After starting her career in marketing at a large retailer in South Africa, Samantha Wessels teamed up with a female colleague to start a small consulting firm, offering one-to-one marketing. The aim was to drive personalized marketing to a large number of people, and Wessels realized very quickly that in order to do anything personalized and at scale, you needed to be in technology.

As she was discovering the importance of tech to marketing, she was headhunted by systems integrator NTT (formerly Dimension Data) to take a role selling Siebel CRM systems. Wessels notes:

I didn't know the first thing about technology, I'm not a technologist. And I thought, if that's going to enable one-to-one marketing, I need to go and understand how we do that through a CRM platform.

This was the catalyst for Wessels taking a step down in her career to join the tech sector. She explains:

When I was leading the marketing consulting firm, I had eight direct reports. I went back in my career to be a first-time salesperson cold calling into the mid-market, which was quite different to running and being part of setting up a business. So I went backwards to go forwards.

The role required Wessels to learn how to sell technology at the same time as learning how to be a salesperson. She recalls:

It was very tough. I didn't do very well. As a first-time salesperson doing outbound cold calling, there's lots of rejection. But what I knew was, if I just showed that I could work hard, that I had a high activity rate, that I kept my manager up to date on my activity, even if I wasn't making the number, they would recognize the hard work.

The strategy paid off, with the help of some sponsors along the way in the form of both a male and a female colleague at NTT. The latter wanted Wessels to join her team as a global account director. Wessels says:

She pushed me to phone the CEO of NTT South Africa and ask him for this job. I was like, I can't be doing that. And she pushed me and she said, right, phone him now and phone me right back. And I did, and I got the job.

During her time in sales management, Wessels volunteered for the most underperforming division that nobody wanted to touch. She notes:

In my mind, that's the best place to go because that's where you can succeed because you can't go down, you can only go up, it's a bit of a no brainer. But everybody knew that this division wasn't great and was failing.

Wessels succeeded in turning that division around, via a combination of new hires and introducing operational rigor. At which point, her original boss at NTT called out of the blue with a great opportunity that required a move to London to set up a global sales team selling cloud.

After chatting it through with her husband and parents, they made the move to London, from where Wessels flew around the world for four years building the company’s cloud sales overlay team.

Wessels spent 18 years at NTT overall, working her way up the ladder with the help of sponsors and volunteering for the difficult jobs nobody else wants.

Interspersed with taking on the unpopular roles and travelling the world, Wessels had two children, who are now 17 and 19. This had a direct impact on the speed of progression of her career. She explains:

A lot of that time, I could have accelerated my career, but I made a conscious decision for eight years to focus on having the children and raising them while keeping my career going. But I certainly could have accelerated my career if I chose to, which I made a conscious decision not to.

After five years in London, another call came out of the blue, this time from open-source startup Elastic. The firm was looking for someone with a systems integrator background rather than from the SaaS or software industry. Wessels took the role, despite the company telling her they were taking a risk on her. She adds:

I've heard that a lot in my career. But I knew it wasn't a risk for them, because I would do whatever it took to be successful. I’d proved myself in all my five other roles leading up to this point.

She turned the organization around, built its Middle East and Africa business, and was there at the right time for its IPO. After two years at another startup, Wessels received another unexpected call, from the COO of Box, which she joined in July 2024 as President of EMEA. She says:

I've gone from inside sales, sales manager, global sales leader, now running Europe and moving countries, while having two kids. And I've always made sure that I've gone where the puck's going. Whether it was the data center, cloud, cybersecurity, and now it's unstructured data and AI, you always want to have one eye on your career. And I've always known where I wanted to be, from the age of 20, where I was going to finish my career.

Over the course of her career, Wessels has learned to take roles where her strengths are valued. When she moved to Elastic, she was interviewing the company as much as the company was interviewing her. She says:

I really didn't want to put myself in a situation where I would feel like the dumbest person in the room, because that wouldn't be good for my own self esteem. So if I was going into a boardroom where they needed deep technical expertise, I would need somebody supporting me in that conversation because I couldn't do that, and they knew that, and they weren't hiring for that. Because there are many, many people that understand the features and functions of your software, but there are not many people that can connect and match the solution with the business pain. And that's where my strength comes in.

The belief you need to be an expert in technology to work in the sector isn’t something Wessels agrees with, especially as that's what puts off a lot of women. She adds:

Everybody thinks you need to be a software engineer and that's just nonsense. That's why, when we have diversity initiatives at Box, it's all about making people comfortable that you don't have to be technical to have a career in tech. I feel quite strongly about that because otherwise, I wouldn't be here.

What’s more important is to have an appreciation for technology and its impact on the world. Wessels notes:

You need to be curious about it. But you don't need to be selling the features and functions of how an LLM is actually built. I don't need to know that. Or how the blockchain's built. There are enough people who know that.

Coming from South Africa, diversity, equity and inclusion is at top of mind all the time for Wessels. She explains:

Because of the country I was raised in, with apartheid and all the terrible challenges that South Africa had to go through, I'm always very, very conscious about making sure that everybody's represented, whether that's religion or race or whatever it may be.

One major change she’s seen 30 years on from the start of her career is that women are a lot stronger in themselves than they used to be. This is especially the case with the younger generation, who ask Wessels for advice on how to negotiate or get a promotion. She says:

They take the careers more seriously, and they are a lot more forthcoming about their ambition, which is wonderful. I'm very conscious about tapping each one of them on the shoulder, understanding their career, what motivates them, where do they see themselves in five years. If they don't have a plan, I want them to build a plan, I want a five-year plan, a 10-year plan.

When Wessels thinks back to particular challenges she’s faced in her career, some relate to self-doubt.

[Women] want to know we're going to be successful. We don't want to put ourselves out there, and I've had that in my career and a lot of self-doubt. My message is, self-doubt is going to pull you back if you don't manage it. You've just got to back yourself.

She  has acted on her own advice at various times during her career. Once was when a promotion she’d been promised had been signed off by the board, but her boss didn't give it to her because growth was 30% instead of 70%. She explains:

I had a major problem with that, where he held a promotion back. I left that company on principle because I can't work for somebody like that.

Another time, Wessels took a role where she knew the shares she was getting weren’t equal to her male counterpart’s, because the company said it was taking a risk on her and she had to prove herself. She adds:

Looking back, I wouldn't have tolerated that. I've learned from both of those. Number one, if you deserve the promotion, go and fight for it and get it, or leave on principle. Secondly, negotiate your salary as if you are the single breadwinner of the family.

She advises asking to see a company’s salary data for the mid-range, below the mid, and the high range of your salary band, and then negotiate. 

If Wessels could share some advice with her younger self, it would be to be more aggressive about her career. She says:

Just because you're a mom, doesn't mean you need to take a backseat. Know where you're going and where you want to be and have that very clear in your mind. Take the opportunities and don't wait for them to come to you, go and ask for them, according to your own timeline and your own goals.

Although she stresses that reaching those goals also requires hard work, being good at your job, playing to your strengths and being passionate about the industry. She notes:

You've got to do more than the basics to reach the top.