Before Midddleman became a startup, it was a string of side hustles. While working full-time in marketing, Omolara Sanni was juggling e-commerce experiments on the side, testing ideas, and figuring things out along the way. She didn’t know it then, but those long nights and small wins were setting the stage for Midddleman, the startup she now co-leads.
In this interview, she talks about what it’s really like building in the African tech space. She also shares how she builds her team, lessons from early missteps, and the mindset that keeps her grounded when things get hard.
If your career journey were a movie, what would the title be and why?
I think ‘Evolution’ would be a good title because that’s exactly what my journey has been over the past few years. I’ve done a lot of different things: starting with an internship at Utiva when I moved to Lagos, then working as a bank teller for a few months, moving into cybersecurity, then marketing, and now I’m fully focused on entrepreneurship. And honestly, I feel like there’s still so much more I’m yet to learn.
What led you to pursue a career in tech, and how did it all begin?
During my final year of school, I attended an employability training program that introduced us to concepts such as project management and entrepreneurship. It was my first real exposure to the tech world and what life after school could look like. That training stuck with me and actually motivated me to move to Lagos after graduation. I ended up interning at the same company that ran the training, and that’s where it all really began. From there, I became curious, started reading more about technology, explored different career paths, and even dabbled in cybersecurity for a while. But honestly, cybersecurity didn’t excite me; I found myself drawn more to the marketing side of things. One day, I decided to resign and fully go into marketing.
Did you ever think you’d end up as a co-founder? What made you take the leap?
While I was working full-time as a marketing professional, I was also running e-commerce businesses on the side with the same person I’m now building Midddleman with. So entrepreneurship has always been part of my journey, even during my nine-to-five.
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Over the years, I’ve had several ideas, some of which I never got around to executing, but I always knew that one day I’d go all in on building something of my own. Running those e-commerce businesses eventually inspired the idea for Midddleman. At some point, we decided it was time to shut everything else down and focus fully on building it.
What do you know now about building in African fintech that you didn’t know two or three years ago?
I think the first surprise for me has been how tough it still is to raise money here. When the whole funding winter started two or three years ago, no one thought it would drag on this long. I definitely didn’t expect that by the time I was ready to build, I’d still be facing the same challenges founders have been talking about for years.
The second thing would be realising that there are still ideas our market just isn’t ready for. And that can be really surprising; it’s 2025, and there are concepts that have already come and gone in other parts of the world, yet here, the market is still not prepared for them.
What’s your approach to hiring and building a team?
For us, the approach has always started with our network. I’m not sure if that’s unconventional, but we’ve mostly worked with people we’ve collaborated with in the past. So, the early team, our founding team, was made up of people we already knew and trusted. We’d just reach out and say, ‘Hey, we’re building something new. Want to be part of it?’ But over time, something really great started happening; people we didn’t know began reaching out because they loved what we were building. They’d pitch themselves, we’d have a conversation, and if it made sense, they’d join the team. So it’s been this mix of pulling from our immediate network and building something that genuinely attracts people who want to be part of it.
Because of how we bring people in, cultural fit becomes just as important as technical skills. Apart from hard skills, one of the biggest things I look for is teamwork. It’s something we take seriously; everyone needs to be able to get along and collaborate well. The second thing would be adaptability. In the startup world, things move fast. New technologies, new directions—it’s a lot. And humans, by nature, resist change. Most people prefer to stick with what they are familiar with. So I really value team members who are open to change and can move quickly when things shift. That mindset makes a huge difference.
What’s something that looked like a small decision at the time but ended up having a big effect on your career?
I don’t know if I’d call it a small decision, but looking back, one of the most impactful things I did was choosing to be more vocal about my work, just putting myself out there, especially on LinkedIn. That single decision changed my life significantly. It helped me build credibility in my field and made the transition into working on Midddleman full-time a lot smoother. People already saw me as someone who knew what she was doing, and that opened up opportunities; speaking engagements, collaborations, and even customer acquisition.
It’s interesting because we actually ask users how they found Middleman, and without any incentives, around 10% say it was through referrals. I genuinely believe a big part of that comes from my co-founder and I consistently talking about what we’re building. Even when the people seeing our posts aren’t our direct customers, they often know someone who needs what we’re offering, and they refer us. So being visible and vocal has had a compounding effect.”
What app do you secretly wish you had built?
It’s going to be Canva. I just love the company. They’re incredibly innovative, and I really admire that. Plus, it’s even more inspiring knowing a woman founded it.
What has been your lowest moment building Midddleman, and what pulled you through?
I think one of the toughest moments was really early on, even before the product launched. Maybe I wouldn’t call it a low point exactly, but it was definitely frustrating. Since my co-founder and I are non-technical, we had to hire engineers to build the product. The first person took our money and delayed us for months. We had to get a refund and find someone else, but that experience pretty much repeated itself. It was a really tough process. Eventually, we found someone willing to join as part of the team, not just a freelancer you pay and move on. That made all the difference, but those early struggles were definitely challenging.
Have you encountered any challenges or biases as a female founder?
I wouldn’t say I’ve faced direct bias. It’s not like a VC will come out and say, ‘We’re not giving you money because you’re female.’ It doesn’t work that way. You’ll usually get other types of feedback or reasons why they’re not backing the idea. Personally, I haven’t had anyone tell me outright that my gender was the issue.
That said, I’ve been intentional about approaching VCs that are more female-friendly. These days, there are firms that specifically back female-led teams, or at least require there to be a woman on the founding team. I tend to lean towards those, as well as grant opportunities that are designed to support female founders.
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