“What’s the first step a B2B SaaS company should take when expanding into overseas markets?”

“I’d like to hear the experiences and insights of those doing business in a global environment.”

We’ve invited Daiani Macedo, a global serial entrepreneur who can provide clear answers to questions like these.

CEO Macedo, who has built tech startups that make complex technologies accessible to everyone, shares the formula for success she has personally validated while running a tech-based startup in a global environment. She emphasizes that in the AI era, trust between people is more important than anything else, even in B2B business.

From advice born of the experience that “if you try to sell to everyone, you’ll end up selling to no one,” to the importance of building a self-directed culture based on trust in team members—discover the insights of CEO Macedo, who has achieved two exits in the span of five years.

🪄 We create services that anyone can use easily.

Q. Hello, Ms. Daiani Macedo. Could you please briefly introduce yourself?

As a co-founder and Product Lead at Raia, I’m responsible for product development and establishing the product roadmap. Currently, I’m focused on developing the core features of our AI agent platform and formulating our go-to-market strategy. I’m also working to find the right positioning that reflects market demand in order to achieve product-market fit (PMF). I also work closely with our early customers to gather feedback on the product and make improvements based on their input.

Daiani Macedo, CEO and serial entrepreneur

Q. I understand that you’ve started several companies before Raia. I’m curious about the experiences you gained in your previous career and how those experiences led to the creation of Raia.

We create services that make complex technologies accessible to everyone.

I co-founded two B2B SaaS startups and saw them through to their exits.

My first startup was a company called HTBASE. We provided a solution called Juke that enabled enterprises to centrally manage diverse cloud environments. Founded in 2013, it was acquired by Juniper Networks in 2018. My second startup was a company called Shipa, which developed a solution to assist with app deployment management. Founded in 2020, it was acquired by Mirantis in 2023.

What both companies had in common was that they simplified complex technologies so that anyone could use them to solve their customers’ problems. Through this experience, I realized just how important it is to help even non-experts easily access the latest technologies.

In a way, you could say we’re doing the same thing at Raia. Our goal is to turn AI agents into intuitive and practical business tools. We’re building services that allow teams without deep AI expertise to leverage AI in their businesses.

🧭 The most important things are PMF and a great team.

Q. You have founded HTBASE, Shipa, and Raia—all of which are businesses targeting the global market rather than operating solely within a specific country. What are some key considerations for B2B SaaS companies preparing for global expansion?

If you haven't found your PMF, nothing else matters.

One common mistake companies make when expanding globally is doing so before they’ve fully established product-market fit in their domestic market. When starting a business, finding product-market fit is the most important thing. If you don’t find PMF, nothing else matters. Always conduct user interviews before building a product. Don’t assume you already know your customers’ problems.

Another common mistake is applying the same messaging, positioning, and sales strategies that worked domestically to other markets. When entering overseas markets, you must treat them as entirely different markets and start from scratch to find product-market fit.

Q. You’ve gone through several startups and exits. I’m curious how the insights you gained from your previous ventures have informed your next business. In particular, are there any lessons you’ve learned that you’re determined to apply again?

Build a "One-Team" that can rapidly iterate through improvement cycles.

First, fail fast. Build an MVP, gather feedback, and repeat this process quickly. If you spend months creating a perfect product only to realize later that it’s not what the market actually wants, the loss would be significant. It’s important to pivot quickly when necessary.

The second step is building a great team. Find people you enjoy working with. Create an environment where team members can focus on what they love doing. And it’s important to foster a win-win culture where everyone succeeds when the company succeeds. I believe a strong team isn’t one filled with many talented individuals, but one where everyone is moving toward a single goal.

Q. I was struck by your comment that a team working toward a single goal is a strong team. The Raia team, which runs a global business on a small scale, seems to be exactly that kind of small but strong team. I’m curious to know what efforts you’ve made to build such a team.

We’ve created an environment where every team member can work independently, based on trust.

First of all, keeping the team small is intentional. A small team allows us to move quickly. We eliminate unnecessary meetings and give team members full autonomy so they can take the initiative in their work.

We also maintain a culture that allows employees to work according to their own schedules across different time zones. We focus not on how many hours are worked, but on the results achieved.

To sum it up, I’d say it’s about fostering a self-directed culture where team members trust one another.

Raia: Running a global business with small teams based on trust

🎯 You need to clearly define your target audience and really think about what they want.

Q. On the flip side, have there been any lessons where you thought, “I’ll never do this again”?

If you try to sell to everyone, you won’t be able to sell to anyone.

First, you shouldn’t try to do everything yourself. This seems to be a common mistake when starting a business. It’s important to set clear priorities. Focus on tasks that can make a big impact, and don’t hesitate to eliminate the minor, trivial tasks.

Second, we shouldn’t try to sell our service to everyone. In the early days, we tried to create a product that would satisfy everyone, for fear of missing out on opportunities. This made both development and marketing strategies more complicated and drove up costs. In the end, we ended up with a product that couldn’t satisfy anyone.

Q. When someone with an entrepreneurial mindset, like you, looks at a sales and marketing organization, what is the most important perspective to consider?

We need to understand who our customers are and what motivates them.

From the perspective of sales or marketing teams, metrics like the number of leads or ad impressions tend to take priority. While these metrics are important, if we focus solely on them, we risk losing sight of the core customer problems we need to solve.

What really matters is understanding who our customers are, what they want, what they fear, and what motivates them. To do that, we can’t just stop at analyzing personas; we need to approach our customers with curiosity and actively listen to what they have to say.

When doing B2B business, it’s easy to think of clients solely in terms of company names and job titles, making it easy to forget that there are real people behind them. However, recognizing that the person on the other end is an individual is essential for building a stronger, more trusting relationship. It is this kind of trust that leads to business success.

🤖 How to Build AI Services That Drive Revenue

Q. We’re seeing a lot of AI-driven businesses emerge these days. As someone who has been conceptualizing and implementing AI-based services, I’d like to hear about any clear-cut insights you’ve gained—such as “This definitely worked well” or “This approach didn’t work in the real market.”

AI alone isn't convincing anymore.

The most important thing is to create user-friendly products. While this applies to other fields as well, AI technology in particular is still relatively unfamiliar to the general public and lacks accessibility. It’s important to make it accessible to everyone, even those who aren’t experts.

Another key factor is clear positioning. There are simply too many AI-powered services on the market. AI alone is no longer enough to convince people. What people want isn’t flashy technology—it’s practical tools that solve their problems.

Q. For B2B SaaS products that prioritize technology, “reliability” and “sustainability” often pose challenges for companies. What strategies proved effective in persuading customers who could serve as early references and in building trust?

Let’s identify the small group of customers who truly need our product and create compelling success stories.

I believe trust is key in B2B. In the early stages, trust is built through reviews from other customers.

You need to start by clearly defining your Ideal Customer Profile (ICP). While many companies could be our customers, who are the ones who need our product enough to tolerate the limited features of the MVP and the bugs that are bound to arise in the early stages?

Even if you offer the product for free, start by securing 3 to 5 partners. After all, revenue isn’t the initial goal. Gathering feedback from our ICP, rapidly iterating through improvement cycles, and creating solid success stories are far more important than revenue.

👭 Even in the age of AI, what matters most is people and relationships.

Q. What is the issue you’ve been most focused on lately?

Thanks to advances in AI technology, the time it takes to develop products is rapidly decreasing. Not to mention marketing content. While this is welcome news from a business perspective, the sheer volume of services and advertising messages seems to be causing significant fatigue among consumers. I believe it’s particularly important in marketing, sales, and customer communication to build trust with customers by maintaining our service’s unique identity. I’m currently exploring how we can wisely leverage AI and automation while preserving this human touch.

Q. Finally, what message do you plan to convey at this year’s B2B Roadmap 2025?

B2B is ultimately a business that connects people.

The point is that behind every business decision there is a real person with desires, fears, ambitions, and anxieties. To succeed in B2B, you need to focus not on the company, but on the real people behind it. After all, every business decision is made by the people behind the company name.

I believe Korean companies already possess the necessary technological capabilities. However, technology alone is not enough. What’s needed is a people-centric approach, an understanding of customers’ needs and pain points, and the ability to build trust. It’s important to remember that B2B is, at its core, a business that connects people.

I’ll share more details at the B2B Roadmap 2025 Conference. See you in Seoul this May!

Want to hear more insights and firsthand stories fromDaiani Macedo, the global serial entrepreneur?

B2B ROADMAP 2025 ConferenceMeet B2B industry leaders at the B2B ROADMAP 2025 Conference.
Don’t miss this opportunity to expand and connect your business—from practical strategies to networking!

Interview with Serial Entrepreneur Daiani Macedo: How a Global Serial Entrepreneur Builds a Successful B2B SaaS Company