The Good-Guy Hackers: Inside Sprocket Security's Rise at StartingBlock Madison

Some companies build a better mousetrap. Sprocket Security built a better hacker.

Since joining StartingBlock Madison in 2023, Sprocket Security has grown from an eight-person team gearing up for a Series A round into a 50-employee company recognized by Gartner, GigaOm, and a growing list of industry awards. We sat down with founder Casey Cammilleri and co-founder Gaurav Kulkarni (GK) to talk about what Sprocket does, how the company has grown alongside StartingBlock, and what advice they'd give to founders just getting started.

The Good-Guy Hackers

Ask Casey what Sprocket Security does, and he'll give you the plain-English version first: "We're the good guy hackers. We break into companies, and then we tell them how to fix it, before bad guys take advantage of it." The technical term for that work is continuous penetration testing, and it sits at the center of Sprocket's mission: to help as many businesses as possible secure their infrastructure and applications.

Penetration testing itself means mimicking the cybersecurity adversary attempting to break into a system, doing it in a structured way, and reporting every vulnerability discovered so it can be fixed before someone with worse intentions finds it first. Traditionally, that work has been done by a single human tester, working one organization at a time, for a tightly bounded window of a week or two.

Casey started Sprocket in 2018 because he was tired of exactly that model. "I wanted to open that up and just do it continuously, all year long, without constraints on time or targets," he explained. Making that possible meant building real technology, not just hiring more testers. Sprocket had to engineer a platform that could scale the judgment and creativity of a skilled human tester into something continuous and always-on. That technology backbone is what differentiates Sprocket from traditional, point-in-time security assessments, and it's the foundation the company has kept building on ever since.

Growing Up at StartingBlock

Sprocket joined StartingBlock in 2023, right as the company was approaching its Series A and starting to hit real traction in the market. GK recalls the appeal clearly: "StartingBlock was a great location for us to start collaboration. It gave us a lot of flexibility in terms of office space, and it put us near like-minded entrepreneurs who were trying to do the same thing."

That flexibility turned out to matter more than either founder expected. Sprocket started on the second floor in a cube built for six people. As the company grew, it expanded into larger office space within the building, tracking almost exactly with its business milestones. "I think when we hit our Series A, we realized we didn't have to go anywhere," Casey said. "StartingBlock had resources and space for us at that next stage." Today, with 50 employees, Sprocket is still there.

Gaurav Kulkarni and Casey Cammilleri, Sprocket Security

For GK, the value went beyond square footage. Joining StartingBlock as an eight-person team without a clear picture of what the next year would hold, the ability to flex space, power, data center infrastructure, and even dedicated ISP phone lines up or down as needed removed a whole category of operational risk. "It gave us the reason we've stayed with StartingBlock so long: continued flexibility. As we grow, we have options to expand into other suites right here."

The two also pointed to specific programs that shaped their early months as members, including the Lunch with the Founder series and monthly member lunches, which gave them direct access to other founders working through similar problems. As Sprocket prepared to fundraise, StartingBlock's pitch workshops and dry-run sessions helped them sharpen their story before it mattered most.

Milestones Worth Marking

Every growing company collects a few moments that stick. For Casey, it's landing a client whose name everyone recognizes. "When you secure clients that everyone knows, everyone uses, and you're responsible for testing their cybersecurity, that's an honor. Definitely a milestone."

GK points to a different kind of number: 100 customers. "During our journey at StartingBlock, we hit our first 100 logos, and that was a big milestone. Crossing that first digit, we actually had to stop and look at ourselves and go, that's a big deal." Since then, Sprocket has kept expanding that customer base, much of it made up of household names GK can't always name on the record, but recognizes every time he shops, eats, or uses a product from one of them.

Casey adds a milestone that's less about the market and more about the people inside the company. Reaching 50 employees means, in his words, helping "50 different people build their lives, both professionally and personally," and watching the team succeed and grow has become its own kind of reward.

On the industry recognition side, the list has gotten long enough that Sprocket keeps it posted at the bottom of its website. Highlights include

SOC 2 Type II certification, CREST certification (an industry validation reserved for top firms in the field), recognition from Gartner and GigaOm, a Global InfoSec Award, a SourceForge Top Performer distinction, and a Fortune Cybersecurity Award, among others. Hitting the Series A milestone itself, GK says, was validation of something more fundamental: "We have product-market fit. We're doing something other companies aren't doing, and that growth and interest in Sprocket is there."

What's Next: AI-Driven Security at Scale

Asked where Sprocket will be in five years, Casey's answer, only half in jest, is "hopefully still at StartingBlock, because I don't have to worry about who's cleaning the office." Beyond that, he sees Sprocket leading the way in automation and scalable penetration testing. The company recently launched AI agents that take on work previously done entirely by human testers, though Casey is quick to note humans remain very much part of the process. "We're building the next wave. We've always been innovating in this space."

Advice for Founders

Casey's advice for founders early in their journey goes back to Sprocket's earliest days: "It's easy to get distracted about things that are actually not important, which tool you use, which vendor to pick. It's more important that you have the discipline to do the thing you know you should be doing to grow the business now." He's watched other early founders fall into the trap of over-engineering decisions meant to "set them up for success," when in reality, as he puts it, "I guarantee you will not be using that same tool, that same vendor, or that same process in 12 months. Don't over-index on the things that aren't important."

GK's advice runs in a similar vein, distilled into a phrase he repeats often: "Just work on the next hard problem." Don't try to solve everything at once, he says. And when in doubt about where to focus, follow the revenue. "Revenue solves a lot of those problems. It can help you zone in on where to put your time and energy."

A Physical Space That Attracts Talent

One theme that came up repeatedly wasn't about product or funding at all, it was about people. GK noted that as Sprocket has grown, its team, largely hybrid and based in and around Madison, has increasingly taken advantage of StartingBlock's community programming and events, sometimes even more than the founders themselves do. That turns out to be a real advantage for recruiting. "From a talent perspective, the location and the activities happening at StartingBlock have been great, because our people enjoy being in the physical space, and they enjoy the community around it too. It's actually a benefit for us when it comes to acquisition. People see it and think, "this is cool, we're right here."

Casey traced that appeal back to the very beginning, when he and GK were choosing where to set up shop. "There's a lot of office space out there, but you have to ask yourself: which office space do I actually want to go to every day? What do employees want to walk into every day?" StartingBlock, with its modern facilities and amenities, answered that question clearly, whether the team numbered one person or fifty. "Just having a place you want to go to is huge."

For Sprocket Security, that combination of flexible space, a founder community, and room to grow without distraction has freed the team to focus on what actually matters: building the next generation of automated, AI-powered penetration testing, one hard problem at a time.