Engagement at Scale — How Shearwater Cofounder Jackson Boyar is Helping College Students Finish School

6 min readJun 27, 2017

The initial transition into college is arguably the most trying time in any student’s life. It’s unsurprising, then, that the root cause of a staggering number of dropouts is the failure to adequately acclimate to the demands and routines of higher education. And for students coming from underserved populations, this rings even more true.

This is precisely the problem that Jackson Boyar, cofounder of Shearwater, is solving by using technology to make mentorship an integral part of the college experience for the students who need it most. Read on to learn the story of Shearwater’s origins, why higher education has struggled to link students with mentors in the past, and what administrators should do to better serve students.

This is part 3 of our Boston’s Most Exceptional EdTech series. Check out part 1 (uConnect), part 2 (Door of Clubs), and part 4 (Ready4).

Can you give us your elevator pitch for Shearwater?

More than 30% of college freshmen in U.S. drop out after the first year. Universities are losing revenue, but the attrition is disproportionately represented by underserved populations. A major reason why those students drop out is that they struggle with the transition to college.

We help colleges and universities ensure every student gets the support they need. We help our partners recruit mentors from their community to work with students from matriculation to graduation. Mentors do this through our platform, which houses curriculum tailored to the needs of their mentees.

What was the major problem Shearwater set out to solve?

We initially started by focusing on helping international students. Both my cofounder and I are from the U.S., but we studied abroad ourselves and had some transformational experiences doing it. Many of our friends in college were international students who didn’t understand American culture and became frustrated and homesick.

Universities just didn’t have systems to support the soft side of being an international student, and so it was personal for us to help our friends make the most of their time in the United States. We were doing pro bono work for schools as a side project. Our first partners said that we should be charging for our services, so we quit our jobs and started Shearwater.

One of the key problems is that most onboarding happens during Orientation, but it’s typically a firehose of information and difficult to gauge whether students retain what they learn. Shearwater helps universities scale up and deliver personalized support to more students.

Can you give us a broad overview of how the platform works and how the mentorship process works from beginning to end?

It’s not just technology. The software is important, but the experts we employ help universities and colleges craft a program that fits the specific institution. It’s quite custom.

If you’re a new student matriculating into one of our partner schools, you’re matched with a mentor. The matching process is very data-driven. We start by helping schools identify and recruit great mentors from their own communities. Incoming students fill out a survey to identify their best-fit mentor, and the platform matches them up based on the mentors’ profiles and the students’ answers.

All of our mentors have to receive ongoing training and every mentor has to be well trained before working with a student. Once they’re on our platform, we have personalized curriculum for each student to work through with their mentor. For example, an international student may see different content from a first-generation American student.

Our platform also includes a lot of tools to track engagement over time to gauge the success of the mentorship. Every university has different goals and uses different modules and content. We have curricula for women in engineering, international students, and many other student profiles.

Why have mentorship programs historically been so deficient at most universities?

I wouldn’t say they’ve been deficient. The residential university model is really hard to scale. My alma mater had tens of thousands of students. At that scale, it’s nearly impossible for a department of rockstar administrators to ensure every student receives personalized support.

Another thing we’ve recognized is that most of a university’s budget is spent on admissions — essentially sales and marketing for the school. A large part of it is also spent in advancement and alumni — acquiring donors and building an endowment. That’s how they fund their institutions.

“Customer service” — making the experience as good as it can be — is now becoming very important. Schools are realizing that they need to take care of students after they enroll if they want to retain their student body. If kids drop out, it hurts the school’s ability to attract prospective students.

Our best customers care about the students. They’re in education for a reason, and it’s not all about money. They want to make higher education the best experience possible for the students.

What kind of results are your partner universities seeing?

We’ve invested in randomized control trials to isolate the impact of what our partners do with our solutions. One partner had 50% of its freshman class use our program, while 50% didn’t, and then we tracked their results over the year.

Students in our pilot group were five times less likely to be on academic probation and over 20% more likely to be retained.

We are also exploring ways to quantify the softer sides of our solution. In some instances, we may ask students to name their top five friends at school. This allows us to look at demographic data and understand things like social integration. For example, if a Chinese exchange student had all Chinese friends, it would be an indicator that they hadn’t integrated into the wider student body.

How is higher-education changing in the tech/software and social media driven world?

A big part of it is macroeconomic changes — there’s an overall decline in enrollment post-Baby Boomer era. The current political climate has also impacted international student programs — international students are a big part of any university’s revenue.

Most students entering schools are accustomed to social media — they grew up on it, and in some cases they may not have had the social development older millennials have had in terms of face-to-face interactions.

A lot of deans are telling me that they are seeing an increase in indicator of mental health issues. In particular, young adults and teenagers are often afraid of failure to the point where it is paralyzing. Schools want to tell kids that it’s OK to reach out to mental health professionals and that failure is a normal and important part of the college experience.

We’re using technology to help solve and alleviate some of those problems.

What should universities be doing to stay on top of all of these new media/internet/platform trends?

At a startup, it’s all about empathizing with and understand your customers. The same should hold true at universities. Schools should work to understand exactly what their students — their customers — need to thrive. Unfortunately, senior administrators rarely have time to just go into the cafeteria and talk to students.

Our most innovative partners build student-driven committees and focus groups to ensure that their initiatives always consider the needs of their students.

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Read the rest of our Boston’s Most Exceptional EdTech series here:

If you liked this interview, check out our Future-Forward Fashion Founders series, featuring interviews with notable founders from Boston’s fashion/apparel industry.

This interview was conducted and written by Camden Gaspar, Content Strategist & Copywriter at Ideometry. You can follow him on Twitter @camden_gaspar.

Ideometry is a full-service marketing agency located in Boston helping awesome companies and organizations amplify their growth strategies.