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Case Study
Helpful was a video chat directory for work. In an office, at home or in the field, managers could share video feedback, coaching, and recognition with employees. Helpful was acquired by Shopify in 2019.
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Helpful — a workplace video platform

A phone and earbuds on a table with the Helpful video chat app on an iPhone

Back in 2016, I was an early employee at Helpful — a little startup in Toronto — which was the brainchild of Daniel Debow and Farhan Thawar. My role at Helpful allowed the startup to quickly and continuously test Daniel’s vision, building on old systems and creating net-new ones, with a workplace video messaging app powered by machine learning.

As a product leader, I had my hand in building and validating all of the wild and strategic ideas that came from Daniel and Farhan. The product took many forms and three major pivots over my tenure, however, it was the earliest of days where the nitty-gritty real-world problem seeking was most crucial. 

Reaching out to, and diving deep with prospective customers divulged an interesting systemic blindspot in SMEs — employee turnover meant getting to know both your immediate team, and the broader, larger company was difficult. After much concept exploration, we decided to pursue a kind of intelligent employee directory with a fun game to get to know your team.

Trying to keep things simple, I hacked together clickable prototypes and cobbled together unanswered questions to launch an ongoing series of interviews with potential users at companies in the Toronto area. People seemed to get it, were willing to try it, and were actually kind of excited about getting to know people in their company.

I worked with our amazing engineering team to build a functional app that allowed a manager to launch the app within their team, people could sign up and immediately add a few things about themselves which would be added to the game. Launched in 2016, the Helpful directory and game was very successful in the small groups we tested with.

In early 2017, our team started to explore adding quick, ephemeral video messages to the directory to solve our own pain: standup. The team had grown, and people (including myself) commuted from all over the GTA to the office for 9 — but not always on time. Well before pandemic Zoom remote work, we thought that perhaps adding a video message for everyone’s morning update might be a good way to make sure everyone could contribute asynchronously when they couldn’t make it to standup.

A sketch of the Helpful application's top-level interface structure

My role at Helpful took on many heads: working as product lead, interpreting the vision and ideas from the executives, managing a product designer while interfacing with product management and engineering, and also working in an exploratory capacity with our machine learning/data science experts. We launched exciting experiments starting in the final days of the game (training the system to help people find someone who can help with x), and later on the video platform, creating better ways to transcribe videos, learn from the transcripts, exploring augmented reality, and generative recommendations.

Helpful’s app eventually turned into a fantastic short-format video messaging suite that allowed teams to provide feedback on projects, or for managers to provide feedback to employees. During this period, I lead the product and engineering team to element a comprehensive design system and product exploration/iteration cycle. Along with product management, our feature exploration, user testing, build, launch and measurement practice led to an application that began to take shape as a proper enterprise communication tool. We launched with small business owners with fleets of remote, distributed employees; banks for providing employee feedback and executive updates; and major airlines as a way to allow employees to asynchronously communicate across the vast distances at an airport.

Helpful continued on this path while simultaneously spinning up Dialog, an open conversation platform. Dialog allowed people to create real-time podcasts where listeners could pop in with questions to the hosts. If this sounds familiar, Helpful created Dialog in 2018, two years before Clubhouse.

Helpful was acquired by Shopify in 2019.

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