Huntress discovered that simply finding threats wasn't enough for its MSP customers, who lacked specialized cybersecurity staff for remediation. The product had to evolve into a fully managed, human-powered service that handled the problem end-to-end, moving from alerts to a 'click a button to fix' solution.
Huntress founder Kyle Hanslovan leveraged his nine years at the NSA creating offensive cyber warfare tools. This 'offense to defense' path gave him a deep, intrinsic understanding of how hackers infiltrate and persist in networks, providing an unfair advantage in creating a product that could effectively hunt them.
Founder Kyle Hanslovan saw the first signs of product-market fit at just $1.5M ARR. It wasn't about revenue scale, but the realization that the core business functions—demand generation, a fast sales cycle, and scalable service delivery—were becoming predictable, repeatable flywheels that could be systematically improved.
Initial go-to-market efforts selling directly to small businesses failed because the buyers weren't technical. After five consecutive calls revealed that SMBs outsource their IT, founder Kyle Hanslovan realized he needed to sell to Managed Service Providers (MSPs) instead of the end-users.
While his vision for serving the SMB market via MSPs was consistently rejected, Kyle Hanslovan eventually won over investors by focusing on hard data. By proving the model with strong KPIs like top-of-funnel conversion, net dollar retention, and cash flow, he made the opportunity undeniable, even to skeptics.
During a 16-week accelerator program, founder Kyle Hanslovan slept in his car to preserve every dollar of the $50,000 investment for the business. This extreme bootstrapping, which included showering at a gym, highlights the intense personal sacrifices founders often make to keep their company alive in the earliest days.
Huntress succeeded with MSPs by framing its security product as a way to protect their margins. Since MSPs charge a flat fee, a security incident meant lost time and negative profit on a client. Huntress helped them avoid financial losses and become heroes to their customers, ensuring deep partnership alignment.
A technically brilliant but risk-averse potential co-founder was hesitant to join Huntress. The turning point wasn't the idea itself, but the external validation that came from securing a $50,000 check from a startup accelerator. This small amount of capital was enough to de-risk the leap and convince him to commit.
While his military service involved higher stakes (life and death), founder Kyle Hanslovan found startup life to be emotionally harder in a different way. The all-consuming nature of building a company forced him to sacrifice his health, friendships, and role as a father—parts of his life he was able to maintain while in the military.
Despite strong early metrics, Huntress was rejected by over 60 VCs for its Series A. The primary objections were its SMB focus, its Maryland headquarters (outside Silicon Valley), and its fully remote model in 2018. This demonstrates how VC pattern-matching can cause them to miss high-growth opportunities.