Samantha Wessels brings nearly 30 years of experience in the tech industry, with a strong focus on sales, go-to-market strategies, and business growth. She has played a pivotal role in scaling businesses from startups to large-scale enterprises. She currently serves as the President of EMEA at Box, the leading Intelligent Content Management platform, where she leads all GTM functions. Previously, as Senior Vice President of International at Snyk, she drove double-digit growth in both EMEA and APJ. Before that, she served as Vice President of EMEA Sales at Elastic, where she built the go-to-market strategy across key European markets. 

With her exceptional experience in enterprise go-to-market, we welcomed Samantha to the Earlybird Catalyst program, where she serves as a world-class sparring partner for our portfolio founders. Recently, we sat down with Samantha to gain her insights on building a successful pan-European sales strategy. Reflecting on her own scaling journey Samantha says, "The accomplishment of building and scaling Elastic was so rewarding. Now I have the knowledge and experience, and I want to give back."

A key lesson from her career is that sales and technical expertise must go hand in hand for a startup to succeed. "Founders with unbelievable technical knowledge need the support of a good CRO, VP Sales, or Go-to-Market executive to make it happen: you can’t have one without the other," she explains. The sales function is often underestimated, but serves to ensure that even the most innovative technology reaches the right customers.

One of the biggest mistakes startups make, she explains, is assuming that European markets can be approached identically. "The first step to tackling GTM in a place like Europe, with such diversity, is acknowledging that each market is different. Startups make the mistake of trying to tackle the German market in the same way they tackled the UK market. They need to be treated differently, and you need to show empathy for your team on the ground," she says. While market strategies need to be tailored to each country, she stresses the importance of running common themes across them to maximize efficiency.

The next step is deciding which markets to focus on and developing a clear understanding of them. According to Samantha, "This requires building a European strategy and a separate strategy for each country." Founders need to first consider their target personas, the total addressable market, regulatory requirements, and competitors. What truly differentiates success from failure in GTM, as Samantha explains, is "understanding the nuances of the culture and the customer. We are starting to revert back to sales as I know it, face-to-face, where relationships are built, and that’s where culture becomes quite important."

Once the markets are chosen, another key challenge is determining where to place talent. Samantha advises, “Ask yourself: Am I going to place them in hubs in those regions? Or should I centralize them? The answers will be highly dependent on the market you are working with. For example, some markets don’t mind buying in English, while others do." She warns that sales can’t be the only consideration: "You are also thinking about customer success, asking yourself where it makes sense to put your customer support and business development teams. It is important to think strategically about each of those decisions with both a short-term and a long-term view."

Your market strategy is deeply intertwined with the sales process aligned to a buying cycle, Samantha emphasizes: "Every well-run organization needs to have a sales process." She describes the beginning phase as prospecting and discovery—listening, asking pointed questions, and identifying pain points. She elaborates, "Then you move into technical validation, where you bring in more technical teams to confirm that your technology addresses your customer’s business pain. Finally, you arrive at the negotiation phase. But to get to that point, you must ensure you've done enough listening, strategizing, planning, and dialogue facilitation to become a strategic coordinator & advisor who drives the deal to closure on your terms and at your price." The role of a sales lead, she says, is akin to that of an orchestrator: "You should be managing stakeholders on all sides, at all times."

She describes sales as "a team sport, where you should avoid shortcuts and assumptions while considering every possible reason why a deal might not go through. It’s an entire ecosystem that needs to fall into place, and it's your job as a founder to appreciate and coordinate that."

Winning the deal isn’t the end of the process. Samantha says, "You need to onboard the customer, bring in your customer success team, and ensure that your customers are getting value to avoid churn down the road." No matter the deal size, she explains, "From 100k to 50 million, the sales process follows the same principles."

Need help tackling the GTM beast? Connect with Samantha on LinkedIn and stay tuned for more high-level perspectives from the Earlybird catalysts.