We’re sharing stories of people’s early careers. Everyone we interview has worked for a startup in the first few years of their career. We hope reading about others’ experiences at startups will help you make more informed career decisions!

At Otta, we’re advocating for working at fast growing technology companies early in your career. We think this is where learning opportunities and development potential are highest.

Anselm: iwoca & Checkout.com

Anselm Obi is currently an Operations Manager at Checkout.com. Anselm studied Law at university and started his career at iwoca in the Sales team. During his time there, he held a variety of roles, including managing one of the Operations teams. After 2.5 years at iwoca, he had a stint as a contractor working at HSBC (it was supposed to be a 3-month contract but ended up lasting 10 months!). He then joined Checkout.com in the summer of 2018 and currently leads the company’s MENA Customer Operations department. I met Anselm at Checkout.com’s offices in Fitzrovia.

Tell me about how you got your first job

I studied Law at university, a subject where there is a fairly well-trodden career path. 80% of my peers ended up going to be corporate lawyers, others went to consultancies and banks. Career fairs at university were full of huge companies, so I didn’t really get any sense of what it would be like to work for a smaller company, even though I was considering startups as an option.

After my second year, I did a short internship at an investment bank and knew straight away it wasn’t for me. I felt my career development needed more flexibility than what was offered by most corporates. I didn’t even want to spend one year doing it for the experience!

I was a bit lost on what to do next. I considered doing a Masters degree but that was really just delaying deciding on a job. I planned to do some internships in the meantime to help me figure out what was right for me.

When looking for internships, I came across a few roles on my university careers website. I applied for one at a company called iwoca (who provide small businesses with loans), and they reached out to me and asked me to come for an interview.

I travelled to London for the interview. As soon as I got there, the recruiter looked at my CV and said this job is for German speakers and it doesn’t look like you speak German from your CV… It didn’t say this on the job description!

She called the Head of Sales into the room, he looked at my CV and said straight away “We’re not hiring graduates at the moment, but, since you’re here I’ll give you a couple of weeks, see how you stand up to the test and then we can take it from there.”

So before I knew it, I had an internship! I was thinking I would do this internship, maybe do another one and then go back to school for my masters, but it didn’t work out like that.

After the first few days at iwoca I thought to myself ‘there’s no way I’m going back to school’. I was really enjoying it, and I was doing well. I ended up staying there for 2.5 years.

What were you working on at iwoca?

I started in the Sales team as an Intern, I had no experience so they trained me up very quickly and within a few months, I was up to speed. After another few months, I quickly became a senior member of the team.

Before my first year was complete, I got promoted to a different department where I was responsible for building a new team focused on commercial operations.

The CEO took me into a room to explain the objective of the team and the value it could add to the company. At that point, iwoca had lots of people signing up to the website, and my team’s objective was to ensure we converted as many of them to paying customers as possible.

I became the Head of the newly established Client Onboarding team and was quickly hiring, mentoring and managing people.

The best part of iwoca for me was the education I received, it was like being at business school. For the first 6 months, I was focused on sales & marketing. Then I worked in operations, where I was setting KPIs, learning how to manage teams and develop processes. The latter part of my time was more focused on leadership & strategy as the company grew.

At the end of my time there I was managing a couple of teams and around 12 people. It felt like I had 5 years of experience condensed into 2.

iwoca’s product helps small businesses access loans

What made you decide to leave?

I was at iwoca for 27 months in total, which doesn’t sound like a lot, but when you’re working somewhere that’s growing really fast it can feel a lot longer.

The learning curve was so steep and I wanted to continue on that trajectory. It got to a point where I thought the best way to attain that would be through a new challenge.

I took 6 weeks off when I left iwoca to take a breather and see what was on the market. I’d always advise people never to jump from one job to another if they don’t have to, a small break helps you reflect and refocus.

I knew I wanted a long career in fintech, but I also thought a stint at a more established company could help with my credibility in the long term.

I ended up accepting a 3-month contract opportunity at HSBC. I was working on a project to do with Brexit, and my responsibilities were completely different from my previous job.

It was a regulatory project where we had to migrate HSBC’s clients ahead of Brexit. I was supposed to be there for 3 months but it ended up lasting nearly a year. It was super interesting, but I always knew my days were numbered as I was waiting for the right opportunity in the fintech industry.

How did you end up moving to Checkout.com?

Whilst at HSBC, the Head of People at Checkout.com reached out. I knew very little about payments, but after a quick chat, he managed to get me excited about the company and the role.

The role was for a Senior Onboarding Specialist. The Onboarding function in Checkout.com is responsible for analysing and mitigating against the various risks associated with all prospective clients. I took the job and started soon after.

Within a few months, I was managing the team. As the company grew, I transitioned into my current role as Operations Manager where I’m now responsible for the company’s MENA Customer Operations department. Believe me, it’s not an easy job to explain to my Mum when she asks me what I do!

What made you choose Checkout.com?

For me, the company’s story is truly unique. From our early days in Mauritius to the fact that we were self-funded up until recently. I could feel the company’s aspirations after a few conversations with team members.

The key for me was that I could really relate to the company’s values. We have an aspirational team that truly leaves no room for approximation.

Do you have any advice you’d give to others considering working at startups?

The first piece of advice might sound obvious, but I think it is important to always have a plan, don’t wing your career.

You can always change your plan or adjust it as you grow, but having a plan gives you a sense of direction and purpose.

Secondly, you need to be open-minded to get the most out of your experience in a startup. In most startups, your work will almost definitely go beyond the scope of your job description, but this is an opportunity to add more strings to your bow.

When I started my career, I didn’t even think about a job in sales, but the lessons I learnt from my early experiences still help me on a daily basis.

It’s a shame more people don’t know these great opportunities to learn are out there. That’s why it’s great to see companies like Otta helping to get exciting roles in front of people. More people should be reading about startups and considering them as a career option!

Do you have any other advice?

My last piece of advice is to find a mentor if you can. Having someone you can seek guidance from who’s also invested in your career is invaluable.

Finding the right mentor can be tricky, but at most startups the leadership teams are easily approachable. So I’d encourage people currently at startups to make the most of those relationships!

Want to share your story? We’ll buy you a coffee whilst we do the interview, and then give you £25 towards a dinner as a thank you. If you’re interested, email me at theo@otta.co with a bit about yourself and your career so far (a few short bullets is fine!).

At Otta, we’re rebuilding job search. Our product is the smartest way to search for jobs at startups in London, and we have great companies like iwoca and Checkout.com on the platform.