How these 14 Canadian tech companies scale-proof their engineering teams


Unsurprising to us locals, Canada’s tech scene has blossomed in 2018. Toronto has added more jobs in the sector than any other city, Canadian funds are being announced left, right, and centre, and we have businesses leading the way in sectors ranging from crypto to cannabis.

As our ecosystem develops, more and more Canadian companies will grapple with the challenges inherent to scaling. For many, this will require adding layers to their onboarding process, particularly in engineering teams where technical learning dovetails the interpersonal transition that every new hire experiences.

Through Peersight, I’ve had the chance to chat with 14 engineering leaders, who shared their perspectives on how to run an effective onboarding process for their teams.

The best onboarding starts before the hire does

No hire has ever complained that their employer provided too much context before their start date. CareGuide CTO Ed Lui said that “as soon as a candidate signs their offer, [the engineering team] creates a new checklist,” outlining the many to-do’s that exist prior to the new hire’s start date. This includes sharing “a PDF of [the company’s] last monthly meeting and a peek at [the individual’s onboarding] curriculum” a week prior to their arrival.

There are important expectations to be set with respect to where the organization is headed and how it interacts with users.

Thinking on an even longer time scale, OneEleven CTO George Eichholzer said that, when selecting a front-end framework at Top Hat when he was VP of engineering, “onboarding ease and timeline was one of the most heavily weighted items in [their] selection criteria.” At one point, this enabled them to successfully onboard “over 40 developers in 40 weeks” while still delivering on deadlines.

Don’t assume senior hires will just “figure it out”

While it would be wonderful if senior additions to the team didn’t require coaching, the reality is that much of everyone’s experience is company-specific. “No matter where [your hire] comes from,” said AT&T associate director of software engineering Christine Wood, “it’s imperative to help them through your organization’s processes.”

In the case that your company has a niche tech stack, you’ll likely need to go a step further. To help teammates spin up on their blockchain-based tech application, CTO Thanasi Karachotzitis’ team at Authenticiti created an entire internal Wiki. Central to this are tutorials tying requisite conceptual topics in blockchain to their application within the company’s code base.

Buddy up

While getting developers ramped-up technically is understandably crucial to their success, every leader I spoke to also pushed on the importance of interpersonal integration. For this reason, both Ritual mobile head of engineering Michael Welsh and Ollon CTO Chris Ellefson swear by pairing each new hire with a buddy. This one-step-removed peer allows hires to expand their social circle, while benefiting from an impartial sounding board.

Fundthrough engineering manager Matt Belanger is particularly fond of this approach as it allows “someone on the team to exercise their leadership muscles.” The manager, in turn, is able to better “focus on the parts of onboarding that too often get forgotten… the spoken and unspoken culture of the team.”

Get aligned on expectations

Continuous improvement, more than anything else, is what makes for successful onboarding.

To ensure a robust working relationship between the new hire and their direct manager, many companies set ultra explicit expectations early on. At Uppercase, CTO Jeffrey Ling shared that new teammates and managers “co-create a document outlining expectations and explicitly make it as ambitious as [the hire feels] comfortable with.”

Statflo CTO Steve Pereira is a big believer in having hires define an individual Vision, Values, Methods, Obstacles, Measurements document. “[At Statflo], new hires have two weeks to read the V2MOMs of peers and leadership before sharing their own path. This naturally fosters alignment across the team, and largely prevents early performance issues.”

Take time to zoom out

In addition to expectation-setting for the individual, there are also important expectations to be set with respect to where the organization is headed and how it interacts with users. Freshbooks director of engineering Susan Davis noted that every Freshbooker starts on “front-line phone and email support” to provide “a very thorough grounding in [their] customers.”

At Drop, employees meet with team members across every functional team to get a sense of where each group is headed. Drop VP of engineering Ian Logan advocates that “understanding the bigger picture and making connections” with other teams is crucial to an engineer’s long-term success. Similarly, Kowsheek Mahmood believes that sharing the product vision early and often is a crucial part of keeping new hires “product-focused and oriented towards delivering great results.”

Make onboarding two-way

Tying things together, a number of technical leaders stated that continuous improvement, more than anything else, is what makes for successful onboarding. Software developer Gabrielle Quilliam sees onboarding as an opportunity to expand “the skillset of [her] team [by] ensuring that the knowledge [new hires] have from previous experiences translates to positively impact the company.”

Maple CTO Stuart Starr encourages new hires to revise the companies onboarding Wiki, allowing them to improve the process for future hires.

Photo via Unsplash.


Mike Gill

Mike Gill is the co-founder & CEO of Peersight, an employment marketplace that helps job seekers get to know their potential colleagues before accepting an offer. As CareGuide’s former Director of Performance Marketing, he led the team responsible for over $7 million in annual paid acquisition spend. Venture for Canada Alumni & McMaster Mathematics/Integrated Science Grad.

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