A conversation with Dana Stephenson, Co-Founder & CEO of Riipen
by Sally Sorte
“Everyone tells you to do something you are really passionate about and something you can relate to,” recalls Dana Stephenson.
At the time, Stephenson and his co-founder, Dave Savory, were in their fourth year at the University of Victoria in British Columbia. As they were talking to friends and reflecting on their own lives, the omnipresent question was, “What’s next?”
That question was what Stephenson and Savory decided to hone in on. Or more specifically, they sought to help more students get the right experience to facilitate a more successful and seamless post-graduate transition.
“What we realized is that [Dave and I] had tons of [work] experience — but our peers did not have that experience. Our focus right away was: How can we help more students get access to high quality, high impact work experience alongside their education?” says Stephenson.
Stephenson and Savory saw these work experiences as a gateway to helping students “gain career clarity, help them build up their portfolio, help them showcase to employers and articulate the experiences and skills they built throughout education, and to help them land employment.”
For students, there is this chicken and the egg dilemma of how to get that first experience when employers prefer to hire someone who already has experience. Riipen’s curriculum embedded, micro-internship offering reduces the barriers to entry for students.
The short-term, project-based format also benefits employers who are looking to attract and vet new talent with a lower lift in terms of time and cost.
Since inception, Riipen has built a 122-person team and a two-sided marketplace for students and businesses to connect. Riipen has delivered over 88.5k student experiences while helping more than 12.5k companies vet and recruit new talent, solving a key pain point for both sides of the equation.
Riipen fits into the EduLab Capital investment thesis of focusing on transitions within the learning and workforce continuum. These inflection points are not only ripe for disruption and product improvements, they are also opportunities to create impact as inequities tend to be more pronounced.
Imagine the compounding effect if you are able to increase your earning potential by 25 or 50% at early transition points, as opposed to 2–10%.
As EduLab Capital Managing Partner, Liam Pisano puts it, “A broad mosaic of work experience expands horizons and expectations — simply put, the more you see and experience, the more you want to see and experience. Riipen enables and accelerates this process, and we’re watching actual impact as they grow, which is exciting.”
Stephenson’s Path to Entrepreneurship
Dana Stephenson was not initially on a path to become an entrepreneur.
“I always wanted to be an engineer,” says Stephenson. “In school, I was interested in science, physics, math, and really interested in engineering.”
That said, Stephenson had been exposed to entrepreneurship from a young age.
“I was born and raised in that environment,” describes Stephenson, “My dad had his own business, which was originally a mechanics shop that worked on German cars.”
“That business ended up not being successful earlier on in my life, so I learned a lot from him and lessons from him as I saw him go through different phases of growth, reducing the size of it, and eventually moving on to something else.”
Stephenson’s mom also had a key influence on his career trajectory.
“After I graduated high school, I took a year off. I was working construction at the time and broke my thumb playing football, so I couldn’t work for a few months. My mom was sick of me sitting on the couch… so she found me a job, or paid training for a sales job.”
“I hadn’t done any sales before, in fact, I was extremely shy at the time, so I was terrified at the idea of it. She said ‘Get up, just do it, do a week of paid training and worst case scenario you can leave after a week.’”
Stephenson says that one week of sales training really “opened his eyes” and that he felt like he learned more tangible, practical and applicable skills in that one week — “communication, building relationships, asking the right questions” — than he had in all of high school.
That first sales role changed things for Stephenson.
“All of a sudden I started to feel like… I was more in charge of my own destiny.”
“It was a sales role, so it was very commission driven… The harder I worked, the more I put into it, the more I trained, the more I educated myself, the better I could do, and I could really see the impact of that every week on my paycheck.”
Stephenson switched gears and went to school for business instead of engineering. He used Craigslist to find sales jobs and paid his entire way through University.
He notes that “they were all pure commission, so there was no safety net or weekly paycheck other than producing results.”
“I loved the freedom that it provided. I felt like on a personal level, I was running my own organization — I was in charge of my own hours, my own paycheck, how I wanted to work.”
Eventually Stephenson transitioned to building teams for these organizations. He took the management and leadership skill sets he developed from organization to organization, pitching them on building a team and adapting the structure to each unique role.
Stephenson enjoyed growing a team, motivating a team, and helping them realize the same success that he had realized in sales.
“It wasn’t my own organization or my own venture… but at the time it felt like the closest thing to it, and it got me super excited. I was passionate about motivating people and it made me want to start my own company.”
Stephenson continued this work across multiple industries, yet he reached a point where it was not enough.
He explains, “I kept realizing that I was really good at what I was doing, but at the end of the day, even though I had all this freedom, I was paying my way through University, making really good money, building teams and motivating them… I really didn’t feel like what I was selling was making an impact.”
“[This realization] really encouraged me to start to explore how I could take this skill set and experience that I had developed and put it to good use, to make a positive social impact or environmental impact in our world, and that’s really what I wanted to start a business around.”
Stephenson met his co-founder, Dave Savory, in school and they joined the entrepreneurship program together. The two had similar backgrounds — building and growing teams (Savory founded College Pro Painters) and both had worked their whole way through university — so they were similarly committed to taking this opportunity to start a business right out of school.
“The hypothesis was, if we can help more students get experience and get the right work experience while they are in school, then they would be better prepared to transition into the workforce,” says Stephenson.
Stephenson and Savory had access to Canada’s Co-op model, a program designed to connect students with industry, but they identified an access gap: only 80k of 2M students had access to Co-op at the time.
As they investigated and interviewed Co-op coordinators, they found that the Co-op model was expensive to manage and grow at scale.
This led Stephenson and Savory to ask, “What if there are other alternatives to the traditional 4 month Co-op? What if we could bring work experience that wasn’t necessarily 4 months long, but was more flexible, more customizable, shorter in duration, varying levels of intensity? What if we could bring that to students earlier on also, so they weren’t waiting until the 3rd or 4th year [of University] — but throughout their entire education?”
The duo landed on a project model.
“In school you do so many projects, but most of those projects are fictitious, made up by the professor, or out of a textbook. The skills you’ve developed are trapped in the academic transcript. You get feedback from your professor, but you are not necessarily getting feedback from an industry professional.”
As serendipity would have it, their professor tested their idea before their very eyes. Ripping up the case study, he brought in his friend who was a CEO and the class was tasked to solve his challenge.
As Stephenson recalls, “Engagement skyrocketed, a woman got hired straight out of the class.”
When Stephenson and Savory interviewed the CEO, they couldn’t wait to find out if they had solved his challenge, which was a blue sky case to help him make $10M in the next two years so he could retire.
The CEO chuckled, “If you think the reason I came here was to learn how to retire, you’re out to lunch. Sure, we got some golden nuggets and lots of fresh insights, but what I was really looking for was talent.”
That’s when the light bulb went off for Stephenson and Savory: their micro-internship marketplace was value-add for both sides of the equation.
Riipen ran with their project-based model — first selling into student clubs and then using those case studies to sell directly to professors and embed the projects into curriculum. Things took off from there.
Perhaps it is only fitting that Riipen was born from the minds of college students looking to answer their own “What’s next?”
Reflections on the past year of the pandemic
Stephenson emphasizes, “I can’t tell you how proud I am of our team…” and how they “adapted quickly to a remote environment and adjusted to the rapidly changing landscape.”
This was of particular note given the young tenure of the team.
“For many it’s their first job,” says Stephenson, “And we certainly walk the talk — so we hire a lot of recent graduates and have interns ourselves.”
“This past year really opened our eyes — opened my eyes — to the benefits of going remote.”
He explains, “We always had a very open and flexible WFH policy, but people were not taking advantage of it. I think it had a bit to do with this feeling or stigma that you have to show up at work to demonstrate that you’re working hard. We have seen a huge amount of productivity gains in going 100% remote. It has really changed how we think about the future of our workplace environment.”
Since Covid, Riipen ended one of its leases in Toronto that naturally came to an end. Stephenson does not think the team will go 100% remote permanently, but they are reconsidering what that space will look like and how it will be used.
According to Stephenson, “We are rethinking what the offices will look like… we are not sure if we will have areas where more of our employees will book space in a shared environment, so there’s that community, or whether it’s having our own space, changing what we think of the office, so it’s more for training, onboarding, collaboration, brainstorming, community, and internal events. As opposed to a place you have to show up to demonstrate that you’re working.”
While their brick and mortar footprint may be up in the air, their reach and impact are full steam ahead. We look forward to seeing great things to come from Riipen.
Read and view more student testimonials here: https://www.riipen.com/love