Dana Stephenson is the Co-Founder and CEO of Riipen, a future of work platform dedicated to scaling experiential learning opportunities for learners of all backgrounds. His entrepreneurial journey began with a mission to end underemployment by ensuring every learner has access to authentic, career-relevant experiences that create smoother transitions into the workforce. Under his leadership, Riipen has partnered with hundreds of academic institutions and tens of thousands of employers and non-profit organizations to make project-based learning more accessible and impactful. Dana works closely with universities, industry associations, and government agencies to expand experiential learning programs internationally, advancing both workforce readiness and educational innovation at scale.
Recently, in an exclusive interview with Higher Education Digest, Dana shared insights into his entrepreneurial journey and vision for transforming education and workforce development. Dana emphasized the importance of collaboration, scalability, and inclusivity in education, aiming to end underemployment by connecting learners with meaningful work experiences. He also highlighted Riipen’s growth and impact in creating a more equitable and sustainable talent pipeline. The following excerpts are taken from the interview.
Hi Dana. Can you walk us through your career journey and how you came to co-found Riipen?
My co-founders, Dave Savory, Jordan Ell, and I started Riipen in 2013 as part of a capstone entrepreneurship project at the University of Victoria. We noticed a challenge shared by our peers and ourselves. As students, we wanted meaningful work experience, real employer relationships, and a way to prove our abilities, yet we kept hitting the same classic conundrum: you can’t get a job without experience, and you can’t get experience without a job.
We set out to build a solution to bridge the gap between education and employment by embedding real-world, project-based learning directly into the student experience. Since then, Riipen has grown far beyond what we initially imagined. We’ve built a platform that has connected hundreds of thousands of students with tens of thousands of companies. Even with our global reach, our goal has always remained the same: to end underemployment.
What do you think sets Riipen apart from other companies in the education and workforce development space?
What sets Riipen apart is that we go beyond connecting students to employers. We get to the heart of the problem by making sure every student has access to the experience and professional connections they need to build portfolios with industry-vetted skills. Without that, job boards often feel like sending resumes into a black hole. Through Riipen, students work directly with employers on real projects that solve real challenges. Unlike a typical business case study or simulated internship, these projects are live. The deliverables students create are actually implemented by employers, and students receive feedback, mentorship, and validation of their work. This interaction helps them develop the human skills that AI can amplify but not replace while producing tangible outcomes they can demonstrate and discuss with future employers.
Embedding these experiences into the classroom ensures that every learner, regardless of background, geography, or personal network, has equal access to meaningful opportunities. Because projects are online and asynchronous, students can participate from anywhere and balance them with other commitments. For educators, these experiences replace traditional assignments with authentic work that aligns closely with existing learning objectives and builds career readiness. Institutions can track, measure, and report on the impact these projects have on student employability as well as the measurable value they create for businesses and non-profits locally and globally.
What do you believe is the most pressing issue in education and workforce development today?
The most pressing issue in education and workforce development today is the widening gap between what students learn and what the labor market demands. The rapid adoption of automation and AI is transforming industries and redefining the skills required to succeed. Long before generative AI entered the conversation, there was already a deep mismatch between graduates’ skills and employer needs. According to the Strada Education Foundation, nearly half of college graduates are underemployed after graduation, and 45 percent of those remain underemployed a decade later.
The challenge isn’t that academic leaders or educators don’t recognize this problem or want to fix it. It’s that the current incentive structures rarely encourage change. That’s where intermediaries and technology partners like Riipen come in to remove as much friction as possible and make it easy for institutions to integrate meaningful work experiences at scale. There’s no reason we can’t develop socially engaged citizens and ensure meaningful employment outcomes. Too many schools treat it as an either or, but with the right partners, it’s an attainable both and.
If we’re preparing students for a world of uncertainty, we need to put them in it. Project-based learning does exactly that. When students work on real, messy problems with real people, they learn to adapt, listen, take feedback, and figure things out. They learn to learn, unlearn, and relearn. That’s the mindset and skillset the future demands, and the one we’re helping institutions deliver.
What role do you think technology plays in transforming the way we approach education and career development?
Technology is one of the most powerful tools we have to bridge the gap between the classroom and careers. It can make meaningful, work-based learning accessible at scale in ways that were never possible before. Through Riipen, professors can connect students with companies across the country and around the world to give them hands-on experiences that build real, industry-vetted skills. More than just providing access, technology allows us to capture data on which skills students are developing, how they’re applying them, and where the gaps are.
That insight helps institutions design programs that better align with labor market needs and gives students a clearer picture of their strengths and growth areas. It also helps employers identify and nurture talent early, making hiring more about proven ability than pedigree. When used thoughtfully, technology doesn’t replace human connection in education—it amplifies it. It helps create feedback loops between learners, educators, and employers that make learning more relevant, equitable, and future-ready.
Can you share a mentor or role model who has had a significant impact on your career, and what advice they gave you?
Dr. Karen Bakker was one of the most inspiring people I have ever worked with. She was a scholar, entrepreneur, and changemaker who showed what it means to bridge academia and innovation with purpose. I first met her early in my journey when we were both building education technology companies in Vancouver. From the beginning, she led with curiosity, integrity, and an unwavering belief that collaboration could achieve more than competition ever would.
Karen taught me that true leadership in education is about generosity—sharing knowledge freely, lifting others up, and making space for new voices. She constantly reminded me that learning should be an act of connection between disciplines, between people, and between ideas. I feel fortunate to have learned from her example and to carry her lessons forward in the work we do today.
What is your favorite quote?
“Leadership is not about how people experience you; it is about how people experience themselves in your presence.”
This quote was shared with me by Mohamed Mansour, Chair of Riipen’s Board, and it has stayed with me ever since. It’s a reminder that great leadership isn’t about authority or visibility—it’s about creating the space for others to feel confident, capable, and inspired to grow.
Can you share a book or resource that inspires you, and why?
The Connected College by Elliot Felix. It’s one of the best articulations I’ve seen of what higher education can be when it’s designed around connection—connecting learning to purpose, and students to the people, experiences, and opportunities that shape their future. It reinforces the idea that education works best when it’s collaborative, experiential, and focused on real-world outcomes. That philosophy is at the heart of what we’re trying to achieve at Riipen.
What are your long-term career aspirations, and how do you see yourself evolving as a leader over the next five years?
My long-term goal has always been to help end underemployment by ensuring that the jobs people want and the skills they have align with what employers need. Work-integrated learning helps people find purpose, contribute to their communities, and build lives that are fulfilling and sustainable. When people can support their families through work that matters, communities thrive, and so does the broader economy.
I believe we now have the infrastructure to build national talent networks that strengthen both education and the workforce, fueling economic growth for everyone. We’re seeing real momentum—not just from individual departments and faculty, but from presidents and senior leaders who want to integrate work-integrated learning across their institutions. Over the next five years, I see myself continuing to advance that mission: scaling the reach of work-integrated learning globally and ensuring that every learner, regardless of background, can access meaningful experiences that lead to real career outcomes. For me, leadership is about building ecosystems where opportunity, purpose, and prosperity reinforce one another.
What advice would you give to entrepreneurs looking to start a business in the education or workforce development space?
Education is one of the most interconnected systems in our society—a network of students, educators, policymakers, and industry. My advice is to start by listening. Talk to the people your solution is meant to serve and understand their needs before trying to solve them.
You can’t create lasting impact in education by working in isolation. Be a true partner, collaborate deeply, and stay focused on outcomes that move students, institutions, and communities forward. Success in this space is challenging, but it’s also some of the most meaningful work you can do.