Shopify’s Inflection Point - The Revolving Talent Problem

SaaS
Written By Rick Watson

Shopify executive departures are the biggest story in 2021. Big roles, and bigger implications - make no mistake this is an inflection point.

First what's happened? Chief Talent Officer, Chief Technology Officer, Chief Legal Officer have all just departed. On the back of the Chief Product Officer transitioning out last year.

A few notes:

  • I expect few outsiders will fill these new roles. Shopify needs to preserve its culture. In particular in the Chief Product (again, if they even fill it) or Chief Technology role - you likely don't get this role if you haven't known Tobi for a long time - especially given his outsized influence on these teams.

  • To be clear, if a bunch of new outsiders do join the organization, I would worry for it.

  • Of these, I think Chief Tech and Chief Talent will be most missed. Both are long-time players with big influences on the org. That doesn't get replaced overnight. However, all executives with big influences leave behind learnings for many others.

  • Almost all of these executives (including the CTO) have cashed in shares in the past few months leading up to this - signaling sometimes nothing, but noted.

  • Another exec frequently trading? The current CFO who started only 3 years ago.

Rick Watson

Rick Watson founded RMW Commerce Consulting after spending 20+ years as a technology entrepreneur and operator exclusively in the eCommerce industry with companies like ChannelAdvisor, BarnesandNoble.com, Merchantry, and Pitney Bowes.

Watson’s work today is centered on supporting investors and management teams incubating and growing direct-to-consumer businesses. Most recently, in partnership with WHP Global, Rick was a critical resource in architecting the WHP+ platform, a new turnkey direct to consumer digital e-commerce platform that powers AnneKlein.com and JosephAbboud.com.

Watson also hosts a weekly podcast, Watson Weekly, where he shares an unbiased, unfiltered expert take on the retail sector’s biggest players.

In the past year alone, Rick has spoken at many in-person and virtual events as well as podcasts on topics ranging from retail/ecom to supply chain/logistics and even digital grocery including CommerceNext IRL, ASCM Connect, and Retail Innovation Conference.

https://www.rmwcommerce.com/
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