Brie Wolfson

Stripe alum (operations and Stripe Press) whose writing on Stripe’s culture is a recurring source across Kyle’s essays. She wrote Writing in public, inside your company on Stripe’s writing culture, and a widely-shared essay on her time at Stripe — cited in Toil We Must, where Kyle notes its divisive reception (some saw a bigger vision worth working toward, others a company having a negative impact on employees).

In the talent-vortex survey (The Talent Vortex - Research) she credited Stripe with developing talent — “Hired young but smart and open-minded people who loved getting critiqued and critiquing others” — and lots of reviewing each other’s work to make it better.

She also supplies a key caveat Kyle carries into Contrarianism and Likability: the framing of “likability as a jail” can encourage people to be difficult for the wrong reasons — conviction over likability shouldn’t be weaponized into being difficult for its own sake (Conviction-Led Contrarianism).

Where this appears

• The Talent Vortex - Research — survey response on Stripe developing talent through mutual critique.
• Toil We Must — her Stripe essay and its divisive response.
• Conviction-Led Contrarianism / Likability / Contrarianism — her caveat against weaponizing conviction-over-likability.

LinkedIn

Storytelling Studio at Positive Sum. Connected with Kyle on LinkedIn on November 23, 2021 — profile.