Samantha Wessels is SVP and President of Box EMEA where she leads business growth in the region.
Box is a leader in Intelligent Content Management, helping organisations worldwide simplify how they work through its secure AI-powered content platform. With over 20 years of technology experience, Samantha has held leadership roles at high-performing SaaS companies and large-scale systems integrators. Prior to Box, she was SVP of International at Snyk and drove double-digit growth in both EMEA and APJ. Before that, she served as VP of EMEA Sales at Elastic, where she established a successful go-to-market motion across key European markets. Samantha also held leadership roles at NTT, including SVP Global Cloud Sales and SVP for Group Sales Operations and Enablement. She is passionate about bringing more women into tech sales and is an advisor to EarlyBird, a venture capital investor offering Europe’s tech innovators financial resources, strategic support, and access to a vast international network.
How did you land your current role? Was it planned?
You don’t decide to become a leader – it’s a long work in progress. My role as President of Box EMEA is the result of years of growth, learning and taking on challenges that stretched me. I started in sales and progressively moved up to leadership positions within the tech sector. My time at Elastic where I lead EMEA Sales in a company deeply focused on AI, and later at cybersecurity innovator Snyk gave me the experience needed to lead a region at scale.
Both roles sharpened my understanding of high-growth environments and prepared me for what we’re building at Box. At Box we empower organisations to securely manage and extract valuable insights from their business critical content, and transform their enterprise workflows with AI.
To become a leader, it’s crucial to never shy away from difficult paths. I’ve embraced situations that appear challenging as opportunities to learn and to stand out. Taking the path that pushes you out of your comfort zone forces growth, and therefore helps you elevate your career.
What does an average work day look like for you?
What I love most about my job is the variety it brings. In previous sales roles, my focus was more contained to that function. As President of Box EMEA, my day-day spans multiple teams – from sales and customer success, to marketing, consulting, operations, HR and legal. That cross-functional collaboration brings real breadth and energy to what I do, and keeps every day dynamic.
Right now a significant part of my daily focus is supporting how our teams help our customers become AI-first organisations. We’re working with European businesses across sectors including Life Sciences, Financial Services, Legal, Media & Entertainment and more to leverage Box’s secure AI-powered content platform to achieve real business outcomes. Our State of AI in the Enterprise report shows that 60% of companies anticipate achieving AI transformation within two years. Helping customers identify and act on those AI opportunities with Box to stay competitive is one of the most exciting parts of my job.
Are there any specific skills or traits that you notice companies look for when you’re searching for roles in your field?
The short answer is it’s always changing. The most important trait I’ve seen both in hiring and career growth is initiative, grit and adaptability. Skillsets evolve fast, especially in tech, and those who thrive are the ones who stay curious, keep learning and don’t assume yesterday’s toolkit will solve tomorrow’s problems.
Right now, AI literacy is critical. That doesn’t mean everyone needs to be a data scientist, but we all need to understand how AI is changing the way we work and how it can make us more effective. Put simply, if you’re not willing to learn AI, someone else will be – and they’ll get the job.
Have you found the tech sector supportive in helping you learn and develop in your professional life?
I’ve found the tech sector to be an exciting space, full of opportunity for those who are curious and willing to learn. It rewards a growth mindset. The pace is fast, but that’s part of what makes it so energising.
Mentorship and sponsorship have been key to my development. Some of my biggest champions have been male senior leaders. The industry is actively encouraging more women into senior solutions leadership roles, and I’ve felt that support from male peers.
That said, this definitely isn’t an easy industry. It’s competitive by nature, and the pressure to succeed is real. Building resilience and backing yourself is absolutely necessary to thrive in this sector.
Have you ever faced insecurities and anxieties during your career, and how did you overcome them?
I think most people suffer from a bit of impostor syndrome at some point. I certainly have. Impostor syndrome isn’t something you fully overcome; it’s about learning to manage it and preventing it from holding you back. There are moments where you simply have to back yourself and “fake it until you make it,” stepping into situations with confidence, even when it feels uncomfortable.
I’ve found that having supportive people who remind you of your strengths is crucial. Making the effort to stay knowledgeable and informed builds confidence and silences inner doubts. Once you truly understand your strengths and leverage them, it becomes easier to push anxieties aside and keep moving forward.
What are you most excited about in your career ahead?
I joined Box at a pivotal moment – we’re helping our customers become AI-first companies. 70% of business leaders we surveyed in our State of AI report believe AI will reshape their industry within five years. Plus it’s clear that this shift won’t just boost productivity – it will redefine how entire industry sectors operate.
The real excitement for my career ahead lies in how we help customers navigate that business transformation. Many organisations are closing the AI skills gap by upskilling their teams, and we’re working with them to ensure they’re choosing the right tools, workflows, models and prompt strategies to unlock real value.
At Box we’re focused on how to embed AI as a strategic asset (not just a tool) to drive smarter decision-making and accelerate innovation across industries. That’s what energises me. It’s an opportunity to not just keep up with change, but to shape it.
Did you (or do you) have a role model in tech or business in general?
I wouldn’t say I’ve had a single role model. I tend to draw inspiration from different people, depending on the context. You learn different traits and ways of thinking from different people. Each leader brings their own strengths, and there’s always something to take away if you’re paying attention.
Right now, I’m inspired by leaders driving large-scale digital and AI transformations. I admire their ability to lead with vision, adapt quickly and bring people with them in the face of constant change.
As you’ve said, AI is reshaping how we work. Which AI innovations are the ones to watch in your opinion?
AI agents are the real game-changer and they’re already joining the workforce at speed. From simple task automation to fully autonomous processes, they’re transforming how businesses operate, innovate and scale. Our State of AI report shows right now, 87% of organisations are using AI agents in some form.
The biggest opportunities for agents are in areas where demand has always existed, but cost or complexity made execution impractical. Think lawyers swamped with unread contracts, engineers buried in backlogs of non-core dev work and marketers itching to scale campaigns but lacking time or budget. AI agents reduce the cost of doing this work dramatically, which means it finally gets done – and because these tasks are all part of wider workflows, they of course still benefit from human oversight.
The bottom line is if there’s a task that’s valuable but rarely done, there’s probably an AI agent ready to take it on. This is happening in every vertical, and the window to lead, not lag, is right now.
Entering the world of work can be daunting. Do you have any words of advice for anyone feeling overwhelmed?
Back yourself and believe in what you’re capable of achieving. I try to focus on the positives and not stay hooked on the negatives, but aim to see the opportunities in everything. You won’t get far if you let the first hurdle stop you, so change how you think about the problem. Growth rarely happens without discomfort. The moments that feel tough are usually the ones that stretch you most. Focus on learning and progress, not perfection.
It’s also important to know what good looks like in your role, ie: how you’re being measured, and what success means in your team or organisation. Ask for quarterly feedback – don’t wait for someone else to start that conversation. Take the initiative and own that dialogue. Clarity builds confidence.
At Box we run a placement student year where several university students join between their studies to gain their first real-world business experience. They all start out nervous, which is completely natural, but finish the year with a huge boost in confidence and a strong new set of skills. It’s a fantastic initiative and I’m proud of the culture of trust and support we’ve built at Box that helps make those students successful.
What advice would you give other women wanting to reach their career goals in technology?
Technology is a sector for everyone, regardless of gender. It is important that young women know they belong in this space just as much as anyone else.
We need more women in tech and sales. These remain very male-dominated fields at the moment, and they stand to benefit hugely from diverse perspectives and voices.
If you have the skills and the drive, don’t let doubt or bias hold you back. Let your talent speak for itself – a good leader will recognise it and the right environment will help you to thrive.
One piece of practical advice: study AI. Read about it, experiment with it, and look for ways to apply it in your work. It’s already reshaping our industry, and understanding how to use it will set you apart. More broadly, find ways of differentiating yourself – whether it’s through expertise, creativity or the way you communicate your ideas.
