In Conversation: Rachel Weston Rowell on Scaling Startups, Regulation, and Building Global Teams

Scaling a tech business across borders is more than just duplicating your HQ playbook—it’s about local nuance, strategic clarity, and internal alignment. In this in-depth conversation, we spoke with Rachel Weston Rowell, a product and technology leader whose path into software has been anything but conventional.

Senior Vice President at Insight Partners, Rachel brings a multidisciplinary lens to one of the most critical challenges facing tech leaders today: how to grow globally without losing focus locally.

With experience ranging from business publishing to special education to fast-scaling software companies, Rachel draws on a rare blend of technical depth and human insight. Her work centers on helping C-suite leaders navigate high-growth environments, align product and engineering strategy, and lead through cycles of rapid change.

Rachel shares her firsthand insights on global expansion, compliance, hiring strategy, and the hard-earned lessons that come from moving fast without enough clarity. Her advice is grounded, specific, and full of practical takeaways for leaders navigating international growth.

Welcome, Rachel—and thank you so much for making time for this conversation. I’ve been following your work. You’ve had a non-traditional journey into tech—from publishing to startups—and I have to say, it’s fascinating. How has that experience shaped your approach to scaling businesses globally?

Rachel: Oh, interesting question—yeah, I do have a pretty varied background. Honestly, the way I ended up in the world of software was sort of by accident. But as soon as I started working in a software company, I felt like, “Oh, I finally found a place where I really can thrive.” I really loved the work. 

Having worked in a lot of different types of companies and with a variety of people outside of software helped me gain a broader perspective. It helped me understand how different industries function and how people’s needs can vary so much. There’s just so much variety outside of the typical world of dev tools or standard tech that many in software are familiar with. 

When I think about expansion, that definitely affects my view. It’s about recognizing that things are not always as homogeneous or static as we think. There’s a lot of local information you can miss if you only view things from a 50,000-foot level. 

That’s a powerful perspective. Let’s talk about resource allocation. How do you approach trade-offs when considering a shift in engineering focus for a new market?

Rachel: I think it’s important to be really, really clear about the trade-offs we’d be making if we shift engineering capacity to new work. What would we be leaving behind? 

It may still be the right business decision—maybe the opportunity in the new market is so incredible that we should do it. That’s totally fine. But we have to make sure we’re having that conversation. We shouldn’t just start swinging wildly in one direction or another without clearly understanding what we’re doing and why. 

With international expansion, compliance becomes tricky, especially with data centers and regulations. How should CTOs and tech leaders consider data privacy and local compliance when scaling into new regions?

Rachel: Oh, that’s a good question. One that probably has a more in-depth answer than I can give you in the next two minutes, so I’d be happy to follow up with some notes. But broadly speaking, I think partnerships and external resources are key. 

CTOs can’t do this alone. They need to feel confident they’re working in accordance with local regulations, and there’s no universal answer. Every geography has its own rules, so understanding those is essential. 

This is where partnerships can go a long way. Working with someone who already understands the market helps you take quick steps up the ladder you’re going to have to climb. That doesn’t remove your own responsibility—you still need strong collaboration with your legal team, and your legal team must understand the regulations of the new market. 

You’ll also want to develop relationships with local regulators. But again, finding people who already know the terrain will give you a huge head start.

That’s great insight. Moving to team culture and management—how should companies approach hiring when expanding internationally? What strategies ensure teams are aligned with product and market goals?

Rachel: Most of the time, when I see companies expanding internationally—outside their home geography—the first hires are on the go-to-market side. I don’t often see companies starting with product and engineering hires in new regions. 

Now, of course, there are cases where regulations or technical needs mean you have to hire engineers locally. But generally speaking, sales, marketing, and customer success roles come first. 

From there, it’s critical to have someone in the region who can manage those folks, and who understands what the working situation will look like—whether remote or in-office. You also need some sort of HR presence because you’re entering a region where your company might not yet have all the personnel or legal infrastructure in place. 

Think taxes, employment law—there’s a lot to handle. So, while your first hires might not be product and engineering, your operational and HR setup needs to be ready to support anyone you do bring on. 

You mentioned regulation and data centers in a prior discussion. Data privacy and compliance are major topics right now. How can companies ensure compliance when entering international markets?

Rachel: Great question. It’s a big topic and probably one I could write a whole paper on. But at a high level, partnerships are incredibly helpful. There’s no universal answer—every geography has its own laws and standards. 

CTOs and tech leaders need to build confidence that they’re aligned with local regulations. And the best way to do that is by leveraging people who already know the landscape. That could mean working with local legal experts, compliance specialists, or third-party advisors. 

That doesn’t absolve you of responsibility, of course. You still need a strong internal legal team that understands the regulatory framework of the new market. Ideally, they should build relationships with local regulators too. I think it’s smart to take a balanced approach here—don’t overcomplicate, but don’t assume. 

When companies are scaling globally, they should get a baseline understanding of what data privacy frameworks apply to their business model and then bring in local expertise where things are unclear. 

A few things that can work well: 

Start with a lightweight compliance checklist by region—even something simple like: Do we store/process user data here? Are there consent requirements? Who needs to be informed? For high-risk markets or where there’s a lot of customer scrutiny (e.g., EU with GDPR, certain U.S. states), local counsel or Employers of Records (EORs) can help navigate. 

Think about how their product team builds—privacy expectations are increasingly becoming product requirements, so it’s easier if compliance is embedded in the dev process versus handled as a last-minute legal review. If the company is early in its expansion and running lean, a contractor or privacy-focused legal advisor can be a good bridge. 

That’s really helpful. Let’s switch gears to hiring strategy. When companies scale globally, how should they approach building international teams—especially product and engineering? What strategies do you recommend?

Rachel: When I see companies expanding internationally, most of the early hires are go-to-market roles—sales, marketing, customer success—not engineering or product. 

You might eventually hire engineers in a specific market, especially if there’s a regulatory or technical requirement for local presence, but that’s usually not where companies start. 

One of the most important considerations is management. You need someone in the region who can effectively manage those new hires. And you need to have clarity around your working model—will it be remote, hybrid, or in-office? 

There are also important compliance and HR questions: How will you handle local taxes? What employment laws apply? Do you have the right infrastructure to onboard and support people in that market? 

That’s why it’s critical to have some kind of HR presence or partner that understands the local landscape. Hiring internationally is not just about getting talent—it’s about building a support system that ensures those hires can thrive and stay aligned with your company’s culture and goals. 

Have you come across a technical challenge during global expansion that surprised you—something that wasn’t obvious until it happened?

Rachel: Expansion can surface technical issues that might have gone unaddressed in the core market. Entering a new region can reveal infrastructure limitations that weren’t visible before—things like latency or inconsistent integration performance due to local network constraints. 

In a case like this, a team could treat the symptom as a one-off or workaround. But a more strategic response would be to step back and use the learning to reassess foundational infrastructure choices. 

It’s work that might not have been prioritized otherwise, but global expansion can increase visibility. And when handled well, the result is often a better experience for all customers—not just those in the new market. 

Have you ever experienced a failure during global scaling that later turned out to be a blessing in disguise?

Rachel: I worked with a company expanding from the EU into the U.S. They hired a local sales team and started running at the market quickly. A year later, they weren’t seeing results—deals weren’t closing, and the team was spinning. 

When they took a step back to understand why, it became clear they hadn’t validated product-market fit for the U.S. market. But just as importantly, there wasn’t executive alignment around what success in the U.S. was supposed to look like—which created confusion for the GTM team and often led to people working at cross-purposes. 

The key takeaway: speed without clarity can create drag. Expansion works best when PMF, GTM, and leadership alignment move together. Even that doesn’t guarantee success in a new market, but it gives teams a far better shot at identifying the real blockers—and solving the right problems first. 

This has been incredibly insightful, Rachel. Thank you again for being so open and thoughtful throughout. Before we wrap up, here is just one last question to close on a high note. Could you share an example of a company that scaled exceptionally well on the global stage? Maybe one you admire or have worked with—and what you think made their growth work so well?

Rachel: A good example here is Templafy. They’re an AI-powered document generation platform that started in Copenhagen and have done a nice job scaling into the U.S. market. 

One of the big unlocks for them was realizing that their European brand didn’t quite land with U.S. enterprise buyers. Rather than push ahead with a “global is good enough” mindset, they partnered with Insight’s Onsite team to rework their positioning. That included workshops to dig into buyer expectations and ultimately refine how they talked about the value of their product. 

The rebrand focused on innovation and revenue impact, a framing that made sense in the U.S. context. It drove better engagement and visibility and opened up new opportunities for growth. It’s a good reminder that even if the core product doesn’t change, how you show up in a new market often needs to.