This week we had the opportunity to chat with Adda Birnir, Founder and CEO of Skillcrush. Skillcrush is a leading online education platform specifically orientated towards women in the tech space, with courses in programming, design and much more. A fully distributed team from the beginning, Adda had some great insights into the scaling a remote team, culture and what it takes to build a business! We covered a variety of other topics including leading a mission driven business, how to hire the right people, technical education and much much more.

Adda has an interesting back story from beginning her entrepreneurial adventure in the depths of the 2009 great recession, to building an original product (hint, it’s probably not what you think) and evolving the Skillcrush community to a team of 20+ people helping thousands of students find careers in the tech space. What struck me most about Adda is her passion for the day to day of building a business and her love of constant improvement. I hope you enjoy this half as much as I did!

Be sure to check out Skillcrush’s Ultimate Guide to Getting a Remote Job You Love handbook, found here: https://skillcrush.com/go-remote

Also, check out skillcrush.com and follow Adda on twitter at @addabjork

[00:00:00] Matt H: Hello, everyone. My name is Matt Hollingsworth, and welcome to another episode of the Remote Show where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.

[00:00:24] My guest on today's show is Adda Birnir. Adda is the founder and CEO of Skillcrush, an online tech education company with the mission to empower women to learn the digital skills they need to enter high-paying and flexible careers. Adda is passionate about making tech and flexible careers more accessible and inclusive to all. She was named one of the 30 Most Important Women in Tech by Business Insider, and she has served over 18,000 students from 127 countries with Skillcrush. Learn more about her work at skillcrush.com.

[00:00:54] So, Adda, thanks for coming on the podcast. We really appreciate it.

[00:00:58] Adda Birnir: Thanks for having me.

[00:00:59] Matt H: It's great.

[00:01:00] Why don't we start with just a bit of background about yourself? Tell us a little bit about your background and how you got started with Skillcrush.

[00:01:08] Adda Birnir: Yeah, my background is that I was a liberal arts major in college. One of the most common questions I get is whether I have a computer science degree, and the answer is a resounding no. I started my career off working in the world of photography. I was working as a photo assistant and then went into photo editing. That is actually what led me into tech because I was working in an online magazine. This is 2008, 2009. Tech was starting to become really big in New York, and I thought it was interesting. I wanted to learn more about it and started poking around a little bit.

[00:01:44] Then, the recession hit and I managed to survive one round of layoffs at the online magazine I was at, but I got nervous and so I took a new job at a digital agency thinking that the agency world was going to be safer. Which, in retrospect, I'm not sure where I got that idea.

[00:02:00] I knew where I was wasn't very safe, so I figured anywhere but there was going to be better. I got that job, and then within seven weeks, I got laid off along with a third of the company at that agency.

[00:02:10] Matt H: Wow.

[00:02:10] Adda Birnir: That was tough, and it was 2009, so it was not a good time to be out there looking for a job. New York especially, it felt like you were just watching all these industries crumble around you. I had been thinking about really digging in and learning more technical skills at that point and that was just the kick in the ass that I needed. I had a lot of time on my hands and felt like applying to random Craigslist jobs postings has a real diminishing returns and decided to take that time to try to teach myself some more technical skill.

[00:02:43] That process was both frustrating because there weren't, at the time, a lot of options available to you. I literally was just walking into the Barnes & Noble and buying a computer science book and trying to make sense of it. But, at the same time, I found that the payoff was pretty

[00:03:00] immediate for me. Pretty quickly, I was able to start freelancing. I was a freelance developer doing small projects for small businesses, and then I was able to land a more technical production job and then keep freelancing. It was a very, very different experience than what I had had working in photography and media, which felt like you were beating your head against a wall, so that was really awesome.

[00:03:21] Then, a couple years later, I found myself having started my own design agency, design development agency, with a friend of mine, and we were doing all these really fun projects and stuff like that and really enjoying it. But, we were really frustrated because we were two women and there really were not very many other women working in tech. As a side project, we started this thing that we called the Digital Divas. The thinking there was we were trying to talk about technology and technical skills.

[00:03:51] I don't know if we really thought about it in this way at the time, but really start to educate people about technical skills in a way that felt more representative to

[00:04:00] our own experience of it and that felt like it talked about technology in a more accessible and more fun and practical way, in particular, in a way that would appeal more to women. When we started that, we really did not see it at all as a business. It was totally a passion project on the side we were just doing because we cared.

[00:04:20] Slowly, over time, and this is one of my first major lessons in market validation, it was the only thing we were doing. We had a couple of different pots going, and it was really the only thing that anyone would ever respond to and get excited about. Slowly, over time, we would meet people and started to learn more about how to really start more of a traditional startup business where you're not doing services, you're producing a product. Over time, basically, this project that was this total side project for us ended up evolving into this germ of an idea for an actual business, which was Skillcrush.

[00:04:53] Matt H: Wow. You started that in 2009 or 2010?

[00:04:56] Adda Birnir: Skillcrush itself we started in 2012.

[00:04:58] Matt H: Oh, 2012. Okay.

[00:05:00] You mentioned you started out with a passion project on the side. What was the response typically that you got from women in tech or those that wanted to get into it? What was the response typically from the people that you were interacting with?

[00:05:10] Adda Birnir: It's an interesting question. I think it was just one of those things. We would find ourselves in different circles. There weren't a lot of instances where we were necessarily pitching this project or talking about this project to women who were already in tech, largely because it's hard to come by. More than that, it was often we were in startup-y circles, so it was a lot of people who were all interested in the startup world and were trying to figure out their way into it and in those circumstances. We had some other business ideas that we were playing around with. We would present different ideas and then we'd say to them, "Then, we have this side project."

[00:05:41] I can't overemphasize how much we did not consider it a business. The product was, as far as we were concerned, was actually a deck of cards that we produced. It wasn't a digital business at all. We weren't even doing it digitally. It was literally a deck of cards, and the deck of cards was a stack of 15 cards that was those study cards that you would make where it would have

[00:06:00] a technical term on one side and then it would define the technical term on the other side. It was really just a fun thing that we had made for ourselves.

[00:06:08] I think we just felt like the way everything was talked about was so dry and boring. Honestly, I still feel like for the vast majority of technical education today, it's still that way. It felt like such a lack of imagination on the part of everyone producing this technical education and it's such a missed opportunity to connect with a much wider audience. We were creative people, and we just wanted to play around with this idea that we had that you could present this material in a much more interesting and engaging way.

[00:06:37] Then, I think what would happen is that we would be in these circles with people who were interested in technology and also just trying to get into it and break into it. I think for them it was the answer to this problem that they've had, which is all the jargon was being thrown around and they didn't really understand it. Here we had this cute little pack of cards that we'd pass around and they'd be like, "Oh, this really explains what HTML and CSS is and JavaScript and Ruby and programming

[00:07:00] languages and some other major terms like that."

[00:07:01] For us, it was just really interesting because it was we would present these other business ideas and they'd be like, "Boring." Then, they'd see our deck of cards and they'd be like, "Wow, this is amazing," and get really engaged with it. That was what it looked like.

[00:07:16] Matt H: That's fascinating. That's quite a pivot from your original product to where you are now.

[00:07:20] Adda Birnir: Definitely. It was actually good for me because we had actually been working on this tablet publishing software ... Because this was 2012 when tablets were all the rage. This is before responsive became really big, so everyone was freaking out trying to figure out how to optimize for mobile. Especially in media, they were really concerned about that because I think the idea was that the tablet was going to be the new magazine.

[00:07:41] We were really thinking about how do you make it easy for companies to publish the tablets and create good, nice experiences on tablets at scale. That was a problem we were solving. That was the problem we thought we should be solving, and so we were working on some software that would do that and make that easy for people. But, it was great because it

[00:08:00] gave us this really accidental opportunity to see what is a positive signal from the market and what's not, if that makes sense. Because we didn't mean to set up this A/B test, but it ended up being that way. What we found was people were just not interested in the tablet publishing software and really interested in this Diva Deck.

[00:08:18] It was also hilarious because it's like, again, we weren't even pitching it as a product. That was a really good lesson for me because we had put a lot more time and effort and work into the other product, the tablet publishing software, and very little work comparably into this deck. I think that was a really important early lesson to me about learning how to put things out there and not over-invest. Also, the pain of having over-invested in something and not have it work out ... I feel like those lessons have served me really, really well in terms of the following seven years of brutal startup building after that.

[00:08:54] Matt H: Yeah, I'm always fascinated to hear about how communities grow and why they grow, and what makes them successful long-term.

[00:09:00] It seems like what you're describing there was that the community came maybe not easier, but more naturally just based on your mission. Did you find that was the case? Did you find out the community grew naturally and then you could pivot your product and services based on the feedback you were getting from them? How did the community grow for you?

[00:09:18] Adda Birnir: Yes and no. I think looking back on it, I can have the perspective that it did grow very naturally actually. All things considered, it was not that difficult for us to build an audience and engage that audience. I think at the time, it felt very difficult because I think when you don't have any experience with this, all you have to go on is the stories that you read in the media. For us, the big one that hung over me always was that right around this time Codecademy had launched Code Year and they had 250,000 people sign up overnight.

[00:09:48] That was my benchmark of what it meant to succeed, which is completely unrealistic and is a once in a lifetime ... I don't even think most entrepreneurs experience anything of that

[00:10:00] sort. I think, at the time, it felt like the 5,000 people or whatever we got to sign up was puny. It's just hard. You just don't have any benchmarks. You just don't know what is working, what's not working.

[00:10:10] One thing for us, one experiment we ran was that we actually went to South by Southwest in 2012 and I had just read Lean Startup. So, I was like, "I'm going to make a lean experiment." My experiment was that we would try to "sell" women a newsletter. It was basically going to be the Digital Diva Deck but in a newsletter form, so emailed newsletter. It was going to be free, so the purchase was just going to be with an email. It wasn't going to be a monetary transaction, but we considered that as currency.

[00:10:40] Our thinking was, "Okay, if we can't get women at South by Southwest to sign up for this, then there's no hope for us." Right? Because that's a really primed audience, hypothetically, for this kind of product. I think our goal was to signup 1,000 people. We were doing this, mind you, all in person. So, this was direct sales.

[00:11:01] We quickly figured out that 1,000 people ... We weren't going to be able to talk to that many people because exhaustion would set it. But, I will say, we had an incredibly high rate of conversion. I don't know the numbers, but very few people turned us down when we pitched it to them. I think, at the time, I knew it was a positive signal. I don't think I understood how positive of a signal. If you can get people to even just talk to you for two to three minutes, much less give you their email when you're engaging with them about a product and you can do that repeatedly for over 100 people, I think that's actually a pretty good sign.

[00:11:33] Matt H: Yeah. You mentioned that it's hard to compare yourself to others in the process of starting up your own business, especially in your case given the context and given what the tech community looked like then and still looks like today. Did you find that there's anybody else that was doing a similar thing or was pitching a similar mission? Did you have any other benchmarks in that sense of a community of women in tech and that sort of thing?

[00:11:57] Adda Birnir: Yeah, certainly. Obviously, Codecademy, in a lot of ways, is very similar to us. I think

[00:12:00] they had a similar mission of trying to make tech education very open. I think their approach to it is very different. The other thing, there's always been a lot of nonprofit efforts to get women into coding. So, there is RailsBridge and Rails Girls and PyLadies and Girl Develop It was another one that we were definitely very good friends with, the people who started that organization.

[00:12:23] I don't know if they really provide us with benchmarks because all of them are in person. Again, it was different for us. The other one that we looked at quite a bit because it was started also around the same time is Team Treehouse. With both Codecademy and Treehouse, I gave up relatively early in comparing myself to them because I think there's important ways in which their product is different and therefore their numbers have always dwarfed our numbers. But, that hasn't stopped us for being able to build a totally sustainable, productive business.

[00:12:53] I think having that attitude has taken time for me. I think that for a long time I had a lot of doubt about the

[00:13:00] viability of the business because we didn't have maybe that astronomical growth or the huge user base. Something that I have learned over time is that most businesses, they either have an audience problem or a revenue problem. Meaning that either they can build a big audience but have a hard time converting them to paying customers, so they have a hard time transacting those people. Or, they can transact people, but they have a hard time building up the audience and scaling it really quickly.

[00:13:30] If you have neither problem, then you're going public, and you just are riding that gravy train. That's obviously the best situation to have neither problem, but, in my experience, the vast majority of businesses have one problem or the other. I think for me, with Treehouse and Codecademy ... And, I don't know, obviously. I'm not inside those businesses, but I think that in both of those, I would guess that their problem ... Actually, I shouldn't speak for Treehouse. I don't know. But, my sense with Codecademy is probably that their problem is more on the transacting side and less on the building audience side.

[00:13:59]

[00:14:00] Whereas our problem has always been more on the building audience. So, it's relatively easy for us. Once our typical customer finds us, it's not hard for us to get them to purchase a product and to stay with us and then repurchase and build a relationship with us over time. What has been harder for us is just getting that scale of audience. We grow, but we don't grow exponentially.

[00:14:21] Matt H: Right. I guess maybe we should take a step back just for the listener and just describe a little bit about what Skillcrush does on a high level and what makes you different from the companies that you mentioned there. Can you speak to that a little bit about how are things going now and what does Skillcrush do that's different than the other company (inaudible) ?

[00:14:39] Adda Birnir: Yeah. Absolutely. What Skillcrush does is we teach online courses in technical skills. We take a pretty expansive definition of what technical skills mean, which means that we did always start with coding, but design has always been a really important aspect of what we teach and now we're also venturing into things like digital marketing. Everything that

[00:15:00] falls under the umbrella of digital or technical skills. I think our thinking in the greater scheme of things is marketable, future-focused.

[00:15:09] What makes us, I think, particularly unique is that our focus is really on women. It's not exclusively on women. We're not a women-only school or anything like that, but about 80% of our audience is women. That is by design. The way that we attract women is that we have really designed the product for them in mind and have worked really hard to understand what makes their experiences different and unique and what their specific needs are when it comes to online technical education. And, have really worked very hard over the last seven years to create a product that specifically and uniquely, I think, meets the need of that target audience.

[00:15:44] Matt H: Right. What has the success rate been for people that have gone to Skillcrush and had skilled training in the areas that you work with them?

[00:15:53] Adda Birnir: Yeah, you're getting one of my biggest points of self-consciousness, I think. I always look at those bootcamp

[00:16:00] reports, and they can track all their people. One of the challenges for us is that we've occupied this funny, middle space where we're not a bootcamp that has people in person and it has a tiny, little cohort that is vetted ahead of time. Then, we're not one of these super big players that just has hundreds of thousands of students.

[00:16:18] At any given time, we have almost 2,000 students enrolled with us. There is no criteria to enter the program. Then because we don't place people, made a lot of efforts to track people down, but all we really have at this point is anecdotal stories that we're able to track with our students. I would say the largest percentage of our students will start with freelancing work and then ... This is where it's challenging, especially for us, because tracking them further down the line becomes all the more difficult for us.

[00:16:46] Yeah, they go into all kinds of different jobs. We have a lot of people who do end up as developers, software engineers, and stuff like that. Then, a lot of people end up in design and digital marketing and runs the gamut.

[00:16:58] Matt H: Right. Have you seen

[00:17:00] any trend of consistency with the people that come to Skillcrush in terms of their background and their training? Is there any sort of typical user that comes to you in terms of their background that you can speak to at all?

[00:17:12] Adda Birnir: Yeah, the traditional Skillcrush user is usually in her late 20s, early 30s. Usually, has a college degree, but not in a technical field. Then, traditionally, what we find with a lot of our students ... And, I think this is just really common for a lot of women, is that they graduate and then they end up at these jobs that are basically, they call them admin assistants, but it's basically just a new term for a secretary.

[00:17:36] They've usually worked for three to four years and are extremely frustrated because they're really smart, really hardworking, but find themselves in a position where there really is no forward momentum. There's no ladder to climb in the position that they're in and they feel totally underutilized and frustrated and believe correctly that there is more to life than this and are looking for that. That's the typical situation that we find where students come

[00:18:00] to us.

[00:18:00] It's interesting because obviously things like making more money and stuff like that is important to them, but I'd say probably one of the biggest motivations for most of our students is just creative fulfillment. They want to do work that they're excited about and that they feel like is going to carry them into the future and provide them with more opportunities.

[00:18:16] Matt H: Right. I think that the mission of Skillcrush ... I was mentioned this actually to somebody the other day because Skillcrush came up. It seemed like this is one of those companies where the success that you've seen is fantastic and well-deserved. If you continue on this way and if you succeed at the level you have previously or do better than you're currently doing in terms of the user rates and all that kind of stuff, success rates, it's only going to serve everyone better to have you succeed. It's a cool company to hear from and learn from and it's a unique position to be in, I think, as a company, as a startup, and as a full-fledged, successful company. So, kudos to you and your team.

[00:18:52] Adda Birnir: Thank you. It's hard. I think sometimes when you're working a business you just take a lot of the positive aspects for granted.

[00:19:00] Obviously, us having this mission and being focused on this audience, if you think about who is out there looking for technical skills online, the majority of people out there doing that are not women. So, we have created a situation for ourselves where we're swimming slightly against the current or whatever you want to say.

[00:19:17] I think sometimes you're just like, "Why are we doing this?" At the same time, the mission is the core of the business. That is everything. It's why every single one of my staff works for me or works for Skillcrush really. It's been very important for me as I run this business for longer to make sure to continuously be in touch with that because I think I, like any other CEO, get lost in spreadsheets and numbers and looking at growth and all that stuff. It is important and it is different. I don't have a comparison really because I've never started another company, but I imagine that it would be very different if we didn't have that to fall back on.

[00:19:55] Matt H: Yeah. I do talk to a number of companies on a regular basis, but it's rare to have

[00:20:00] the mission be so important to everybody. I think that's a really unique and really cool thing to be a part of.

[00:20:06] Adda Birnir: Yeah, and I think part of what we're trying to do to is prove that you can both have a mission and work in these ways that we believe are more sustainable and more flexible and still have a successful business. We're not Google or Facebook. I'm not trying to suggest that. I'd like to believe those businesses could also mission-oriented and do as well as they're doing, but it is also important to know that you can run a profitable startup even with a mission and lots of ideals around how you work together with everyone at the company.

[00:20:38] Matt H: Right. That's a good segue for me actually to talk about remote work in your case. One of the questions I love to ask is for you personally and then we'll get to the company. What, for you personally, has been difficult about both starting a company in a remote context and just working remotely on a daily basis?

[00:20:57] Adda Birnir: When it comes to starting a company, I think everything is

[00:21:00] challenging. I'm like, "How do you even begin to choose?"

[00:21:02] Matt H: That's a loaded question.

[00:21:03] Adda Birnir: Yes, exactly. In terms of working remotely, when I started the business I ran before, we worked with people remotely. I think, to a certain extent, I just got so accustomed to that that I took that for granted. Sometimes I'm actually very curious about what it would be like to work in person. I will say that we've had lots and lots of challenges scaling the business, and I think is really hard for anybody, but I think it's harder sooner for a remote company. Because my sense, at least from talking to other people about this, is that for us, when we got to 16 people, we didn't really have any processes at that point in place for anything really. You're just running in eight different directions or whatever.

[00:21:40] It was around 15 to 16 people, it felt like everything fell apart and the communication became this huge problem and everything became a huge problem in terms of how to get everyone to be coordinated and working together or towards one thing. My sense is that that doesn't happen that early when you're in person because there's a certain amount of communication and passing of information that

[00:22:00] happens naturally in person that isn't going to happen naturally remotely, so you really have to work extra hard at it.

[00:22:16] Right, and it's probably come a long way since you started your business and got to that 16 person mark within your company. Because, right now, of course, we're seeing this surge of remote work as a concept in new companies that are starting out remote or companies that are even established already that are going remote. There's just more resources out there. That's what, I think, we were trying to do with this podcast too is to talk to people and talk about their experience with working remotely and to give people a more broader sense of what's out there in terms of people's processes and things like that.

[00:22:49] That's one thing, but it probably has come a long way since you were forced to implement processes for Skillcrush remotely just because it just wasn't very many other companies maybe that were doing what you were doing.

[00:22:59] Adda Birnir: Yeah.

[00:23:00] Definitely.

[00:23:01] Matt H: Can you speak to some of those processes individually or as a company that you do on a daily basis or a weekly basis?

[00:23:08] Adda Birnir: Yeah, absolutely. It all was a process for us to develop them, of course. I just can't underemphasize, again, how disorganized early-stage startups are and how much things are done completely ad hoc, even just things like setting up regular meetings and that kind of thing. Probably about four years ago, we actually all transitioned to Scrum. So, all the teams became Scrum teams, which, in retrospect, I think that that was probably overkill. I spent a lot of time arguing with the sales and marketing teams because they were like, "We don't understand this." I think in retrospect, I don't necessarily think that it was the right thing to do, but I think I was just so desperate for some process that was clear and standardized.

[00:23:51] That did give us a framework, which is really helpful, just in terms of the cadence of this idea of doing sprint planning, committing to a certain set of

[00:24:00] work for the week, not changing it over the course of the week. Because I think that can be so chaotic in early stage startups is that everything is changing all the time, so you have to try to find ways to control the chaos. It's ironic because I think traditionally, Scrum is actually designed to do the opposite, right? It's to take people who are used to these really long timelines and waterfall and try to get them to iterate more. For us, it was really the opposite. We were just complete chaos and we needed some sort of limitation on it.

[00:24:30] Then, we adopted Jira. We use Jira for every team. It's a totally unsexy software. I personally love it, but it's funny. People, whenever I tell them that we use Jira, they turn their noses up and are mortified. Yeah. Then, actually, we use HipChat for a long time until we were forced into moving to Slack because Slack bought HipChat. Yeah, I think it's still a challenge. Information

[00:25:00] dissemination with a remote team is really hard and we do things like we have a weekly management team meeting and then that gets translated into something we call the Big House Bugle, which is our weekly newsletter. Then, we do things like we do a PO daily, which is traditionally in Scrum it's called Scrum of Scrums. It's basically where all the POs get together and coordinate. We actually do it three times a week. It's not every single day. That helps us stay coordinated and in sync.

[00:25:27] Another challenge I find that we still struggle with is information overload. It's not always that the information isn't being shared, but it's just too much for any individual to take in. We spend a lot of time on Hangouts, a lot of time on Slack. It's funny, I think part of me is, "Isn't this what everyone does?" I'm like, "Oh, I guess they meet in person instead." I just take so for granted working remotely that it's hard for me to even imagine what it would look like otherwise.

[00:25:55] Matt H: Yeah. This is one of the most interesting parts of this podcast is because I get to

[00:26:00] see where people are coming from, what perspectives they bring to their remote work. This is a case where, obviously, the remote aspect of it is what you're most comfortable with rather than the opposite which is mostly what I hear from people that move to remote companies. It's just harder to get a grasp on.

[00:26:15] Adda Birnir: Yeah. it's really interesting for me because from my perspective, it feels so much easier. It's really exhausting to be the CEO of a 30-person company and if I try to imagine doing that in person, I'm terrified by it. I'm like, "Oh, my God." There are moments where I feel like sometimes things get just caught in the weeds or communication is just not very efficient.

[00:26:38] There's a fair amount of I'll go around and poke people and say, "Get on a Hangout. Get on a Hangout." I find that people often default to Slack. Basically, we don't use email at all. We just use Slack. We use Zoom, I guess, at this point, but whatever. We do video calls. I will say that I do think that there are problems where people get overly comfortable in Slack, and I just find that you can spend an hour in

[00:27:00] Slack trying to work something out that will get fixed or taken care of in five minutes on a video call. There's a certain amount of reluctance to do that.

[00:27:06] Although, I would imagine that that plays out with email and not wanting to walk over to someone's desk in person too. I don't necessarily think that's a remote culture problem, I guess. It's just the remote culture version of the problem.

[00:27:19] Matt H: Yeah, that's interesting. I hadn't really thought about that, but I guess that's true. I worked in an office before I worked here. Yeah, there was a sense of it's easier for me to send an email, so I will avoid the possible uncomfortable interaction that I will have face-to-face and just send the person an email, which is definitely, in some cases, not the most productive way of going about it. Yeah, that's interesting.

[00:27:40] I often hear that people have to more intentional or deliberate about the interaction that they have with their coworkers in a remote team that doesn't have to do with work necessarily, that is just getting to know the people on a higher level that isn't maybe directly associated with work, but plays a part in building a culture and getting to know people better. Is there anything that you do as a team that is intentional in that respect?

[00:27:59] Adda Birnir:

[00:28:00] Yeah, we do this thing called Paircrushing, which is basically ... It's everyone who says that they're willing to do it, gets thrown into a hat and then, once a month or so, they get reshuffled. So, you get a person to Paircrush with. The idea is that you spend half an hour just chatting with them. It's probably the single most intentional thing. We also have done things like movie nights and that kind of thing. Then, I think the culture of our organization in Slack, it's important. Celebrating people's birthdays and having special Slack channels about totally non-related-to-work stuff.

[00:28:32] This is funny because this is not something we've necessarily forced, but, I will say, my staff has always gone to visit each other or has traveled quite a bit and then met up with one another. We do do management retreats where we meet up as the management team. Usually, we'll do it in a place where maybe there's some other staff members, so we'll meet them where we can, try to actually meet face-to-face. I've also visited quite a few of my staff when I've been traveling and that kind of thing. It is obviously a big

[00:29:00] part of our culture, but it's not something that we decree from the top down.

[00:29:04] Matt H: Right. It probably comes down to hiring effectively too, so that you don't have to be as deliberate or spend as much time making sure that people are interacting in a positive way or doing that sort of thing when you hire people that would do that anyway, right?

[00:29:19] Adda Birnir: Yeah, definitely.

[00:29:20] Matt H: Is there anything different that Skillcrush does specifically in the hiring process to make sure that people are the right sort of people that you want to be working within your company?

[00:29:30] Adda Birnir: Yeah, I think there's a whole bunch of things that we do in terms of how we vet people. I think what we have really working for us is actually to go back to the mission of the organization. I think in the hiring process, we do really look for your investment and commitment to that mission. That is very, very important to us that you're not just applying to Skillcrush with a bunch of other companies, but you really understand what makes Skillcrush unique and why what we're doing is so specific. That plays

[00:30:00] out, I guess, in a million different ways, so I think that is a very, very fortunately effective way for us to end up with people who are a good fit for us. Because we are such a different company and our expectations are so different and the way that we work together is so different.

[00:30:13] We also have this thing, which maybe you've come across, but we implemented a salary tier system a couple years ago. It's pretty straightforward, and it is something that's common to a lot of especially government organizations and stuff like that. The idea there is we really are focused on pay parity, so making sure that there are not discrepancies in terms of people doing the same role and making different pay. Also being really transparent about what people are getting paid and also really upfront with people about it. Sometimes I think it gets misinterpreted as a no negotiation rule. It's not really no negotiation rule, it's really a minimized negotiation rule. Basically, an effort to maintain fairness between roles.

[00:30:50] All of those types of ways in which we run the company, I think, help us create an environment where the people who are attracted to that tend to be better fits for our

[00:31:00] organization.

[00:31:00] Matt H: Right. Depending on who you're hiring, I'm sure that you're more involved or not depending on who it is. But, what does the hiring process look like for Skillcrush and how long is it and what specifically is unique about the hiring for you?

[00:31:13] Adda Birnir: Yeah, so it depends a little bit on what role we're hiring for, obviously. But, we usually just begin by putting together a job description and really thinking through things like what's the overarching goal of this position, what are some outcomes that we'd like to see. In an ideal world, what would this person accomplish in the first three months, the first six months, nine months, 12 months, that kind of thing? What is our big laundry list of all the things that we would want if we could have them?

[00:31:41] Then, we put it out. We work really hard to get a diverse candidate. Again, we're fortunate to the extent that both being remote and then also having this mission, I think, predispose us to a more diverse pool of applicants than your run of the mill company. But, we still have challenges with diversity and try to really think

[00:32:00] hard about how to find more diverse candidates. What that looks like is that my director of operations spends a lot of time finding Slack groups and smaller groups like that. We've had a lot of success with that kind of approach. So, not going to the big job listing sites. We don't find those bring great candidates.

[00:32:18] We will sometimes do LinkedIn sourcing, which is where we so outbound contact with people. We will try to find people who we think are a good fit on LinkedIn and reach out to them, but that's a tactic we use not in every situation. I will also say we're also fortunate that especially for certain roles, we're able to really take advantage of our customer base. A lot of my staff was a customer before they were our staff. We love hiring our students because they're amazing and smart and super motivated and totally aligned with everything that we're doing. They also are very familiar with the company and our product, so that makes our onboarding and training much easier.

[00:32:55] Matt H: Right. A couple of things that I wanted to ask you about being a CEO in general. Obviously,

[00:33:00] you're in a unique position and I think a lot of our listeners would be curious to hear a little bit more about your experience and what it's like being a CEO just in general. So, I have a couple questions for you about that. The first one is just what's the most important component or aspect of being a CEO in your experience?

[00:33:17] Adda Birnir: That is an interesting question. I think your ability to learn quickly, but also really be self-reflective. I think that a lot of people get themselves in trouble in business by being overly attached to their specific idea or their way of doing it. I think that one of the things that has allowed us to have the success that we've had at Skillcrush is that we're committed to the mission, but that's basically it I would say. It's not literally it, but I think as long as something is driving towards that mission, I am not overly invested in exactly how it plays out.

[00:33:51] Honestly, I find that the process of iterating on things and learning about them and getting better at them is so interesting and exciting to me and I've

[00:34:00] learned so much. The company and their product and the team couldn't have imagined it like this, which is why I'm glad that I wasn't attached to being the person who imagined it all, right? I think that if I had been really attached to that and really thought that it had to be totally executed against my vision at all times, I would have really limited the possibilities of what it could be. I think that's hard, and I think that takes a lot of having to check your ego over and over and over again and admit over and over and over again that you're wrong or that your way isn't the best way, and reflecting on that and learning from that and then joining that process versus presenting it.

[00:34:36] Matt H: In your executive meetings, I imagine that there are interesting conversations there just given your outlook on leadership. Do you have to do anything specifically or deliberately to get people to discuss these things or is it here we have a strategy that we want to try or we have something that we want to test or whatever and then let's just talk about it kind of thing? Or, do you have to ask people specifically for their opinion,

[00:35:00] or how does that work with those brainstorming aspect of the strategy of the business?

[00:35:03] Adda Birnir: I don't think I had a challenge getting people to brainstorm ideas. I think everyone comes to the table with a lot of ideas. I guess I would pivot the question a little bit, or my answer, because I actually think that one of the biggest problems in business is that everyone tends to have a lot of ideas. This is language I'm totally borrowing from a woman named Teresa Torres who's really amazing and everyone should read her. What she calls it is solution orientation versus problem orientation.

[00:35:32] If we were to have a meeting right now and we were to all come to the table and brainstorm a bunch of cool ideas that we had, that would be us being solution-oriented. Because we're coming to the table like, "Oh, I think this thing would be cool," versus us coming to the table and saying, "This is the problem that we have and our customers have. Do we fully understand this problem and what are some different ways that we could solve this problem?" What we try to do instead is really be problem-oriented. That, I think, goes back to the statement I was making

[00:36:00] about how for us, it's all about the mission.

[00:36:02] For us, what we do is we try to really emphasize and really focus on the problem, make sure to really take the time to understand the problem that we're solving, which means a lot of talking to our customers and asking them lots and lots of questions. We also look at quantitative data as in user behavior and all that kind of stuff. Then, the idea, or our thinking, is to actually be very unattached to the solution, meaning we want to obviously come up with our best ideas for the solution, but also understand that we're definitely not going to be able to come up with the perfect solution on our own and also not on the first try.

[00:36:38] Instead, what we do is we go with our first two to three best ideas as far as a solution and then to the extent that we can, practice this thing called co-creation, which is where we do a rough prototype of whatever solution it is and we try to get it to that point where it's enough that it can clearly articulate what the proposed solution is, but

[00:37:00] not so well-designed and well-thought out that it seems done. Finding balance, but you're trying to basically get it to the point where when you show it to a customer, they will feel comfortable telling you what's wrong with it. If it looks too good, they won't feel comfortable even if they hate it.

[00:37:16] Then, we'll show it to customers and get their feedback on it and iterate from there. I will say that the hardest thing for me as a leader, and I think this is just a natural human problem, is really getting everyone to accept and really embrace this idea that all of their ideas are probably terrible and that's totally fine. It's not about being the person who has the idea and comes up with the magical solution. It's really about creating a process where together, and especially with our customers, we come up with what is actually the best solution.

[00:37:51] I would not say that I'm perfect at it at all, and I totally fall victim to all the same problems that everyone else does. I struggle sometimes to get the team on board, but

[00:38:00] my MO in terms of how to do it is to be that example of really calling out when my idea completely flops, which it does. I would say 100% of the time our ideas are at least five degrees off of where they need to be and then probably another 60% are like 50 degrees off of where they need to be or 80 degrees or 180. That's fine. As long as you have a quick way to figure that out and recalibrate.

[00:38:24] Matt H: Right. You touched on my next question there in that answer, which I thought was really great. Is there anything specifically that you look for or that if you have any role models that are CEOs, or just people in general in technology ... It doesn't have to be in technology. Is there a specific attribute of those people that you admire that is consistent among them? What is something that you really admire in other leaders that maybe goes unnoticed amongst regular CEOs or just in popular media?

[00:38:53] Adda Birnir: It's funny because I struggle with this myself in that

[00:39:00] rationally I know that this is problematic, but in practice, it's hard. I would say one of the things that's really depicted a lot in popular media is this idea, this visionary leader, the Steve Jobs, who has all the answers and comes and waves a magic wand. Poof! Magic happens. I think that in my experience, building a business is absolutely nothing like that. Like I said, I guess I don't have the magic that they had and I'm not sure that I've ever seen anyone who has that magic.

[00:39:33] What I tend to really be attracted to in leaders is just people who are really tied to reality, which sounds obvious, but I don't know. I am consistently surprised at how many people and how many "CEOs" that I meet are just not that attached to reality and are living in this visionary world. Obviously, it's important to have a

[00:40:00] vision. For us, it's really our mission, but I think in terms of translating that into actual mechanics of what you do every day, it can be really, really challenging. A lot of people I've known who are very good at that visionary part are actually not very good at translating that into boots on the ground.

[00:40:17] I tend to be a person who's very much about that translation. I know my numbers really well. I'm really in the weeds like we're talking about in terms of product development. I love to work with our customers and talk to our customers all the time. To me, I feel like I'm almost a modern-day carpenter or something. I love the process of building a business and being really a part of it in a really material kind of hands-on way. I tend to be really attracted to leaders who talk really practically about stuff, who really understand what it is to build a business, who are really in it. Really in the trenches, I guess, is a good metaphor for it. They are trying to tinker with it and work it out and figure out how to build that machine.

[00:40:59] Matt H:

[00:41:00] Right. Yeah. That makes total sense. In my asking of that question to a few of the CEOs that I've been lucky enough to ask the question to, and my interpretation of that as well, is that my favorite people to talk to are people who are just really real about the problems that they're facing. I think it's a really rare thing for somebody who ... especially who's an executive or CEO ... to be completely honest about the fact that, "Hey, I don't know the answer to your question. We're trying to figure it out. We're doing the best we can, but right now, we don't have a really good answer." I think that's just super refreshing and it sounds like that's something that you feel as well.

[00:41:31] Adda Birnir: Well, I think it's funny too because, to me, that's my constant state. So, it's always funny to me when I meet people who project as if that's not their constant state. I think it's taken me a long time to get to the point where now I realize they all must be either lying to me or lying to themselves or maybe both. But, I think for a long time, I was really like, "What is it that they know that I don't know?" I think it's really easy to think that, but I don't know.

[00:42:00] Listen, if they know something I don't know, I would love for them to share it with me someday, but I'm also starting to doubt that there is anything that anybody knows.

[00:42:07] Matt H: Yeah. Yeah, I'm getting closer to doubting that myself as well as this podcast progresses. That's great. I want to be aware of your time here and you've been so generous with it so far and we really appreciate it. I have a couple more questions here for you. The first one is your favorite (inaudible) product that you think every remote worker should know about.

[00:42:29] Adda Birnir: In terms of my favorite product for remote workers, I'm just obsessed with Google Drive everything. We do everything in Google Drive. I don't really understand how anyone really works on a computer with a team without using that. I know that some people use Dropbox, but I find that Google Drive is much better. It sounds like ... I don't know. I hate to hawk Google because I don't necessarily like that business, but I love in a lot of other ways. I just find my entire world runs on Google Docs and Google Spreadsheets and all that

[00:43:00] jazz. It is actually something that we teach our students how to use for that exact reason.

[00:43:05] Matt H: Segue there a little bit, do you have a remote specific component of a lot of the courses that you offer? Is there a specific segment of it that say, "Hey, this is how you work remotely and this is the best practices and that sort of thing?"

[00:43:18] Adda Birnir: We don't actually call out specifically working remotely in our material. To me, a lot of the things that you have to do remotely are A, things you have to do no matter what and B, things that you would have to do if you were working freelance. We do spend a lot of time with our students working on freelance skills specifically.

[00:43:38] I think in terms of working remote for a company, other than just being very, very comfortable with all of these digital tools that we've been talking about, so project management, softwares, and Slack, and Zoom, and Google Docs, and all that kind of collaborative software that I honestly think that any modern worker working in technology needs to be comfortable with that

[00:44:00] tool, that tool kit. I don't think that is unique to remote workers.

[00:44:04] The other aspects of remote that are a little bit more about managing yourself and managing things across time zones or just managing a relationship with someone you're working with that's not co-located, I actually think is very, very, comparable to what freelancers have to deal with. So, we do spend a lot of time with our students talking to them about workflow for freelancing and professional best practices and that kind of thing. Between the two of them, we cover everything that is remote specific.

[00:44:30] I will also say one of the challenges for us with our students is that we love remote work and our students obviously want remote work, but the supply of remote jobs is so dwarfed by the demand for remote jobs. That can be really challenging for our students. What we work with them on instead is rather than waiting for that job to come up, to really create their own remote job in the form of freelancing.

[00:44:57] Matt H: Right. Interesting. My next

[00:45:00] question here is actually something you've already answered, but I'm going to ask it anyways. What leadership practice or skill do you think is most important? Again, this can be as a CEO or just generally speaking.

[00:45:14] Adda Birnir: It's interesting. I feel like if I were to answer the question of what leadership skill is most important, I feel like that would necessitate me having a really good idea what's working and what's not working. I think I'm constantly in this process of trying to make sense of that. I think in terms of what I do, I think I've always tried to be transparent with my staff. So, they know the numbers and we talk about things as transparently as is appropriate. Obviously, there's certain things that can't be shared with my staff, but I really try to err on the side of talking to them openly and honestly about things.

[00:45:46] I think I just work really hard to be self-reflective and learn from my mistakes. I have an amazing coach who helps me with that and thank God for him because I think he's helped me a lot in terms of seeing where some of

[00:46:00] my weaknesses and growth opportunities are. I don't know. It's such a process. I feel like if I felt like I had reached the end of the road, I could tell you what's most important, but I haven't reached the end of that road yet so I'm still trying to figure it out.

[00:46:13] Matt H: Yeah. Well, that in itself is a great answer. Maybe that's the skill that everybody needs to know about is the fact that you can never be satisfied with thinking you know everything.

[00:46:22] Adda Birnir: I think this is basically my life motto. I don't think it's unique to CEOs. I think that this is basically life in a nutshell. We're all in the process of figuring things out as they come up. You try to be as forgiving of yourself as you can and remind yourself that you did the best you could with the information you had.

[00:46:41] I don't know. I think it's funny. I will say one thing which is that when I started Skillcrush I remember having this discussion with somebody I was working with at the time and they were having these fantasies about the day that we would have ... I think it was around video production specifically. At the time, we were just shooting with one light and a camera by

[00:47:00] ourselves in an office for the videos. They were having this fantasy about having a bigger team and a set and all these things.

[00:47:08] It was funny to me because I was like, "I don't have that fantasy." It's not that I don't want to get there, but it's I felt in my core that once we got to that place, which I believed we would get to, we would look back on this time very fondly and miss the days when it was simpler and we had less. I guess I feel like I'm fortunate in that I enjoy that journey. Obviously, everyone has goals that they want to get to, but, for me, I get so much joy and I just get so much out of the process of getting there. So, I just appreciate that and I'm thankful for it and enjoy that process of being, "Wow, I really screwed that up." As long as it's not horrible because then you feel bad about it.

[00:47:48] We (inaudible) this all the time. We'll look back on the ways we used to produce new products or new offerings or whatever and we'll just chuckle at how bad we were at doing that. That's nice. That's a nice feeling to be like, "We're so much better than we used to be."

[00:48:01] Matt H:

[00:48:00] Yeah, that's really cool and it's something that I don't hear very often is that the process itself is the fun part. My last question here for you before I let you go is what is the best advice you've ever been given? This can be professional or otherwise and you can it then whatever direction you want to.

[00:48:19] Adda Birnir: I'll say in terms of professional advice, I'm very fortunate to have an amazing mentor. There was this moment when I was trying to figure out some stuff with Skillcrush and I remember this was very, very, practical advice, but it was really pivotal. I think that it can be adapted for a lot of different circumstances. Basically, what happened was that we had 5,000 people on a newsletter list and I was telling him all the different ways in which they are so engaged and they open the newsletters and blah, blah, blah, blah, blah.

[00:48:48] He was like, "That's all fine and good, but will any of those 6,000 people ever pay you a dollar?" I was like, "I don't know. I hope so." He was like, "You've got to find out." It was a good example of what

[00:49:00] I'm talking about in terms of just a reality-based leader. His point was it's really great that you've accomplished this thing, but, at the end of the day, if you want to build a business, you actually have to make money and you have to get these people to buy something. You need to figure out as quickly as possible whether they're going to do that.

[00:49:16] That led us to producing this ebook that we sold for $5 and made $1,200 on. So, we were very relieved to find out that some of those 6,000 people would actually give us their money. I just so appreciated it in terms of he just distilled this whole situation that I have made into this complicated scenario and was like, "Here's the question you need to ask and you need to get an answer as quickly as possible." That was such an important lesson for me.

[00:49:45] It's funny because he still plays that role in my life. I will go to him with these extremely complicated questions and he'll just cut through all the BS and be like, "This is what you need to do." I'm like, "God, yes. Okay."

[00:49:55] Matt H: Yeah.

[00:49:56] Adda Birnir: That was phenomenal advice that I got. The other

[00:50:00] thing that I had to come to terms with, a couple years ago I did hit this point where I got really frustrated because I think for the first four years of building the company, I had just run on adrenaline. It always felt like, "Okay, if I just get around this one corner. If we just launch this one product or make this one change, then everything will be different." Then, of course, the goalpost keeps moving backwards, and I got to this point where I became really disillusioned with that and realized that there wasn't going to be anything. You know what I mean? If we launched a product, yeah, maybe it would spike revenue or whatever and that would be great, but then we'd have a whole new set of problems to work with.

[00:50:41] So, I read this book. It's called An Exoneration Fantasy. It's basically this idea that we all walk around with this belief that there is a promised land basically, that there is a place in which we have no problems and we're happy all the time. It's

[00:51:00] whatever variation it is for you. For some people, it's if I just lose 10 pounds or if I just make a million dollars or if I just get a boyfriend or whatever it is. What this book was saying was that part of becoming an adult is letting go of that fantasy and understanding that you will never get to a place where you don't have problems. There's always going to be challenges in life.

[00:51:21] I think that was just such an important learning experience for me in terms of continuing to have the stamina to continue in business. That exoneration fantasy carried me for a while and then maybe it served a purpose that was important to me for that period, but then eventually it runs out. It is a fantasy. It's not reality. Being able to reflect on that and come to terms with the fact that even if my business went public or whatever, achieved whatever fantasy I have for it, that's going to be great in some ways and terrible in others. That's how everything is, which, I think, can be a little depressing. I think, in the end, I find it comforting.

[00:51:58] Matt H: Yeah, yeah. It's liberating, I

[00:52:00] think, a little bit to know that. There's a saying that I like as well that if you threw your own problems into a bucket that was public, and everybody did that, we'd grab our own back. I think that lends itself to the same idea is that we often don't know what the problems are of the other people and the ones that we have right now probably aren't that bad.

[00:52:18] Adda Birnir: Yes. Totally. No, it's funny because I will say also something I've often said about business is that one of the wonderful and horrifying aspects of business in my experience is whenever you solve one problem, usually, all it does is make room for bigger and more problems to show up in its place. Best to come to terms with that quickly.

[00:52:37] Matt H: Right. Well, Adda, I really appreciate it. This was a lot of fun. I think I got a lot out of it. We really appreciate your time and everything you've done so far with Skillcrush and otherwise. Thanks so much for that. Is there anywhere you want to send people to?

[00:52:51] Adda Birnir: Yes, absolutely. You can obviously just go to skillcrush.com and then we also, if you go specifically to skillcrush.com/go-remote,

[00:53:00] we actually made one of our guides available. You can get it totally for free. It's called the ultimate guide to getting a remote job you love and it's just a collection of our best tips in terms of how to find remote jobs and then how to apply for them.

[00:53:12] Matt H: That's great.

[00:53:12] Adda Birnir: I think it actually goes a little bit into what you're asking, which is how to kick ass once you're in the job.

[00:53:17] Matt H: Yeah. We'll link to that in the show notes and we'll link to Skillcrush and to your Twitter feed and anywhere else you want to send people. That all will be available. Yeah, thanks again, Adda. Really appreciate it, and hopefully, we'll talk again soon.

[00:53:30] Adda Birnir: Yeah, thank you so much for having me and I definitely want to stay in touch.

[00:53:33] Matt H: Yeah, for sure. Thanks again.

[00:53:36] Adda Birnir: Take care.

[00:53:37] Matt H: Thanks so much again for listening to the show. Be sure to check out weworkremotely.com for the latest remote jobs and if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone that we should talk to, advice you have, please feel free to reach out to us at [email protected]. That's [email protected]. If you'd like to sponsor the show,

[00:54:00] please go to weworkremotely.com/advertise for all of our available opportunities.

[00:54:06] Thanks so much for listening and we'll talk to you next time