Men in Tech: Greg Stafford’s Journey 

In this latest installment of our Men in Tech series, we celebrate Greg Stafford, whose dynamic career trajectory in the tech industry showcases not only his sales acumen but also his ability to lead and inspire growth. Greg’s journey from an eager beginner to the Director of Sales at Klik is a narrative of resilience, strategic foresight, and unwavering commitment to excellence.

A Fortuitous Start in Tech

Greg’s foray into the tech world began shortly after graduating from Towson University. He seized an opportunity to work with a tech reseller founded by Arthur Olshansky. Reflecting on those early days, Greg says, “Arthur gave me my first opportunity in the industry, setting the stage for what would become a deeply rewarding career path.” 

This pivotal moment led him to various roles across the tech landscape, including a significant stint at Tricerat, where he evolved from account management to Director of Sales over 12 years.

The choice between a career in technology and other paths was straightforward for Greg. He humorously notes, “It was either computers or work for a beer distributor, and I think I picked the correct path.” 

His career is punctuated with milestones that highlight his knack for growth and leadership. At Tricerat, he transformed the sales department and scaled the company’s revenue significantly, establishing himself as a leader who not only meets but exceeds expectations.

Overcoming Challenges with Adaptability and Focus

Greg’s journey wasn’t without its challenges. Balancing the dual roles of coaching a team and managing accounts required a mastery of time management and clear communication.

 “One of the biggest challenges I’ve faced is balancing coaching responsibilities with active account management,” Greg explains. He tackled these challenges by focusing on efficient practices and fostering a culture of open communication and continuous learning.

Current Role and Responsibilities

Greg joined Klik as a member of Arthur Olshansky’s team in 2024.  As the Director of Sales at Klik, Greg’s role is multifaceted. He is deeply involved in setting strategic goals for the sales team, driving revenue, and ensuring the alignment of sales strategies with overall business objectives. “I embrace a player-coach role, which means I am hands-on with our accounts while also steering our sales team towards our collective goals,” says Greg. 

His responsibilities extend beyond sales; he is instrumental in recruiting and training top talent, aligning with marketing strategies, and ensuring customer satisfaction through seamless service delivery.

Arthur Olshansky, owner and CEO of Klik Solutions, notes, “Greg has worked really hard to implement and improve our sales management processes. This also includes improved alignment between pre-and post-sales initiatives within our company.” These efforts highlight his strategic input in enhancing operational efficiency and fostering integration across different phases of the sales process.

Exciting Initiatives and Future Outlook

Currently, Greg is excited about initiatives that enhance Klik’s market position and foster innovative solutions. “Building high-performing teams and developing go-to-market strategies that resonate with our core audience are what excite me the most,” he shares. His focus is on leveraging his deep understanding of the market to drive innovation and growth.

Skills for Success and Tools of the Trade

For success in sales, especially at the executive level, Greg highlights the importance of empathy, active listening, and strong relational skills. These skills are crucial in understanding customer needs and building long-term relationships, a hallmark of the Klik approach. “To excel as a Director of Sales, you need to genuinely connect with both customers and your team,” he asserts.

In terms of tools, Greg relies on technologies like AI to enhance his work. “I use chat GPT every day and believe AI will be dominant in the near future,” he mentions, pointing to the indispensable role of advanced tools in modern sales strategies.

Advice to Aspiring Tech Professionals

Greg advises newcomers to the tech field to choose their company wisely. “Find a great company with a great product and great people. You spend half of your life at work, so you need to enjoy the people you work with,” he suggests. This reflects his belief in the importance of a supportive and enriching work environment.

A Legacy of Impact and Mentorship

Greg’s significant impact on Tricerat, where he increased annual sales revenue dramatically, is a testament to his strategic vision and execution prowess. Applying these skills at Klik, Greg has continued to advance the company’s sales strategies and performance, reflecting the same dedication and strategic insight that fueled his success at Tricerat. 

Greg notes that Arthur Olshansky has been a guiding force in his career, teaching him the value of perseverance and strategic thinking. Arthur’s mentorship has not only shaped Greg’s professional approach but has also imbued him with a robust philosophy centered around driving results through tenacity and smart planning, principles that Greg now applies to lead Klik’s sales team to new heights.

Looking back, Greg would advise his younger self to “Enjoy the ride! It’s a lot of hard work. Trust the process and keep grinding because, in the end, it will pay off.”

Greg Stafford’s career illustrates a unique blend of leadership and hands-on execution that has significantly shaped the companies he has worked with. More than just advancing his own goals, Greg has consistently applied his skills to foster growth and innovation, proving that thoughtful and engaged leadership can create lasting impacts in the tech industry.