Level Up: How I’ve survived over 400 rejections in my career

How this product manager overcame numerous rejections before landing his first role in the UK.
14 minute read
Level Up: How I’ve survived over 400 rejections in my career


In this week’s edition of Level Up, we spoke with Sidiq Rufai, a UK-based product manager. He shared his journey of transitioning from marketing to product management and the many rejections he faced before landing his first role in the UK.

If your career journey were a movie, what would the title be and why?

From pillar to post, because my journey has been a series of pillars to posts, each step building on the last. Everything I’ve done has been a foundation for the next chapter. Being a photographer led me to copywriting, which became the pillar for content management. Content management, in turn, set me up to become a digital strategist.

Where I am now is just another pillar to a post I probably don’t even see yet. But from here, I’m starting to envision entrepreneurship, building something of my own.

Tell us about your journey into the tech industry?

I’ve always loved advertising—not just the ads themselves, but the idea behind the idea. For example, when I see a billboard or a campaign, I’m not really focused on whether it worked for me. I’m more fascinated by the process: how did they come up with this? How many ideas did they trash before landing on this one? That curiosity is what eventually led me to copywriting, though my journey into it was unconventional.

I remember visiting an agency and chatting with the creative director, who happened to need advice on buying a camera. I helped them pick one, and somehow, that conversation turned into a copywriting job. I didn’t grow up dreaming of working in an agency, but I was already dabbling in creative things, so it clicked. 

After a year in copywriting, I transitioned to content management, where I started thinking about the analytics behind campaigns, how they performed, and what could be improved. That shift sparked my interest in digital strategy.

From there, it was a whirlwind. I worked as a digital strategist at X3M Ideas, managing ads, analysing data, and coordinating campaigns end-to-end. Marketing in Nigeria is a unique beast; roles aren’t rigidly defined, so you end up doing a little bit of everything. I eventually realised I wanted to build things. I’ve always been drawn to the how and why behind ideas, so I pivoted toward product management.

X3M  Ideas was pivotal for me. I joined during COVID, a chaotic time for marketing, and worked across pitches, ad placements, influencer management—you name it. That’s where I got my first taste of working with tech companies and shaping product roadmaps. One standout moment was working on BBNaija’s voting subscription feature. I casually mentioned tying voting to subscriptions, and it became a key feature.

Eventually, I decided to pursue a master’s in digital business. I wanted to laser-focus on product management, leaving marketing behind. Now, as a product manager, I’ve gone from helping a fintech launch a global remittance product to managing the mobile app for a major UK retail organisation. It’s been a journey of wearing multiple hats, embracing challenges, and constantly asking, ‘How did this idea come about?

With a marketing background, how did you navigate the technical complexities of your role?

“I’d say ‘agidi’ [means Grit in English] When I want something, I go all in.

For me, I grew into being a growth product manager, though there’s also the technical side. A technical PM focuses more on the coding, UX, and engineering aspects, while growth PMs think about how the product generates revenue or achieves specific goals. Right now, I’m a mix of both.

My experience in a startup really shaped how I approach product management. I even took QA testing classes to build technical knowledge, learn manual and automation testing, and earn a certification. It wasn’t easy—no one warned me about writing Selenium scripts or learning Postman—but it gave me a strong foundation to communicate effectively with engineers. And trust me, engineers can be a different breed; they’ll try to bullshit you if they think you don’t know the technical side.

That said, I don’t believe you have to be deeply technical to be a great product manager. I believe the best PMs aren’t necessarily coding experts—they’re just exceptional communicators. They know what they want, who to talk to, and how to articulate their vision to get it done. It’s about seeing the bigger picture and managing people, processes, and, ultimately, the product itself.

In today’s world, with tools like AI that can query code, it’s more about understanding how to manage and influence people because, at the end of the day, the focus is on the customer. How do you serve them? How do you manage the team building the product and the processes to achieve your goals? That’s what it all boils down to.

What’s the most common reason people fail to succeed in your field, And how do you suggest they overcome it?

In product development, I think many people focus too much on chasing the money rather than truly understanding and meeting customer needs. Yes, the business has its goals, but the customer should always be the priority. I speak to customers regularly, it’s something I do every week. Whether it’s grabbing someone from retail or just talking to a user, I ask them, ‘What do you think about the app? What can we improve?’ It’s a constant feedback loop.

At the end of the day, the customers are the ones who pay us, so building features without speaking to them first is a mistake. You need to be obsessed with understanding them. And while customers don’t always know what they want, they can tell you what they don’t want. If you can understand that, you’re halfway there. The goal is to make sure the product aligns with customer needs, solve a real problem, and then figure out how to get them to use it.

I also believe that the fear of starting is one of the biggest barriers to success. In life, failing is not about not starting; it’s about not trying at all. I applied for over 400 jobs before landing my first job in the UK, no jokes. But I learned from every rejection.

The biggest thing I’ve learned is that you can’t be afraid of failure. You have to give the worst-case scenario a chance to happen so you can learn from it. Keep pushing forward, and seek clarity on what you want. There are so many distractions in the tech world, but focusing on building depth in one area first, instead of trying to be good at everything all at once, is key.

Have you noticed any significant changes in salary offers over the years? If so, what do you attribute these changes to?

In my current role, I’ve received two salary increases in less than a year since I joined. Here’s how I approach it: we have OKRs and clear metrics, so I ensure my contributions are measurable. I present my achievements, compare them to my peers, and make the case that I’m being underpaid. It all comes down to knowing your leverage.

Negotiation is an art; it’s about your knowledge and your relationships. In this case, ‘relationships’ mean how well you can communicate your value. If you don’t have leverage and you’re demanding more, you risk being dismissed. 

For me, leverage is rooted in my role. I own the mobile app section in my company, and while I’m not irreplaceable, I’ve built a structure that would take time and resources to replicate if I left. When negotiating, I pointed out how onboarding someone new would cost the company more in time and money than retaining me.

I also tied my case to tangible benefits. For example, I explained how optimising my efficiency could increase ROI, making my contributions even more valuable. But beyond these arguments, it’s critical to have a good relationship with your manager. My manager values mental stability and believes a happy employee is a productive one. That open relationship made a difference in the conversation.

Of course, negotiation isn’t just about money for me. It’s about freedom. I want the flexibility to work from home for two or three days a week. I’ve turned down offers that required me to be in the office for five days because that doesn’t align with my priorities. For me, it’s not just about the paycheck; it’s about the freedom to live and work on my terms.

That said, not everyone has the same leverage or options. I’m fortunate to negotiate from a place of strength and choice. I know what I bring to the table, and I present it in a way that feels larger than life. It’s important not to come across as desperate, negotiations I’ve done from a place of desperation often backfire.

At the end of the day, negotiation is about understanding your leverage, packaging it well, and knowing the right person to approach. Whether it’s your manager or a director, you need to tailor your pitch to the audience. And always have leverage. Whatever it is, find it and use it. 

What’s your experience with navigating cultural differences in a global tech environment?

Surprisingly, there’s actual work-life balance here, which I wasn’t used to. Coming from a startup environment, you’d understand—it’s a crazy world. Now, I’m at a much bigger organization, Matalan, a UK retail fashion company.

Let me give you an example. One week, I had so much on my desk that I ended up being the last to leave the office at 6 PM. In my previous role, I’d still be on Slack by 9 PM, talking to engineers in India or Pakistan across time zones. It was almost like working around the clock. So when I left at 6:30 and was the first in the office the next morning, my line manager asked me if I was okay. It was such a strange conversation for me.

I’ve had to adjust to this balance. It’s taught me to appreciate life outside of work. Here, if you work extra hours, the company pays you. It’s not just expected, like at startups, where ‘9 to 5’ on paper really means ‘5 AM to 9 PM.’

Another adjustment has been small talk. I wasn’t big on it before. In my previous roles, there was no chit-chat; it was all business. But here, I’ve realised how powerful small talk is. Sometimes, I rehearse what I’ll say to get someone on board with an idea, but then a comment about the weather or something trivia opens the door. Suddenly, we’re chatting and building rapport, and now they’re more likely to support my work. Small talk builds connections in ways I didn’t fully appreciate before.

Adapting to the cultural differences has also been interesting. At first, people struggled with my Nigerian accent, but now, through all the small talk, they’ve gotten used to it. We’ve even had debates about how wasteful English can be with letters! I’ve learned to understand the demographics of both my colleagues and customers. 

In Nigeria, for example, customers are much harder to please; they always want more. Here, people are more appreciative and will go out of their way to give feedback, whether good or bad. It’s a different dynamic.

Ultimately, adaptability has been my strongest skill. I’ve learned to adjust to different people and situations, and that’s made the difference. 

What does success look like for you in your career?

Success, for me, comes down to two things. First, I want to work on a product that 10% of the world can’t do without. That’s the dream—my own Champions League or World Cup moment in product management. 

At one point, I thought that would be Google Maps. I mean, think about it: no matter where you are in the world, you’re likely using some kind of map application. I remember being in the UK and feeling completely lost until Google Maps saved the day. The goal has always been, and still is, to contribute to something that fundamentally impacts people’s lives on a massive scale.

Second, I view my life as a product, and my vision is to achieve true freedom. For me, freedom is the discipline to do whatever I want despite the known and unknown challenges. It’s about having the time, the resources, and the mindset to make things happen, whether it’s travelling to the Bahamas or building an app. 

Success in my career would mean reaching that point where I have both the impact and the freedom: the ability to create something transformative while also having the freedom to live life on my own terms.

What specific technical skills have been most valuable in your career progression?

I’d say communication is everything. Knowing what you want and getting people on board is incredibly hard. I always say that people who can clearly articulate their thoughts are like superheroes; they’re influencing others to take action, which is no small feat. 

A big part of my role involves talking to different stakeholders: engineers, designers, marketers, you name it. It’s about presenting what I think needs to be done and backing it up with data because I’m working with really smart people who question everything.

It’s not just about talking; it’s about building trust. I often have to say no, a lot. Everyone believes their feature is the most urgent or important, but if everything is urgent, nothing really is. So, my job is to prioritise and get others to trust that my ‘no’ is strategic, not dismissive. That’s not easy; it can lead to resentment, people trying to go around you, or frustration. But it’s all about how you say it, how you navigate the aftermath, and how you maintain those relationships.

Even though I’m not a technical person, I rely on analytics to sharpen my communication. I don’t just speak in assumptions; there’s always a hypothesis and data to back it up. If I think something will or won’t work, I can explain why. And when I do get it wrong—which happens—it’s about managing the fallout and moving forward. 

So, for me, communication is the core skill I’m always building. It’s about learning to articulate my thoughts clearly and effectively every single day.

In your field, it’s common for people to mix up the roles of a product owner and a product manager. What sets them apart?

Firstly, I’d say it depends on individuals but a product manager sets the vision. It’s like saying, ‘This MacBook is designed to serve 10,000 designers.’ The product owner, on the other hand, owns the list of tasks to achieve that vision, working closely with engineers to deliver it. Product owners are in the trenches, planning sprints, running retros, and managing day-to-day execution, while product managers focus on the bigger picture, aligning the product mission with business goals.

At the end of the day, both roles are crucial and intertwined. If something goes wrong, the product owner gets the immediate blame, but the product manager faces the most scrutiny because they represent the broader vision.

For me, starting in a lean startup shaped my approach. I was both a product manager and a product owner, juggling strategy and execution. 

It boils down to how you see yourself and how the organisation defines the role. Ultimately, whether you’re a product manager or product owner, the goal is the same: deliver a product that meets the business’s goals and serves its users.


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