Careers in tech often look glamorous from the outside. The job titles, conference panels, and LinkedIn updates all give the impression of a clear path to the top. In reality, the journey is full of pivots, detours and second guesses. Few people capture that better than Benjamin Dada.
His story reflects both the risks and the rewards of building a career in an industry that is constantly changing. In our conversation, Benjamin spoke openly about the choices he regrets, the lessons he has learnt, and why he reminds everyone to view their careers as a marathon shaped by time and chance.
The result is an honest look at what it means to build a career in African tech, told through the perspective of someone who has experienced its highs and lows at different stages.
If your career journey were a movie, what would the title be and why
I don’t have an exact title in mind, but I can describe the movie.
It would be about a boy who started life hitting all the right notes and was destined for the top. Graduated top three in his department, completed five internships as a student, and got a job straight out of school. One career move, a relocation after, an economic downturn (post-ZIRP era), and it’s been full of turbulence requiring a lot of soul-searching. For what comes next, the viewers will need to stay glued, cause even this protagonist doesn’t know yet.
Click to signupTell us about your journey into the tech industry. What initially sparked your interest?
My tech career started during my undergrad. I was fortunate to study Management Information Systems (MIS). Left to me, I wanted to study Psychology (not approved by my parents). So, left to the state of employability in Nigeria, it would have been Medicine, seeing that I was a science student.
I missed out on writing the post-UTME of the University of Ibadan, my first choice University, and very quickly, I was scrambling for a viable backup to not miss going to University that year (2012).
One thing led to another, and my school’s Guidance and Counselling teacher, Mr Adewunmi, suggested I pick Covenant University and study MIS, a new Bachelor’s programme in Nigeria that was offered by only a handful of Universities.
Desperate for a place, I decided to give it a try, telling myself that after the first semester, I can decide properly. Turns out, I loved it. I achieved a GPA of 4.77 (out of 5.00) that semester, where we covered a wide range of subjects, including computer science, programming, accounting, and finance.
Thus, it was my course of study that sparked my interest in tech.
When I went for my first internship at an accounting firm (2014), I found myself using my newly-found programming skills to create a Birthday card application that wished my senior colleagues happy birthday on their birthdays. It was a simple but fun application developed right within our main work tool, Microsoft Excel, via Visual Basic (a programming language) macros.
Then in 2015, I did my SIWES at Softcom, a company founded by an alumnus of my department. That was also the year I heard about Andela, a Silicon Valley-like startup paying people to learn how to code. I couldn’t believe it. We were battling with coding for our final year projects, and Andela was offering money to learn it.
My friends and I at Softcom applied. I got in, extended my internship by a month, and joined Andela. It was my first experience in a startup-y culture where the company had a rooftop with games, a common room with bean bags, and a dining area with free breakfast and lunch served.
Being in Andela, attending ecosystem events, and seeing the startup scene firsthand made me lean more towards becoming a startup guy than a consulting guy. If not for those experiences, I probably would be a Director in KPMG’s Tech Advisory division.
Did you choose the startup path intentionally, or was it more a result of timing and circumstance?
The only conscious decision I made at that point was that I wanted to complete my final year project independently, and I wanted to maximise my six-month-long SIWES plus holiday break (a month or two) to do at least two internships.
So, after staying five months at Softcom, I had started considering a move. By June, I had three offers on the table. One was Citi, another was a return to KPMG, and the third was Andela.
Andela’s financial offer was actually the lowest of the three, but I chose it because I wanted to learn how to code well enough to handle my project on my own. I was also open to consulting, so if Andela hadn’t picked me, I would have been fine with KPMG or Citi.
I think that my mindset of being open to whatever comes my way was further solidified by studying MIS. My programme is a hybrid of computer science and business sciences. So, we were often shuttling between two colleges to have classes. Seeing that I was doing well in both categories, I didn’t for once think to specialise in computer science, maybe so I can become a full-on programmer, or to specialise in business courses, so, I can become an investment banker. Rather, it was the opposite; I was looking for a role that could blend both computer science and business studies. It was in that search (2014) that I first heard of product management. But I didn’t get to work as a Product Manager until 2018.
How did your journey from Andela go?
Joining Andela in 2015 gave me a front-row seat to the evolution of what I’ve described above as Silicon Valley-style start-up vibes. And if you watched The Social Network movie (released in 2010), you might have been interested in that Facebook-y culture.
So, to help people live through me, I started writing about my experience on Medium. Over time, a lot of people followed me on social media and on Medium.
After my undergrad, I thought, ‘Okay, the world is my oyster, what next?’ I connected with some folks at CcHuB in Yaba, who turned out to be the co-founders of Stutern, twins running an internship placement platform. Their mission resonated with me because I’d done numerous internships myself and wanted others to have the same experience. I worked with them for a few months before rushing off to the UK for my Master’s.
During my Master’s program, I applied to Google for the third time and finally got in. They needed someone in Nigeria, so I returned home for the internship. After completing my MSc, in February 2018, I reached out to my former Softcom boss, who invited me to join the development of a new product: Eyowo. The sweetener? I get to work as a Product Manager!
Eyowo was an eye-opener.
You see, as a Master’s student, I used tech journalism to solidify my class learnings. In December 2016, I became a reporter for Techcity.ng, writing about startups like Piggyvest (then Piggybank), the digital divide, gamification and more.
I realised that some of the things that I was researching to write about as a reporter still didn’t provide sufficient explanation and context into the realities of founders and operators. So, I decided to combine my journalism experience with my lifelong operator experience by creating a publication on my terms.
Over time, I focused on fintech explainers while doing some investigative reporting and lots of search-optimised content. By 2020–2021, I’d become one of the most recognised tech voices in Nigeria. I got nominated for awards and travelled across Africa on an all-expense-paid trip to interview founders.
Later in 2021, I joined Stitch, putting my media work on the back burner. I left in 2022, relocated to the UK with my wife and joined Moniepoint in 2023 to help them get their cross-border payment and remittance product off the ground. I took a lot of learnings from here as well about the challenges of banking Africans globally, and how to build a cross-border payments business. Had a baby towards the end of 2023.
By 2024, after more than six years in tech, I considered launching a startup but decided against it due to my new life circumstances. Instead, I tilted more towards consulting for people who want to build cross-border payment businesses from Africa or for Africa. And that’s gone very well so far, as many of my clients have now gone live. In mid-2025, I decided to double down on building Condia while I try to figure out what’s next.
In your experience, how important have relationships and people been in your career, and how should others approach building and using them in their own careers?
These days, what people call networking is just attending events, collecting contacts, and keeping them for future use. That is a very simplified version, and it does not really work. Real networking comes from people you have worked with or had meaningful interactions with, whether through work, shared experiences, or even in more casual, “non-networking” settings.
I was able to call on the Softcom founder after my master’s degree (2018) because I had already built that relationship while interning there (2015). So, I’d contributed value to his organisation in the past, and he knew what value I could bring to where he was referring me to (the subsidiary, Eyowo).
The focus should be on building value into yourself. For me, that meant getting the best grades possible, creating a strong CV and cover letter, and making myself employable. I also positioned myself in places where I could be found, such as writing on Medium, building a presence on LinkedIn, and publishing work that demonstrated my capabilities. Those things attracted the right people far more than simply turning up at events and introducing myself.
I like to think of human relationships in banking terms. When you add value to someone, you are depositing into the account that you both share. When you need a favour, you are making withdrawals. It’s not this simple, but please bear with me. Essentially, do not draw on those deposits recklessly. Reach out only when you have a clear reason or a specific ask, not for advice you could easily find online or for roles you are not qualified for.
At the end of the day, systems are made up of people, and people are the ones who decide if you move to the next stage. Your best chance lies in doing good work, showing it, and then knowing when and how to call on the people who influence a thing.
How can mid-level professionals position themselves to be more competitive in the job market?
In my last two companies, I focused a lot on how I was contributing to the strategic objective. For me, that meant looking at the company’s mission, vision and KPIs, and asking myself how my work was helping to move the needle. One reason you need to know this is so that you would be able to tell a coherent story about your achievements in light of how they contributed to the company’s overall objectives, during job interviews, and skilled worker visa applications (like UK TechNation, and US O1)
Broadly speaking, thinking top-down and bottom-up helps you do your job better. If the company aims to make ₦20 million, then each department, manager, and individual has their own share of the responsibility. Bottom-up thinking means asking, ‘When I do all these things, how do they add up to the bigger goal?’
So, I always begin projects by asking what the objective is. That way, the task-giver and I, can clearly gauge my performance and other things being equal, they would be able to speak up for me where it matters and justify whatever is being spent to keep me in the company.
But maybe this big-picture thinking comes with more seniority in the workplace.
What I notice with junior people is that they are often task-focused. They tick off what they are told to do, but they may not see how their work connects to the company’s wider mission.
Once you are mid to senior, you need to move away from just tasks. Publishing ten articles is not the point. The point is whether those articles push the company closer to its goal of being, for example, the leading financial companion in Africa. That kind of end-to-end thinking is what sets people apart.
The next part is upskilling. You need to identify the skills that will take you to the next level. In my case, I knew that without a proper grasp of profit and loss, balance sheets and income statements, I could not become a business leader. So I paid for accounting classes to strengthen that area.
Finally, there is agency. This means taking responsibility, coming up with initiatives, getting alignment and delivering results without excuses. It is about acting without waiting for constant permission. You do the work, pilot new ideas, show early results, and then present risks, mitigation strategies, and timelines. That puts you in a different class.
The challenge in Nigeria is that many people are working multiple jobs, which limits their ability to think creatively or run initiatives that could show their true capabilities. But if you can combine top-down execution, bottom-up clarity, and high agency, then you stand out as someone people trust to deliver.
Looking back at your career journey, what decision or experience significantly impacted your path?
Starting a media company had a significant impact on my career, and that impact has fluctuated depending on the phase of my life. At the beginning, it was exciting. It gave me a way to learn and contribute to the community. But the unintended consequence of its popularity was that people began to assume I was only a media person, some even tried to belittle me by calling me ‘a mere influencer’. Oh, and mind you, there is nothing wrong with being an influencer, its more about the context and intent in which it was used.
My first job at Eyowo was actually in product management, and I had joined before starting the media work. So, product came before the media company. Not the other way around.
As I said earlier, by 2020 and 2021, people largely saw me as a media guy, and the more I grew in that space, the more it overshadowed my work in technology. Sometimes, when I was in companies, people looked at me in a dismissive way. That was frustrating.
At other times, I’m having to shrink myself to make other people feel comfortable around me, cause, for instance, there’d be times when I go for a meeting with my boss and the counterparty is fawning over me being there or meeting me for the first time. While it’s such a sweet feeling, it can get awkward. When I walk around the office, I have to drop my shoulders lower, because people naturally expect me to have them pumped.
Not only did I try to shrink personally, I even caused my media company to suffer even more cause I was trying to distance myself from it for a bit.
The media + working in tech journey is still one I am figuring out. In reality, doing media and working in tech is actually complementary. And there are many examples of people who seem to be doing it okay abroad, like Simon Taylor, author of the popular FintechBrainfood and now a staff member at Tempo, a company by Stripe and Paradigm. Before Tempo, he worked at an AI fraud startup, Sardine.
Media has opened doors for me in many cases, but in other situations, it has raised more questions than answers. Either way, it has played a huge role in shaping my career.
What’s a funny or memorable story from your career that you love to tell?
Once, I travelled without a valid passport because I had to attend a company engagement. Not going to say more cause it’d water down the story, but when I was doing it, I was very afraid.
A particularly memorable moment for me was in 2020/2021 when I won three awards at Softcom. First, I was named Solutions Architect of the Year. Then, within the bigger unit, I received the MVP award. Across the wider organisation, I was one of the recipients of the CEO Outstanding Award. That period was a real high point for me, and I felt genuinely happy about it.
What common blind spots do you notice in how African founders tell their stories?
When I think about telling your story, I see it across three main channels: owned, paid and earned. Many founders do not yet know how to make the most of all three.
Many people focus solely on their owned platforms. They write about company milestones, share behind-the-scenes stories or build in public, which is good, but it is still just one layer of storytelling. Ideally, your owned content should also feed into earned media, so that when people think about a sector, your name is the one that comes to mind. For example, when you think about HR, you might think of Seye from PaidHR, and when you think about remittances or cross-border, Benjamin Fernandes often comes to mind because of how much he has written on the subject. Their consistency on owned platforms has made them top of mind for earned media opportunities.
What I also notice is that many founders shy away from paid media, especially when a project calls for a 360-degree storytelling approach. One of the key lessons I learnt at Google is that marketing should be 360. Earned and owned are great, but paid media has a role too. It can drive awareness, activation, retention, revenue or referral. Not all paid media delivers conversions straight away. Some, like billboards or above-the-line campaigns, are just for awareness. Some are for activation. Others are purely about brand equity. For instance, Chowdeck recently gave people ₦100,000. Yes, the by-product will be increased sales, but it is also about the feeling people associate with the brand. Paystack invested heavily in community content and events. That did not always translate directly into sales, but it built a lovable brand, and brand love matters when you are competing in a crowded space.
Of course, to do this well, you need growth and marketing people you can trust to guide you. Earned media is never fully in your control, but paid media is. You can decide where to show up, whether that is on a platform with broad appeal or a niche one where your audience lives.
The gap I see today is that many founders have yet to evolve their approach. They are still stuck at early-stage tactics and need to think beyond that as they grow towards becoming brands at the storytelling scale of Coca-Cola.
Do you see African talent moving abroad as a loss for the continent or as something that still benefits Africa?
The sheer size of our population means we produce more than we can consume. Of course, Nigeria sometimes feels unreal. You can have 80 million young people, but only a fraction of them will be graduates. When you look at percentages, it can feel discouraging. Yet regardless of the percentage, the absolute numbers still place us ahead of many countries. Nigeria is estimated to have over 230 million people, while Kenya is around 57 million. Even if every young person in Kenya were highly skilled and educated, Nigeria would only need about 10% of its youth to match that scale.
That is why I find it lazy when people say all the best talent has left. The real issue is discovery. Many companies do not know how to find the right people. Sometimes your best hire may be someone from FMCG who has worked on System Applications and Products (SAP) systems. That same experience could be repurposed into growth marketing or even building core banking systems. So yes, there is a discovery challenge, but there is also a visibility challenge. Nigerian youth need to do more to be seen.
I also think that talent going abroad is not necessarily a bad thing. On one level, it improves Nigeria’s reputation. When people work with excellent Nigerians at companies like Google, they are more likely to expect that the next Nigerian they encounter will also be strong. That changes stereotypes in our favour. On another level, there is a long play where some of these people return and contribute directly to the country’s development.
That said, companies in Nigeria also need to do more to compete with what is obtainable abroad. It is not always about salary. Many people leave due to poor work culture, toxicity, or a lack of work-life balance. These are areas where Nigerian employers can and should improve. In many cases, you cannot compete with the salaries offered abroad, but you can focus on other aspects that matter to your employees.
Ultimately, the brain drain debate is something for ministers and policymakers to wrestle with. For the average entrepreneur who employs maybe a hundred people, it will not make or break you. The key is to build the right culture and find the right talent.
Is it better for young professionals to take the generalist path or focus on becoming a specialist?
I think it depends on what you are prioritising at any given time. For a young person starting out, the popular wisdom I agree with is to specialise. Build deep expertise in one area first. Once you are established and strong in that, you can branch out, pivot, or even switch careers.
But if your long-term plan is entrepreneurship, being a generalist can be very valuable. You get to experience different functions and organisations, from a one-person company to a ten-person team, a hundred-person company, or even a thousand-person one. You see how they behave, how they grow, and sometimes how they scale revenue that can fund your next venture. As a generalist, you are exposed to more opportunities because you are raising your hand for almost everything, whether in the same company or elsewhere.
In my case, I took the generalist route. At different points, I thought perhaps I should have been a specialist instead. I wanted to go into product management, but I did not quite get the role I hoped for. Then an opportunity came up in solutions architecture, which is essentially a pre-sales role. You create proposals, run demos, and demonstrate how your systems can integrate with clients’ systems. I took it on, learnt quickly, and made it work.
Later, when the company restructured, I was offered the role of business manager. Sometimes the move is not one you initiate, but you always have the choice to say yes or no. I said yes. After a while, I decided I wanted to earn more money, partly because I was thinking about eventually going into entrepreneurship full-time. I had already started a media company, and I told myself that if it were still alive after three to five years, I would focus on it fully. I began job-hopping, which recruiters often dislike, but the truth is, everyone has different goals and priorities.
The long and short of it is that you should choose the path that works for you in the medium term, and be willing to adjust as circumstances change. If you are a specialist and you lose a job, you can often rebound into the same line of work, building a continuous career in one area. If you are a generalist, your CV may show shorter stints across roles, which can be harder for recruiters to process. That is where you may need more tailored job hunting, reaching out to people who are willing to look beyond the CV to the bigger picture of your skills and experience.
There are many ways to build a career. Some are more straightforward and others are more complex, but what matters most is aligning them with your goals and being flexible enough to adapt when opportunities present themselves.
What would you say are the downsides of taking the generalist path?
The downside of being a generalist is that you will almost never get through mass recruitment processes. There will always be someone who has done the exact thing you are trying to do for much longer. It also depends on the stage of the company. When companies are scaling, they prefer specialists. When they are just starting, they prefer generalists because a generalist can take on multiple tasks. It saves them money by eliminating the need to hire two people. They can hire you, knowing you will figure it out or cover everything.
So, if you are growing your career, consider where you want to be. Do you want to start in a bigger company, where you can learn from specialists and follow that path for a few years, and then later move into a smaller company where you can have more oversight, broader responsibilities, and probably higher pay? That is one way of looking at it.
However, starting your career as a generalist in the first few years does not always set you up well for a successful career as an employee.
How should mid-level professionals think about money and career growth? Should they play the long game or take quick opportunities when they come?
I like to answer this question using three quotes. The first is, ‘you can play the long game and still lose at the end.’ The second is from Bill Gates: ‘Many people overestimate what they can achieve in one year and underestimate what they can achieve in ten.’ And the third is, ‘life is usually about time and chance.’
A career is a marathon. The excitement of being young, combined with the pressures around you, can make you forget that. In a marathon, you can start fast and burn out, or you can build momentum steadily and press harder later. If you change jobs or roles too quickly at the start of your career, it is like sprinting in a marathon. You may get the title of manager early on, but you risk deceiving yourself about your readiness. If it comes with money, by all means take it, but keep yourself grounded and remember that the gaps in experience remain.
I learnt this the hard way. I left a role too soon, chasing more money and impact, when I should have stayed to build deeper expertise. On the surface, it worked, but in the long run, consistent growth would have served me better. Timing also plays a huge role. Some organisations shine in a season and others fade. Careers are shaped by the cycles of capitalism as much as by personal choices. If you joined a high-growth startup during a boom, your trajectory might look very different to someone entering later, even with the same skills.
The biggest lesson for me is that consistent money is often better than short-lived windfalls. Nigeria makes this especially tough. Many of us do not have the cushion of wealthy parents, so the need to make money quickly can push us into short-term decisions. Still, the principle remains: a career is long, and you should give yourself grace.
I tell people, stop tying your value to what an organisation pays you. When I was an intern, I earned next to nothing, but the work I did there became my strongest story in a Google interview. Companies pay according to what they can afford, not always what you are worth. That is why your CV should not just describe tasks but outcomes achieved.
Give yourself grace and stay grounded enough to play the marathon game. Even those who dream of retiring at 40 will work for at least a decade. The question then becomes: what will you do today to set yourself up for the next ten years?
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