Rethinking the First Four Years of Startup Leadership

Brian Skinn [00:00:01] Hello, everyone, and welcome to today’s Open Teams community event. Open Teams gives you access to the best open source architects in the world to help you train, support and deliver your software solutions. I’m Brian Skinn, the open source Architect, Community Manager here, at Open Teams, and I’ll be your host for today. 

Today, we’re joined by Oshri Cohen, fractional CTO for an Open Source Architects Spotlight event entitled “Rethinking the First Four Years of Startup Leadership”. Oshri is here to make the case that startups don’t actually need a full time CTO in many cases, but instead can get all the strategic leadership they need from a fractional CTO and at a fraction of the cost. And I’m really looking forward to hearing from the ex CTO/ex VP of Engineering and a professional developer with 23 years of experience. And he now works with startups from ideation through to Series B as their fractional CTO. Oshri is able to cover every aspect of technical leadership from architecture and engineering management functions to director, VP and CTO positions, and can switch between these roles in sync with a startup’s rapidly evolving needs. 

Before we get started, I will note we are open for audience questions. Please post any you might have in the comments and we’ll take some time at the end of the conversation to address as many as we can. So, thank you all for coming. Oshri, welcome! How are you today? 

Oshri Cohen [00:01:14] Fantastic. After that intro, I can just leave now. That’s it. I’m good. 

Brian Skinn [00:01:18] Okay, fair enough. Yeah. [laughing] 

Oshri Cohen [00:01:22] Let me call my mother. Can you tell her that? 

Brian Skinn [00:01:24] Totally. Absolutely. 

Oshri Cohen [00:01:25] She has no idea what I do. So. [laughing]

Brian Skinn [00:01:29] So, tell us a bit about yourself. How did you get into software development to begin with? 

Oshri Cohen [00:01:33] Oh, my gosh, how did I get into software development? Right? Straight out of high school. I actually jumped into a vocational school, I didn’t even go through university for this. Later on, I formalized my education in it, but straight into a vocational school. And I remember having so much difficulty with software development. It took three months for me to grasp the concept of a variable. It took that long, but then I finished the entire year in the next three months. [laughing] Because it’s vocational, so you can do the whole thing as quickly as you want. And I just blasted through it once it all clicked, it just the brain lit up, right? 

Brian Skinn [00:02:18] Sure, Sure. 

Oshri Cohen [00:02:19] That’s how I got into it. And back in 2000 something, 1999 – 2000, I am dating myself at this point, right? Employers weren’t hiring without a degree. That’s it. There was no concept of the startup. There were small businesses, there were no startups. There were just big players. You try to apply at IBM, and Cisco, and all of them. And they’re like, “If you don’t have a university degree, don’t even talk to us”. It was actually very challenging. It, actually, kind of forced me well, to start my business a little bit after that, right? [laughing] 

Brian Skinn [00:03:02] Indeed. So, what kind of business was that? Was that your first step towards what you are doing now, called CTO roles or… ? 

Oshri Cohen [00:03:08] No, back then it was just development roles, just contract roles, and, eventually, I got hired by a video distribution company to write a video streaming server. And then later on I switched on to a consulting company to implement ERPs. I mean, I went from engineering to business consulting, but I knew engineering. 

So, it really really worked well. And then from that point on, I said, “You know what, I outgrew my bosses or I think I did, I’m not sure”. Maybe it was just ignorance of a new worker, right? So, but I felt like I outgrew my bosses and I said, “You know what? I’m smart. I got $3,000 in my pocket”. Which was a lot of money for me back then. And I said, “You know, I’m going to start my own shop, my own full-on consulting company.”

And I went off and I did it completely ignorant of all aspects of business. [laughing] Completely. There was no startup school. There was, you know… You wanted to learn business? So I’m like, “I guess I have to do an MBA. I have no idea”. Right? “I have to do a business degree for three years to understand business”. But it turns out that it’s actually much easier than that. [laughing] It’s something you’ll learn in the School of Life, I guess. 

Brian Skinn [00:04:22] Yeah, as with many things, the exposure to reality. You can learn things in school, but the exposure to reality will teach you that little else can. 

Oshri Cohen [00:04:30] I learned about customer acquisition cost before I knew that the term even existed. I was doing it in Excel. [laughing] 

Brian Skinn [00:04:38] It works. Lots of things happen in Excel and you get there. So. Well, when did you get to the point of being you said that you’re ex CTO, ex VP of Engineering. Fast forward a bit. What were those roles like for you? 

Oshri Cohen [00:04:52] So, my evolution to executive. And I don’t take that lightly because in startups, you’re an executive, because you have the title. So my evolution to that, I attribute to the eight years where I ran my consulting firm, where I had to hire people, I had to fire people, I had to lay a lot of people off, I had to close my shop. After the 2008 financial crisis, I was dead in the water. It was done. I was finished. 

And I attribute it to my ability to speak business and technology, and speak to business without using technical terms, and speak to technology without using business terms. And that perfect translation in between, because otherwise I wouldn’t be able to sell a contract if I start to talk to a CEO about database schema. They don’t care about it. What they care about is when am I going to get the application and will I be able to evolve it, right? So, I attribute a lot to that. 

I evolved into leadership about, I’d say 15 years ago. I went into a director role and then a little bit later into a CTO role. You know, the CTO role, I loved that job. It was one of my favorite jobs ever. My favorite role ever. But I hated my employer. [laughing]

Brian Skinn [00:06:35] Oh, no. 

Oshri Cohen [00:06:36] Yeah. Actually, my employer made me quit. That’s how bad it was. It was just so toxic, they made me quit. Because they misunderstood the CTO role to begin with. I felt I knew it and they misunderstood what it meant. I had to be the developer. I had to be the EM. I had to be customer facing. I had to do implementations. I’m like, I’m burning out. I’m doing 14 hour days. Too much.

Brian Skinn [00:06:59] Too many different roles, all piled in one. 

Oshri Cohen [00:07:01] Yeah, too many different roles. And that’s when it started to click and I’m like, “Okay, something’s wrong here”. So, then I moved on. I got another director role again. That’s not really a director role. It is more of an EM role. Okay, fair enough. Then I went into a VP of Engineering role. You called it a VP, but it’s not a VP role. This is a team lead role. What’s going on here, right? Then move back and forth continuously.

And for a good seven years, I didn’t hold the same job for more than a year and a half. Because it was just so misaligned and so much frustration until I left my last job about a year and a half ago. And I said, “You know what? I’m going to be a fractional CTO”. I didn’t even know the term existed. I knew fractional COO, I’ve seen that. Fractional CFO, obviously. You’ve never heard of a fractional CTO. And I’m like, “How would that work”? So I started my practice and then I researched it. Again, the ignorance of the entrepreneur, right? [laughing]  

Brian Skinn [00:08:12] Just go do it. It’ll be fine.  

Oshri Cohen [00:08:14] And I started selling, and people started buying because it made sense. And then I researched it more, and I found some early innovators in this space, but they’re all in Europe. None of them existed in North America. And European culture is all about renting. It’s a lot less about ownership. It’s, “I’m going to rent, I’m going to borrow, I’m going to use what I need, I’m going to give it back”. It’s just, you know, cultural in some countries. I’m not generalizing. 

And so I brought that to North America. And I started pitching. Well, I didn’t stop shutting up on LinkedIn until maybe this morning because I’m too busy. Just nonstop. Nonstop. And people tell me this, like, “How do you come up with all this”? I have no idea, frankly, to be honest. It just comes up in the morning at 5 a.m., and I start whipping out some content that I think makes sense. And that’s how I kind of got into it. The genesis was frustration over years of this misalignment and misunderstanding. 

Brian Skinn [00:09:28] That misalignment between what the title was and what the role associated with the title was across all the roles? 

Oshri Cohen [00:09:33] Exactly. What they expected the role to be, what they wanted you to do and what you needed to focus on. Right? 

Brian Skinn [00:09:42] In order to be effective. 

Oshri Cohen [00:09:45] When I was CTO, I needed to focus on technology strategy – how,why are we going to implement it? I needed to be, you know, tied at the hip with the product, be in front of the customer as well, really understand, deeply understand how the business works, how the whole system works. And I wasn’t allowed to do that. And by definition I was set up to fail. The CTO role was set up to fail.  

Brian Skinn [00:10:17] Not intentionally. 

Oshri Cohen [00:10:18] No, not intentionally, not out of malice. You’re going to fail because what is expected of you is not what the job actually requires you to do, right? And there’s that misalignment that the founders misunderstand.  

Brian Skinn [00:10:35] So, it sounds like what you’re describing is almost like a general. There’s some misunderstandings about these roles, that’s kind of industry-wide almost. The understanding of the roles is still developing to a certain extent. 

Oshri Cohen [00:10:47] Absolutely. And I looked into the statistics of this. Out of memory, I don’t have the actual statistics in front of me, but out of memory. Most startup CTOs or even founding engineers will last about two years. That’s it. They last two years, but they’ll get a nice chunk of equity. Which is interesting to me because that also doesn’t make a lot of sense. And I’m going to digress a little bit, but I’ve consulted with enough clients who took over from their departing CTOs, departing founding engineers. Some of them did a spectacularly beautiful job and some of them did a spectacularly horrible job. And I’m like, “How do you even hold a job after looking at the work you’ve done? How is it even possible”? Like, you can’t eat with a fork. That’s how bad some of them were and there are more bad ones than there are good ones, right? 

Brian Skinn [00:11:51] Again that’s the technical strategy in the CTO role you’re speaking that there was something.  

Oshri Cohen [00:11:56] Exactly. Just the technical strategy. The inability to even prioritize between A and B on a mathematical basis alone. Like what’s business valued? They don’t even understand that concept. It’s not because they’re inadequate. It’s because they’re not trained for this and they’ve never gone through it, right? How do you evaluate the business value of going in path A or path B? 

Brian Skinn [00:12:25] Yeah. My background is engineering and that was chemical engineering. And it is very clarifying the chemical engineering approach of what is the dollar value of a project. Finding the right metric and being able to reduce this complex thing to that single metric is a critical part of evaluating the strategy. 

Oshri Cohen [00:12:48] Exactly, exactly. I remember, I was the CTO of this particular company. We were doing implementations. We had to implement the software because some software, even cloud based, still needs to be implemented locally because you need the local resources, right? We needed to import data continuously with every single new client. We needed to import data that was never the same. And I was seeing the integrations team that really kind of fell under the COO, under operations, which really shouldn’t because they were dealing with code and data. And seeing what they were doing, and they were spending 80 hours on something that, you know, if we spent 300 hours building a proper tool for them, they would then spend 10 hours at a time. I saw the opportunity. But because of how the company was organized, it never happened and they still spent eight times more money and thereby eight times less capacity instead of optimizing. Because they just didn’t know it was even possible or they didn’t want to hear about it. 

Brian Skinn [00:13:53] Okay. All right. I really appreciate those insights into the CTO role: what the role is for. That’s a great deal there that I didn’t know before. So, the fractional CTO has the same function. Instead of being full time on a given startup, they divide their time among multiple. Is that pretty much at a high level as simple as it is or there is more to it than that? 

Oshri Cohen [00:14:21] A little bit more to it than that. Yes, there’s the fractional CTO and there’s actually even the CTO on retainer. So, the fractional CTO is even sometimes on retainer. It’s like, here you get a bucket of my hours, you get to tap into my years of experience and across, you know, ten industries that I’ve played with and that I’ve acquired knowledge of, and I get to solve your problem right there and then. The fractional CTO allows you to borrow 20, 25, sometimes 30 years of experience of a person that will not work for you full time. They don’t have enough work. It’ll be boring for them. Half the time within three months I find it hard to find even 2 hours of work with some of my clients. 

Brian Skinn [00:15:13] You’ve solved, you’ve addressed all the problems today. Yeah. 

Oshri Cohen [00:15:17] I’ve solved the problems. They can now move forward. And on LinkedIn, I say something like “Another client graduated”. And I’m actually happy about that. I’m like, “Yes, I worked myself out of it”. Because that’s the business. I’m supposed to work myself out of a job. If I’m always there, I’m in the middle. I’m not supposed to be in the middle, right? I get in the middle, but then I rise up very quickly and oversee how things operate and then let people do their jobs. 

Brian Skinn [00:15:40] And then they might move into a new type of problem or different problems. But then that’s like a different cycle turns over almost. 

Oshri Cohen [00:15:47] Well, so, I actually split everything into three phases. You bring me in because there’s a problem or you don’t know something. There’s one of those two. Or you’re smart enough to know that a fractional CTO is good for your bank account. That’s the reality of it, right? So, that’s when you bring me in. 

So, the first three months, I typically deal with foundational issues. You have a team. It might take four months to fix foundational issues if they never had a really proper engineering leadership. And then there’s engineering leadership and then there’s technological leadership. Those are very, very different. It’s like a Venn diagram, but they barely touch. And in the middle somewhere is how they touch. Because engineering is building, technology is running what was built. A completely different approach which most startup CTOs don’t have that experience because they’re hired to develop, right? And we’re going to go into the arc of the startup CTO role soon enough. I think I lost what I wanted to talk about.  

Brian Skinn [00:17:00] Yeah, three things – there was the evaluation. 

Oshri Cohen [00:17:02] Yes, yes, yes. So, there is foundational. Then there’s evolutionary. And now we’re evolving. So, now that we have a proper foundation, we can evolve. What does that mean? Now we’re going to make the system more performant, faster, less lag, higher quality; even though, in foundation, higher quality comes into play. But still even then, foundational is very much focusing on engineering and if there’s product, then product interaction with engineering. In evolution, we’re going to take a look much bigger and once we say, “Okay, now we have to evolve this system because the company’s goals at Series A is 100,000 active daily users or daily active use (DA use)”. And so we know the system can’t handle it. Now we’re going to evolve it to that point. It could take three months, it could take six months. All depends. All the while, even during foundational, we’re still delivering features on a daily basis. So it’s playing kind of both roles where I’m focusing on creating the proper foundation, and the existing leadership focuses on delivering current business value. Because I can’t stop everything, I wish. I did that once at a startup. I’m like, “We’re stopping it all and we’re rewriting this because this is impossible”. Well, once in a year and a half, once in my whole career actually, because it was just that bad. It’s not something I take lightly because it would take $1,000,000, pour it in the garbage, right? 

Brian Skinn [00:18:27] Oh yeah. 

Oshri Cohen [00:18:29] So, that’s evolutionary. And then there’s growth. So now we’re going from series A to, let’s say, Series B. Now, let’s say, we are at 100,000 daily active use (DA use). Now we’re going to set you up from 1,000,000 DA use or 100,000 or whatever it is, right? And now you’re grown. And we’ll set up the system so that business has to catch up to technology. You have this untapped capacity. You have to go now. Go, grow your business. 

Brian Skinn [00:18:59] Find the customers. 

Oshri Cohen [00:19:00] Yes. I’ve created this buffer for you. So, one of my clients could barely do a thousand orders an hour. After five months with me, we set it up to 100,000. But then they got to, like, 5,000. I’m like, “Guys, you don’t need me anymore. You’re not growing fast enough to retain me. I’m going to put a principal engineer in place. I’m going to coach them. I am still on retainer. You don’t need me anymore”. There it goes, my fee now just dropped dramatically because they don’t need me, right? And they can move forward. 

Brian Skinn [00:19:40] You provided only the amount of benefit that they needed. And then let them loose, too. Cool. Yeah. So, that’s the arc of given interaction with a given client. So, you mentioned in there and again it’s right there in the title of the event “The first four years of a startup”. So, how does that cycle interact with the first four years of startup and what is your vision, your view of that arc of the first four years of the startup? How do things change? 

Oshri Cohen [00:20:15] So, I talk about these first four years, but it’s actually not the first four, it is the first four generations of your startup. Because your startup can evolve from one generation to another within a year, within less than a year, even. Until you’ve got a major amount of funding, you’ve got a major client. You have now something, boom, evolve, and grow, rapidly. Your current leadership may not be able to do that or they may stumble, whatever it may be. 

So, the first generation is your CTO is really the founding engineer. Great coder, excellent developer. They can design, they can build, they can code, they can do whatever. But then suddenly they have a team and they’re not coding as much. And now they are managing. Now, here’s problem number one to the transition from a deeply creative role. Developers are artists that use science. That’s it. They’re just artists that use science. It’s like engineering. There’s a lot of science involved, even though there’s math. It’s like, “How am I going to compose this? We are creative beasts. We are artists”. I said all the time… My upcoming book is actually called “The Art of the Code”. It’s about the art of it all. So, yeah. Shameless plug, you know. Entrepreneur. I got to tell you. [laughing]

Brian Skinn [00:21:39] It’s reflexive. It’s instinctive at this point.

Oshri Cohen [00:21:40] I can’t stop. I sell it to my mother. I have no idea why. [laughing] So, you’re asking this engineer who’s used to coding all day long and solving problems rapidly to now manage people. Do they have the skill set? Do they not? Even if they have the skill set for it, do they want to do this? That’s the key. Most don’t actually want to manage. And I’ve seen this over and over and over – “My best engineer left”. “Why”? “I asked him to manage. He doesn’t want to manage. He wants to just code”. “Why don’t you let him keep coding”? “Yeah, but he’s my founding engineer. He’s supposed to be the CTO”. “Oh, okay. All right, then”. 

There’s a misunderstanding here. There’s a lot of education. So, they got a manager. Let’s assume they’ve evolved. Or after about a year or so, usually right at the cliff they vested their 25%. They bought into the company. They are out. They leave. It happens all the time. And they leave. And I challenge founders to ask themselves “What did they produce”? [laughing] “What did they produce for a chunk of your company? You paid them a salary, a decent one”. Because nobody’s working for equity anymore. This isn’t 2005. “What was working for equity? What did they produce for that equity? For that chunk of the company”? Really, that no other developer could have produced with proper technical leadership. There’s a value differential that is. It’s hard to quantify. It’s really, really hard to quantify. I advise founder to do a two year cliff, not a one year, wait two years. If they last you two years and they still did a good job, you know what they deserve. And at the two year cliff, give 50%, not 25%. So, they’re still getting the same amount. You just spreading it a little bit longer. You know, whether people will listen or not is that’s up to them. That’s their money, right. 

So, they’re going to a manager role. Ok, so, they’re managing now. It’s easy enough to manage three, four, six developers. That’s pretty easy, right? A little bit of coaching. You know, you manage the process. You don’t manage the people, you grow the people, but you’re still not coding as much, you’re coding maybe 20% of the time at that point. Boom. Now you need to evolve a bit more. Now you need to add up multiple teams. Right. So now they’re going from “I’m still an engineer in my mind. I have to manage. It’s difficult. Now I have to lead multiple teams and lead managers”. Okay. That’s when it gets challenging, because now you’ve got to get really excited. 

Brian Skinn [00:24:36] It can really be…scary. 

Oshri Cohen [00:24:37] It’s insane. It’s actually very scary. Yes. I’ve been in it and in that position, I’m like “Why would they listen to me? Why would they listen to me? Who am I that they would listen to me? And how do I do it? How do I even approach it”? You know, coaches for developers barely exist as it is. And I coach a lot of developers, but there’s not enough in the market. So, if anyone’s listening to this, if you’ve got developers, hire a coach for them, don’t even give it to your CTO expecting them to coach. Another job on top of their job is to coach people, which not everybody is designed for. Most people can’t even interview other people properly. 

Brian Skinn [00:25:21] It’s challenging. It’s own skill set. 

Oshri Cohen [00:25:25] Yes. Incredibly, incredibly challenging. So, we’ve got that. So, now they have to be a leader and now they have to keep track of metrics and they have to interact with product and customer service and help them, you know, formalize and adjust their processes to help engineering, right? Half my job is working with product and with customer service and with sales to adjust their processes, not their customer facing process, but their business interfacing processes, their internal processes to help engineering. Because if you take a look at a funnel, engineering is at the bottom. It receives signals upon signals built on other signals and finally gets to them. That’s why so many engineers are frustrated. Because you’re just getting all these signals of all these problems and they don’t even know how to get out or how to navigate away from it. So then they create this shell. 

Brian Skinn [00:26:28] And so, what you are saying, most of the signals from higher up in the funnel are not relevant to them. Is that it? And that it’s a noise overload or… 

Oshri Cohen [00:26:36] It’s wrongly attributed to them, right. The CEO says, “Well, why aren’t we releasing features fast enough”? Product will say, “Well, engineering is slow”. Engineering will say, “Well, product isn’t giving us proper specs or they’re giving us tasks that last three weeks”. Because nobody has the leadership credentials to say, “No, product. That’s not how you work. This is how you work and let me help you and let me show you and then we’ll sell you on this so that you accept this. Not because I’m telling you to, but because you will see the light on how it’s better for you and how it’s better for the business and how it helps engineering. Let’s be best friends”. 

I’m literally a technical talk therapist. C’mmon, talk to me. At every first engagement, my first meeting with all stakeholders is technical talk therapy. I just sit there and I start taking notes. I’m like, “Talk to me about your father now”. [laughing]

Yeah. So, and then you go from leader and you have this thriving team you got to go into visionary. Now you have to think beyond the CEO. Now you have to think, “Shall we keep cloud or should we go to a private data center? How do I even do this math”? You’ve got to do this math now. Or “Are my VPs working well or they are not working well? Are my directors doing their job? How do I know? How do I optimize the team topology? Should we implement a different process altogether”? You have to start thinking. And in many cases, some of my clients ask me to do this… well, the Research and Development Project says, “We don’t have anyone to think about the future of the business. Can you do it”? Sure, I can do that. I’ll sit with the CTO. I’ll sit with the director of engineering. I’m like, I’ll write it all up for you. I’ll start thinking creatively. 

Brian Skinn [00:28:28] What is Gen2 and Gen3?  

Oshri Cohen [00:28:30] Because they don’t have the time to do that. They’re knee deep in the process because they’re missing a few roles and skill sets. So that’s those four generations. And you kind of need four different people. That’s the reality. Four different full time employees. So, good luck finding that. [laughing] 

Brian Skinn [00:28:48] Right. But then the fractional CTO says, “Well, you don’t need full time. Just find the right fractional CTO or fractional role for what you need and plug it in”. It sounds like. 

Oshri Cohen [00:28:59] Exactly. So, you know, because I fulfilled the EM role, the director role, the VP role, the CTO role. I found the role… I had two startups. I have a third one now that’s launching soon. And I can think and operate at those levels. And because it doesn’t impact my career to become an EM. It doesn’t hurt my career. That’s why people hire me, because I can be a chameleon and then I can leave. It doesn’t impact my career. So, if I need to be a principal engineer and sit down with the Devs and design a system and review code, I’ll do it. That’s it. I’ll just do it. If I need to now become the hiring manager and do a whole ton of recruiting, I’ll do it as well. It doesn’t impact me. My resume doesn’t change. Because my success is not tied to my rise in this company and what I’ve done. Where for employees, it really, really does. You can’t just ask a director of engineering saying, “Hey, you know, can you go see this client?” “What do you mean ‘”Go and see this client”?” Yeah, I’ve done client facing – fly out, meet a client because they needed to see the technical leadership that the company didn’t have. So. 

Brian Skinn [00:30:22] Yeah. So it’s totally a side step to the rigidity of a career arc, so to speak. You’ve had the experience in all those roles, and you can bring them in at just whatever the client needs. You can supply it. 

Oshri Cohen [00:30:35] Exactly. So I’ll give you another use case for this which just came out. Really. You know, I had this founder call me. He’s like, “Listen, we love our CTO, love him, but going on maternity leave and we want to keep him, obviously”. They are not mean people. “But we don’t want to hire someone full time because we feel like maybe, you know, there’ll be some anxiety. Can you fulfill that role”? I’m like, “100%”. I’ll meet with the person, download everything that they need. If they want to stay in touch with me afterwards once a week or once every two weeks to make sure that everything is working fine, by all means. I come in, I manage, I take over, and then guess what? I leave. Because I’ve got  no vested interest. It’s not my career. I’m not there to replace you. So people actually kind of like that because they like their CTO. It’s like, “Oh, this person is just kind of standing in?” “Yeah. When I return from maternity leave, this person’s coming in”. “Okay, fair enough”. That’s it. 

Brian Skinn [00:31:47] Yeah. I mean. Go ahead. 

Oshri Cohen [00:31:51] Yeah. It’s just something that kind of came up. And now I’m reaching out to HR reps and telling them this is an opportunity to really provide an amazing experience for your employees that are of that age group. They’re having their kids, they’re getting married and whatnot. To allow them to have, you know, a four week vacation because they need it or a sabbatical because they need it. Why not? 

Brian Skinn [00:32:24] Indeed. Yeah, it’s the flexibility just from a planning standpoint. The ability to tailor the spend and all of it seems like it would be extremely attractive. 

Oshri Cohen [00:32:37] And it’s cheaper. [laughing] It’s so much cheaper because I’m not there full time. I’m there 2 hours a day – I talk with the directors, I adjust things. They’re out there with me on Slack and that’s it, you know. 

Brian Skinn [00:32:49] But at the same time from your side you can have multiple clients. And so the overall effort is full time career and income for you. So, it works on both sides. 

Oshri Cohen [00:33:00] Yes, yes, yes. I typically work a good 10 hours a day. I usually have five clients almost at all times, right? Almost at all times that require 2 hours of my time. I’ve got another six or seven that are based on retainers, and they’ll contact me when they need me. And kind of works very well.It’s exhausting, though.  

Brian Skinn [00:33:25] Well, but it sounds like a lot of fun. 

Oshri Cohen [00:33:26] I literally need a vacation every three months with zero electronics. And I’ll go to a cabin somewhere with no Internet and I’ll just lie down in quiet. 

Brian Skinn [00:33:36] Decompress, totally. 

Oshri Cohen [00:33:38] Totally decompressed. But I love it. It’s fantastic. 

Brian Skinn [00:33:41] Awesome. One thing you mentioned in there is the recruiting aspect. Fractional CTOs are recruiting. Talk a bit more about that. What are the advantages there? 

Oshri Cohen [00:33:52] Man… Hiring a fractional CTO to actually do the recruiting for you is a very interesting experience both for the candidates and for the teams. So, when I’m hired as a fractional CTO, obviously, I’ll take a look, I’ll keep the existing team as is, I’ll learn, I’ll see what’s happening. It takes about a month to really fully immerse yourself in the situation and the problems of the company. And I’ll say, “Okay, I think we need to hire about three people and this is how we would use it”., and so on and so forth. And because we’ve got proper leadership, we can go a bit more junior so we don’t have to get these superstars, right? Which by the way, if you have proper architecture and proper processes, you don’t need your superstar Cowboy Ninja, technics, developers. You can have a couple of really strong Devs and the rest are juniors and give people a chance to get in and start in the business. I mean, junior developers, and I digress again, sorry. But how many junior developers call me and say “I’m having a hard time finding a job? Nobody wants to hire a junior”. It’s a very, very difficult situation for new entrants into the industry. 

So, my client says, “Okay, well, we need to hire a recruiter”. I’m like, “Not a problem. Either you can hire a recruiter and I will work with them or you can hire me and I will recruit for you off hours”. And I do some recruiting and only do recruiting really for clients that I really like. I mean, I’ll only work for clients that I really like. It’s kind of the benefit of entrepreneurship. If I don’t like you, I’m not working for you, I’m just out. See you, contract canceled, we’re good. I get to do that, right? They get to do that as well, which is kind of the risk, but still. 

So I’ll do the technical recruiting. Usually far cheaper than a recruiter would normally charge, but I provide a far better service. Because I know technology. I actually understand technology. I intimately understand what the team needs. It’s my team. So when I’m hiring for them, and I’m interviewing them, half the time, I’m like, “You’re going to be hired. I just need you to meet the team first”. Within the first interview. 45 minutes. Have you ever seen a technical interview? If you know technical interviews or you’ve gone through it, it’s usually three or four interviews – jump through hoops, how many squats can you do?, can you code also?, show me that, oh, we need another three weeks, another six weeks to wait. It’s horrendous. Frankly, half the time it’s demeaning. I’ve been a developer enough, and I had to go through the recruiting process. It’s honestly 99% demeaning. 

Brian Skinn [00:36:36] Does it really take this much? Is this process actually what it takes to…? 

Oshri Cohen [00:36:41] No. People are just afraid of making a decision. So, I need to look good to my superiors.  And if you hire normal recruiters, you’re going to get a flurry of resumes because they looked at keywords and said, “Oh, you know, get. Great. I think they need that as a skill”. Excuse me. What? [laughing] What do you mean? Maybe use a keyboard as a skill set now?  

Brian Skinn [00:37:06] Right. There’s no perspective on what’s fundamental, the things that everyone ought to know versus what really is necessary for the role. 

Oshri Cohen [00:37:12] So I’ll go over everything, you know – I’ll rewrite the job description, I’ll do the technical interviews. That’s very much related specifically to the challenges. So I’ll craft specific questions that I want to see who this person is made of. But I say and I tell this to my candidates and I tell this to my clients as well. I’m not going to try to filter people out. I want to try and position them one way or another. Sometimes I can’t position people because they don’t have what’s required. So my questions are not to trip you up, it’s to evaluate what you’re made of, how your mind is wired. That’s what I want to know. I can teach you programming. Frankly. I can teach you the code. Most of the time I’ll interview someone that has dot net experience and we’re doing Golang and Python. There’s not even any relationship to those languages. But if they can think in a certain way, teaching them the language, it’s, you know…

I learned Python and Golang in about three weeks together, and I was deploying to production in one of my jobs. And I didn’t know any of it. That’s why I did that because it was one of the first times, it was the best interview I’ve ever had. There was one employer, the best employer I’ve ever had. I love him to death. And I tell them on LinkedIn all the time. I share all of their job roles all the time. They’re amazing people. You know, if people want to know, I’ll tell them who they are afterwards. So, that’s it. So, I rewrite the job description, do all of that, find the candidates and then hire them in record time. I could hire an entire team in two weeks. 

Brian Skinn [00:39:03] And then, you’ve been in the strategic role also. You know how you plan to deploy them and where they can better invest. And then the technical progress just flows naturally. You know, the team comes in, and they get better positions. 

Oshri Cohen [00:39:19] Yes, exactly. And now I started doing technical recruiting outside of fractional CTO mandates for clients that ask really nicely because they’ve heard of me and they’ve heard of what I can do. So, I do the same thing, I just bring someone else to help me source because it takes so long. But I do all of the technical interviews. You know, one of my clients said, “I’ve never hired a recruiter where I could listen to the interview. It’s so entertaining while going for a run”. [laughing] Boom, boom. I send them the video, the audio, here are my notes. You want to listen to it? Listen, go for a run, pop some squats, knock yourself out. And if you want to talk to them, book it. It’s never happened before. I don’t know any recruiter who’s ever doing that. 

Brian Skinn [00:40:09] Interviews as podcasts. 

Oshri Cohen [00:40:12] Basically. Because it’s entertaining. This style of conversation is my interview. 

Brian Skinn [00:40:16] Yeah. Awesome. 

Oshri Cohen [00:40:17] Yeah, that’s fun. 

Brian Skinn [00:40:19] Cool. So we talked a lot about benefits and advantages as a fractional CTO. I’m curious, are there any situations, contexts, environments where a fractional CTO might be the wrong choice for a startup or a larger company? What do you think? 

Oshri Cohen [00:40:33] So in a startup, if there’s a problem with existing technical leadership, do not bring in a fractional CTO as a coach. It’s a failed endeavor. It’s happened to me. I’ve learned which clients just will not accept the role. Will not accept the fractional CTO concept. Because if I’m coaching a technical leader who also has the personality not to accept the information, not to accept the coaching or the leadership, they really have a personality problem, incompatible, I’m going to fail. 

Brian Skinn [00:41:20] It’s a human factor. 

Oshri Cohen [00:41:22] Yes, it is. 99% of the time a human factor. So now I tell my clients and it’s part of my contract, “I take over everything”. I don’t care if you’ve got a CTO. You want me in. I take over everything if I’m fractional CTO or show me CTO on retainer and do some work for you. Not a problem. I don’t really talk to anyone. I do some work. I help out a little bit because you need me for a couple of hours here and there. But if you need me consistently, I need to run the shop. I will give back the reins afterwards to the technical leader, and I tell them that I’m here, I’m taking over, I’m reducing your stress load, reorganizing, and I’m going to drip it back to you as we move forward because I’m not here permanently. My job is not here to be permanently. My job here is to fix a problem and then leave. 

Brian Skinn [00:42:11] Okay, so there’s that. Those are the main situations, just about most others, you know, technical issues, business issues, the fractional. 

Oshri Cohen [00:42:18] That’s it. If you’ve got business issues, I can actually help here. I’m currently at an offsite with a client and 99% of my assistance is around product, is about positioning of the business and some use of technology. Because I have that skill set. I can’t speak for other fractional CTOs, but I have that skill set. I’ve seen enough in business to be able to advise, and to do some design thinking and whatnot and whiteboarding exercises. 

Brian Skinn [00:42:51] Right. Sure. Excellent. Okay. That’s all the questions, topics I had. Any last points you want to make before we close out? 

Oshri Cohen [00:43:02] What does it look like, the fractional CTO? You hire someone so what does it look like? What does the first day look like, the second day, the first week, the second? So, at first, there’s a lot of learning, so don’t expect much. Don’t expect them to change the world. You hire a CTO, don’t expect them to change your whole company overnight. Same thing. There’s no difference, right? 

Brian Skinn [00:43:25] Right, right, right. 

Oshri Cohen [00:43:28] Don’t be afraid of the hourly rate as well. Because, yes, it’s much higher than a full time employee, but over a whole year, keeping me for over a whole year barely scratches the surface of a mid-level engineer. Barely. But you get 20 years of experience, right? Because usually I come in with the answer to the question, and sometimes I come in with the re-questioning of your question because your question was wrong to begin with. You didn’t ask the right question. Let me rephrase the question for you and then I’ll give you the answer as well. Because that’s what comes with experience, right? And…that’s it.  

Brian Skinn [00:44:15] Terrific. All right. Well, thank you so much, Oshri, for your time today, for all of this. 

Oshri Cohen [00:44:20] Thank you very much. 

Brian Skinn [00:44:21] Background and detail about the fractional CTOs and the advantages they can provide. We did not have any questions come in, so we’ll just leave it there. 

Thank you to everyone who attended. This was, I got to say, this was incredibly informative for me and I hope our audience thought so too. The event is being recorded. That recording will be posted to the Open Teams YouTube channel and to our site once we have it prepared. That’ll probably be a few weeks out. And that’s it. 

Remember, just remember that Open Teams gives you access to the best open source architects in the world to help you train, support and deliver your software solutions. Go to openteams.com to learn more and to get to know our open source architect network. Or if you, if you’re interested, apply to be an architect yourself. Thank you very much. Have a great rest of your day. Thanks, Oshri. 

Oshri Cohen [00:45:12] Thank you.