There are different personality types. If you’ve ever taken a Myers-Briggs test, you’ll know how differently people approach life, work, and relationships. For Ololade, who might show up to work with blonde dyed hair on a Monday morning and wine-red dyed hair by Friday, you could tell she falls on the spontaneous side of life. This spontaneity doesn’t just reflect in her hair colors but also in her approach to life. 

Her career trajectory is a testament to this. For Ololade, nothing is unachievable. As someone who naturally shies away from client-heavy roles, I often found myself in awe whenever Mallick, our CEO, would challenge the Sales and Account management team about their quarterly targets. Ololade would always respond assuringly, “Yes, we’ll meet up. It’s achievable.” And quarter after quarter, she has proven it true that she “achievesss”. 

I eventually sat down with her to understand where this unwavering optimism comes from.

Where it all began

I checked Ololade’s LinkedIn to get a feel of how she started, but Ololade’s career journey can’t be summed up within the walls of LinkedIn; in fact, it doesn’t give much away about her career. 

“In this short life that I have lived, I have lived different lives,” she says. “I’m someone who strongly believes in the moment.”

Ololade’s career began in the media industry. She studied Mass Communication and became a radio presenter because people loved her voice, opening a YouTube channel as a portfolio where she shares her presenting nuggets. She also had a stint hosting red carpets. At the time, many of her friends thought she’d become a journalist because she wasn’t the “friendly” type, but she insisted on taking her own path.
Around 2016, she co-founded a social media blog, which she has decided not to share with me for fear of digging up her past. Driven by her curiosity and creative energy, she learned digital marketing during the lockdown and managed an online radio for a friend. She thought she’d stay in freelancing forever until her spontaneity led her somewhere else.

In 2020, when the FinTech buzz was everywhere, Ololade found herself in an unexpected place, working full-time at a tech company. A friend referred her for an internship at Cellulant, and she got in without an interview.

Despite not being paid for her previous gigs in media, she always believed in doing excellent work because fulfillment mattered more than money to her, as at that time. “Maybe this is me shooting myself in the leg,” she laughs, “but I think I’m part of the lucky few who just see an opportunity and grab it.”

At Cellulant, she joined as a Product Marketing Intern and quickly proved herself indispensable. She redefined the product messaging and went an extra mile by identifying a major potential client, a deal that later earned her a full-time position. When the internship ended, multiple departments wanted her, and she was retained as an Account Manager. She worked there for a year and eight months before joining Startbutton, referred directly by her boss to the CEO, Mallick Bolakale.

How it comes together 

All of these career transitions have one thing in common: people. Ololade is a firm believer in meeting people by chance, long-term relationships, and kindness. “We owe ourselves an epitome of kindness,” she says. “You don’t burn bridges, you sort of build them.”

As a Sales and Account manager at Startbutton, managing merchants' expectations is an everyday firefighting work; there is always something Ololade’s merchants are facing, and she has to be there to quench that fire.

The Merchant of Record (MoR) model, Startbutton operates in, solves a unique problem for her merchants. Having spoken to different businesses, read articles, and done comprehensive research on the challenges Businesses face, she concluded that “The MoR model is the future.” 

While Ololade was working at Cellulant, she saw firsthand how the Compliance team turned down some of her merchants due to them not being locally incorporated in the country. She could relate to what Startbutton is solving because it has been a roadblock for some of the merchants she had tried to onboard, so it was easy for her to be sold on this vision.

Her merchants' challenges revolve around currency volatility, difficulty transacting across African borders, and complex legal regulations. “Unlike Europe with a single currency, Africa’s diversity makes it hard for businesses to transact easily,” she explains. “What business owners really want is for their customers to pay them and get paid easily, without stress or delays.”

She believes that the Merchant of Record (MoR) model is the solution: “If the MoR model had gained traction earlier with the FinTech buzz, trust me, businesses would have found it easier to scale across borders. It’s a powerful value proposition, we’re solving a problem of now and of the future.”

When I asked her what she would tell a business owner about Startbutton, she said, “Startbutton is what your business needs to grow in Africa.” 

The dual persona

Ololade admits she wears two personalities: her firefighting persona at work and her personal self. “My work personality wears an armor,” she says. “Even when I have personal struggles, I can’t afford to let them show because if I lose a big customer, it would take time to win them back.”

Work takes up most of her life, and she finds deep fulfillment in helping her customers. “If I’m not getting the results I want, I get disappointed,” she says. “But seeing my merchants grow and succeed makes everything worth it.”

The most challenging part of Ololade’s role is managing constant demands. “Sometimes, I wish I could just ‘lock in’ and not get disturbed,” she admits, “but my day is defined by my customers.” Managing expectations from both customers and internal teams can be tough, but she’s learned not to take frustrations personally.

Still, the results make it all worthwhile. She’s spent over two years at Startbutton, and seeing the merchants she onboarded still transacting gives her immense joy. 

One of her favorite success stories is of a merchant who processed a huge amount of money. “At that time, the company wasn’t processing that much,” she recalls. “We promised we’d deliver, but there were protests in Kenya, banks were shut down, and operations were chaotic.”

Still, she refused to disappoint her merchant. “We had to process the money manually. We came to work every day, and it was during the rainy season. If we could have delivered the money to every doorstep ourselves, we would have.”

Her “I-can-do” personality believes there’s always an unblocking tool for every blocker. 

Ololade’s day-to-day activity looks like this:

The way Ololade’s day plays out is heavily dependent on her merchants, but this is an overview of how it plays out.

7:00 AM  - Ololade admits she is not a morning person, and she often starts her day with a bad habit of opening her laptop first to see if there are any issues to resolve, like missed calls from a merchant or Slack messages that need to be acknowledged and then escalated. Lately, though, she’s been more intentional about giving her Creator the first moments of her morning.

She orders her food when she notices she is close to fainting, and hunger is affecting her productivity, but there’s no rigid structure to her day; she simply adapts to whatever her merchants want. 

Her day-to-day activities include managing merchants' needs, pain points, minimizing churn, expanding merchants' usage, and working closely with internal teams to satisfy merchants' needs.

Ololade’s perfect Friday night when she is not in her firefighting mode or tying up some loose ends for her merchants would be with a bottle of wine, a lit-up scented candle, dim lights, and a really nice playlist, preferably with Alternative music like Asa, or Brymo singing her lungs out to their lyrics.