Kyle Caffrey

Tell us more about your background – how did you get started in the transportation industry?

I entered the transportation industry later than most. After graduating from college I spent my early career teaching social studies and coaching football in Connecticut and South Carolina. I began my transportation career at a Super Regional Carrier during a period of turmoil for the company. That afforded me a great opportunity to have multiple different roles in a very short time.   

What about Pyle made you want to work for this company?

The company’s reputation for a commitment to excellence and customer service. A. Duie Pyle was ascending where my employer at the time was descending. Moreover, Pyle’s family-oriented culture and focus on employee development resonated with me on a personal level. At the time I had a growing young family and a desire to grow personally and professionally.

Describe your role at Pyle.

At Pyle, my role as VP of Sales & Training encompasses overseeing all aspects of the sales development process, from formulating growth strategies to nurturing client relationships and developing training content. I work closely with our portfolio sales teams to ensure we are delivering tailored solutions that solve our customers’ problems and evolving needs, while also aligning with Pyle’s objectives and core values.

Considering the evolving landscape of sales technologies, how do you envision incorporating innovative tools or methodologies to streamline the sales process and stay ahead of the competition?

In today’s fast-paced business environment, leveraging innovative technologies is crucial for staying ahead of the competition. We’re continuously exploring new sales tools and methodologies to enhance the efficiency and effectiveness of our CRM tool and market research practices.

As the VP of Sales, how do you approach developing and maintaining strong partnerships with customers, and what role do you see these relationships playing in the long term success of Pyle?

Developing and maintaining strong partnerships with our customers is at the core of our business philosophy at Pyle. We prioritize building trust, understanding our customers’ unique challenges, and offering solutions that exceed their expectations. We still have our very first customer, a relationship that was established 100 years ago. Where many publicly traded companies play for short-term success, Pyle plays the long game. We work to lay the foundation for long-term partnerships that foster mutual trust and growth. Our goal is to be a trusted advisor to our customers, providing them with innovative solutions that help them succeed in their own businesses.

In your view, what key qualities or strategies do you believe are essential for building and leading high performing sales teams?

When building and leading high-performing sales teams it’s essential to foster a culture of collaboration, empowerment, and continuous learning within the team. Providing ongoing training and development opportunities helps keep our sales professionals motivated and equipped with the skills they need to succeed. Additionally, setting clear goals, providing regular feedback, and recognizing and rewarding top performers are all critical aspects of building a winning sales team.

What achievement are you most proud of during your time with Pyle?

One of the achievements I’m most proud of during my time with Pyle is successfully adapting my skills to align with our organization’s successful expansion into new markets and verticals. By leveraging our significant investments in People, Technology, Facilities, and Equipment we’ve been able to diversify our customer base and drive sustainable growth for the company.

Any closing thoughts?

In closing, I’m incredibly grateful for the opportunities I’ve had at Pyle and feel privileged to be able to work with such a great team of professionals. In my 27 years I have seen tremendous change as the company has grown by over $700 million. However, they key element that makes Pyle a great company remains the same. Excellent family leadership and an unwavering commitment by everyone to fostering and maintaining our Core Values.