Shopify’s big people investment: how a startup scaled coaching beyond its executives

Boris Wertz
Published in
3 min readDec 7, 2015


By boris, December 07, 2015

We know that companies are successful (or not successful) because of their people. Over the past few years, it has become relatively acceptable to work with a leadership coach and investors typically have a handful of good coaches in their rolodex ready to support and develop young founders. Yet even with this rise in popularity, leadership development is still primarily limited to CEOs and select executives.

Shopify is the first startup to really understand the value of coaching and leadership development across the organization. It’s about to launch “Managify 101,” an ambitious at-scale leadership program geared for all company managers. The evolution of coaching at Shopify from executive to at-scale offers important lessons for other startups.

The evolution from one-on-one to full-scale production

Coaching at Shopify began ordinarily enough. Cody Fauser, one of Shopify’s first employees, was promoted to CTO. It’s a common situation at tech startups: Cody was one of the best and brightest, but didn’t have C-level leadership experience. Executive coach Cam Gregg began working with Cody one-on-one. Soon enough, Cam began coaching other Shopify executives as well.

At the beginning, there was concern that having the same coach working with multiple executives would create conflict and tension. These concerns proved unfounded, primarily because Cam “provokes, but doesn’t force” (his words).

If Cam thinks a conversation should take place among upper management, he’ll provide the catalyst for it, but won’t act as a go-between. As Harley Finkelstein, Shopify’s chief platform officer, explained, “Coaches often become conduits between executives. But, that’s silly: we need to be talking amongst ourselves.”

One of the remarkable things about Shopify is that they hired Cam as a part-time coach when the company had around 60 employees and full-time when they reached 160 employees. Cam now heads up Shopify’s Talent Acceleration group which offers two levels of coaching services throughout the company. One-on-one coaching for executives includes the full coaching toolkit: 6–10 hours of assessment, and regular biweekly meetings over the course of 6–9 months. Then, there’s ad hoc mentor coaching for 1stand 2ndlevel managers.

Now, Cam’s group is about to launch “Managify 101,” a 90-day leadership development program that brings the benefits of coaching to the whole organization. Designed for newly promoted managers and new manager hires, Managify kicks off with a keynote from Shopify’s CEO, Tobi Lütke, with other executives sharing real-world leadership stories. The one-day kickoff will be followed by a set of workshops and peer coaching over the next 90 days.

This program is an impressive investment in talent development. As Cam explained, “if you’re prepared to play at your edge the whole time, what you’ll get from us is an incredible commitment to your ongoing development.”

Management buy-in has been critical to the successful development of coaching programs at Shopify. Harley lets all of his direct reports know that he has been working with Cam for over four years and has seen a huge impact from the experience. From day one of any training session, Cam already has the social proof that Shopify execs believe in the results.

“Where I’ve seen other companies get tripped up is they caravan in a coaching team for middle managers without any executive buy-in,” said Harley. “You can’t just drop coaching into the middle layer of the company and expect it to have an impact.”

Talent development is often an afterthought or an obligatory check on the checklist once a company reaches a certain size. It’s refreshing to see Shopify develop such an innovative approach to making sure company leaders are nurtured and developed at all levels of the organization.

Originally published at on December 7, 2015.



Boris Wertz

Entrepreneur turned investor. Co-founder AbeBooks (sold to Amazon), early-stage investor through @versiononevc, board partner @a16z. Husband and dad of 4.