Debbie Otuagomah, Founder and CEO of Pineway, is building software designed to simplify the messy behind-the-scenes work that coaches, consultants, and independent experts deal with every day. From forgotten follow-ups and proposals to scattered booking and payment tools, she believes these everyday hassles should not get in the way of people doing what they do best. It is a busy category to build in — scheduling, proposal, and payment tools such as Calendly, HoneyBook, and Dubsado already serve independent professionals — which makes simplicity the core of Pineway's appeal.

Like many women in tech, a group that remains underrepresented in the industry's global workforce, Debbie is driven by a long-standing desire to make life easier for others — a desire that has shaped both her career and what she is building today.

From Engineering to Entrepreneurship

With eight years of experience in tech, Debbie's journey has taken her from frontend engineering and technical writing to technical support and support engineering leadership. She spent six years at Customer.io, a customer engagement and messaging platform, where she led a globally distributed support engineering team.

"I've always loved figuring out how complicated things can feel simple, and how to lead people in a way that doesn't leave everyone burnt out. It's also shaped how I think, lead, and build," Debbie said.

Now based in Dubai and building Pineway alongside co-founders in Dubai and Romania, Debbie is bringing that philosophy to entrepreneurship. She said the product was born from a desire to remove the operational chaos that often comes with running an independent business, allowing experts to focus more on their actual work.

Away from tech and building, she enjoys reading fiction, playing games on her Steam Deck, sketching, singing, and making things.

Her Morning Routine

"My mornings start with a walk, then honey-lemon tea (or whatever I have at home, to be honest), time in my Bible and a little prayer, before I ease into work," she said.

Workspace and Devices

"I do all of my work on a 14-inch MacBook Pro that goes everywhere with me, a Google Pixel, my Sony headphones, and an LG monitor for the days I need more room. I work from home most of the time, unless I'm at the office in town," she explained.

The Tools Behind Pineway

"Linear is where the product currently lives. It's how we track everything we're building at Pineway, from tickets to sprint scope.

"Slack is where we do all of our team comms, and we're spread across Dubai, Nigeria, India and Romania, so it's the closest thing we have to an office. Notion is where I think things through and write them down so they don't disappear, and Loom comes out whenever typing would take longer than just talking. Granola handles all my meeting notes, and Arc is my favourite browser for everything web.

"Claude and ChatGPT have become part of how I think, not just how I work. I use them to draft messages, pressure-test strategy, and talk through founder decisions out loud when I need a second brain in the room."

Her use of AI assistants as a thinking partner reflects how widely chatbots have been absorbed into everyday knowledge work in the few years since their public release.

How She Resets and Generates Ideas

"The first thing I do is walk away from my desk. I'll usually pace around, talk out loud to myself, or take a quick break and do something completely different. Sometimes that's reading a few pages of a novel, cranking up a playlist to rejig my brain, or watching someone on YouTube who's already done what I'm trying to do and seeing what I can learn from them.

"If I'm stuck on something specific, I'll go back through old customer conversations to reorient myself.

"Typically, though, the best ideas always hit me when I stop thinking about Pineway as a product and start asking what people are actually struggling to do. Building a business is all about finding ways to help people who need what you have and getting obsessed with how to serve them, so anchoring to that always helps."

Her Favourite Apps

"Honestly, it's a tie between Spotify, Substack, and TikTok. I've spent years curating each of them so they actually reflect different parts of what I like, from the music I listen to while thinking, to the writers I want to read, to the corners of TikTok that make me laugh or teach me something new. They're the best apps that make my phone feel like mine."

An App She Wishes Existed

"Something that completely takes the thinking out of food. I'd love to wake up and just know exactly what I'm eating that day, prepped the way I like it, balanced for what my body actually needs, with zero decision-making on my part. No scrolling through delivery apps, no staring into the fridge, no opening recipe tabs I'm never going to use.

"Food is one of those quiet daily decisions that takes up way more mental space than it should, especially when you're building something. Whoever cracks that, in a way that's actually personal and not just another meal-kit subscription, will give a lot of people their brains back, and I would be their first customer."

If She Could Invest in Anything

"I'd invest in young people. There are so many brilliant young people in the world with huge dreams and a crazy work ethic, and most of them are stuck because nobody's backing them early enough to do real work.

"I wouldn't fund them to build startups, necessarily. I'd fund them to tinker, to create freely, to follow ideas without having to justify a business case for every single one.

"So much of what shapes where human society is heading comes from people who were given the space to think and build before they had to prove anything. I'd love to be the person who gives that space to more of them."

Her Tech Role Model

"Ire Aderinokun. She was the first female tech founder I ever found on the internet, and watching her career shaped what I thought was possible for myself early on.

"She's deeply technical, design-minded, and builds with intention. She's also Nigeria's first female Google Developer Expert, co-founded Helicarrier and helped build some of the earliest crypto-fintech infrastructure on the continent, and now she's investing in the next generation of African founders.

"She's done all of that while staying unmistakably herself, never shrinking to fit any of the boxes the industry tried to put her in. That's a standard I still measure my own work against, and I genuinely admire."

A Quote She Lives By

"Nothing in this world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan 'Press On!' has solved and always will solve the problems of the human race."

The passage is widely attributed to US President Calvin Coolidge.

"It reminds me not to rest on talent, or genius, or education, or anything else that feels like it should be enough on its own. None of those things finishes the work; only persistence will. Whenever I'm building something hard or in a season where progress feels slow, this is what I come back to."

Who She Recommends Next

"Eloho Omame, co-founder of FirstCheck Africa. She's been steadily backing the next generation of African women founders, and I think her perspective on what actually moves the needle for early-stage women builders on the continent would be a brilliant read," Debbie said.

Read also: Tech Trivia with Funmito Makanju-Osho, Regional Product Lead at Google