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Building a structure to enable scale.

Square’s former CEO on the two crucial components of org design

This week, Alyssa Henry — former Square CEO, AWS's first GM, and 12-year Microsoft veteran — shares org design best practices from tech's bluechip companies.

How to Intentionally Design Your Org, From Square’s Former CEO

When Alyssa Henry left Microsoft and joined Amazon, she was shocked at the lack of quality assurance testing. “We just built stuff, deployed, and watched to see what happened — it felt insane,” she says. Quickly, she learned that this team structure depended on context from both the business needs and the people driving those needs. In this case, it was the difference in ROI and risk between shipping physical and digital products.

This is one example that shows no two orgs are alike, but how they're built has similar underlying considerations. Henry has identified key components of their design from her experiences as Square’s former CEO, building AWS from the ground up as the company’s first GM, and 12 years at Microsoft in product and engineering roles:

  • The environmental condition — this is the business context. It takes into account the business model, constituents and customers as inputs when thinking about org structure as it relates to product strategy and resource allocation.
  • The human condition — these are your people, and the core human elements that shape your culture, like creating a way for candidates to self-select into it, motivating your team and operationalizing company values.

In practice, Henry gives the example of “taste” at Square, which is a traditionally squishy and subjective value, making it extremely difficult to truly operationalize. Taste was part of the company’s operating principles, and it was a factor in decision-making — from product to hiring and performance reviews.

“The trick to building a business that can scale is putting in the scaffolding. Strong communication and value systems make up the foundation that will allow you to scale without crumbling,” Henry says.

Organizations are living, breathing things that founders and executives at companies of every stage must continually assess. Whether you’re a first-time founder or someone in the C-suite restructuring your company, Henry’s lessons are timeless.

As always, thanks for reading and sharing.

-The Review Editors