From bootstrapped to AI exit — Zoomin’s Gal Oron on timing, trust, and getting acquired by a tech giant

The first time Amit Karp learned about Zoomin, it didn’t strike him as the obvious investment choice for Bessemer. The bootstrapped company was growing, but it wasn’t exactly a high-flying startup. The website was poorly designed, the go-to-market strategy wasn’t established, and the leadership team was small—and yet their customers? Fanatical. “Over and over on diligence calls, I heard the same refrain,” shares Amit, “‘They’re not just a vendor, they’re a partner.’”

Gal Oron, CEO and co-founder, along with his co-founders Hannan Saltzman and Joe Gelb, weren’t just building another SaaS company—they were pioneering a new category in knowledge orchestration. “I fell in love with their vision and the team, so I took the leap to be their first investor in 2018,” shares Amit.

Zoomin’s founding story wasn’t the typical tale of two founders launching a startup in a garage. The three co-founders saw a massive unaddressed problem in enterprise product content, so they bootstrapped a business to solve the problem.

Companies were generating huge volumes of documentation, manuals, and knowledge base articles, yet customers struggled to find the right information when they needed it. Product content was fragmented across multiple platforms—SharePoint, Confluence, Google Drive—making self-service frustrating and inefficient. Zoomin was the centralizing solution to turn content into a strategic advantage for enterprises.

“Riding shotgun on this seven-year journey has been a wild ride,” says the Bessemer Partner. “So when Zoomin culminated in a successful acquisition by Salesforce in 2024, I knew Gal was a rare founder who could share the kind of advice you can only get by actually living through it.”

In this conversation, Gal shared what it takes to build a resilient business, the mental frameworks founders need to navigate hard times, plus the story of how a well-timed AI pivot positioned Zoomin for a strategic exit.

Founder lessons from Zoomin’s Gal Oron

1. Bootstrap for discipline, raise venture for horsepower

“In the early days, we deliberately chose to bootstrap instead of raising capital to validate that we were solving a real problem before bringing in investors,” shares Gal. “Too many startups rush to raise money before proving product-market fit. We didn’t want to make that mistake. Instead, we focused on building something customers truly needed and were willing to pay for.”

This approach comes with a cost and can be limiting at times. In the early days, Zoomin wasn’t looking like the hottest startup. But given their goals at the time, it didn’t matter that much to Gal. “We didn’t care about financial KPIs beyond one metric: cash flow. Our goal was simple: build a product, sell it, deliver results,” he says.

Zoomin bootstrapped to 20-30 enterprise customers, including ServiceNow, McAfee, and Dell EMC. “This gave us full control, allowing us to prioritize customer success over investor expectations. But over time, we realized that while bootstrapping gave us discipline, it also limited our ability to scale.”

Gal and the team had strong customer traction, but growth was constrained by lack of resources. “We could only hire as fast as our cash flow allowed,” shared Gal. “To take Zoomin to the next level—hiring top talent, accelerating product development, and expanding our reach—we needed external capital.”

So this scrappy, revenue-driven, and laser-focused team went out to raise those dollars.
“But let’s face it,” Gal remembers. “We weren’t built for fundraising at the time. Our website was terrible, and we had no formal go-to-market strategy. We were built for delivering value.”

“While I had my initial concerns,” Amit admits, “Zoomin proved to be a dark horse ready to create a new category in turning content into a strategic asset.”

“Our first meeting with Amit was a turning point for us,” Gal says. “Bessemer understood our business strength, the deep trust we had built with customers, and the massive opportunity ahead. Turning to Bessemer as our first venture partner was one of the most important milestones in Zoomin’s journey.”

2. Customer fanaticism will drive your growth trajectory

Without a massive marketing budget or a sophisticated go-to-market strategy, the Zoomin team relied on customers to become their biggest advocates.

“Rather than treating them as transactions, we treated our customers as true partners—listening intently, adapting to their needs, and ensuring they weren’t just satisfied but truly successful,” shares Gal.

The customer obsession was the biggest signal to Amit that they were a bet worth taking. Customer-centricity created a powerful dynamic: Zoomin’s customers weren’t just using Zoomin. They were selling it for them.

“Our customers were our greatest salespeople. They spoke about Zoomin at industry conferences, championed our value internally, and drove adoption within their organizations,”says Gal. Some were so invested that they left their jobs to join Zoomin—a testament to Gal’s inspiring vision and the powerful product the team had built.

“This customer-first approach also shaped our product roadmap,” continues Gal. “Many of Zoomin’s most impactful features were driven by real-world pain points, not assumptions. Our goal wasn’t just to sell software—it was to make our customers look like heroes within their companies.”

3. Raising money doesn’t automatically mean you’re ready for hypergrowth

Balancing growth and focus can be one of the toughest challenges for founders. “Bootstrapping teaches discipline—every dollar counts, and you only invest in what truly moves the needle. That mindset kept us lean and customer-obsessed, but once we raised capital, expectations changed,” shares Gal. “Suddenly, it wasn’t just about sustainable growth. It was about scaling fast.”

But for Gal and the team, the hardest part of transitioning from bootstrapped to funded was knowing when to accelerate and when to exercise restraint.

But here’s the lesson most early stage and VC-backed entrepreneurs have to remember: “Raising money doesn’t automatically mean you’re ready for hypergrowth. Scaling requires strong foundations—a predictable sales motion, solid quota attainment, strong unit economics, and a clear focus,” says Gal.

Gal encourages founders to grow at the pace their business is ready for—not the pace the market expects. “When we realized we were moving too fast, we course-corrected quickly—we refocused on efficiency, and ensured every hire, investment, and decision aligned with long-term success,” he says.

4. Be open with your board about your problems

Always wanting to seem perfect in front of your investors can be an entrepreneur’s fatal flaw. Don’t. Bring the board into all your problems. “I was always impressed by Gal’s masterful ability to keep the board engaged and aligned during difficult times — it deepened our trust in his leadership,” shares Amit.

“From the start, I made a point to be completely open—I didn’t try to sell a rosy picture or hide challenges,” says Gal. “Instead, I laid everything on the table: These are the issues we’re facing. Here’s what we know. Here’s what we don’t know.”

“I also involved them in problem-solving, rather than just updating them,” he continues. “When you share your struggles candidly, board members don’t just observe. They become active participants in helping you solve your problems. This created a sense of shared responsibility and deepened trust. There were no surprises, no last-minute crises they weren’t prepared for—just clear, honest conversations about where we stood and what we needed to do.”

“I wanted to make sure everyone was focused and knew the direction we were headed in, so I wasn’t just transparent with my Board, but also the entire company. After every Board meeting, I presented the same updates to the team, ensuring alignment from the boardroom to the front lines. This level of transparency kept everyone motivated, even in tough times. When your investors and employees believe in the mission—even when the road gets bumpy—it makes all the difference.”

5. Be extremely vigilant with partnerships

“Enterprise partnerships can be game-changing—but if not managed properly, they can kill your company,” warns Gal. “From the start, we knew that working with Salesforce had massive potential, but we also understood the risks. Partnerships with large incumbents can be a huge distraction—they consume time, management focus, and resources. That’s why I approached it with extreme discipline.”

Zoomin first made sure there was real customer demand in this early partnership. “Customers were already asking for Zoomin inside Salesforce, which gave us leverage,” says Gal. “Second, we structured our efforts carefully—we didn’t throw the entire company into the partnership. Instead, we built a lean, focused team to work on Salesforce while keeping the rest of the company running as usual. This way, if the partnership failed, it wouldn’t derail our core business.”

Successful technology partnerships require co-development, and that starts with building trust with the people you work with on “the other side” and gaining their buy-in at every stage of the process. “Gal navigated this precarious venture adeptly,” shares Amit. “We both reflected on an important lesson for founders to remember when attempting to vault into a partnership like this one: Big companies don’t do business with companies—they do business with people."

“I made sure we built deep relationships with the right stakeholders, aligning with folks inside Salesforce who were personally invested in our success,” says Gal. “Timing also mattered—when AI took off, Salesforce needed what we had. Because we had already built trust and demonstrated value, we became the obvious strategic fit when they looked to expand their AI capabilities.”

6. Be agile enough to respond swiftly to emerging opportunities

In early 2023, one of Gal’s VPs casually mentioned using ChatGPT for a work task. “‘Let me consult my friend,’” Gal remembers this colleague saying. “That was the first time I really paid attention to the possibilities of LLMs being layered into software.”

Within days, Gal realized that AI wasn’t just another tech trend—it was a fundamental shift that could either render Zoomin obsolete or unlock massive new opportunities. Given that Zoomin’s core business was structuring and delivering enterprise knowledge, it became clear that AI needed high-quality, proprietary data to be truly useful. And Zoomin had the fuel to power AI engines.

“Once we saw the opportunity, we moved fast,” Gal says. “We didn’t spend months debating strategy. We acted. First, we launched a quick AI-powered application, even before we fully understood our long-term AI play. That rapid execution helped us test demand and gain immediate traction. Then, we took a hard look at our positioning—instead of being just an end-to-end knowledge orchestration platform, we leaned into what we did best: ingesting, structuring, and harmonizing unstructured data for AI models like Salesforce’s Einstein.”

This shift wasn’t just about adding AI features—it was about redefining where Zoomin played in the AI ecosystem. “We streamlined our focus, repositioned our messaging, and quickly became the go-to partner for enterprise AI initiatives,” says Gal.

That agility—catching the wave early instead of reactively hopping on the bandwagon—made all the difference in securing Zoomin’s spot as a leader in the AI landscape. And it was this type of strategic pivot that ultimately led to a successful acquisition.

7. Three things Gal ‘wishes he knew’ — Learn to live in uncertainty, lean into your customers, and play the long game

Amit ended his conversation with Gal with our classic, Bessemarian question: What do you wish you knew in the beginning of the journey? His perspective is a comfort and guidance for founders.

Learn to live with the questions

“It’s okay not to have all the answers. As founders, we want to solve every problem immediately, but in this journey, you’re constantly operating with uncertainty. Learn to live with the questions. Instead of rushing to find the perfect answer, focus on staying in the game long enough to recognize the right opportunities when they come.

Lean into your customers during the good times and the bad times

“Tough times aren’t setbacks—they’re opportunities. Every company faces challenges, but the best founders use those moments to make their biggest leaps forward. When things get difficult, don’t retreat—lean into your customers. Every time I wasn’t sure what to do, I went back to them. If they’re seeing value, you’ll survive. If they’re struggling, they’ll show you what needs to change.”

Imagine the future-state of your platform, and build towards that

“Build for scale from day one. Early on, we were so focused on execution that we didn’t think about how our platform would need to scale as we grew. At a certain point, fixing foundational issues becomes almost impossible—so invest in scalable infrastructure early. And finally, never underestimate the power of marketing. In the enterprise world, it’s easy to focus entirely on product and sales, but if you don’t control your narrative, the market defines it for you. Storytelling isn’t just a nice-to-have—it’s critical for building a category, attracting customers, and driving growth.”

As a final note, Gal admits that not knowing everything is intrinsic to the entrepreneurial journey: “If I had known how hard it would be, I might not have started…But sometimes, blind optimism is what gives you the courage to take the leap—and course-correct along the way.”