Click to watchIf life came with a plotline, Jeremiah Ajayi clearly missed the memo. He started out studying Law but somehow ended up building content strategies for global tech brands. In between, he wrote romance novels, got rejected by Piggyvest (only to be hired later), quit jobs, and lost everything. Twice.
He’s led content at startups like Stears and RemotePass, and built a personal brand that opens doors. In this conversation, he talks about lying his way into his first SEO job, learning to negotiate, losing it all, and how embracing chaos helped him build a career that makes sense only in hindsight.
If your career journey were a movie, what would the title be and why?
I’d call it Zigzag. That’s the best way to describe my career. Nothing about it has been linear. Sometimes I even ask myself, ‘Jeremiah, when do you stop living such a chaotic life?’ I was in school, doing well, but dropped out when my tech career started to take off. I’ve fallen and risen more times than I can count. It’s been messy, unpredictable, and full of detours, but that’s also what makes it mine.
Tell us about your journey into the tech industry. What initially sparked your interest?
I didn’t start out planning to work in tech. I was studying law at OAU when I started freelance writing, mainly because my friend was already doing it. My first gig was a romance novella that got rejected, and the client even asked for a refund. But that didn’t stop me. I kept writing, got my own clients, and eventually stumbled into SEO.
Around 2018, a friend referred me to a small digital agency hiring an SEO trainer. I lied about being an expert, got the job, and had to learn SEO quickly just to keep it. I didn’t get paid a dime, but it set me on this path.
My real introduction to tech came in 2019 when I pitched myself to Kelechi Udoagwu after reading her BellaNaija article. She gave me a shot at her company, Week of Saturdays, where I managed content and communities. That job exposed me to how digital products and online communities actually worked. I started ghostwriting for tech companies and built a network that still shapes my career today.
Leaving Week of Saturdays was one hard decision I had to make. It had become my comfort zone, but I knew I’d grown past it and needed to see what else was out there. After that, I dabbled in freelance work while trying to transition into SaaS content marketing. I reached out to Victor Eduoh after seeing his B2B SaaS agency (VEC Studios) and ended up landing a full-time role there.
I’d also applied to Piggyvest before and got rejected, which stung a little because I really admired what they were building. But I didn’t take it personally. I just kept learning and improving. Then, in early 2022, they reached out again. This time, I got in. That became my first official tech role, and the moment I finally felt like I’d arrived in tech.
How did you transition from freelance writing to leading content strategies for top African and global tech brands?
Most of the big turning points in my career transition came from serendipity, not some perfectly mapped-out plan. I messaged Kelechi on a whim in 2019, and that opened one door. I met Victor through a LinkedIn DM, which led to another opportunity. Even PiggyVest, I wasn’t supposed to apply. I sent the job to a friend, and she said, ‘You’d be a good fit too.’ I applied, got rejected, but followed up with Daniel and left a good impression. Months later, he reached out when they were hiring again, and that’s how it happened.
Same thing with Investor’s Corner on Condia. I started it after a rejection. I wanted to help founders get access to the kind of information they needed to grow. That project opened a lot of doors. I later worked with The Earthshot Prize (a global environmental award awarded to five winners yearly for their contributions towards the environment) because Yemi Kuti, whom I’d met through Investor’s Corner, referred me. I even got a job offer from Kola Aina, Managing Partner at Ventures Platform, after interviewing him in 2023. I didn’t take it; I chose RemotePass instead, but it showed me how much comes from putting yourself out there.
What were some of the biggest challenges you have faced in your career, and how did you overcome them?
When I started out, my biggest challenge was getting people to give me a chance. I couldn’t get clients on my own, so my friend subcontracted me. It took time to build enough credibility for people to bet on me directly.
Once I became a good freelance writer, a new challenge came up: breaking free from freelancing itself. I didn’t want to be stuck writing for clients forever. It felt repetitive, soulless even. I wanted something more sustainable, something that felt like a real career. But back then, there wasn’t as much information or guidance as there is now, so figuring that out was tough. I had to look for internships, reach out to people I admired, and take chances.
Joining VEC Studios came with new pressure. The standards were sky-high, and I was constantly worried about keeping up. I had reached out to Victor Eduoh myself because I felt this need to prove I deserved the opportunity. Piggyvest was smoother, but juggling it with school and another role was chaos. Eventually, I had to choose between school and work. I chose work. I dropped out of my law degree, and honestly, it was one of the hardest but most defining choices I’ve made.
Each phase presented new challenges, whether it was gaining recognition, achieving stability, or keeping pace with fast-paced global teams, such as those at RemotePass. But the common thread through all of it is courage. I’ve always been scared, but I’ve never let that stop me. I don’t even think I’m that smart; I just think I’ve mastered how to make fear look like confidence. Every time I’ve pushed past fear, I’ve found out I was more capable than I thought.
What has contributed the most to improvement in remuneration in your career?
Between Stears and RemotePass, I 12xed my income. It’s been a mix of learning when to leave, how to negotiate, and how to build a personal brand that works for me.
At Stears, I negotiated a higher offer than initially proposed, and this continues to influence my approach to negotiations. Everything is negotiable. Never take the first offer unless you want to shortchange yourself.
Another thing that helped was knowing when to move on. I don’t job-hop recklessly anymore, but I also don’t stay where I’m undervalued. I’ve become more stable and intentional with every move.
And honestly, building a brand on LinkedIn changed my life. I didn’t have any tech connections. But by showing up online, sharing my work and thoughts, I built visibility. Now, brands pay me to post, earning over $1300 from brand influencing for two clients. That’s money I didn’t even see coming.
What’s one financial lesson you’ve learned the hard way in your career
I’ve lost it all twice in my life. In 2022, I was working two jobs, earning well in both dollars and naira, and living what felt like the good life. I was young, making good money, partying almost every other day, and feeling untouchable.
Then everything flipped right after my birthday. I’d just thrown this big, flashy party, and the very next day, I got demoted at work. Not long after, I left the company after an argument with my boss. My income dropped from around $1,800+ to just ₦360,000 a month. Meanwhile, my rent for a serviced apartment was ₦300,000 monthly. That was almost my entire salary gone before I even considered anything else.
Debt piled up fast. At one point, I almost got evicted. I couldn’t move because I had nowhere to go, and paying monthly rent meant that missing even one payment could cost me the apartment. It was rough. I went from earning in dollars and living comfortably to struggling to get by. That fall was painful.
Eventually, I got a new job at Stears. It brought some stability, but more than half of my salary still went to rent, and the rest barely covered upkeep. Saving wasn’t even an option. That period taught me hard lessons about money, discipline, and timing. I learned that you can’t assume the good times will last forever.
That season humbled me. It showed me how quickly money can disappear and how important it is to save and invest when things are good. Now I’m more intentional with my finances and my life. Losing everything gave me perspective; it’s why I try to stay real online. People see success stories, but not the moments when you’re broke, scared, and trying to rebuild from zero.
What’s a failure you’ve had that people would be surprised to hear about?
One of the biggest mistakes I’ve ever made in my career happened while I was at Stears, during the 2023 elections. We were publishing real-time election results, and at some point, I inadvertently sent a test notification to the live environment instead of the sandbox. It was a small error that escalated quickly. We trended online, people mocked it, and it became a big deal. The CEO called me immediately. The tension was heavy.
That period was rough. I was burnt out, barely sleeping, and constantly under pressure. Then came another mistake—I accidentally pushed out a wrong election update that said Peter Obi had won Kano. Everyone in the suite turned to me. I knew instantly what had happened. I got asked to step back from work that night, and it felt like everything I’d built just crashed.
It was a painful time, but I learned a lot. I saw how unforgiving corporate environments can be, especially when you make a visible mistake. I also saw how easily people can turn when pressure comes from above. Still, it taught me resilience. It made me tougher and shaped the kind of professional I am today.
How do you approach creating content that drives real business results, not just engagement? And how do you measure the impact of your work beyond traditional metrics like clicks or engagement?
Different things work for different people. For me, content that drives real results starts with a clear hypothesis. I form that hypothesis from conversations with the client or employer, understanding their goals, and knowing exactly who they’re trying to reach.
Once I get that, I dig into audience insights, sometimes by speaking directly to customers or analysing existing interviews and data. That gives me clarity on what motivates them and how they behave, which then shapes my content approach.
From there, I test my ideas through a few quick-win pieces, track their performance, and refine the strategy based on what works. The goal is simple: every piece of content should tie back to the business results we discussed at the start. Otherwise, it’s pointless.
Looking at African startups today, what’s the most common content marketing mistake you see brands make?
For many African startups, the biggest issue I see is the lack of a real strategy behind their marketing. Most of it is reactive. A Fintech company sees another brand doing something and decides to copy it, not because they’ve spoken to customers or have data to back it up, but just to keep up appearances.
Another common problem is the ‘emperor culture.’ In many startups here, whatever the CEO says goes. It doesn’t matter if you’re a marketing expert with years of experience; if the founder says no, that’s the end of the conversation. And the irony is, most of these ‘emperors’ don’t have marketing backgrounds. So teams end up executing ideas that don’t make sense strategically, and when those campaigns fail, the marketers get blamed.
There’s also a lack of data-driven thinking. Many teams don’t track results or do post-mortems after campaigns. It’s just one-off efforts—no reflection, no testing, no iteration. Even in content marketing, very few people speak to users or validate ideas with research. So a lot of the content you see isn’t grounded in insight; it’s just assumptions dressed up as strategy.
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