From failed startup founder to top-level cloud engineer: The inspiring story of Yekeen Ajeigbe

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August 16, 2022
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20 mins read
Yekeen Ajeigbe design

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For this week's episode of Expert and African, I sat down with Yekeen Ajeigbe, a senior software engineer with six years of experience. He's the senior engineering manager at Deimos, an Africa-based cloud-native developer and security operations company.

After putting his all into a startup idea that failed earlier in his career, Yekeen decided to focus on a specific role and get better at it. In this conversation, he shared how he moved up the ladder to become the preferred choice for leading tech companies; and he also talked about his love for farming.

Yekeen had a startup idea, OurOja, and started working on it as he rounded off his undergraduate studies. He calls it a crash course because it formed the basis of his knowledge in product development, software engineering, marketing, sales, user experience, people management, and other skills required to run a tech business. Although he was disappointed because OurOja never took off, Yekeen didn't give up.

Not deterred by that, he went ahead to hone his software engineering skills. His first stop was at a software-as-a-service startup where he spent a few months before heading to Konga, one of Africa's leading eCommerce platforms, to lead one of their engineering teams a short time after he joined. 

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In less than two years at Deimos, Yekeen went from senior software engineer to principal software engineer and then to engineering manager before assuming his current responsibility as the senior engineering manager, where he works with multiple engineering teams and engineering managers to build products and provide value for clients. 

As someone who started coding in 2011 and rose to become a senior software engineer, some qualities sped up his transition. Can you guess what made the difference? Years of experience or project quality?

Let's learn a bit about his early days

Having a conversation with Yekeen Ajeigbe
Yekeen Ajeigbe, Senior Engineering Manager, Deimos

Yekeen got his first computer, a desktop, when he was nine years old. And that meant only one thing: he had something to tinker with quite early in life. But that didn't last long because bad voltage destroyed the computer. 

And this put him back in the same situation as his classmates at the government secondary school he attended, where students had only one hour a month to play around with a computer. Maybe this was why his parents wanted him to be in touch with current trends, and Yekeen is grateful for their push; of course, it helped that he loved to read. 

“For my parents. I can't really say exactly what their motivation was. But as a parent, you would want to give your child the very best things of life. It was more like computers look like [they] are taking over the world. I think that was more or less the train of thought for my parents. And of course, I spent most of the time on the computer playing games and switching between words.

“It wasn't like I was writing code or anything, but it was pretty interesting. And then I was lucky enough to go to a school where, twice in a month, you'll get to go to the computer room, and just play around for 30 minutes. And that was like the highlight. And that was if there was power. That really stoked me because I loved its technical nature.

“I love reading. When I finished secondary school and got admission [into university], I used to have this flash drive that I took literally everywhere with me. The flash drive contained books. Like lots of books from everything around the Harry Potter series to books around software engineering, which I probably didn't read back then. But it was just like collecting PDFs. People collected movies back then, but I collected books mainly. And so with that I would go to a cyber cafe. Even when I didn't have a computer, I'll go to a cyber cafe. I'm happy to spend my lunch money on it, and just plug that in and read.

“So I think that was what gave me that exposure. When you grow up, you can't allow yourself to be defined by just the environment you grew up in. You need to broaden your horizon, you need to read a lot more. It was that continual reading that I would say gave me the exposure to say, ‘This thing looks technical, it looks weird, but it's actually doable.’ It's not that bad, especially when you start looking at the underlying principles.”

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Speaking with Yekeen Ajeigbe
In conversation with Yekeen Ajeigbe, Senior Engineering Manager, Deimos

Yekeen’s baby steps in tech

“Yes, I've always been in tech. My very first job was being [sic] a founder. Being a founder, you have to wear a lot of hats. At some point, I had a team of up to six or seven. I'm not really a one-direction kind of person. I love knowing exactly how something works, so I would say I was very interested in not just building products, but building very good products. 

“I started out my career trying to build a small startup that never really took off which is called OurOja. It gave me a lot of insights and knowledge into product development and software engineering, marketing, and sales. It was literally a crash course, a very good learning experience. So it was the days of UX. I attended a lot of Google trainings on UX in Lagos then.”

Yekeen’s career before OurOja

“Before that, I was literally learning how to code, more or less. I love technology. For me, I see it as a tool to solve problems. And software is one of the best tools for us in Nigeria because as long as you have a laptop and Internet connection, you can literally access unlimited resources to get started with it. I spent a lot of time in operating systems, programming, [and] Python before I eventually decided to try to solve a problem with this.”

Wondering what inspired him to go into software engineering?

“My love for technology is what really pushed me there. But a little bit of it also, from the pragmatic side of things, was [because] I studied microbiology. And it's a very interesting field. I love science. One of my dreams when I was younger was to be a researcher. I read science books for fun, even till now. 

“I studied microbiology and if I want to make a career in microbiology, potentially, the highest I could probably do is be some kind of lecturer. If I wanted to take the next step, I'd probably have [had] to figure out a way to get into a top-level research company or something like that. There isn't a lot of room to grow there. There isn't [sic] a lot of areas to explore there. 

“I've always loved computers. I remember when I got my very first computer when I was small, those few months, it was revolutionary for me, it was game-changing. Being able to type one word and see it. It was cool. So that's where I started leaning more into technology. I started understanding [that] I love this thing already. 

“That was [sic] the days of Facebook, it was like every startup was coming out. Everybody wants [sic] to be the next Mark Zuckerberg. There were startups coming up, solving problems. People like the Kongas and Jumias were coming out. And Nigeria is definitely a place full of problems. And we see people solving these problems every day. We see people using technology to solve them. 

“It wasn't even really necessarily about the money though. Of course, if you do it properly, you can go a very long way. And that's one of the beautiful things about technology or software engineering in Nigeria. I've worked with so many people, mentored so many people that are now in Europe. Some of them didn't even study technology like me.

“And the beautiful part is [that] software engineering is that great equaliser, where, regardless of where you are in the world, with a computer and an Internet connection, you can learn and upskill. You can potentially get to Silicon Valley levels if you're willing to put in the work. It’s just mind-blowing. You can get lots of materials just for free. Lots of careers to make you very profitable with very good careers. And you can do it by yourself without having to wait for anyone to mentor you or to train you.”

The story behind the startup that never took off after over 2 years of effort

Yekeen Ajeigbe
Yekeen Ajeigbe, Senior Engineering Manager, Deimos

It was [my] final year. I actually took a year off school. You could imagine the kind of chaos it caused back home. Because at that point, I wasn't remotely interested in my degree anymore. For my final year, I just took a year off and spent some time. I worked from Idea Hub back then, which was close to CcHub. 

“I did that for close to a year before I did have to go back to school. I spent one or two years just playing with that. Towards my service period, I realised that I don't think I'm ready for it yet. Because it's exceedingly hard to build something for a large set of people when you don't have the skillsets or, you don't have the experience or the knowledge. I spent more time making mistakes and learning, which was a positive side. 

“So that was pretty interesting. We never really got any traction or even got out of the idea or conception phase. If I could have concentrated completely on engineering, maybe that would've been a good idea. But instead I was trying to do engineering, product management and then sales and so on.

“And a little bit of that is actually also down to the personality trait I had back then, I wanted to do everything. I was like a one-man wrecking machine, which really doesn't scale. You can't build things with just one person. It's just about taking the best out of everybody and getting the best skill sets from everyone. Using everyone to the best of their capabilities. 

“Yes, I did really feel bad because ultimately, who would want to actually fail? It was like when you try to go your own way and everybody says there's no road there and you went on to try it. Our society hates failure, but failure is just a good learning point. So it felt like crap, but I'm happy for the experience and I can look back honestly and say it failed more because I wasn't ready; I didn't have the skill set or mindset to even go for it. 

“I've been very intentional about building up those skills, being very hungry for the kind of experience, working in a place where there are always people better than you. Sometimes you just have to surround yourself with people who help you become better. And that's been very helpful for me so far.”

From failed startup founder to a sought-after senior software developer

“And then after that, I joined Formplus, which is a really cool software-as-a-service platform where I started working a little bit because of my people skills. I was working with the customers, taking customer requests and also doing a lot of software engineering. Eventually, I just ended up spending much more time with software engineering. 

Yekeen Ajeigbe posing for a picture
Yekeen Ajeigbe, Senior Engineering Manager, Deimos

“I met with the founder of Formplus, and he was someone I could actually learn from. This is software-as-a-service, Nigerians doing software-as-a-service is weird, at least back then, anyways. Because this was a startup that almost no Nigerian was using, a startup that people across the world were using. But it was based in Nigeria. And that was pretty interesting for me. It was a great experience. It also set the bar a little bit high for me.

“Doesn't matter if you're Nigerian, you don't necessarily have to churn out "trash." You can also churn out some of the best products in the world, regardless of the geographical location. After Formplus, I joined Konga. Konga was great at that point and still is one of the biggest eCommerce platforms in Nigeria. 

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“Within a very short period of time, I was leading one of the engineering teams which is one of the lead architects which re-architected and rebuilt the Konga platform to some extent. Then after Konga, I joined Deimos. At Deimos, I pretty much started out doing a lot of senior software engineering stuff.

We work with companies across Africa, some very cool companies in Nigeria, even some companies in Europe and so on, giving them solutions to technical problems.”

Yekeen didn't even have to apply before getting these jobs.

“The weirdest part is I've sent in a lot of applications and applied for a lot of jobs in my life so far, but I've never really gotten a job based on applications. My very first job, which was just like a contract gig, was from a community that was born out of CcHUB. It was just like frontend, or something like that, in Nigeria. So that's how I got my very first gig. Someone just called me from the community and said, ‘Oh, Yekeen. I know you do frontend, there's this company…’ so just called me out of the blue, that was it. 

“And then Formplus was literally just a mutual friend to the founder going you two have to meet. And I was like, ‘Okay, sure, why not.’ I just thought it was gonna be a waste of time, but then, [it] turned out to be not. Getting into Konga was literally someone from Konga just dropping me a message on my LinkedIn and going, ‘Hey! I really like your skill sets, let's meet’ or something like that. And even my current company. Keeping my LinkedIn up to date, even though it's not really active, just make sure that it's not completely stale. It keeps a lot of offers coming in.

“I was a little bit just obsessed with it. I take my personal development very seriously. For a very long time even till now, I code a lot. So it was just like, even at work, I see this paradigm, I try it. As you're working, you are learning on the job. But also, there are some things that you don't even need to figure out. You can just read a book because somebody has already figured that out for you in the past.

“So a lot of my early growth was just that I read more than almost anybody else. So if you say a problem, I would say, ‘Huh, maybe this tool is actually a [sic] right tool for it. Maybe you could have solved that problem also, or you'd have come out with the same conclusion that I have, but just because I had some better tools.’ And as I'm exploring different aspects of software engineering or, just spending more time on management. So that's really helped to some extent also. 

“Then at Formplus, we were working with some Polish engineers, when I started, he was very critical of my code, not even of me, I didn't even take it personally. So I turned what could potentially have been negative. And also I've always asked for feedback. So I would ask my coworkers for feedback. I would ask the founder for feedback. So I think when you are working anywhere or even where you are, you should always know exactly where you stand at every given point. If I suck, please tell me. So that I can do something about it, right? Yeah. There's no point in you telling other people that I suck because they won't be [the] ones to do something about it. So it's being very helpful having that direct feedback and being just very open. Literally everywhere I've worked, I've enjoyed all the products I've built to varying levels.”

Moving between companies as a software developer

“I think so far, it's been relatively straightforward. It hasn't been too difficult. Another thing also is when you know what you're looking for, you try to be very intentional about the kind of companies that you work with. In some companies, even if you announce that you're resigning, it's like all hell breaks loose, you must never leave, you become persona non grata or something like that. 

“But at every single place I've worked at, for example, with Formplus, it was very cordial, I'm still in touch with the founder. Same thing with Konga. Not burning bridges when you are leaving, right? Yes. There's always that sadness about, ‘Oh, these are people that I've spent over a year with,’ right? You sometimes spend more time at work than at home. But there's also that assurance like I'm not burning bridges. I can still chat with these people if I want. Because we're not working together doesn't necessarily mean we are now suddenly enemies.”

Is Yekeen ready to build a startup now?

“To answer your question, yeah. Can definitely run a startup. For me, I'm just very selective in terms of what problems I wanna solve, what problems do I want to work on? It's in the roadmap. I would like to get back into it. I think I've learnt a lot of skills along the way, but I'm also just very happy to keep growing, keep getting those skills. 

“Because the way you approach problems on a smaller scale is different from when you are thinking about multiple layers, multiple interrelations and also building up a network area of being able to actually attack problems with good resources and good backend.”

Getting into software engineering

The demand for software engineers is high! And there's a projection that it would grow by 20% before 2030. So, there's a worry that the space is becoming saturated, but Yekeen has a different opinion, which would help if you're considering a career in software engineering.

“Definitely, the market is saturated, but on the other side the weird thing is ... I and a client were talking about how hard it is for them to actually find engineering talent. Even for us, you know, it takes us roughly two to three months to find good software engineers. Even for an intermediate role, you can get literally 2,000, 3,000, or 4,000 CVs. 

“But, by the time you do CV screening, you are getting maybe 400/500 people. You do an initial assessment and then it drops. And then at the end of that, you're barely able to find one or two candidates actually. So there is a lot of quantity in the pool but quality is also very ... there're some great gems out there, like a lot of great engineers in Nigeria. Like I know, like I've worked with a lot of them. What I'm trying to say is people just coming in should not be disheartened or sad or think it's not possible.

It's still very much possible. Software engineering's a place that rewards... if you actually know your stuff, if you're not fluffy. Nigerians know how to sell themselves. People sometimes spend more time selling themselves than actually developing those skills that they should be developing. It's not insurmountable. 

“If you're starting out, focus on one or two aspects. For me, for example, when I first started, that's one thing that didn't help too much, it doesn't allow you to grow very quickly. So you want to focus on a specific. Do your research, pick one or two areas, focus on it. Don't learn the technology, learn the fundamentals, learn the principles behind it. So in terms of joining a team, there are some invaluable experiences you'll just learn in a team. But there are also a lot of things that you can learn on your own. You don't have to be in a team to learn about engineering, to some extent, anyways.

On the other side of that, Nigeria is now getting to a place where there are lots of startups. , there's always one coming out of the woodwork every other day. And it's actually the same thing consistent across the world. There's usually always somewhere to start, really. If you've gotten your skills to a certain level, right? Companies encourage you to learn, they give you the skills to learn but, no company wants to take you from zero to hero. They don't start from zero, start from maybe like 40, 50%. 

“And then, like I said, okay, maybe there's something here to invest in. You can provide some value to me. Because, ultimately businesses are meant to make profits. They're meant to bring value to their shareholders, they're not necessarily meant to upskill people, right? Though, of course, as a business, you also wanna think that, oh, if I upskill my people, it provides better value for me in the long run. 

“But again, I don't want to now say, okay, I'll take you on board. You spend six months or one year learning things that you could have learned at a bootcamp, you could have learnt at your own time, and pay you salary, with you not returning any value. And then in, after one year you decide, oh, I'm going to leave or something. Because retention is a big problem across tech nowadays. So usually people are resigning the jobs every one to two years, or they're changing jobs every one to two years”

How to become a senior software engineer

Scaling as a software engineer is one question that ordinarily comes to mind at the start of this career. But how your journey would go is not set in stone, there are many factors that can contribute to one's growth to becoming a senior software engineer. And Yekeen shared his thoughts on this.

“So currently, in my current role, I do a lot of recruitments. I'm reviewing CVs, sitting in interviews. And it is giving me just a better understanding of... seniority in software engineering, the years aren't a direct correlation.

“Generally, maybe it takes five years for someone to be a senior software engineer. But it's also not necessarily that. So if you've spent all your career working on WordPress, right? No offense to WordPress. You may be a senior at WordPress, but like you probably wouldn't have gained other actual, very good software engineering skills or transferable cloud-native engineering, building microservice architectures, and so on.

“So that is where the difference... now, compared to someone working on... for example, I've worked with literally people who have gone from junior engineers to intermediate in one or two years because they started their career working in advanced... we're talking about the Microsoft Azure architecture, for example, the standard architecture that people like the Facebooks and the Googles and so on. 

“So that's the architecture that a lot of them work with. So if you grow up in engineering, working with that kind of architecture, you'll probably have a shorter path to seniority than some people. So, it's hard to directly measure in terms of years that's to say. 'Cause there are some people that have spent 10 years working on, for example, Magenta or WordPress or something like that. Especially if they're working on just the surface-level things and not necessarily the backend things. 

“I can't even give them a rating of intermediate. Because they only know how to do a specific technology. They may be able to, you know, slay a dragon on WordPress, for example. But that doesn't necessarily mean they understand a lot of cross-functional engineering skills. No offence to WordPress. Okay. But it depends on where you're spending your time, depends on the kind of company you're working with. Depending on the scale, really?

“If you're building software for 100 users, trust me, like they won't see all the potential bugs that would happen in your system. But if you're building for 1 million users... I remember Black Friday or Yakata then at Konga. When lots of users are using your system, they use it in unpredictable ways. So it actually now goes away from programming to actual software engineering. 'Cause if you're not writing properly or you're not developing your products properly, if you don't have the tools to even know when there's a bug or something. So a number of things like that affects seniority.

“So it just boils down to, when you have some contexts. But it can take anywhere between three to five years to become a senior. But caveats around the kind of person you are, the amount of efforts that you're putting into your own personal development, the kind of companies you are exposed to, or the kind of products that you're exposed to.”

Having a career in cloud engineering

“I think cloud engineering is much more accessible than it ever has been. So for example I was at a Google event, like you sign off for Google, they give you $300 of credits for you to just play around with for three months. Amazon does something similar. You can literally get started by exploring some of these platforms. 

“Have a little bit of an understanding about what they work. Definitely learn about containers. They are not particularly special, but they're also just a very good starting point. So that's maybe one of the best ways. And then just having a good understanding of what are the considerations for deploying an application? What are the scale considerations? What are the observability considerations? The security considerations, right? Which is usually an underlooked area of development also.”

The 'not so fun' part of engineering.

“Engineering is brutal. It's brutal where the skills that you learnt today are potentially obsolete in one week. That's probably an exaggeration, but... in engineering, I always say standing still is the same thing as going back, right? So if you're someone that's, you are not that interested, you just wanna learn one thing and do that one thing for the rest of your life, that's going to be tricky.

“ If you are someone that loves challenges... in fact, a lot of engineers are thrill seekers to some extent, it's about slaying the next dragon. If you have that kind of mindset, that aggressive growth mindset. Engineering is a discipline that doesn't suffer people that just wanna do the bare minimum. If you have the fundamentals, you can maybe relax a little bit.

“The other thing also is working conditions in different companies vary quite a bit. So it's usually very good to just spend some time just having a better idea of what company am I joining? How do they work? Or something like that.”

Making leadership work as a senior software engineer

“For me maybe leadership just come easily to me, to some extent. But I've also evolved a lot, I'm also very intentional about growing as a leader. You get actual feedback from them just to get a better idea of where you could be better. And then, you keep reading, you keep evolving and developing yourself. 

“That's more or less the same cycle. But on the other flip side of it, some of us may be more prone or have more affinity for certain skillsets. But also, I don't think it's something that can't be developed. It's putting the effort actually to become better. Your emotional intelligence is also very important as a leader, right? As a leader, you don't have a luxury of just thinking about yourself. You think about how your energy affects your team, how what you're doing affects your team, right?

“I'm usually a big fan of the servant leadership approach where... get your team, get what they need, know what they need to grow and help them grow. Because the key thing is always if I'm not there, I want you to be able to own a problem and solve it. Not wait for me to say, this is how you do it. This is how you do it. This is how you do it all the time. So if you don't have that autonomy to actually grow yourself, I'm just creating more work for myself.”

How to stay productive

“So it's usually, different problems, different approaches to them. You use different tools for the right job. I think a key thing is your calendar, just in terms of productivity. My calendar is usually very tightly packed but it's also very helpful because then I know exactly what I'm doing. I know exactly what I'm working on. I know exactly what I'm up to. Notion, I just use it as the headquarters of my thoughts. 

“I think one of the better tools that I've discovered recently has been, at the start of every day. Just take five minutes, look at your calendar, look at what you need to do, look at what are the deliverables and just, flesh it out. It helps very much because it just helps align you, you know exactly what you're working on. You're not spending time jumping from meetings to meetings.

“And then also just prepping for meetings. That's a very important tool. Prepping for meetings can take just as little as less than five minutes. Okay. What meeting are we going into? What do we want to do in here? What's the point of this? Getting your thoughts in orders. Right? One of the worst things is when you're in a meeting, nobody's prepared. Then somebody's asking every five minutes, 'um I'm sorry, what did you say?' Or 'what are we here for?' It's very unproductive. And you're all wasting time.”

Life outside coding

“Oh, I would be a farmer. I love farming and also, being in touch with nature. We're in a country that doesn't pay as much attention to our impact on the environment.. We consume too much, we're actually spoiling where we live in. There's definitely room for producing smartly. And it's a problem that affects the rich, the poor. It doesn't really matter because. whoever you are, you're still going to have to eat. I would potentially wanna be a farmer at some point. I already farm commercially actually, just a small commercial farm. It's integrated agriculture, so it's like a lot of veggies and also poultry and livestock and so on.”


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Human enthusiast | Writer | Senior reporter | Podcaster. Find me on Twitter @Nifemeah.
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