Alignment is Critical: What I’ve Learned About Leading a Cross-Border Startup

Leading a cross-border organization has taught me that success depends on understanding and adapting to unique challenges. It means navigating cultural differences and bridging communication gaps. But the challenge is worth it. Talent knows no geographical bounds.

At Scribble Data, we have built a global team across India, the US, and Canada. Our journey has been one of pursuing first-principles thinking, focusing on deep customer value, and having the conviction to be contrarian. We have learned that there is no one-size-fits-all approach. Success requires a willingness to learn, adapt, and continuously build bridges between teams.

In this article, I will share insights from my journey as an entrepreneur who transitioned from academia to building a technology startup that spans multiple countries and cultures. I will explore strategies and mindsets that have been crucial in overcoming obstacles and unlocking the potential of cross-border collaboration.

The Dynamics of Cross-Border Organizations

Running a cross-border organization involves navigating two key dimensions: alignment and operational coordination.?

Alignment refers to the degree to which teams are on the same page conceptually, in terms of goals, interests, and mindset. Operational coordination, on the other hand, encompasses the tools, methods, and processes that enable teams to work together effectively.

In my experience, startups rarely begin with perfect alignment and seamless operational coordination. The path to success involves starting from a point of low alignment and low coordination and gradually improving both aspects over time. For startups, the high level of uncertainty makes it crucial to prioritize alignment before focusing on operational coordination.

In the early years, we made the conscious choice to bootstrap Scribble Data. This allowed us to gain clarity on our product-market fit and value proposition before scaling up. We focused on aligning the team around the central artifact of data and the goal of delivering deep customer value. Only after establishing this foundation did we start building out more sophisticated operational processes.

Investing in alignment from the outset lays the foundation for success. It creates a shared understanding that keeps teams in sync, even when faced with differences in context or experience.

Once alignment is established, operational coordination becomes easier to achieve. With everyone working towards the same objectives and with a common understanding, implementing tools and processes to support collaboration becomes straightforward.

Four Levels of Alignment

Achieving alignment in a cross-border organization requires work at four distinct levels: goal/purpose, culture, process, and tooling. Each level plays a crucial role in ensuring that teams are working in harmony towards a common objective.

Goal/Purpose: The foundation of alignment is a shared understanding of the organization's goals and purpose. Teams need to be clear about what they are working towards and why. When everyone is on the same page about the desired outcomes, it becomes easier to make decisions and prioritize tasks that move the organization in the right direction.

In our case, the overarching goal has been to build AI assistants and agents that transform how work gets done in complex domains like financial services and insurance. By constantly reinforcing this mission, we ensure that teams across geographies are rowing in the same direction.

Culture: Cultural alignment is about creating a shared understanding of how things are done within the organization. This includes aspects like communication styles, reporting structures, transparency, and documentation. When teams have a common cultural framework, it reduces misunderstandings and facilitates smoother collaboration.

At Scribble Data, we have tried to foster a culture of intellectual honesty, first-principles thinking, and respect for the customer. We believe that technology should be an enabler, not an end in itself. By hiring people who resonate with these values, we make it easier to maintain cultural alignment as we scale.

Process: Process alignment involves synchronizing the way work is handed over between teams in different locations. In a cross-border organization, there may be differences in roles and responsibilities, with some teams being closer to the customer and others focusing more on implementation. Aligning processes ensures that everyone understands their part in the workflow and how their work impacts others.

We have invested heavily in building domain expertise within the team. We believe that to deliver real value, it's not enough to have great engineers - you need people who deeply understand the customer's context and can bridge the gap between technology and business outcomes.

Technical: Finally, technical alignment is about ensuring that teams are using compatible technologies and platforms to collaborate effectively. When teams are using different tools, it can lead to communication breakdowns and inefficiencies. Aligning tools does not necessarily mean using the same version of Slack or Teams, but rather ensuring that the tools we are using can integrate seamlessly.

Interestingly, Scribble Data’s approach to tech has been somewhat contrarian. Rather than chasing the latest trends, we've focused on using simple, proven technologies that allow us to optimize for speed, accuracy, and trust. We have found that this "boring" approach actually enables faster innovation in the long run.

Achieving alignment at all four levels is no easy feat, but it is essential for the success of a cross-border organization. In the next section, we will explore some strategies for building alignment and fostering a sense of shared purpose across teams.

Strategies for Achieving Better Alignment

Aligning teams across borders is no easy feat, but I have discovered some strategies that can make a world of difference. These approaches have helped us at Scribble Data build the kind of alignment that drives real results.

Storytelling: Stories have the power to connect people across even the widest of divides. Encourage your team members to open up and share their experiences, triumphs, and challenges. You might be surprised at how quickly those narratives become the glue that holds your organization together.

As a leader, I spend a lot of time sharing stories from our entrepreneurial journey - the failures we've overcome, the insights we've gleaned from customers, and the moments of serendipity that have shaped our path.

Informational Parity: When teams don't have a shared understanding of the market, customers, and problems, it's like trying to solve a jigsaw puzzle with different pictures in everyone’s mind.

We have found that creating opportunities for team members across geographies to interact directly with customers is incredibly powerful. It allows everyone to build empathy and develop a firsthand understanding of the problems we are trying to solve.

Shared experiences: There's nothing quite like breaking bread together to build a sense of connection. I am a big believer in creating shared experiences for teams across borders, whether it's through short-term visits or longer-term assignments. Giving team members the chance to walk in each other's shoes can work wonders for fostering a shared culture.

Shared rewards: When teams feel they are working towards the same goal and their contributions are valued, it creates a powerful sense of unity. Ensure that rewards and recognition are distributed fairly across borders, so everyone feels invested in the organization's success.

We have tried to create a culture where victories are celebrated collectively, regardless of which geography or team they originated from. When an engineer in India solves a tricky technical challenge, it's a win for Scribble Data as a whole.

Bridge builders: Cultural differences can sometimes lead to misunderstandings or communication breakdowns. Seek out individuals with high emotional intelligence who can smooth over rough patches and keep everyone on the same page. Empower these bridge builders to work their magic, and you will be amazed at how quickly teams can find common ground.

As someone who straddles the worlds of technology and business, I have seen how vital these individuals are in a cross-border context.

Conclusion

Here is the key – alignment must come first. Trying to force operational coordination without first building that foundation of shared understanding is like putting the cart before the horse. It might work for a little while, but sooner or later, the lack of organizational unity will catch up with you.

At Scribble Data, we have learned that building deep alignment is a never-ending journey. It requires constant self-reflection, humility, and the courage to question your assumptions. But when you get it right, the results are incredible.

Teams across borders start to operate like a single organism. They anticipate each other's needs, challenge each other to be better, and find creative solutions to even the thorniest problems. The world starts to feel a lot smaller.