Level Up: What this founder looks out for when hiring

Jesutofunmi Adedoyin -

In the spotlight this week is Oreoluwa Olaitan, co-founder of Enif.ai, an AI-powered CRM solution that helps businesses in Africa use the power of AI to drive growth.

He shares insights on the challenges of scaling a startup in Africa and what he looks for when hiring talent. 

🔎 In the spotlight with Oreoluwa Olaitan

What inspired you to launch a tech startup in Africa?

I’m a firm believer in the potential of the Global South. Having completed my MBA in Southeast Asia, I witnessed firsthand how countries like Malaysia, Vietnam, Thailand, and Singapore are rapidly transforming into tech hubs. Africa is the next frontier for this kind of development, offering immense opportunities for those willing to take the risks necessary to lead a tech revolution on the continent.

In my field, AI, there’s vast potential to drive significant change across Africa—from healthcare and security to agriculture and business efficiency. Of course, these opportunities come with risks, but as we know, higher risks often lead to greater rewards. 

I believe Africa’s greatest resource is its people, so it’s more of a commitment to creating value for Africans.

What are some of the biggest challenges when scaling a startup in Africa?

One of my biggest surprises was realising that Africa is not a single market. It’s common to hear people in Europe refer to Africa as if it were one country, but once you start doing business, you quickly discover just how fragmented the continent is. This fragmentation means that a business strategy that works in one country might not be effective in another. The business environments across these nations are vastly different, and the real challenge lies in the lack of standardised regulatory frameworks across the continent. This can be a significant hurdle, especially for startups that don’t have the resources that larger, established companies do.

Of course, funding is critical. Raising capital for African startups has become increasingly difficult, and scaling across the continent is cash-intensive. Whether hiring teams in different countries or navigating the various regulatory landscapes, all these activities require substantial capital.

Beyond skill level, what other qualities do you prioritise when hiring employees for your startup?

The main qualities I look for are passion and enthusiasm. In the world of startups, you never have all the answers from the beginning. You can’t predict every challenge you’ll face, so working at a startup demands high adaptability. You have to learn quickly as new needs arise. Without the grit, desire, and commitment to the project, someone won’t be able to handle the challenges that come with it.

What’s your approach to hiring talents?

When considering someone for the team, I focus on specific traits. I assess how well they understand situations, whether they grasp what the role requires, and how quickly they can adapt and start making a significant impact. For instance, I often present a scenario during interviews and ask how they would handle it. This helps me gauge their understanding of the role, their approach to problem-solving, and whether they are enthusiastic to learn what they don’t already know.

If you could have any superpower related to your career, what would it be and why?

It would be the ability to really understand customers and understand customer's pain points. When you have a good understanding of the customer's problems and what they're facing, you can always build the right solutions. Not a nice to have but a “oh, you’ve solved my life’s problem, take my money.”

From a hiring perspective, what advice would you give to early/ mid-level tech talents to help their job search?

Startups don’t have the luxury that larger organisations do when it comes to hiring and training programs. In the early stages, when a startup is trying to go from zero to one, they need people with very specific skill sets. Either you have those skills, or you have transferable skills. Even if you don’t have the exact skills, you should be able to demonstrate a track record of learning quickly, adapting, and acquiring new skills to deliver value.

There are also times when you may not have any direct experience, but you’re genuinely passionate about the role. In these cases, taking an unconventional approach can help. For example, you could create a presentation or show something tangible, demonstrating how you would contribute or add value. Another tip is to build a portfolio, even if it’s based on side projects, not just work done for a company. Document your work so that when the opportunity arises, you can provide evidence of your abilities—even if you haven’t done it professionally before.

Recently, I hired a social media intern who’s just finishing university and had never worked for a company before. Despite this, she had volunteered for several organisations, managed accounts in the past, and earned certifications in relevant courses. Her passion and willingness to learn were clear. Sometimes, you won’t find the perfect candidate, but you’ll see potential and a strong desire to grow, and that can be enough.

If I have a candidate who’s a 90% fit but has a closed mindset and another who’s an 80% fit but shows hunger and the capacity to grow, I’ll choose the 80% candidate. I know they’ll surpass the 90% candidate over time, potentially reaching 95% or higher.

As a founder, I can tell you there’s a lot of randomness in the recruitment process that’s beyond your control. That’s why I advise people not to take rejections too personally. If you can get feedback from the recruiter, that’s valuable too. Sometimes, when I interview four candidates who are all closely matched in ability, the decision isn’t about proficiency anymore—it’s about other factors. That’s why it’s important not to focus solely on qualifications; soft skills can be the differentiator in these situations.

You’ve previously worked at eTranzact and Branch. While you were in the job market, what were the job search strategies that worked for you?

When I’m targeting specific companies, I start by making a spreadsheet. Let’s say there are ten companies I really want to work for, and I list the roles I’m interested in within those companies. My next step is to find someone who works there. If it’s a Nigerian company, there are usually plenty of people to connect with. For foreign companies, I look for a Black person, an African, or a Nigerian working there. I connect with them and try to learn more about the company. 

The fact is, if you apply directly, your application might not get past the Applicant Tracking System (ATS). But if you get an internal referral, it significantly increases your chances of getting noticed. Once your CV is seen, you have a better shot at landing that first interview. So, I network my way in—sending LinkedIn messages like, ‘Hi, I see you work at this company. I’d love to connect and learn more about it.’ Once you connect, you can then mention that you’re interested in an open position and ask for more information. Don’t ask for a referral right away. After gathering info, you can casually ask if they’d be willing to refer you or mention your name to the hiring manager. I’ve had people do this for me, and it works.

If you secure the interview, the next step is to research the company thoroughly. I always try to consume as much information as possible about their culture, publications, and even YouTube videos. This way, when I’m speaking to the hiring manager, I’m using the company’s language, aligning with their culture, and showing that I understand their perspective.

Finally, make sure you can defend everything on your CV. Practice answering questions using the STAR method (Situation, Task, Action, Result). It’s best to rehearse with a friend to ensure your answers are concise and clear. The goal is not to sound robotic but to be ready to deliver your points effectively, even if time is limited, and to keep the conversation flowing smoothly.

Describe a day in your life as a founder

My day starts early. I wake up, pray, exercise, freshen up, and dive straight into work. There's always something to work on—whether it’s putting out fires or pushing forward on a project. My mornings usually include a stand-up meeting where the team discusses progress and aligns on goals. These meetings are crucial for identifying any issues early on so we can make contingency plans if needed.

The rest of my day is filled with meetings—whether it’s with investors, customers, or internal teams. I also handle demos to show the product’s value and make time to talk to customers regularly. Understanding their pain points helps us ensure that we’re building solutions that truly address their needs.

A lot of nitty-gritty is involved, and my workday doesn’t have a typical closing time. Sometimes, I’m working late into the night to wrap things up. Even after dinner, I often find myself back at my laptop, working until it’s time to shower and call it a night.

I rely on my support systems to manage the pressure. Going to church helps, and spending time with my girlfriend is also important to me. These things keep me grounded because the demands of work can be overwhelming.

If you could take a break to learn something new, what would it be?

It would either be learning to cook or advancing my guitar skills. I’m self-taught on the guitar but haven’t had much time to play lately. I’d like to take advanced courses because music is a great way for me to relieve stress.

Tech News: New African countries added to Medium’s Partner Program

Medium has opened up its monetisation program to Nigerian writers, along with those in 76 other countries. So, if you're in places like Ghana, Egypt, Algeria, Kenya, South Africa, Gabon, or Nigeria, you can now earn money from your blog posts on Medium.

Plus, they’ve extended their nomination program to these countries. This means independent editors within the Medium community can now find and nominate your stories, giving them a chance to reach an even bigger audience.

You can read more about the requirements here.

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