Career History
Mastering the Craft, Building the Brand
Over a decade in, I've put in the unglamorous hours: testing, breaking, recovering, rebuilding, and reading the data until it talks back.
Along the way, I picked up an Executive Education in B2B Marketing Strategy from Columbia Business School and a Product Marketing Manager Certification (PMMC), on top of a Computer Science degree that still shows up every time I'd rather build the tracking myself than wait on someone else.
What I actually do with the power of Creativity and Artificial Intelligence: demand generation, performance marketing, and growth. The full revenue engine, from the first cold impression to closed-won and expansion. Lead and pipeline generation, paid media at real scale, conversion rate optimization, analytics and attribution, lifecycle and retention, GTM strategy for B2B and D2C, and the unit economics holding it all together.
In a world where I find myself the only marketer in a group of 100 friends, I held on to my purpose and still stand today. I never blamed my environment; every successful step made up for many failures. Yes, it was hard; I lost my job multiple times. I worked 12-hour days for years, and I sunk a lot of marketing investments.
My one rule has never changed: more math than magic, common sense, and no vanity metrics.
Hey there! I'm Oludotun Oyebolu a.k.a Dots.
Most people just call me Dots, and yes, I've heard every "connecting the dots" joke, so I made it my brand. Connecting dots is the actual job: spotting the pattern between data, buyers, and revenue that everyone else walks right past.
My story with this stuff started during the 2005 internet boom and never really stopped. Five years later, I shipped my first 360-degree digital campaign out of my dorm room, and that was it. The growth marketing bug had me for life.
I spent my early career as a digital marketing director in Nigeria, working with some of the biggest brands in the country through 2019, then took a run at the global freelance world and helped level up more than 100 businesses across five continents and 20-plus countries. In 2019, Canada came calling, and I packed up the playbook to go prove it in new markets. I've been based here ever since.
Career Impact
As a marketer on a mission to deliver outstanding results, I share how I’ve impacted brands. I'm not here to win awards for prettiest dashboard. I'm here to move the number. A few highlights from the last stretch.
Check out some of my achievements over the years:
At Directive, I run demand generation across a portfolio of B2B SaaS clients, steering north of half a million dollars a month in aggregate paid media. The work lives where it should: closed-won pipeline, server-side conversion tracking, answer-engine and search visibility, and ruthless budget allocation toward the channels that actually pay.
At Content Allies, I led marketing for a B2B podcast production agency and added a full $1M in ARR, taking the business from a flat $2M to $3M. Our account-based podcast strategy drove a 10% guest-to-closed-won rate and pulled in brands like Siemens, AWS, Cisco, Zendesk, and Wiley.
I co-founded Listen Network, a US-based podcast ad-tech company, where I'm Senior Director of Ads Strategy. We've built proprietary rich-media programmatic adtech for B2B and D2C brands and crossed $1M in bootstrapped revenue, no outside funding required.
Earlier, at Clickspace Interactive, I ran an entire marketing unit solo, beat a $170K ARR target, and generated 1,500-plus quality leads and 1,000-plus e-commerce transactions across 10 clients.
At ARM, one of Nigeria's largest financial groups, I grew web traffic 500% to 2M annual visits and drove over $1M in investment deposits per quarter. Picked up the ARM Ambassador Award (2015) and the Service Champion Award (2017) along the way.
Not to toot my own horn, but here are a few things I built with bare hands
Strategy Maker™, my own go-to-market framework, built on five pillars: Market Intelligence, Brand & Positioning, the Growth & Revenue Engine, Performance & Economics, and Market Expansion. It's the transparent, math-first system I use to take brands from "industry player" to category leader.
Two whitepapers, B2B and B2C, including Target Acquired, my 2026 guide to building a GTM engine that secures product-market fit and funds its own growth.
The Marketing Leadership Podcast, where I've traded notes with some of the sharpest CMOs and marketers in the world (Neil Patel, Rand Fishkin, Chris Do, and a long list more).
ToolSplit on YouTube, where I co-host and led the growth strategy that took the channel to thousands of subscribers.
Off the Clock
When I'm not heads-down in an activation curve or a CAC payback model, I'm usually deep in a history documentary or embracing the remote, work-from-anywhere life.
As a proud member of the diaspora, I've led social-impact campaigns and given free strategy to small businesses that needed it.
Off the keyboard, I'm a husband and a dad to one very excellent daughter, and I volunteer as a Youth Church Leader, helping the next generation find their footing.