# Stewart Butterfield

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The Onboarding Opportunity

The Cost of a Bad First Window Fenergo — “Global Financial Institutions Struggle with Rising Client Losses and Compliance Costs as AI Adoption Increases” (2025 survey of 600 senior decision-makers; 70% lost clients to slow onboarding, up from 67% in 2024 and 48% in 2023; onboarding abandonment ave…

Ep. 165 | Side Quests That Spark Growth (Ep. 143 Replay)

How to Disrupt the Monotony: Side Quests That Spark Growth (SuccessFlow Podcast Ep. 143 Replay). Steven Harris introduces a replay of SuccessFlow Podcast episode 143, focused on “side quests” as intentional, growth-oriented pursuits that disrupt day-to-day monotony without necessarily being a side …

Amplify What Makes You Special

What if I told you that I haven’t sent an email to a co-worker in almost two years? You’d probably say, “no way”, but short of an administrative email here or there, we’ve almost entirely eliminated email communication from our day-to-day operations at Proof. So the next question you might be aski…

The impossible dream of good workplace software

I’m talking with my good friend David Pierce, Vergecast co-host and The Verge’s editor-at-large, about something he spends an ungodly amount of time thinking and writing about: software. Scores of new workplace apps are cropping with clever metaphors to try to make us work differently. Sometimes t…

How Slack changed Apple’s employee culture, with Zoë Schiffer

Apple has had a lot going on lately: we did a whole episode about the controversial child protection photo scanning features, which have now been delayed. A law in South Korea might force the company to change how App Store payments work; the company settled a Japanese case about the App Store rece…

Recode Decode: Stewart Butterfield

Slack CEO Stewart Butterfield talks with Recode's Kara Swisher about how coronavirus changed everything for Slack and its customers, the sudden transition to "work from home" across the country, and how the company is handling a surge in usage at the same time that other plans and resources are bei…

Recode Decode: Slack CEO Stewart Butterfield, Apple Music

Kara Swisher interviews Slack CEO Stewart Butterfield, Lauren Goode talks about Apple Music and more.

Stewart Butterfield - We Don’t Sell Saddles Here - [Founder’s Field Guide, EP. 43]

My guest today is Stewart Butterfield, founder and CEO of Slack. Stewart’s 2014 essay “Why We Don’t Sell Saddles Here” had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner’s delusion, how to frame the bou…

Microsoft Offers 60,000 Exits: Slack, Trust and AI Influence

What happens to culture after a deal is done, and who is really making the decisions when AI is in the room? This week Chuck brings the stories: Slack’s absorption into Salesforce, Microsoft’s huge voluntary exit offer, the growing job description for CHROs, Deloitte’s model of trust, and an Anthro…