As we kick off 2025, we sit down with Gary MacAskill, Managing Partner at OSL, to explore the company’s ongoing growth, celebrate standout achievements, and envision what lies ahead. Gary’s candid insights, infused with humor and hard-earned wisdom, highlight why OSL continues to thrive as a people-first organization.
Reflecting on your journey with OSL, what moment stands out as a defining “this is why we do what we do” experience?
There are countless moments that reinforce our mission, but one always stands out. Early on, when we expanded with our foundational client, Walmart, we were fully immersed—opening hundreds of stores and transforming perceptions. At the time, Walmart wasn’t seen as a destination for wireless sales. Having worked on the carrier side, I knew the industry underestimated their potential.
A pivotal shift happened in Q4 of that first year. Walmart’s market share soared from less than 1% to double digits. That moment sent shockwaves through our carrier partners, who asked, “What just happened?!” It was clear—we were not just selling, we were changing the game. This experience reaffirmed that with the right vision and effort, we could redefine expectations and create something truly special.
Throughout the years, OSL has experienced remarkable growth and transformation. What has been the most rewarding aspect of that journey?
The greatest reward is seeing the impact we create. The mobility industry, though vast, is deeply connected. I’ve had the privilege of working alongside incredible people—many of whom are now influential decision-makers. Witnessing OSL’s evolution and influence over the past decade, with Walmart, our carrier partners, and the industry as a whole, is truly inspiring. We’ve built something extraordinary, and that sense of pride continues to fuel our ambition.
What lessons have shaped your leadership style at OSL?
I believe in one guiding principle: “You can be right, or you can be happy, but you can’t be both.” Success is about collaboration and connection. Even when you have the right answer, bringing people along on the journey is essential—ensuring they feel valued and empowered. It’s not just about issuing directives; it’s about creating an environment where everyone contributes to success.
I’ve repeated this mantra countless times, and it resonates across business, personal life, and client relationships. True leadership is about empowering people, not just achieving results.
2024 was a significant year for OSL. What accomplishments stand out, and how do you plan to build on that momentum in 2025?
One of our proudest achievements is implementing our “One Best Way” program. This framework is revolutionizing how we operate, providing clarity, consistency, and precision in the field. It wasn’t built overnight—it took months of dedication and collaboration. What makes it powerful is its ability to break down silos and align our teams towards a shared vision.
As we move into 2025, One Best Way remains a cornerstone of our operations, evolving to support our teams and drive excellence. It’s more than a process; it’s a mindset that propels us forward.
As OSL embarks on 2025, what foundation are you building upon?
Resilience. Every challenge is an opportunity to grow stronger. I constantly remind our team to rest, reflect, and refuel—especially after our busiest periods like Q4. With over 9,000 people in the field, our success hinges on having the right systems and support in place. In 2025, our focus is on refining what works, embracing innovation, and staying aligned with our core mission.
What message or mindset should every OSL team member embrace in 2025?
I encourage everyone to embody the “Four Rs”: rest, reflect, refuel, and remain resilient. Celebrate achievements, cherish time with loved ones, and return recharged and ready to take on new challenges. Our journey is about progress, not perfection. Success lies in building upon our strengths and remaining committed to continuous improvement.
If you had to choose a single word or phrase to define OSL’s focus for 2025, what would it be?
People, Performance, Precision—these values have been our guiding force for over a decade. They are more than words; they are the foundation of everything we do. When we prioritize our people, performance follows, and precision ensures we deliver exceptional results. These principles drive our decisions and actions every day.
If you could give the entire OSL team a rallying cry for 2025, what would it be?
Our rallying cry is simple but powerful: “Great People Doing Greater Things Every Day.” This embodies who we are and what we strive for—making a meaningful difference for our clients, customers, and communities. The pandemic underscored the vital role we play in keeping people connected, and that purpose continues to inspire us daily.
Conclusion: Gary’s insights highlight that OSL’s strength lies in its people and its unwavering commitment to excellence. Here’s to a resilient, innovative, and purpose-driven 2025!