Keyhole Software was born from a shared vision—and a strong friendship—between founders Chris DeSalvo and David Pitt. They first met in the 1990s while working at the Kansas City division of CrossLogic Corporation, an application development consulting firm renowned for its technical expertise and high standards.
At CrossLogic, David was a hands-on expert consultant passionate about software craftsmanship, while Chris focused on the business side, building relationships with companies seeking David’s and the team’s specialized skills.
After CrossLogic was acquired—first by Number Six Software and then Advanced Technology Systems Corporation (ATSC)—Chris and David saw firsthand the business models that made IT consultancies successful. In 2008, they used that knowledge to strike out on their own and create Keyhole Software.
In 2008, Chris and David founded Keyhole Software with a clear goal: to build a consultancy centered on top-tier talent, technical excellence, and genuine client partnership—while having fun doing what they love.
Starting from Scratch
Launching Keyhole wasn’t easy. A six-month noncompete agreement meant they couldn’t work with former clients—and just months after founding the company, the global economy collapsed. With no clients and a shrinking market, they relied on personal savings and grit to build software, establish their company infrastructure, and pursue new opportunities.
While early efforts to secure out-of-state work yielded minimal revenue, the team shifted focus to smaller, local businesses and startups—companies that lacked IT departments and needed modern, efficient software solutions to weather the downturn. This pivot turned out to be a defining move, introducing Keyhole to cloud computing, mobile development, and data storage technologies that would soon dominate the tech landscape.
Growth Through Trust and Technical Expertise
By 2009, Keyhole began growing the team. Their work with innovative, early-stage clients helped build a reputation for agility, deep technical knowledge, and practical problem-solving. That reputation began attracting large enterprise clients once again, especially as the tech sector rebounded.
One such client, American Century Investments, partnered with Keyhole on a major 90,000-hour architecture upgrade—thanks in part to a long-standing relationship and the ability of Keyhole’s consultants to seamlessly collaborate, share knowledge, and lead with technical credibility. Training and education sessions became a cornerstone of Keyhole’s value, helping clients stay ahead of tech trends and reinforcing trust in the partnership.
These challenging beginnings gave the Keyhole leadership team valuable experience in adapting and pivoting in response to shifting market demands—whether embracing new technologies or navigating economic crises. In fact, Keyhole approached the COVID-19 pandemic using many of the same strategies that proved successful back in 2008.
The Keyhole Philosophy
From the beginning, Chris and David built Keyhole Software on four core principles:
- Hire only the best software consultants—people who are smart, curious, and passionate about their craft.
- Create a culture of continuous learning and innovation, working across a wide range of technologies.
- Act as true partners to our clients, embedding within teams to drive outcomes and long-term success.
- Have fun doing what we love: building quality software with people we trust and enjoy working with.
What’s in a Name?
Despite common assumptions, the name Keyhole doesn’t refer to a locking mechanism. It was inspired by the Keyhole Route on Long’s Peak, a 14,000-foot mountain climb in Estes Park, Colorado. To our founders and many of our team members who have climbed it, the Keyhole represents pushing beyond “good enough”—a philosophy we bring to every client engagement.
Privately Held. Purposefully Independent.
Keyhole has always been a privately held company with no outside investor funding. This independence allows us to focus entirely on our team, our clients, and doing great work. In fact, our approach to growth was featured by the Kansas City Business Journal for overcoming early obstacles with creativity and tenacity. (PDF)
Today and Beyond
Today, Keyhole Software operates with a growing team across multiple cities, supporting a diverse range of clients across industries. We continue to embrace new technologies, expand our technical capabilities, and recruit top-tier developers who value craftsmanship, collaboration, and continuous improvement.
We’re proud of our journey and excited about what’s next—whether it’s helping a client modernize a legacy system, mentoring the next generation of devs, or hosting one of our beloved Lunch & Learns.
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