Member story: How curiosity and feedback shaped Damilare’s marketing journey
Member story is a monthly Smarketers Hub series where we connect closely with a member of Marketers Room, our Slack community, to explore their career journey, capture their industry opinions and work philosophies, and document what being a Smarketer means to them. Each story will leave you with a fresh perspective on doing excellent work and growing your career through community.
For this month’s entry, we sat with Damilare Olasinde, a freelance B2B content marketer, to talk about his mindset behind great writing, what he’s learned about growth through feedback, why he believes B2B should embrace aspirational marketing, and how his journey, from a teenage entrepreneur to a thoughtful strategist, is guided by curiosity and deep work.
If you were creating a time capsule to represent your marketing career so far, what three items would you put inside, and what story do they tell about your professional journey so far?
First, the book SOAR by Bishop T.D. Jakes. I read it when I was around 18 or 20, trying to grow my first business, which I started at 17. The book speaks to faith-driven entrepreneurs and teaches how to turn an idea into a successful business. It introduced me to aspirational marketing, the kind that companies like Nike and Apple do.
I’m a self-improvement guy, so that was the kind of marketing I wanted to do. But mine was a food retail business, and I felt; What does motivational and aspirational stuff have to do with food? It seemed like two different things that shouldn’t mix. This book showed me my idea wasn’t crazy or even new. That realisation gave me the permission I needed to pursue it.
Second would be Deep Work by Cal Newport. Its main argument is that most people have lost their ability to create rare, valuable work because their attention is always fragmented.
The war for our attention is real. Thanks to tools like social media and whatnot, we’re becoming increasingly addicted to distraction. Cal’s thesis is that we can create rare, valuable work by protecting our attention and honing our ability to focus. This implies that a deep work habit is crucial to thriving as a knowledge worker. This idea resonated with me.
There were lots of references to writers in the book. Plus, Cal often geeks out on the writing craft on his YouTube channel. Since I’m a writer, too, we connect on that level, too. I see Cal as a wiser and more refined version of me. He’s one of my role models, so it shouldn't be surprising that I own (and highly recommend!) all his books
The last item would be a yellowish scroll with two things written on it:
Don’t tolerate imposter syndrome. If you’ve been given an opportunity, chances are the skills you need are already at the edge of your current abilities, and you can learn the rest.
Don't be intimidated by the gap in knowledge between you and the marketers you admire. No one is born with marketing knowledge. Your heroes learned their way up, and so can you.
Those two lines have carried me through moments of doubt.
Lovely picks. Tell us a bit about who you are as a person and as a marketer
I’m a Christian, a self-improvement nerd, and a movie guy. I unwind by reading my bible, non-fiction books and watching films, especially anything by Christopher Nolan. Actually, I’ve only seen a few of his movies — Inception, the Dark Knight trilogy, Oppehiemer — (blame it on adulthood), but he’s certainly my favourite director. I’m a huge Avengers/MCU fan as well.
I often joke that I have a sense of humour that's kind of like Nigeria's, like Nigeria’s power supply — on and off.
As a marketer, I work as a freelance content writer focused on B2B — mostly MarTech, sales, and SaaS. I’ve been freelancing for most of my career, and I love helping companies produce long-form content that’s genuinely informative and compelling.
Ouu, I also love Christopher Nolan. Let’s talk about how you work. What values guide your collaboration with clients or teams?
There are four values I try to carry into every relationship.
First is feedback. I’m fanatical about it, as many of my clients will tell you. I ask clients two questions after a major project: “On a scale of 1–10, how satisfied are you with my output?” and “What would you like me to do better next time?” It helps me grow faster and produce work that meets client expectations.
Many professionals fear feedback, but I’m comfortable asking these questions because I'm self-assured, so negative feedback rarely gets to me. I see it as useful data, not personal criticism.
Secondly, initiative. I believe in stepping up, especially when no one’s giving clear direction. I’ve noticed that in some team settings, people wait too long for instructions. I try to be the person who says, “Let’s get something moving.”
Third is excellence. Go above and beyond, be the person who is known to deliver excellence. Or, at the very least, be the person who is known for always doing their best.
Fourth is overcommunication. You can't go wrong by overcommunicating. You may go wrong, however, by undercommunicating. For instance, it’s one thing to miss a deadline. It’s another thing to go AWOL.
I’ve missed more deadlines than I’d like to admit (In my defence, this occurs because I consider it a bigger betrayal of client trust to ship mediocre work). However, I never ghost my clients in such situations. I update them and provide my reason for the delay. As you might imagine, missing deadlines has cost me a few clients. But I believe I preserve some credibility by maintaining communication.
Tell us about a project or a memorable work experience that has shaped your career
Sometime in 2023, I worked on a ghostwritten thought leadership article for a client in financial services. The audience was senior marketing executives and CFOs.
At first, I felt underqualified. I didn’t have direct experience in that industry. But I remembered something simple: if I don’t know their problem, I can figure it out. I dug into industry pain points, then found companies that have broken past that. Research led me to brands like Wise and Cowrywise, companies that managed to stand out despite regulatory constraints — a major challenge in financial services marketing.
That project taught me something critical: I’m not a writer or creator, per se. I’m a curator. My job isn’t to invent knowledge or conjure something from nothing. My job is to understand readers’ challenges and solve them by gathering existing) knowledge from subject matter experts. It sounds simple in hindsight, but that realisation has been liberating.
What’s something you haven’t seen in marketing yet that you’d love to see more of?
Aspirational or missional marketing in B2B. We don’t see enough of it.
I can't think of any one B2B company that is aspirational in their marketing. You could mention examples like Apple, but I don't consider Apple B2B in this context because they cater to a large consumer base. For strictly B2B businesses, you don't see a lot of aspirational marketing.
I once heard Peep Laja, founder of CXL and Wynter, suggest that Start with Why (referring to Simon Sinek’s book) has no place in B2B marketing. I beg to differ. I believe a strong mission can be a powerful differentiator for B2B brands and will become a competitive edge in the future.
Humans still make the decisions on B2B teams. So, I believe there’s space and even a need for storytelling, purpose-driven messaging, and creativity. I’d love to see B2B brands that are bold enough to root their marketing in purpose, versus, say, product features that competitors eventually copy.
But B2B is a strict industry and often demands a more serious tone. How do you think aspirational marketing can thrive in that kind of environment?
First, I should say I don’t have all the answers yet. But I’ll share three thoughts.
One: I use the terms “aspirational marketing” and “missional marketing” interchangeably. And missional marketing isn’t about promoting personal achievement or self-actualisation like Nike does or as Apple did with its famous Think Different ad campaign. It’s about having a clear, strong, compelling mission that’s woven into business processes and messaging.
Two: We’re already seeing signs of unconventional marketing in B2B. Take HockeyStack, for example — a Y Combinator-backed attribution company. They once released a rap track on LinkedIn to explain what their product does. That kind of creativity is rare in B2B, but it worked. I still remember it. In fact, HockeyStack is the only attribution tool I can name, and that’s because their marketing stuck.
Three: Even in B2B, you’re still talking to humans. Yes, decisions are made by committees, but each committee is made up of real people. If your message resonates with even one internal champion, that could be enough to tilt a deal in your favour. As the LinkedIn thread below reveals, B2B professionals are frustrated with the lack of deeper purpose and are actively seeking ways to bring more meaning into their work.
The bottom line is, I believe we’re heading into an era where B2B brands will win not just by being useful, but by being meaningful. The companies that combine strong products with a relatable mission will stand out and attract the best customers… and talent.
So no, it’s not the norm yet. But I believe it’s coming, and I’m excited to see (and possibly build) more of it.
What does being a Smarketer mean to you?
Being a Smarketer is about learning in community. For someone like me who freelances, it’s easy to feel isolated. But the Hub has connected me with smart marketers I now call friends.
I originally heard about Smarketers through my cousin, and I was immediately drawn to Aisha’s work. I made a mental note: “Here’s someone I can learn from.” Even before I joined Marketers Room in Slack, I was following the Hub’s resources on LinkedIn.
But I didn’t really engage until after the Lagos meetup. That in-person experience gave me the nudge I needed. Since then, I’ve had rich conversations, exchanged insights, and built connections that go beyond just “networking.”
It’s a space where I can learn from people ahead of me, collaborate with peers, and give back to folks who are just starting out.
What’s your favourite thing to do in the Marketers' Room?
My favourite thing to do in the Marketer's Room is bantering with other marketers.
I love the mix of serious conversations and lighthearted moments. Sometimes someone shares a wild job posting — like one looking for an “electrician + marketer”, and we just laugh.
Other times, someone needs help, and you get to see how different marketers approach the same problem. It’s like the office gossip I never get to have because I work freelance.
With what you know now, how should marketers approach community for career growth?
The one thing I’ll recommend is to be present.
You can quietly observe and still gain value, but the real benefits come from participating, answering questions, sharing perspectives, and engaging with others.
That also means you need to choose communities intentionally. I belong to five, but I actively participate in only one: Marketers Room. You can’t spread yourself too thin. It’s like dating five people at once; it might be fun for a while, but it’ll drain you.
What’s your hope for the future of your career?
If you asked me late last year, I would’ve said I want to pivot into growth marketing, and that’s still true. But writing a sales “state of outbound” report reconnected me to my original love: sales.
I’m a natural. Talking to people, doing a cold call, or asking for the sale, having hard conversations doesn’t scare me. So I see myself doing a mix of marketing and eventually sales going forward.
So my short-term goal is to blend marketing with B2B sales. My long-term goal? Entrepreneurship. Everything I’m learning, writing, strategy, and sales is preparation to run my own successful business.
Would you like to give a shout-out to a marketer who’s impacted your journey?
Yes, my friend Olaitan Aiyeyomi is the reason I started content marketing. Back in 2019, he told me, “You write well. Why not make money from it?”
That suggestion was where it all started. Four years later, I’m still on this path because he nudged me in the right direction. He deserves this shout-out.
Connect with Damilare on LinkedIn, Instagram, and X(formerly Twitter). And join Marketer's Room to engage with more like-minded professionals and build a thriving career.
