Celebrating 30 years of Insight Partners: A conversation with Peter Sobiloff

As Insight Partners celebrates its 30th anniversary, we’re launching a blog series that spotlights key milestones and the people who have shaped the firm into a leading global software investor. From first deals and IPOs to pivotal market moments, this series will reflect on the experiences that have defined Insight’s journey.

To kick off the series, we sat down with Managing Director Peter Sobiloff. Sobiloff has been with Insight since its early days and has played a central role in the firm’s growth and evolution. His career spans several decades, multiple market cycles, and countless lessons. We couldn’t think of anyone better to help us launch this retrospective.

Q: Peter, you’ve been at Insight for nearly three decades. How did you first get into venture investing?

Before joining Insight, I was an operator. I started my career in tech sales in 1978 — back when computers occupied floors in office buildings and I wasn’t technically versed. But I was good at selling, and I rose through the ranks: sales manager, VP of Sales, Executive VP of Worldwide Operations, President, and CEO. One of those companies, DataLogix, was a turnaround where I created a partnership with Oracle. DataLogix went public and was ultimately sold to Oracle later on.

That partnership taught me how to navigate high-stakes environments, deal with ambiguity, and manage complex cross-functional teams — all things that later translated well to venture investing. During that period, I got introduced to Insight through Jeff Horing. That’s how it started.

Q: What do you remember about your early days at Insight?

It was very different than the environments I’d come from. I went from running global operations at public companies, with assistants, travel teams, and resources, to showing up on my first day at Insight and sitting on the floor because no one had opened the office yet. I was used to a big-company structure, and Insight at that point was a handful of people, a couple of desks, and a big vision. But that rawness was part of what made it exciting. 

It was clear Jeff had big ambitions, and there was a real opportunity to do something different. I had worked as an operator with several venture capital firms, but this lens felt very different. I knew how to build and scale companies, and that turned out to be exactly what we needed.

Q: Tell us about Think Systems, your first deal with Insight.

That was a wild one. The founder was brilliant at product but had never scaled a company. Jeff brought me in to help build the business. I had a previous relationship with the folks at i2, and five months later, we sold it to i2 Technologies for $150 million of public stock.

That success helped shape Insight’s operator-led model and proved that my go-to-market background brought something different to the table. Jeff was ahead of his time in that regard, as most firms weren’t hiring former operators as Managing Directors. It wasn’t just a win for me but also for Insight, as it was a defining moment that validated our early thesis on backing strong products with hands-on operational support.

Q: What made Insight different then, and what still makes it different now?

It’s always been about the will to win. That hasn’t changed. We were scrappy back then. Jeff did the Think Systems deal out of the back of a beat-up car. But even now, after all the success, it’s still about working hard, staying focused, and doing what it takes to help companies win. That mentality, plus our focus on software and tools like Insight Onsite and our sourcing team, sets us apart. We’ve scaled, but we haven’t lost the grit. That combination of scale and intensity is rare.

Q: You’ve lived through several major market cycles — 2000, 2008, and post-COVID. What lessons have stuck with you?

The fundamentals never change. No matter how hot the market is, it always comes back to building real, profitable, growing businesses. In downturns, you may need to cut fast and deep. Small cuts don’t always work. You can preserve optionality by acting early. I’ve seen the same pattern repeat itself over and over, and I try to help founders navigate those cycles with discipline. Also, it’s often critical to resist the delusion that “this time is different.” Every cycle has its own flavor, but the outcome is usually the same if you’re not grounded in fundamentals.

Q: Has the nature of company-building changed since you first started?

Absolutely. Back in the day, you sold perpetual software licenses and hustled to close big deals by quarter-end. Now, it’s all about SaaS, recurring revenue, and metrics like net and gross retention and CAC. The analytics are better, but the core is largely the same: Create a product that delivers real value to their customers and build around that.

What’s changed is the speed and ease with which companies can scale. Cloud infrastructure, global remote talent, proven go-to-market playbooks, and AI have lowered the barriers to growth. But despite that, discipline and focus still matter just as much, if not more.

One thing I always emphasized was helping customers succeed in a way that got them promoted — because if you do that, they’ll become your biggest advocates. You can market those wins. It’s part storytelling, part psychology. You need to think like a buyer, understand how people make decisions, and design your sales process accordingly. The best companies get that: They deliver value and make their customers look good doing it.

Q: What’s one deal that stands out to you as especially meaningful?

Medidata. We were up against another firm that was a bigger name at the time and promised all these connections. We lost the initial bid, but we maintained the relationship; Hilary Gosher and I continued to work with the founders. When that other firm tried to re-cut the deal, the founders turned to us instead. After getting the other firm’s blessing, we invested at a $30M valuation, and the company went public and ultimately sold for $6B in cash. That’s one I’ll never forget. What made it even more memorable was how we built trust with the team over time, showing up, doing the work, and never wavering. We earned that deal the old-fashioned way.

Q: What advice would you give to someone just entering the investing world?

Work really, really hard. Every detail matters. One objection from a potential decision maker can change the course of your life, so be prepared, execute flawlessly, and don’t get distracted. Focus on creating value and making customers happy. That’s how you win. And don’t get caught up in the noise, just stay focused on what moves the needle. It’s easy to be busy; it’s harder to be effective.

Q: After all this time, does investing still excite you?

Absolutely. The winning never gets old. The best part of this job is helping founders and teams succeed — being part of that — that’s the fun of it. I don’t take a day of it for granted. There’s nothing quite like seeing someone buy their first house, send their kids to college, or create generational wealth because of the work we’ve done together. That impact keeps me going.

Q: Looking back on your career, is there anything you would have done differently?

Not much. I’ve taken a lot of risks, some that made sense on paper, and others that didn’t. But those risks shaped my path. If anything, I’d remind myself to trust my instincts more and to act faster when I knew something, or someone, wasn’t right. I’ve sometimes stayed too long trying to make a situation work when the writing was already on the wall. But overall, I’ve been incredibly fortunate. I’ve had a front-row seat to building great companies and a great firm. I wouldn’t trade that for anything.

*Note: Insight has invested in Think Systems and Medidata.