Editors’ Note

Joshua Richards serves as Chief Executive Officer of Boundless Learning. He brings with him more than two decades of industry experience, including a history of impressive leadership roles in the technology and education solutions space. In his prior role as Chief Product and Technology Officer for Boundless Learning, Richards brought new products and services to life while also enhancing the technology capabilities that support employees, learners, and academic partners. He helped lead the transition of Boundless Learning to a standalone company, including the creation and optimization of the global organization and infrastructure to support stability and growth. Previously, at global education company Pearson, he held multiple technology and business leadership roles that drove continued digital transformation in education. Richards holds a bachelor’s degree from Penn State University.

Company Brief

A pioneer in edtech for more than 30 years, Boundless Learning (boundlesslearning.com) is leading the way in designing personalized, workforce-aligned experiences. Its global portfolio serves approximately 17,000 learners in more than 150 countries. Composed of online learning solutions experts working across three continents, Boundless Learning has launched more than 450 online programs that boost access and create economic mobility around the world. Boundless Learning leverages its data-driven insights and workforce trends to build programs that align with industry demands. From upskilling to professional development, the company’s innovative solutions help enable universities and other learning institutions to reach new audiences through high-quality online learning experiences.

Will you discuss your career journey?

Technology has been the constant thread throughout my career – both in how I have shaped it and how it has shaped my leadership approach. My journey began in high school in the ’90s, when technology was only starting to make its way into the classroom. I was fortunate to attend a school that had secured funding from industry leaders like Kodak, Microsoft, and Apple. This wasn’t just about putting computers in front of students – it was about equipping us with the tools needed to understand and apply technology in real-world scenarios. In addition, as we learned, we were then leveraged to educate and empower teachers to use new solutions in the classroom to enhance the traditional learning experience. This approach took a bottom-up methodology to technology adoption, which I would later see mirrored in enterprise-level digital transformations.

When I started college, I initially pursued a marketing degree at the University of Central Florida. Two and a half years in, I recognized that I was ready to take a risk and follow my passion for technology. That realization led me to a role as a support analyst at Penguin Books, based in New York, which was then part of Pearson. Even in that early role, I focused on providing meaningful and personal interactions, ultimately improving how technology moved the business forward. My work started to gain visibility, and I soon transitioned into the heart of the company’s textbook and digital learning operations. That move began my 23-year journey leading large-scale technology implementations and business transformations.

Will you highlight your progression at Pearson and the pivot to Boundless Learning?

Within a year of joining Pearson Education, I moved into a senior role and started to grow in my career. I established strong relationships across the business, particularly with leaders driving the modernization of textbook development and product creation. From there, I moved around various business and technology teams, taking on exciting roles that helped establish multiple global platforms and led Pearson through many aspects of its digital transformation. This trajectory led me to Pearson Online Learning Services, the predecessor to Boundless Learning, where I worked with amazing colleagues to implement a new Salesforce infrastructure that would become the foundation of a business in need of change. It wasn’t just the platform that made the difference. It was the alignment of technology strategy with broader business objectives to create a better experience for employees and learners, while also generating positive ROI for the organization and success for our partners. At that point, technology wasn’t seen as being auxiliary for the business – it was a critical driver of our future. I joined the executive leadership team in an expanded role, providing me an opportunity to oversee technology, product, and business operations, ensuring that all our initiatives in these spaces directly supported business efficiency and growth.

You recently assumed the role of Chief Executive Officer of Boundless Learning. How did your time as Chief Product and Technology Officer prepare you for this new role?

When Pearson Online Learning Services was acquired by a private equity firm and transitioned out as a stand-alone organization, Boundless Learning, I stepped into the role of Chief Product and Technology Officer. This experience taught me so much in a short amount of time. We not only needed to rebuild ourselves as a new company, but we also needed all the technology to stand on our own. The organization also underwent massive changes that had a real impact on all aspects of our company. Every leader on the team had to work through rebuilding trust in the organization, while also focusing on achieving our aggressive business goals. Through all that, one thing became increasingly clear – if we want to win, we need to innovate and rely on the technology we invested so much in.

Technology would have to go even further and become a strategic enabler of growth and differentiation. In addition, the learner experience we provided through our products and services became a key focus area that we rallied around and brought connectivity to the organization. Getting to the next level required intense collaboration across the business to reimagine processes and strategically use the right tools at the right time in areas like marketing, recruitment, student retention and learning design. We also started to concentrate on growing the company and thinking about how we utilize the products and services that had been built to start promoting our competitive advantage.

At that point, the opportunity to become CEO of Boundless Learning presented itself and all those recent and past experiences came together simultaneously, allowing me to step up to take the lead, bringing my unique energy to the table to create urgency and excitement in the business. I have the privilege of working with a motivated executive team and resilient group of employees dedicated to keeping technology and learner experience at the core of how we innovate, providing personalized experience for our learners, creating value for our partners, and expanding our market reach.

How do you define Boundless Learning’s mission and purpose?

Boundless Learning has always been about creating opportunity – both for our academic partners and for learners. That mission hasn’t changed, but how we execute it continues to evolve. At our core, we’re in the business of enabling universities and other learning institutions to reach new audiences through high-quality online learning experiences. It’s not just about offering online programs, but it’s also about redefining how students engage with education. Personalization, data-driven insights, and seamless digital experiences are key to making that happen. A great example of this evolution is our partnership with Sassoon Academy. This collaboration extends learning into nontraditional spaces – bringing a hands-on discipline like hairdressing into an online format through technology-driven solutions. It’s a prime example of how we’re expanding the definition of education, focusing on equity and ease of access for all types of learners, creating new revenue opportunities for brands, and delivering innovative learning models.

Our success is tied to the success of our partners. Whether their goals are financial growth, brand expansion, or increasing student enrollment, our role is to provide the technology, insights, and strategy that help them achieve those objectives. That’s the future of education – meeting learners where they are and providing institutions with tools to grow in a digital-first world.

Where do you see the greatest opportunities for growth for Boundless Learning?

Online education has evolved beyond traditional program constructs. It’s about career mobility, understanding that learning doesn’t end at a point in time, and expanding access to knowledge in ways we hadn’t previously imagined. One of the biggest growth opportunities we see is aligning our technology and learner-centric products and services to higher education, corporate clients, and associations in alignment with their growth and monetization goals. We’ve proven we can do something different by helping a globally recognized brand like Sassoon translate its in-person training into an online offering that can reach a wider audience. There is more to come for us with additional collaborations, in addition to potential B2B partnerships with other businesses.

What do you feel are the keys to effective leadership, and how do you approach your management style?

Leadership is about more than making decisions – it’s about fostering a culture where people can do their best work. Emotional intelligence is key to that. Understanding what motivates people, how to navigate change, and how to inspire teams to align around a shared vision are critical to leading effectively. For me, leadership is also about listening – whether to employees, learners, or customers. Throughout my career, I’ve prioritized open communication and collaboration. Maintaining that sense of connection and shared purpose was a top priority as we transitioned from Pearson to Boundless Learning. I believe in having a strong sense of ownership over the areas you are responsible for while placing equal importance on respect. That’s what enables a business to not only navigate change, but to come out stronger.

At Boundless Learning, we’ve built leadership teams at all levels of the organization who are aligned with our core values and vision, something that we had the opportunity to reinvent as a new company. Our HR team and Culture Committee are crucial in fostering a workplace where people feel valued and empowered. Even through the challenges of restructuring post-acquisition, we’ve focused on building a culture that drives innovation and success.

What are your priorities for Boundless Learning as you look to the future?

Simply put, I want to keep our momentum going and not let up. Our focus is twofold: reinforcing the strengths that set us apart while also identifying new opportunities to push us forward. Looking ahead, we will be promoting Boundless Learning even more and sharing our passion for learning with others. Growth is coming and I am confident our organization is ready for what’s next; we are proud of our 30-year legacy in online learning, excited to tell our story, and more importantly, eager to realize our full potential.