Returning the favor

Over a decade ago, Craig Miller was recruited to work at Shopify as its VP of Marketing. The problem: he had just bought a home in Toronto and his life was there, and Shopify was Ottawa-based. They were not flexible with the location, and neither was he. So he passed on the job offer.

In his rejection note, he wrote a postscript that involved seven tactics to tide them over until they found a VP of Marketing, mostly on getting better results from paid acquisition through Google Ads. 

A week later, they called and asked how they could make it work. 

Miller would go on to work at Shopify as its chief marketing officer and chief product officer for nearly a decade.

It’s one of the best lessons at any given point; adding value, relationships, etc. It’s also extremely contextual and situational. 

There’s a specific stage of company that these types of favors are perfect for. The team was somewhere around 10 employees, and was literally just in between raising its Series A and Series B rounds. It was hungry for talent and needed it urgently. There’s no room for people who were “strategic”-only; you needed to be able to execute, which Miller demonstrated.

There was also not as much red tape; the leaders were hiring for an executive and could make a decision that overruled prior principles or constraints (like location). Compare this to Fortune 500s which have to fight and claw for head count, HR policies and permissions for remote work; it’s not even close. (There’s a narrative that startups are chaotic, but Fortune 500s can be just as messy.)

There’s probably a ton of context that isn’t public, which I would love to find out more about; the only final clear one is that Shopify was originally based on Ottawa, and Craig was based in Toronto; Shopify might’ve seen this as a chance to expand, but also realize that this situation was an indicator of a larger one—that it would need to tap into the Toronto job market at some point. (Shopify acquired Jet Cooper in 2013, Tiny Hearts in 2016, etc.)

Hiring has always been difficult; the so-called great resignation has only made that narrative clearer in people’s heads. The best leaders and companies know this and will work around the talent to make it work; the more desperate the situation, and the more appealing (or less risky) a candidate, the more flexible any given hiring situation will be.

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