Every Manager Needs a Bench of Agents

I wrote recently about the real AI platform shift happening at the substrate layer: the formats your work lives in and where it’s stored, not the models. That argument was about the substrate. This one is about what the org does with it once the substrate changes: what happens to the people in the middle.

The Old Model

For thirty years a “deliverable” was a file some person made in some app and sent to some other person. The org chart and the file system were separate universes. People sat in HR. Files sat in folders.

Middle management existed to bridge those universes: relaying information up and down the hierarchy, making sure the right context reached the right people. The hierarchy was the coordination system.

Roles Replace Apps

That starts changing when you stop opening tools and start talking to a role.

Not “open the spreadsheet” but a conversation with your COO. Not “start a deck” but asking your Head of Growth for the picture. Chief of Staff. Head of Ops. Each one is a project: its own context, its own scope, its own set of files it’s allowed to touch.

I use Claude Desktop as the concrete example because, with its projects and plugin model, it’s where this pattern is furthest along today. But it isn’t Claude’s pattern to own. Any system with a capable model, tool use, and a way to scope context can host roles. The vendor names will change; the move won’t.

The move is small to say and large to live: from “I’m using Excel” to “I’m working with my COO.” The org chart stops being separate from the file system. The org chart is the file system.

What Happens to the Managers

Block put the clearest version of this in writing on March 31, 2026. One month after cutting roughly 40% of its staff, Jack Dorsey and Roelof Botha published From Hierarchy to Intelligence, laying out what the new org actually looks like.

The framing was blunt: “There is no need for a permanent middle management layer. Everything else the old hierarchy did, the system coordinates.” The system, in their framing, is an AI that maintains a continuously updated model of the entire business and uses it to coordinate work in ways that previously required humans relaying information through layers of management.

When it works, that’s exactly what the role-based system does. The context that used to travel through humans now travels through the substrate.

Block’s replacement structure has three roles: individual contributors who get context directly from the system and make autonomous calls; DRIs (directly responsible individuals) who own cross-cutting problems and customer outcomes across teams; and player-coaches, who replace traditional managers.

The player-coach stays hands-on and develops people. They supervise and they do the work.

The Player-Coach Builds the Bench

Block’s framing is correct but stops one step short. “Manager who also does IC work” describes what the player-coach is, not what they do differently once the substrate changes.

The new job is to build and own a bench of agents for their team.

The human individual contributors are the starters, the people on the field doing the work. The agents are the bench: specialist depth you sub in for specific spots. The player-coach’s mandate is to build that bench and set the standards for how it’s used.

A player-coach who runs a growth team doesn’t just manage people and write copy sometimes. They own the team’s skill and agent standards. They decide which repetitive work gets packaged as a skill — “how we qualify a lead,” “the way we structure a weekly pipeline review,” “our launch checklist.” They build the agents that do those things, and they raise the bar on what counts as good enough. Their job is leverage on the team they already have, not a case for net-new headcount.

A skill, in this context, is the executable form of that judgment. Not a document. Not an SOP. A packaged set of instructions plus the assets it needs, such that any role can pick it up and run it. The player-coach is the one who decides what gets packaged and what the quality bar is.

That’s the actual leverage: not a smarter model, but a player-coach who keeps raising the team’s effective output by building better bench depth.

The Deliverable Categories Are Being Redrawn

On both sides of a team, the shape of what gets built is changing.

On the engineering side, the internal admin app nobody outside the team could run becomes a slash command any role can invoke. The background automation becomes a subagent. The internal library becomes a skill. Same engineering effort, far wider reach inside the company.

On the operations side, artifacts replace static documents. The weekly report stops being a deck somebody assembles on Sunday night. A role produces it on demand, with the numbers pulled fresh. That’s where the format-and-storage argument lands in practice: work that lives in markdown, JSON, or HTML in a repo can be pulled, rendered, and composed by any agent on the bench. A report sitting in a Google Doc cannot. The substrate shift is what made the deliverable shift possible. Anthropic’s Thariq Shihipar made the case for HTML as the natural agent deliverable in May: a single HTML page becomes the report, the spec, the dashboard, depending on what the role was asked to produce.

What to Watch For

If you run a team of any size, there’s probably one process someone on that team redoes from scratch every week. A pipeline review. A launch checklist. The way you qualify a new lead. None of it is formally named. It lives in someone’s head, or in a doc nobody updates, or in the way one person just knows how to do it. That’s a skill waiting to be packaged. A player-coach’s first bench job is to find those and give them a permanent form.

You don’t need Block’s infrastructure to start. Paste this into Claude, ChatGPT, or whatever you’re already using: