The Grand Problem

Higher education has consistently proven to be one of the best ways for students to get ahead, particularly in a world that is rapidly automating away some of the most widely held jobs available to those without it.

While colleges have sought to reduce barriers to entry for students, they are increasingly criticized as drivers of inequality, with low and middle income students being left behind by an increasingly complex system that favors those who can afford personalized help.

Regardless of their socioeconomic status, students are let down and left behind by a system that favors the kind of one size fits all advice pushed by the college admissions industry and an overwhelmed guidance infrastructure where the average counsellor is advising over 400 students of vastly different needs, strengths and goals. With administration budgets already stretched thin, high schools are unable to provide the kind of one to one guidance that makes a real difference in students’ lives and greatly improves outcomes.

The vastly different schools, programs and majors that students apply to makes it incredibly difficult to find informed mentors who can provide guidance from first hand experience. The internet should solve this problem, but has yet to.

The Beginning of Something New.

In 2016, my partner and cofounder Alex Thorburn-Winsor founded IvyApps.org: a content website that shared profiles, essays and written advice from students admitted to competitive US schools like Stanford, Harvard and Yale.

We realized there was an opportunity to broaden the scope of IvyApps as more and more students reached out to us asking about the possibility of connecting with the essay authors themselves for one-to-one help and review of their own essays. Their experiences directly inspired the creation of a new platform that alllowed for students to meet and chat with mentors who’ve done it before.

We began to see IvyApps as more than just an archive of successful college applications. It was time for a new brand, and a new name.

The Great Leap Forward...?

The second iteration of Squired saw a huge departure from our old approach to design. We had a better picture of how we wanted users to interact on our site, and was really the moment we began properly planning the layout of the site. We updated our website typography from using three fonts to using one single font (Lato) with a variety of weights and widths. We also created user flow charts that mapped the ideal customer journey.

We began transitioning the site off Wordpress towards a modern stack with the assistance of an external development agency. We were eager, excited, but ultimately naive.

How does it work?

After brainstorming potential solutions and analyzing pain points based on user feedback, we created a detailed site map outlining where each of Squired features would be developed. This allowed us to get a grasp into how the platform would work system-wide.

Student User flow: Book a time

We saw that many students felt more comfortable booking after an introductory conversation with a mentor. As such, we’ve directly integrated personal messaging within the booking process.

Mentor User flow: Complete your profile

We realize a major paint point for Mentors is  setup. We’ve since redesigned the ‘complete your profile’ flow towards an intuitive “step-by-step” process that guides the mentor through the initial setup.

Too much, too fast.

Everyday the project became more and more complex, and further out of scope from the original goal of just a new design.  We were working based off our intuition of what we thought made sense, with little feedback from users on its usefulness and viability.

As we were nearing the application season, the project continued to experience more delays to a point where the migration of the site became near impossible. We weren’t considering the training of mentors to this new system, the extra content we had to make, and the inevitable bugs we’d encounter that’d need more contract help to resolve.

In the end, the best course of action was to shelve the project and continue improving upon our current site based on what we knew worked.

V2 is dead. Long live V3.

Here comes the growth (and change)

Despite a rocky couple of months, we began seeing incredible growth in and around October 2020 with traffic numbers and new user signups hitting all time highs, and new mentors with about one mentor onboarded each week.

This period of time also marked the beginning of a new brand story.   We were shifting away from the idea of “explore different essays that worked” and began emphasizing the essay as just one part of a mentor’s story. The design problem became: how do we showcase each mentor’s uniqueness, guiding students to actively engage with and create relationships with like-minded peers and learning from their experience?  How do we tell that?

Through more user interviews with both students / mentors, and data-informed design with Google Analytics we began refining our message until we felt we knew who we were.

Controlled, Manageable, Informed.

Our first priority was to address fundamental issues we were facing with Wordpress. We moved our hosting away from Siteground onto Google Cloud Platform to solve the frequent issue of our site crashing. In combination with global elements standardization and plugin optimizations, we managed to address the page loading speed issues that plagued our SEO.

As well, we began fully leveraging the Google Analytics suite for goal-setting/tagging and A/B testing important pages to quantifiably measure the impact our changes made.

A Unified Application

We noticed many new users were dropping off early in the funnel and not exploring the site beyond the first couple of essays. For a new user unconditioned to Squired, it is unclear as to why they should view a mentor’s full profile.

From analytics we saw a negligable amount of users reach lower level of funnel, at ~0.01% reaching the view book me page, We sought to improve this by prominentely displaying mentors and parts of their profile relevant to a college application alongside their essays to entice the user to read more about them.

Micro-iterations

Cards were updated towards a greather emphasis on the mentor’s identity. We wanted a visual distinction between featured mentors and all mentors in the directory as we noticed a correlation between featuring a particular mentor and increased bookings with then.

Old Card Design

New Card Design

Old Essays “Cards”

New Essays Card

Visual Standardization

We’ve designed much of the site’s components ad hoc which has led to various inconsistencies in design even up to this day. We’ve since create a design guide for future additions, and have been working backwards to find components and update them towards the new standard.

We updated our website typography from using three fonts to using one single font (Lato) with a variety of weights and widths. We also created a web style guide, that included everything from buttons, forms, modules, and sections and made sure to include all of the various states.

Reflection

In all honestly, I had a fairly difficult time writing this case study. Part of the reason for that is this persistent feeling of incompleteness: “I’m missing stuff about the marketing strategy, and the technical learning, and the mentor onboarding strategy, and the ad ops, and the team management, etc. etc.”

I realized that it would be impossible to fit everything in, so I decided to focus on one theme: change. When I first began working on IvyApps, I had no real experience with product design. Through my  experience witnessing the effects of my creative decisions, direct conversations with real users,  guidance from those more around me, and the difficult lessons I faced with failures, I can honestly say that my time with Squired has helped me develop as both a designer and an entrepreneur.

There is still a lot to be improved on Squired’s site. The past few months have been scrappy, fast-paced, and challenging. That being said, I’m proud of everything we’ve learned and been able to accomplish.

Squired was my first exposure to entrepreneurship, and a real taste of the chaotic, stressful, and cyclical nature of bringing an idea to life. What continued to drive me was knowing we were helping real people achieve their dreams, and that feeling is incredible to me.

I’ve sinced moved on to complete my degree, but I take some comfort knowing the project is in the capable hands of my partner Alex.  Goodbye, Squired.

The Team

Alex Thorburn-Winsor - Co-founder & CEO
Martin Zhang - Co-founder & Head of Product
Yann Youten - Head of Mentor Relations
Syed Ahmed - CTO (Interim)
Kanav Petkar - Lead Developer
Jared McGrath - Developer
Toan Nguyen - Email Marketing
Candice Chow - Product Marketing
Teo Salgado -  Lead Advisor & Education Consultant