The Modern People Leader: Forward-Thinking HR

280 - Being Async-First, Building an AI Ops Squad, & the “Embarrassing V1 Method”: Chase Warrington (Doist)

Feb 6, 2026

Chase Warrington, Head of Operations at Doist who leads async-first systems and AI ops, breaks down Doist’s squads-based operating model. He talks about the “embarrassing V1” one-day spec trick, rituals like async standups and demos, and how async work makes AI adoption and non-engineer prototyping practical. Short, practical, and focused on scalable remote operations.

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ANECDOTE

Embarrassing V1 Accelerates Planning

Doist compressed a two-week spec process into a one-day "embarrassing V1" to force fast iteration and questions.
The change increased company velocity and made teams move much quicker across quarters.

INSIGHT

Async-First Needs Systems And Reinforcement

Async-first requires intentional systems: a searchable handbook, decision frameworks, and a bias for action.
Leadership must repeatedly reinforce values and connect them to async practices to sustain the model.

ADVICE

Bias For Action: Ship, Then Iterate

Embrace a bias for action: ask forgiveness, not permission, and bake safe failure into processes.
Hire for comfort with fast iteration and normalize retracting or fixing mistakes later.

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Chase Warrington, Head of Operations at Doist, joined us on The Modern People Leader to break down how async-first work enables faster decision-making, stronger culture, and scalable operations. We talked about building trust without offices, the systems and rituals behind Doist’s execution velocity, and why async workflows are foundational to effective AI adoption.

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Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode280

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(07:30) Chase’s Origin Story

(11:15) What Doist Does: Productivity Tools, Todoist, and Async-First Principles

(14:45) Why Async Work Changes How Leaders Think, Decide, and Scale

(17:28) Independent Decision-Making as a Non-Negotiable at Doist

(20:44) The Doist Operating System: Squads, Quarterly Cycles, and Decision Frameworks

(23:17) Rituals That Power Execution: Async Standups, Demos, Retros, and Dashboards

(26:30) Communication as Infrastructure: Async Guidelines, Transparency, and Trust

(30:45) How Async Enables Better AI Adoption and an Organizational “Brain”

(33:44) Inside Doist’s AI Ops Squad: Redesigning Planning, Search, and Workflows with AI

(38:17) Vibe Coding, Non-Engineers, and the Rise of AI-Enabled Builders

(47:22) Partnering with Head of People Nadia Vatalidis and Scaling People Systems

(53:30) The Biggest Misconception About Remote and Async Culture

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Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.