Level Up: How a DM got this product manager a role at Future Africa

🔎 IN THE SPOTLIGHT WITH TOSIN OLADOKUN

In today’s spotlight, we’re chatting with Tosin Oladokun, who shares his journey from coding to becoming a product manager. Plus, he tells us about the unexpected moment when a simple DM on X led to him landing a product manager role at Future Africa.

Tell us about your journey into the tech industry. What initially sparked your interest?

In my fourth year at the University of Ilorin, I remember Cowrywise launching a campus ambassador program. I didn’t join, but I was really curious about it. Around that time, I was becoming more financially conscious because I was running a small business on campus and had some liquidity. I kept wondering how Cowrywise could offer interest on my money and how it all worked behind the scenes. 

That curiosity sparked my interest in tech. I wanted to understand how they did it, how mobile apps were built, and everything else. After graduating, I landed a job in the IT department of a financial services company, where I learned how to code. That experience gave me a real understanding of how things work internally, especially in fintech. That’s how my journey in tech began.

When did it all start coming together for you in Tech?

During my internship at a financial services company, I was tasked with developing a machine-learning algorithm to predict stock prices. It was exciting. I wrote a script that actually helped the stockbrokers in the company recommend better stock options for their clients. That experience made me realise just how powerful technology can be as a leverage point for businesses. Around the same time, COVID hit, but thanks to remote work, I was able to keep working and take care of myself, even during all the uncertainty. 

That’s when it really clicked for me that I wanted to pursue a career in tech. The constant innovation and problem-solving are never mundane. Writing code, shipping it, and seeing the impact it made, I knew I was in the right place.

What did you wish you knew about your career path before you started?

As a product manager now, what I wish I had known earlier is just how much communication is involved. Public speaking, writing, and the constant need to convince and influence others were things I had to learn on the job. If I had known that, I probably would’ve taken a communications course at university or done something around storytelling. Half of the work is getting people on board and convincing them to move in a particular direction. It’s less about building the technology or even solving the problem yourself and more about persuading others.

How did you switch from writing codes to becoming a Product Manager?

After my first internship, I applied for another one—this time at a product company instead of a financial services firm. They were building an API for account transfers, and I didn’t care what role I got; I just wanted to be there. They offered me a product management intern role, more like an associate PM position, and I figured I’d give it a try. Because of my technical background and my understanding of how financial services and payments work, I adapted quickly. 

I found that I loved talking to engineers, customers, and basically everyone involved; I just enjoyed making things work. That’s when I made the switch to product management. It wasn’t some deep introspection; it was just meeting the right opportunity.

If you could swap jobs with anyone for a day, who would it be?

Honestly, it’d be someone who works with the Liverpool football club, maybe on the social media team or as an assistant to the players. Just being around them, talking to the players, and watching the games live; would be such a fun job.

But if we're speaking professionally, I’d love to be a product manager for Postman. It's a platform engineers use to test APIs, and the product is complex. I’d really like to dive into that. Another cool option would be swapping with someone at Spotify, maybe on the developer platform team. That would be a great experience as well.

What’s a funny or memorable story from your career that you love to tell?

My first interaction with Iyin Aboyeji was pretty memorable. He made a tweet that I didn’t agree with, and instead of reacting like most people do—getting rebellious or combative, I sent him a DM explaining why I disagreed. Surprisingly, he asked for my number and called me. We had a really good conversation, shared our perspectives, and found some middle ground. At the time, I was working for another company, but after that interaction, he ended up hiring me at Future Africa, which really accelerated my career.

It taught me a lot about how powerful a respectful conversation can be. People aren’t as unreachable as we sometimes think. If we can just treat each other like human beings and have respectful dialogues, even when we disagree, I think we’d see more positive outcomes in our lives.

Can you share an example of a project or role that significantly advanced your career?

My time at GetEquity was really special. I was the first product hire there, and I joined when the idea was literally just a piece of paper. I’ve always been passionate about financial services and making sure people are included in the financial world, so the concept of allowing people to invest in startups with as little as $10 really resonated with me. Leading that project, building the application, and pushing hard to bring it to life was an incredible experience. The team I worked with, the customers we served—it was amazing to see how an idea can become a reality if you keep at it. That’s definitely a project I’m really proud of.

What would you say were the things you did right that has helped you progress in your career? 

My advice is to not focus too much on your position. It’s more about staying curious, staying humble, and always pushing yourself to do more. I’ve learned to stay hungry, knowing that I haven’t reached my peak yet, and I just keep pushing that peak further. Sometimes, you have to gaslight yourself into believing you can do more. 

Being curious—asking how things work and why they work that way has really helped me grow. Networking, which people often see as a cliché, has been crucial too. It’s not just about money; it’s about offering value and asking, ‘How can I help?’ Most of the opportunities I’ve had weren’t ones I actively chased. They came from me being open, offering value, and connecting with people. That mindset has made a huge difference.

Describe a time you had to learn a new skill quickly for a project. What strategies did you use to accelerate your learning?

There was this time when we needed to quickly build a data dashboard to gather insights and understand the performance of the application we were working on. The product had already launched, and we had a lot of users, but we didn’t have a way to actively measure progress. To make improvements or figure out what was going wrong, we needed real data. 

Everyone was busy, our engineers were tied up with other tasks, so I had to learn Mongo Query Language (MQL) because the app was built on MongoDB. I had to pick it up fast, and honestly, the pressure to get it done is what pushed me through. I didn’t have tools like ChatGPT back then, so it was just me Googling stuff, watching YouTube videos, and learning as quickly as possible. It was hectic but also fun in a way.

What's the most interesting interview question you've ever been asked? How did you answer it?

One of the most interesting questions I got in an interview was a behavioural culture fit question. They asked if I would prefer to be appreciated by the CEO publicly or privately. It caught me off guard because I’d never really thought about it before. 

I ended up saying, 'It depends.' That’s usually the safest way to approach any tech question! I explained that if I were leading a project, I wouldn’t need public praise; it’s my job, and I’m responsible for it, so a private acknowledgment would be enough. But if it was a situation where I needed recognition for a promotion or something like that, public appreciation would definitely help. It was an interesting question because it made me think about how context can really change things.

What are some interview tips that have worked for you?

I think the number one piece of advice I’d give is to maintain professionalism. Even though tech environments can be casual, it's important to look presentable. We might not wear suits, but how you present yourself matters. As someone on the other side of the interview table, I can tell you that if you can’t play the part, it raises doubts about your ability to do the job. A clear background, a good haircut, and a crisp outfit are basic but crucial.

Secondly, talk to people within the company to get a sense of the culture. Is it a product-driven environment where tech is the focus, or a sales-driven one where metrics are key? Understanding the company's vibe is essential.

And lastly, just be yourself. It’s really obvious when someone is being fake. People can tell when you’re not speaking naturally. Keep your introduction crisp—no one wants to hear a long monologue about yourself. Aim for about five minutes at most, and make it engaging. Include fun facts about yourself, along with your achievements and background, to set a foundation for the interviewers to build on. The best sign you’re nailing an interview is when they start to deviate from their script.

So, optimise that 'Tell me about yourself' question in a way that reflects both the organisation and your authentic self. That’s my advice.

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