Diamond McKenna is the CEO of Diamond Assets, a leading technology sustainability company focused on helping organizations maximize the value of their Apple devices. A mom to three children, two dogs, and a wife to a pretty amazing man, Diamond leads with authenticity and relies on her gut to drive decisions. Passionate about ensuring schools and businesses receive meaningful returns on their tech investments, she has cultivated a culture of innovation and impact, empowering institutions to be part of the sustainability journey the world is on.
Recently, in an exclusive interview with Digital First Magazine, Diamond shared the inspiration behind establishing Diamond Assets, insights on the most significant opportunities and challenges faced by women in leadership positions today, significant career milestones, future plans, words of wisdom, and much more. The following excerpts are taken from the interview.
What inspired you to start Diamond Assets, and what drives your passion for sustainable technology solutions?
The inspiration behind Diamond Assets came from a deep frustration with seeing school districts not receiving the value they deserved for their Apple devices. Too often, they were taken advantage of, missing out on opportunities to maximize their technology investments. I wanted to change that narrative. My passion lies in creating sustainable technology solutions that not only help schools recover a meaningful return on their initial investments but also allow them to reinvest those funds directly into new technology for their staff and students. Our goal has always been to make this process seamless, hands-off, and hassle-free, so educators can focus on what truly matters—empowering the next generation.
What role do you think education and government institutions play in promoting sustainable technology solutions, and how can they work together to drive change?
I believe education and government institutions have a significant role to play in driving sustainable technology solutions, but there’s still a lot of room for growth in this area. Right now, the process of trading in devices is often treated as an afterthought—a secondary step that only happens when new technology is purchased. To create truly sustainable technology environments, this mindset needs to shift. Device lifecycle management should be at the forefront, fully integrated into the broader technology strategy. By prioritizing sustainability from the start, these institutions can maximize their resources, reduce waste, and create lasting value for their communities.
How do you stay up-to-date with the latest developments and trends in the tech industry, and what resources do you recommend for others?
Staying ahead in the tech industry is all about collaboration, partnerships, and having a great team. At Diamond Assets, we’ve built a diverse team where everyone brings their unique passions and perspectives to the table. This diversity fuels innovation because passion drives people to stay curious, informed, and forward-thinking. Beyond that, engaging with industry leaders, attending conferences, and fostering strong partnerships help us stay connected to emerging trends. For others, I’d recommend surrounding yourself with diverse voices, staying open to new ideas, and never underestimating the power of a passionate, knowledgeable team.
Can you describe your approach to leadership and management, and what qualities do you think are essential for effective leadership?
My approach to leadership is simple: people first, always. I believe in providing clear direction while empowering my team to take ownership of their work. Leadership isn’t about having all the answers—it’s about fostering curiosity instead of just asking questions. I create space for thoughtful reflection, embracing quiet moments and leaning into discomfort because that’s often where the most meaningful ideas, perspectives, and concerns surface. I also believe that a healthy level of conflict is essential; when approached constructively, it challenges us, sparks innovation, and pushes us beyond the status quo. Effective leadership is about trust, curiosity, and creating an environment where every voice matters.
What do you think are the most significant opportunities and challenges facing women in technology and leadership positions today?
Honestly, this question itself highlights the challenge. When I enter a room with the intention of assessing who’s there, I notice that I’m often one of the few women. But when I show up simply as my authentic self, I feel that I belong—I’m welcomed, respected, and valued for what I bring to the table. The truth is, women before me have already shattered the ceiling in ITAD, and I’m fortunate to walk through the doors they’ve opened. Now, it’s about keeping those doors wide open for more women to step into leadership roles in tech. The real shift happens when we stop creating ceilings altogether and focus on building environments where everyone, regardless of gender, can thrive.
Who has been a significant influence or mentor in your career, and how have they helped shape your professional journey?
I’ve been fortunate to have a few professional relationships that have grown into deep, lasting friendships. These individuals have become my first call when I need advice or a fresh perspective. They challenge me in the best ways—calling me out when I’m wrong, pushing me to see things from different angles, and encouraging me to think beyond my comfort zone. What makes their influence so powerful is that they show up for me not just when things are going great, but also during the tough times. Their honesty, support, and unwavering belief in me have been instrumental in shaping both my career and who I am as a leader.
What has been your most career-defining moment that you are proud of?
The most career-defining moment for me isn’t tied to a single event—it’s the environment we’ve built at Diamond Assets. We’ve created a space where people can truly thrive by being their authentic selves. I’ve had the privilege of watching team members grow both personally and professionally—finding their purpose, changing career paths, and discovering passions they didn’t know they had. I’ve seen people share life’s biggest moments here, from engagements and marriages to the birth of their children. In a world that often focuses on the wrong things for the wrong reasons, we’ve fostered a culture where the right things happen naturally. That’s what I’m most proud of.
How do you prioritize your well-being and self-care amidst a demanding career?
Honestly, it’s something I’m still working on. Prioritizing self-care requires intention, and sometimes it takes a wake-up call to realize when I’ve let it slip. What I’ve come to understand is that my family and my business both need the healthiest version of me. That perspective helps me reframe self-care—not as a luxury, but as an investment in my ability to show up fully for the people and responsibilities that matter most. It’s a continuous process, but I’ve learned that time spent on myself isn’t just for me; it benefits everyone around me.
What are your long-term career aspirations, and how do you see yourself evolving as a leader over the next five years?
I think it would be exciting to write a book someday—once I figure out exactly what story I want to tell. As for my professional journey, when the next chapter begins, I want to take everything I’ve learned from my roles at Diamond Assets and use those experiences to help other businesses solve problems, overcome challenges, and achieve their goals. I see myself evolving as a leader by continuing to grow, staying curious, and finding new ways to make an impact beyond my current role. It’s all about applying the lessons I’ve learned to create meaningful change, wherever that may be.
What advice would you give to entrepreneurs just starting their journey?
Entrepreneurship isn’t for everyone—it comes with risks, the fear of the unknown, and growing pressure as your business expands and you become responsible for a team. It’s not just about escaping a 9-to-5 or not wanting to work for someone else. It’s about passion, resilience, heartbreak, all-nighters, second chances, and even third tries. It requires both humility and confidence—sometimes even faking it until you make it. But here’s the thing: if you’re on the right path, you’ll feel it deep down. The challenges won’t disappear, but the journey will be worth every twist and turn because it’s yours. Trust that feeling, and keep going.