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.