How Funke Olasupo became one of Africa’s leading voices in technical documentation

Funke Olasupo’s father had no idea he was planting the seeds of a tech career when he dragged her to cybercafés in Port Harcourt, Rivers, to learn Microsoft Word and Mavis Beacon at the age of 12.

His daughter was supposed to become a neurosurgeon, complete with hospital internships and grand family expectations. Instead, she became something her traditional Nigerian household hadn’t anticipated: a senior technical writer shaping how developers across the world interact with complex software.

The transition wasn’t smooth. When Olasupo changed her Joint Admissions and Matriculation Board (JAMB) form from medicine to information technology without telling her parents, the fallout was immediate and theatrical. Her mother blamed her father for those cybercafé visits. But she held firm, and they eventually let her go, even if the acceptance came wrapped in typical Nigerian parent scepticism. 

Today, Olasupo is the Senior Technical Writer at Rocket.Chat, where she’s spent three years transforming scattered documentation into a comprehensive knowledge base that even competitors reference, and her journey from an aspiring medical student to a technical writing leader reveals how careers actually unfold when you stop forcing them into predetermined moulds.

Technical documentation has become the invisible infrastructure holding the software industry together, yet it remains one of the most undervalued disciplines in tech. According to the 2024 Stack Overflow Developer Survey, 84% of developers use technical documentation to learn, and 90% rely specifically on API and SDK documentation. Yet despite this reliance, documentation remains inconsistent across the industry. The 2024 Postman State of the API Report found that 39% of developers cite inconsistent documentation as their primary obstacle, whilst 58% rely on internal documentation tools to understand APIs. 

The gap between what developers build and what users can actually understand continues to widen as software grows more complex, and technical writers like Olasupo stand in that gap, translating intricate systems into accessible knowledge. 

From volunteer projects to getting paid to write

University changed everything for Olasupo, though not in the way her parents expected. After those initial cybercafé lessons, she kept going back during each holiday, where she started learning HTML and CSS.

Eventually, she got into the university to study information technology. There, she met a group of engineers building a community from scratch and determined to leave a legacy by training the next generation. When they came to evangelise about the community, Olasupo almost didn’t join because she felt a bit proud about the HTML and CSS she had picked up during those holiday programmes. But she showed up a few weeks later, and that’s when she realised this wasn’t just about tinkering in cybercafés after graduation. There was an actual career here, with real opportunities and people who were building things that mattered.

The community started with HTML, CSS, and JavaScript, for new intakes, but Olasupo quickly discovered that front-end development wasn’t her thing and switched to back-end, diving into PHP and Laravel. By her third and fourth year, she was teaching the next batch of first-year students, though she wasn’t working yet, just building projects with friends at that elementary stage of a career where you’re figuring things out through trial and error.

She had already started documenting her work on personal blogs like Dev.to and Hashnode, mostly as a way to preserve knowledge for her students because she was tired of explaining the same concepts repeatedly. If she wrote an article, students could read it first, then come back with questions for deeper conversations.

Then a mentor mentioned guest author programs, where companies like Twilio, LogRocket, and Honeybadger where developers could volunteer, share and create content for their blogs. As an ambitious engineer, she quickly saw this as an opportunity to develop her documentation skills, though front-end developers had loads of opportunities, while back-end guest author programs were harder to find. Olasupo saw it as a natural extension of what she was already doing; she could stay up one night, write an article, and build up her resume and writing. Her first break came with Honeybadger, followed by multiple pieces for Twilio, though at this point, she still didn’t know technical writing was a career. She was just a software engineer who’d found a lucrative side hustle.

Her first engineering job came through volunteering on an edtech project called CodeVixens, and during the technical interview, she ran into the classic “it works on my system but not yours” problem. What saved her wasn’t the code working but the comprehensive guide she wrote after the assessment, documenting her entire process as if she were teaching someone else how to complete that same technical test. Her manager later told her that’s why they hired her; they could see her approach, her methodology, and writing had made the difference again.

The turn towards documentation

After working as an engineer for a couple of years and moving up to mid-level, Olasupo stumbled upon Google Season of Docs in 2022, a programme where open-source projects pitch documentation needs to Google, receive funding, and hire technical writers to complete specific projects. She applied mostly to learn how it worked and didn’t expect to get in on her first try, but somehow she did.

She joined Open Food Facts, a French company, and her job was to build their OpenAPI documentation from scratch using YAML and JSON which she had to master with learning Python and Perl first, languages she’d never touched before. The contract wasn’t full-time work, just a few dedicated hours alongside her engineering job, but it was her first paid role where she led documentation efforts and had a genuine voice in a company’s documentation process.

After the programme ended, Olasupo started wondering what a long-term career in technical writing might look like, though she wasn’t abandoning engineering, since recruiters kept telling her that her technical background gave her an edge. She applied for both back-end engineering and technical writing roles with one condition: if it was writing, it had to be for a developer-focused company because she didn’t want to drift too far from engineering. In December 2022, she joined Rocket.Chat as a technical writer, and that was her first full-time documentation role. When she started, the company had minimal and distorted documentation, but now they have a comprehensive, standardised knowledge base.

She’s stopped calling herself just a technical writer and prefers “customer advocate” because her job isn’t just writing, it’s ensuring customers have a smooth onboarding and user experience. Conversion and sales matter, but if users can’t figure out how to use the product, they’ll never convert. Her focus now is on making life simpler for customers while maintaining the accuracy and thoroughness that keep the product functional.

Measuring clarity with outcomes

The challenge never changes, regardless of industry: Olasupo has to maintain accuracy while making things easy to understand for people who don’t have the patience to read anymore. When she worked with fintech companies, compliance was everything because it’s people’s money, so she had to explain not just how things worked but why they worked that way, with particular emphasis on edge cases. For payment gateway documentation, speed is critical because developers test multiple providers simultaneously and don’t have time to sit through lengthy onboarding; they need the fastest path to their first win, and once they get that initial success, you can offer progressive learning.

Her process starts with one non-negotiable rule: she doesn’t take anyone’s word for it. Even if a developer explains something perfectly, she tests it herself and experiences it as both a developer and a customer before she writes a single sentence. If they need to build a chatbot with their APIs, she builds that chatbot so her documentation isn’t based on what someone told her but on exactly how it works. She stays close to the source code, popping into repositories to test things directly, and she maintains release notes so when updates roll out, customers know what’s changed.

For her, success is measured in three ways: feedback systems embedded in documentation pages with where users can leave comments in each page especially if it’s a thumbs-down so the team can take follow-up actions; a roughly 50% decline in customer support tickets over the years, as people no longer ask basic product questions the doc easily answers; and conversion rates, measured by the percentage of prospects who become paid customers after engaging with well-documented products. Support and professional teams can now focus on custom requests and unique environments instead of repeatedly explaining basic features, which means they’re doing more impactful work with less overall volume.

The impact of good documentation extends far beyond individual companies. According to Postman’s 2024 report, for 21% of companies, APIs drive over 75% of their total revenue, making documentation not just a support function but a critical revenue enabler. The numbers back up what Olasupo has seen firsthand: when Rocket.Chat improved their documentation, support tickets dropped by half, but more importantly, the questions they now receive are sophisticated ones about custom implementations rather than basic “how do I get started” queries. That shift signals not just operational efficiency but genuine product understanding, and it’s the difference between users who abandon a product after the free trial and those who become long-term customers.

Writing for humans and machines

The industry is changing, and Olasupo’s job has evolved beyond writing for humans. People ask ChatGPT or Gemini before they ask Google now, so she has to write in ways that large language models can easily understand and retrieve. Companies are also embedding AI assistants into their documentation search bars so users can type a question, get a conversational answer immediately, then see links to related pages if they want to dig deeper. This matters because the current generation has less patience, and if you can’t capture their attention quickly, they’ll leave.

Beyond AI, she also points out that technical writers like her are doing more advocacy work because writing is just one way to help users. At Rocket.Chat, Olasupo’s team recently launched video tutorials, and she never thought she would be editing YouTube content, but now she’s putting together large-scale content in different formats because it helps customers understand the product better. She sees this trend continuing because companies are looking for people who can think holistically about customer education, not just write documentation, though AI will still require human intervention to oversee quality, accuracy, and communication.

Looking back, some of Olasupo’s proudest moments are not just professional milestones but also the times when her parents finally said “well done,” and the mentorship she’s provided over the years, helping people transition to technical writing and guiding them in growing their careers.

The girl who was supposed to become a neurosurgeon ended up advocating for customers in a completely different way, not saving lives in an operating theatre but making sure developers and users can navigate complex software without hitting walls, and in a world where technology moves faster than most people can keep up, that advocacy matters more than ever.