Content as the Compass

Funmi Ajike’s career seems to have taken off like a rocket straight out of university - but it hasn’t come without its challenges. 

From starting her first role at Wealthsimple fully remote during the pandemic lockdowns to establishing herself as a multi-hyphenated marketer, Funmi has built a solid foundation for herself in the Toronto tech space, and extended that to NYC working remotely as a content strategist at Air.  

I chat with Funmi about our common ground in marketing fintech products on social media, and how she has approached her marketing career with a mindset of “choose your own adventure”. 

Kaley Ross: It’s great to finally connect, Funmi! We’ve been LinkedIn connections for a while but haven’t had the chance to chat. Thanks for making time today!

Funmi Ajike: Yes, it's great to meet you officially. It feels like we've known each other for a while on LinkedIn, but this is our first real conversation.

KR: I know! I was convinced we had met in person already. I’m excited to chat and learn more about your career. Let’s dive in! 

When did you first decide to pursue a marketing career, and how did you start that journey?

FA: It started back in high school. I’ve always loved writing, and wanted to do something creative with it. I initially thought about journalism or law, but also explored other options like marketing and business. I ultimately found that marketing allowed me to tap into my creative side while staying in a business context—it felt like a great fit.

I eventually moved to Montreal and pursued a degree in marketing. My first big break was an internship at an agency, and from there, I’ve continued to grow in the field. I’m currently in my fourth career role, all still focused on marketing.

KR: That’s amazing. Was your first full-time role at Wealthsimple?

FA: Yes, it was, and it came during a pretty tough time—2020, right in the middle of the pandemic. Job hunting was brutal then, especially for recent graduates. People with much more experience were getting laid off, and the competition was fierce. I remember applying for a social media role at Wealthsimple, and they told me there were over 1,000 applicants. By God’s grace, I landed the position, and I stayed with them for about three years.

KR: Wow, over 1,000 applicants? That’s wild! You obviously were so excellent at what you do to have stood out. 

Was there a serendipitous moment that made you realize this was the right path for you?

FA: Definitely. When I started my job search, most of my offers came from agencies. But Wealthsimple stood out because it wasn’t an agency—it was a brand I was genuinely interested in. 

I was already learning about financial literacy as an early twenty-something year old, and I loved the content they were putting out. So, getting the opportunity to work with a team that was creating something I was personally passionate about felt like it was meant to be.

KR: That’s really cool. I love how it aligned with your interests. 

Switching gears, was there a time in your career that felt particularly challenging, and how did you overcome it?

FA: The early pandemic period was definitely a challenging time. There were layoffs across teams including mine, so it was tough to stay motivated and avoid burnout. The key to overcoming that was advocating for myself and ensuring I had the support I needed. I gave a lot of upward feedback and tried to be part of the solution by suggesting ways we could restructure, which eventually led to us hiring more people.

It’s also important to recognize when it’s time to move on, and I think that was a big lesson for me—knowing when to leave a role is as important as knowing when to stick it out.

KR: Absolutely—that’s great advice. 

Social media marketing is often fun and energetic, but doing it in a highly regulated industry like fintech is a whole different ball game. How did you approach that?

FA: It’s definitely different. In fintech, there’s a balance between being creative and staying within legal boundaries. At Wealthsimple, we worked very closely with our legal team to ensure we stayed compliant while still pushing boundaries with our campaigns. I had a great relationship with our legal counsel, who was always open to finding alternative solutions rather than just saying “no.”

We also leaned heavily into brand marketing, which really helped us stand out in a relatively traditional space. When we launched products like Wealthsimple Cash, we did a lot of giveaways and innovative campaigns to build interest. A big part of that success was the team’s ability to make financial products more engaging and relatable through creative marketing.

KR: I remember seeing those campaigns! I always loved the visual branding for the content. 

As a marketer, what do you think are your greatest strengths, and what do you enjoy sharing with the world?

FA: I’d say my strengths lie in the production and operations side of marketing. People often focus on the creative aspects—like content strategy, copywriting, and art direction—but the behind-the-scenes work of orchestrating everything is just as important. 

I’m really good at bringing it all together—making sure things are running smoothly, from content creation to campaign execution.

That operational mindset is what drew me to my current role at Air. It's a creative operations tool, and it helps teams manage their content workflows efficiently. I’m passionate about creating structure, so creative teams can focus on what they do best without getting bogged down by the process.

KR: That’s such an important skill set.

For those looking to build their marketing career, what advice would you give them?

FA: I’d say, don’t be afraid to explore different paths. Marketing has so many facets—whether it's creative, strategic, or operational—so find what excites you the most. 

Advocate for yourself, continue learning, and don’t be afraid to ask for the support you need. Also, keep in mind that moving on from a role is part of growth. Everyone’s path looks different, and it’s all about choosing your own adventure.

KR: I love that about choosing your own adventure. 

People who start in social media marketing develop so many skill sets – there’s a laundry list that’s required for that role. You’re a copywriter, project manager, publisher, designer, crisis communication manager, community builder, brand strategist, data analyst. There’s a lot of opportunity to apply those skills to different roles. 

How do you think people can break into different areas of marketing, especially when they might feel boxed into roles like social media management?

FA: Exactly! 

It's all about exploring different avenues. Some people might enjoy the analytics side of things, while others prefer the more operational or creative aspects. It's important to have options so you don't burn out. 

If you’re stuck doing just one thing, it’s hard to stay motivated and enjoy your work in the long run.

KR: Completely agree. That leads perfectly into my next question: You’ve been building your personal brand on LinkedIn for a while now. 

What motivated you to start, and how has it evolved over the years?

FA: Oh, LinkedIn has definitely become a big trend recently! 

I’ve had my account since 2017, but I think the platform really grew in prominence during the pandemic. People were online more and job searching, and LinkedIn became a space to build community. 

For me, it was initially a way to document my journey—sharing school projects, case competitions, or trips to visit different companies in Toronto while I was a student in Montreal. It’s  funny how things came full circle this year when I got invited back as an alum.

KR: That’s so cool!

FA: Yeah, it was a full-circle moment for sure. I was already using LinkedIn to show my personality and what I was doing, beyond just being a name on a resume. 

Over time, it became a natural place to share professional highlights, whether it was a post about a recent event or just reconnecting with people. I never intended to become an “influencer” in that space, but I found it to be a great way to stay connected with my network.

KR: For sure. 

So you have a Content Strategist role now - tell me more about your unique POV when it comes to content marketing.  

FA: Sure! At Air, we focus on creating content that resonates with people beyond just pushing products. Like fintech, traditional B2B SaaS can be boring, so we’ve completely thrown out the typical marketing playbook and done some fun things like staging a fake protest, producing a 20 minute mockumentary and running a content series featuring creative directors looking for their next opportunity.

The series was a win-win because we give them exposure to potential employers, while we create valuable, engaging content for our audience. It’s what my manager calls “unimpeachable content”—content that’s positive and hard for people to criticize.

KR: I love that idea for a series—marketing that’s about human storytelling rather than just sales. It feels authentic and helps people connect with the brand on a deeper level. 

It’s such a fresh take in industries like finance as well - I love that fintech generally takes that approach.

FA: Yes! Personal finance is, exactly that, personal because people’s livelihoods are at stake, so it’s important to approach it in a human-centric way. 

KR: You’re only a few years out of university, but have held some exciting roles at impressive Canadian companies already.  

What are you most proud of today, and what are you excited for in the future?

FA: One thing I’m really proud of is how I’ve been able to set up systems, especially around content plans and social campaigns, that have helped streamline workflows in the different places I’ve worked. 

Moving from Wealthsimple to TD and now Air was another proud moment for me—it was a big shift from Canadian finance to an American tech company focused on creative software. I think my ability to pivot and explore new areas of interest, like creative operations, has been a major personal achievement.

KR: That’s amazing. It seems like you’ve been able to build an incredible foundation early in your career. 

FA: I’m really excited to keep exploring creative operations and production. It’s a completely different space compared to my previous roles, but I’m learning a lot. 

Being part of a product that I would personally use in my own work is really fulfilling. It’s a chance to see how far I can go in this field, especially as I work with more experienced professionals who are also navigating these creative spaces.

KR: Love it. I’m looking forward to more updates from you on LinkedIn!!

Thank you so much for this incredible conversation, Funmi.

FA: Thank you, Kaley! This was a lot of fun.

⚡ Bonus Round

Subscribe to discover how Funmi stood out in her Wealthsimple interview, and what advice she would give to university students looking to land their first role.

And of course, Funmi’s Recs!