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Bob appears in the Top 100 

Innovators & Entrepreneurs Magazine

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Bob Rock

Bob Rock, the visionary at the helm of Square & Compass Software, isn't just a CEO and founder; he's a technological trailblazer. With an unwavering commitment to dismantling industry barriers, he has redefined the very essence of business success in the realm of software.


Bob's journey is nothing short of remarkable. Coming from a childhood marked by economic instability, he proudly served in the U.S. Army before venturing into the world of technology. With a relentless passion for innovation and a deep understanding of the industry's nuances, he embarked on a mission to bridge the gap between software developers and the customers who use their products. He realized that in the world of technology, faces, passions, and minds often remain hidden behind lines of code.


Square & Compass Software LLC, founded in 2020, was Bob's brainchild—a company dedicated to helping small businesses, startups, and small to mid-size companies thrive through tailored software solutions. Unlike typical consultants, Bob and his team treat their clients like family, listening closely to their needs and expectations.


The company's growth has been nothing short of astounding, with revenue more than tripling in its first two years. Bob's approach is clear: provide affordable, quality technology to small businesses without compromising their vision, product, or security. Small business owners, busy running their enterprises, often lack the time or expertise to navigate the complex world of technology. One of Bob's key missions is to ensure that businesses don't fall into the trap of producing products that fail to meet their customers' needs. He emphasizes the importance of understanding the customer's perspective, rather than relying solely on assumptions or investor feedback. For Bob, being a technological artisan and a compassionate human being go hand in hand. He believes in caring deeply about the customer, their needs, and their desires.


In an industry where the relationship between engineers and end-users is often distant, Bob is changing the narrative. He passionately respects technology and the artistry behind it, considering software development a form of craftsmanship. He aims to reverse the stories of startups and small businesses, turning their potential horror stories into resounding success tales. He advocates for a fundamental shift—listening to the very people who use the technology and delivering precisely what they want. In his eyes, this is how the industry should operate, and it's what Square & Compass Software is all about.


In this engaging Q&A, we delve into Bob’s inspiring journey and his rise from a humble background to a prominent technical artisan.


What was the inspiration behind your decision to establish a company dedicated to assisting small businesses?


My inspiration came from a simple but poignant moment in my life. My mom was changing the TV channel with the plastic end of a paintbrush by sliding it through the slit where the actual buttons used to be and pressing the button on the circuit board. I reached a simple conclusion:  If it was too expensive to buy new technology, I would build it myself. At that moment, I knew I wanted to be an instrument of change and make an impact on my community and the lives of others. Days before my 18th birthday, I joined the Army. I was set to deploy when I was medically discharged after being diagnosed with Type-1 diabetes via an autoimmune disease. I switched gears and began courses in computer engineering and science at the University of Delaware, where I became deeply passionate about technology, both its science and artistry—specifically, the disconnect between those who created and those who consumed the product, in my case, software.


What sets Square & Compass apart from other companies in your field?


Square & Compass Software is unique in its unwavering commitment to people, both within our company and our clients' teams. Our extensive experience allows us to create efficient processes for product development and engineering, while making a positive impact. We don't consider ourselves mere developers, designers, or engineers; we are “Software Artisans.” Our work is not just what we do; it’s who we are, it’s what drives us, and a discipline we're dedicated to advancing.


What motivated you to establish your nonprofit, Future Software Artisans, Inc.?


My motivation for starting Future Software Artisans, Inc., stems from my desire to share the knowledge and experiences I've gained with others, particularly those who may not have had the same opportunities I did. As a former soldier, it's essential to me to provide people in my community with the resources and knowledge they need to excel in their careers, companies, and communities. It's incredibly rewarding to witness the impact on individuals, teams, and careers through the letters and messages I receive from apprentices. Changing the trajectory and future of families, helping them escape poverty, and igniting passion in their work is truly fulfilling.


As you lead both a thriving company and a nonprofit, what continues to drive you?


When I reflect on what drives me, it's a deep and almost instinctual motivation that's been with me from a young age. I want to provide my future children with opportunities and a life I didn't have. I aspire to spoil my mom and prove wrong those who doubted my capabilities. It's about embracing challenges and having the "Pshh" attitude that fuels me. I’ve had this innate drive since I was a kid, to make a meaningful impact, and I’ve been on this path ever since.


On 9/11, I watched the towers fall on TV and saw smoke fill the New York sky from my window. Shortly after, my dad and I were watching the first deployments of soldiers on the news. I said, “That would be a cool job,” because I felt compelled to contribute in the same way. My dad said, “You couldn’t do that.” I did, though. And those towers are memorialized on my arm in ink.



Bob Rock
CEO and Founder
Square & Compass Software


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