Introduction
On a Saturday, Bolaji Olatoye was directing a sold out choir concert he had built from nothing. On the Monday, he was back at a bank building spreadsheets, junior in the room, expected to follow instructions. That whiplash between what he was capable of and what he was allowed to be defined nearly two decades of his working life. Now, as founder of Altitude AI, he wants to make sure fewer people have to wait that long to lead.
The youngest son, the background player
Bolaji grew up the youngest of three boys in a Nigerian family, a position he describes with a clear hierarchy attached: the oldest is the main one, the middle is next, and the youngest is the one sent to fetch the remote. That role followed him into his church community, where his parents were pastors, and later into his corporate career, where he spent years supporting traders and senior figures in technology roles that sat in the background rather than out front. He describes himself at the time as curious and capable but not loud in public, quietly good at things without anyone necessarily knowing it.
Building "He Lives": proof he could lead long before he believed it
While still in the background everywhere else, Bolaji was already leading in one place: church. As musical and choir director for a small congregation, he pitched his father on an ambitious idea, a self-headlined concert called "He Lives", with no outside act to draw the crowd. He trained the choir, assembled a promotions team, ran early-morning leafleting rounds across Manchester, and wrote original material for a choir that, by his own account, wasn't very good when they started. The concert sold out and ran for four years, growing each time. He also managed a gospel duo with no prior management experience, entered them into a national talent search in Birmingham, and won, earning them a slot opening for Kirk Franklin. None of it, he says, was about money. It was about setting a goal and seeing it through.
Eighteen years of corporate battle training
Bolaji's move into banking technology was largely accidental: his eldest brother was already in the industry, a family dinner turned into a same-week job offer, and he started as a junior team member building spreadsheets. Over 18 years in project-based digital transformation and business analysis roles at major banks, he was repeatedly dropped into chaotic situations where processes had broken down and it was his job to make sense of them. He calls it demoralising at the time, particularly the whiplash between his creative achievements outside work and his junior status inside it, but describes the years now as a kind of battle training that built a reservoir of transferable skill he draws on as an entrepreneur, comparing it to muscle memory he didn't know he had until he needed it.
From Challenger to Champion
Bolaji frames his own development through what he calls a Challenger mentality, drawn from the story of David and Goliath: the unlikely candidate who knows, unseen by everyone else, exactly what he has already survived. He describes carrying that mentality through much of his career, aware of his own capability but holding back, before eventually shifting into what he calls Champion mode, owning his ability rather than deferring to it. That same framing now sits at the centre of his mission with Altitude AI: using technology to help people who see themselves as Challengers step into being Champions.
Staying power: purpose over a slow timeline
Asked how he stayed faithful through 18 years of corporate work before stepping fully into entrepreneurship, Bolaji points to a concept he calls staying power, built on having a purpose even before that purpose is fully defined. He says purpose doesn't always announce itself clearly, but it makes itself known negatively: a strong, persistent sense of wrongness when he's out of alignment with it, even while the destination itself stays unclear. He is candid that he has had to learn to balance purpose against commercial reality, admitting he increasingly understands the case for prioritising profit, while insisting his decisions still have to cohere with his underlying purpose rather than abandon it.
Building Altitude AI and AI Workforce Heroes
Bolaji's company, Altitude AI, has launched AI Workforce Heroes, a suite of AI bots aimed at business owners who want more leads, more sales and streamlined operations. He describes being surprised by its capability even during his own demos. Running the business has also forced a separate set of lessons distinct from his technical strengths: he names hiring the right people and structuring partnerships with clear, upfront agreements as areas where he has failed and learned, describing entrepreneurship as constant, fast cycles of learning and adjustment rather than a single moment of getting it right.
Tech as the great equaliser
Bolaji's central mission is to use accessible technology, AI and automation in particular, to let people achieve outcomes that once required money, time or resources they didn't have. He is direct about who this is aimed at: creative, capable people, citing the Black and African community as one example, who have talent but not always the support or resources to build something from it. He draws a distinction between people raised in the diaspora, who he says grow up believing in what's possible by default, and those raised in Western environments, where it becomes easier to accept limits without ever testing them. His advice is not to avoid limits but to hit them deliberately: to find your own ceiling through action rather than accept a ceiling someone else described to you.
Leadership as pioneering and knowing who you're meant to lead
Bolaji defines leadership in three parts: leading from the front as a servant, rolling your sleeves up rather than only directing; pioneering leadership, being comfortable communicating an idea or concept that has few or no existing reference points; and accepting that not everyone is meant to be led by you, that some people simply aren't on the same journey, and that is not a failure of leadership.
