Ajoy Mallik on Cracking the US Market for Startup Success

In this episode, I’m here with Ajoy Mallik, a seasoned business developer based in the United States. We recently connected with Ajoy when he started collaborating with TokePortal.com’s development partner, Dolphio Technologies, an ICT service provider. Ajoy has taken on several of their projects, specifically focused on enhancing Dolphio’s business development initiatives in the US. Now, as many of our listeners know, entering the US market is a major milestone and often one of the most important goals for startups in Central Eastern and Southern Europe. It’s an ambitious and challenging step—one that brings not only new opportunities but also many hurdles that can be tough to overcome without a local partner. The US market entry process is complex due to vast differences in business culture, the regulatory environment, and consumer expectations. Additionally, for European startups, hiring experienced US-based developers or sales professionals is often prohibitively expensive and challenging to coordinate from abroad. But Ajoy’s expertise and hands-on experience really bridge this gap and bring valuable insights into overcoming these obstacles. He’s here to tell us that achieving a successful US entry is possible. So, I invited him today to introduce himself in more detail. You can also find him on our mentor platform, where he’s available for guidance and advice.

I asked Ajoy to share his journey, including how he started his career during the rise of the internet and what insights he’s gained that can help startups enter the US market effectively.

Ajoy Mallik:

So, a bit about myself: I came to the US from India when I was seventeen. My father was a diplomat, so we were a diplomatic family, which meant I had the privilege of growing up with exposure to many different cultures. I first landed in Washington, D.C., where I completed my undergraduate studies in physics at the University of Maryland. After that, I moved to Miami to pursue my PhD. However, as I started on my dissertation, I realized I had a stronger inclination toward business than academia. So, I took the GMAT, got an 80% scholarship, and completed my MBA at the University of Miami.

After finishing my MBA, I set my sights on Silicon Valley, moving there in the early 2000s. This was when the internet was just beginning to gain mainstream traction, and the Valley was buzzing with excitement and innovation. I joined a venture firm called Skyblaze Ventures, which was heavily focused on internet-based technology investments. My role combined responsibilities in business development and operations, so I was deeply involved in helping portfolio companies with everything from sales and marketing to go-to-market strategies. We worked with startups that were essentially laying the groundwork to bring new ideas and products to the market. It was an exhilarating time, but it also came with challenges as we navigated the dot-com bubble and its subsequent burst.

I was very intentional about moving to Silicon Valley. At the time, I knew that Florida wasn’t a tech hub, while Silicon Valley was the epicenter of technology and venture capital. I remember thinking that it was a lot like New York, but instead of capital markets, it was all about tech. People were always making deals, and the atmosphere was electric. You could walk into a cafe, and there would be people pitching ideas for investment or negotiating tech sales. It was an environment that fostered constant networking, collaboration, and innovation. And I quickly realized that to truly succeed there, I needed to build a robust network across various functions—not just in venture capital, but in tech, finance, and operations as well. That was a bit challenging for me, as I was relatively shy at the time. But I recognized the importance of pushing myself to connect with others and become part of the ecosystem. Looking back, it was an incredibly formative period for me, especially with the internet boom and the dot-com bust happening almost simultaneously. There was this sense of intense excitement mixed with uncertainty, which taught me a lot about resilience and adaptability.

There were definitely a few defining moments, but one that really stands out was with a portfolio company called 123SignUp. When I first started working with them, it looked like we might have to write off our investment. They had just recapitalized and were struggling with sales and operations, facing issues left and right. However, I saw potential in their product and customer base. I spent almost a year with them, effectively becoming their interim head of sales and business development. During that time, we restructured their business model, revamped their pricing strategies, and rebuilt the sales pipeline from the ground up. Eventually, we managed to turn things around, and the company was acquired by Jonas Software. That sale brought in a return of eight and a half times our initial investment. It was a significant achievement not only for the company but for me personally. One particularly pivotal moment was when I recommended to my senior partners that the CEO needed to be replaced. At the time, I was young, and the CEO was more than double my age. It was a nerve-wracking decision, but after the leadership change, the company’s fortunes began to shift, and we saw improvement within just a few months. That experience was both challenging and validating.

We completely restructured the business model from a flat fee to a tiered pricing system with Bronze, Gold, and Platinum packages, each offering distinct features. This change allowed us to cater to different customer segments with specific needs. We also shifted the marketing approach. Rather than a “look at what we can do” stance, we made the pitch more about addressing the customer’s challenges directly. We tailored the message to say, “We understand your business is facing difficulties, and here’s how we can help.” This more empathetic approach resonated with our target market, and it showed them we were genuinely invested in their success. Another key factor was talent. We recruited salespeople purely on commission, offering them a high 50% rate, which was attractive to motivated individuals during an economic downturn. This combination of a new pricing model, a more relatable marketing strategy, and skilled sales talent created the foundation for the company’s revival.

After this role, you joined the founding team at Odesk, which is now Upwork and has become one of the largest platforms for remote work. How did that experience unfold?

Odesk, which, as you mentioned, eventually became Upwork, was actually founded in my living room. The initial concept was a tool to monitor developers’ productivity with a lightweight client installed on their devices. However, early on, we encountered significant resistance. People saw it as intrusive or as “spying software,” and that perception was difficult to shake, even though we had features allowing users to turn off monitoring. It became clear that we needed a pivot, so we reframed it as a project management tool specifically for remote work. Instead of just monitoring productivity, it became essential for managing projects across distributed teams. That shift was critical, especially as the 2007 financial crisis hit, and companies started seeking cost-effective remote work solutions. This new positioning allowed us to grow rapidly, eventually leading to a merger with Elance to become Upwork.

At Tata, I was brought on to establish a venture capital and innovation unit. My role involved finding and implementing tech solutions for some of Tata’s major clients, including Fortune 100 companies like Bank of America. The idea was to go beyond traditional IT services and deliver more integrated technology solutions. For example, we partnered with startups working on server virtualization, which was an emerging solution at the time. By combining their technology with our service expertise, we could offer comprehensive solutions to clients. It was a complex role, requiring me to coordinate across venture capital firms, portfolio companies, and clients. This position broadened my perspective and gave me a deep understanding of how large corporations approach tech innovation on a global scale.

In your experience, what are some of the common mistakes European companies make when entering the US market?

One of the biggest mistakes I see is companies expanding too quickly without a solid pipeline. Some founders come to the US with their families, ready to set up shop, but they lack the customer base needed to sustain operations. I always advise building a sales funnel first, with a minimum of ten active prospects for every two deals they hope to close. This gives them a better foundation before making such a big move. Another key point I emphasize is the importance of having US-based investors. Even if they’re not the primary investors, their presence adds credibility and makes it easier to gain traction. Without this local backing, it can be challenging to break into the market.

Lastly, I’d love to hear your thoughts on how Silicon Valley and venture capital might evolve, especially with AI’s rapid growth.

AI is transforming the industry in profound ways. Salaries in AI are astronomical, which is driving up the cost of living in Silicon Valley. Many professionals are being priced out and are relocating to more affordable states. Remote work is helping to some extent, but with big tech companies enforcing return-to-office policies, this dynamic is shifting. Silicon Valley will remain central to tech innovation, but the landscape will continue evolving, especially as AI grows and reshapes demand.

Thank you, Ajoy. This conversation has been insightful, and I’m sure our listeners gained valuable knowledge. I hope our ecosystem will have the opportunity to work with you and benefit from your experience.

Thank you, Nora. It’s been my pleasure, and I look forward to supporting more companies on their journey to the US market.