricky thing about hiring sales-people early is that a salesperson generally needs to know what they're selling and how to sell it. And unless you're extraordinary lucky most sale and maybe this is a startup fit issue, but it's very hard to put a sales rep into a position where they have to like figure out a lot of the messaging and the target ICP and the what the deck looks like and learn the product and learn the use cases and then you stack that also against not having a brand or having the resources of a larger company. And that is very very hard. And so I kept hiring reps and sales management or leaders thinking that they would be able to figure it out better than I could. And I gave him lots of room to do so because the other interesting thing about sales reps is they like to have a lot of ownership over what they're doing. And so I was like, okay, okay, you got it. Let me just tell you about the product when you need me. And that just did not work at all.

Omer Khan 38:24
And like, where did it end up? Like, do you have a sales team today? And, you know, how big is it?

Sandi Lin 38:32
Yeah, so we're in a great place. I actually love working with a sales team now. So I'm going to fast forward a few years a few sort of failed building go to market attempts. So our amazing sales leader Ray Carol joined in October last year, so October 2019. And prior to that, I had actually run the sales team directly for about, you know, like maybe four to six months before that. So we have nine account executives and a similar number of sales development representatives, which is the top of the funnel when it comes to selling. And I actually I was so afraid and intimidated by it and the sales team thinks is hilarious and I actually really loved it. And you know Skilljar totally different scale now you know, we're upper seven digits of ARR again you have blue-chip customers and a lot more resources in the company. So I get that it's like a totally different experience when we were like 200k ARR and had no idea what's going on. But yeah, our team is really humming now we just put together to sort of record quarters back to back and are really on fire for the upcoming year.

Omer Khan 39:48
And I think from what I'm hearing as well is you realized that you're probably better at selling then you thought you were

Sandi Lin 39:59
I'm so much better at selling than I thought I was I had the impression mistakenly, at least at Skilljar that sales is a bit of a. I don't know, nobody says that they're so excited to talk to a sales rep because they think we're going to get, you know, the slick sort of used car salesman pull something over your eyes type of stuff, right? And, but what I love about our sales team, and what true sort of consultative selling is, is, understand what the customer's problem is, and see if there's a match for the product that we're offering. And of course, as a product-oriented founder and with amazing customers, I fully believe that we are the best solution for customer education in the world. And with that type of confidence. It's almost a moral imperative. I'm sort of groaning as I think that for you know if that we truly solve the customer's problem to be able to have that conversation. And if we're not the best solution, I don't have any problems saying we're not the best solution. And maybe here's some other things you should look at. So I view it as problem-solving and I love that I love problem-solving.

Omer Khan 41:12
Yeah, I think that's, that's a great way to look at it. And I talked to a lot of early-stage founders who are in a similar place, and they sort of feel like, either they don't think they can sell the product or that they are going to enjoy doing that. And a lot of the times it's because we have this kind of preconception or the wrong kind of preconception of like what we think sales is. And when you sort of frame it in your mind as exactly how you described it, which is, I just want to learn more about what problems my prospective customers have. And if I can help solve them great. I'll try to do that. And if not, then, you know, we just say goodbye. It's not like I have to go there. And, and force them to use the product or something like that. I think that's a really powerful shift in the way you sort of think about sales that you don't even think about it sales anymore, as you said, it's like, I'm just I just want to help people solve problems.

Sandi Lin 42:13

Omer Khan 42:15
So you've been on this journey for over seven years. And so this is the third sort of iteration of the business. And now things are really starting to click, you've got, you know, a team of about 100 people you said, you know, in terms of ARR, you're kind of, you know, I guess closing it on like 10 million ARR type thing. And you've also raised 20 million now in in funding. So that's a world's apart from, you know, where, where you were, when you were sort of built this sort of the the Yelp of kind of online learning. If you could go back and give yourself any advice back in 2013, what would you tell yourself?

Sandi Lin 43:07
Oh, gosh, I would tell myself that it will get better and you can do this. It took me a long time to believe in myself. I think in this process the first few months and years were so hard. And especially, you know, I've gone to elite schools I've had, you know, prestigious jobs and to be like, the emotional journey of going of starting a company is so hard. So I would tell myself, you know, first it gets better. And also, you can do this and your trust your ability to problem solve and figure it out as best you can.

Omer Khan 43:56
I think that's great advice for your previous self and for other people. listening. And I think in many ways, you know, there's there's a lot about the, you know, the sort of the execution part in terms of the idea, and how you go out there and talking to customers, and you know, how you kind of build the business. But in many ways, just as important, is that mental, I don't know, equipment situation or whatever, right. It's just having not just the the grit and the determination to keep going and to deal with all of the the challenges you're going to face along the way. But also, learning to believe in yourself.

Sandi Lin 44:41
Yes, we are our own worst enemies, and we are the only thing limiting what each of us can do. It's I think the mental game is so important.

Omer Khan 44:52
All right, I think we should wrap up and move on to the lightning round. So I'm gonna ask you seven quick-fire questions? You ready?

Sandi Lin 45:02

Omer Khan 45:03
Okay, great. What's the best piece of business advice you've ever received?

Sandi Lin 45:07
Treat others with respect and integrity because you never know who or how might be helpful to you down the road.

Omer Khan 45:16
What book would you recommend to our audience and why?

Sandi Lin 45:19
I love “Shoe Dog” by Phil Knight, the founder of Nike. It is a raw and humble story, and will raise the spirits of any entrepreneur.

Omer Khan 45:29
What's one attribute or characteristic in your mind of a successful founder?

Sandi Lin 45:34
Grit. You've got to be able to run through walls constantly, and it's going to hurt and you're going to come back for more.

Omer Khan 45:42
What's your favorite personal productivity tool or habit?

Sandi Lin 45:45
Definitely sleep. I really organize my life to sleep at least eight hours every night. It is one of the most healthy things that you can do for yourself and I definitely recommend a book called “Why We Sleep” by Matthew Walker. To learn more.

Omer Khan 46:01
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Sandi Lin 46:06
Really interested in healthcare tech, I'd love to solve the problem of prescription drug delivery. There's still way too much pain in that process as well as the application of AI to medical imaging and radiography.

Omer Khan 46:21
What's an interesting or fun fact about you that most people don't know?

Sandi Lin 46:24
I really like phone games. I'm a level 40 Pokemon GO player and I'm still grinding it out and wizards unite. I think I'm level 43 right now.

Omer Khan 46:35
And finally, what's one of your most important passions outside of your work?

Sandi Lin 46:38
Spending time with my three lovely nieces?

Omer Khan 46:42
Awesome. So if people want to find out more about Skilljar, they can go to And if folks want to get in touch with you, what's the best way for them to do that?

Sandi Lin 46:55
Email, it's sindy[at]skilljar[dot]com and I spell my name with an I so it's s-i-n-d-i [at] skilljar [dot] com.

Omer Khan 47:03
Awesome. Sandy, thank you for for joining me. Thank you for sharing your story. This was, you know, one of those conversations that I think I would have been happy to keep going for another hour. I just kind of feel like this so much we could talk about I, I really appreciate your openness and transparency. And I think your story is gonna resonate and inspire a lot of people out there. So thank you for taking the time and congratulations on on kind of having survived through that roller coaster ride over the last seven years. I'm sure you know, there's still plenty of challenges ahead. But that's that on its own is a huge accomplishment.

Sandi Lin 47:44
Thank you. It's been really fun.

Omer Khan 47:45
Awesome, I wish you all the best. Cheers.

Sandi Lin 47:48

Omer Khan 47:49
All right. Thanks for listening. I really hope you enjoy the interview. You can get to the show notes as usual by going to, where you'll find a summary of this episode and link All the resources we discussed. If you enjoyed the episode then please consider subscribing. And if you're in a good mood, consider leaving a rating and review to show your support. Thanks for listening. Until next time, take care.

Book Recommendation

The Show Notes