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Bob vs Claude Cowork

For when your laptop’s shut and your team needs it too.

You probably hit one of two walls with Claude Cowork. You handed it a job, closed the laptop, and came back to find it had stopped. Or it did something useful and you wanted the rest of the team to have it, and found it lives in your account.

  • Spending limit on every plan
  • Cost shown under every job
  • Free redo if he gets it wrong
  • Cancel anytime

By Matthew, founder of HeyBob. Every Cowork line was checked against Anthropic’s own pages on September 23, 2026. Sources are at the end.

HeyBob
The ops channel in the HeyBob app. A teammate attaches a supplier price sheet and asks @Bob which price changes hit the top products. In the thread, Bob answers with a small table and a line showing credits, time and tool calls.
Wall one

“It stops when my laptop goes to sleep.”

This one has changed recently. Cowork started as a desktop app, and Anthropic now runs Cowork sessions in the cloud too. Its help center says a cloud session keeps working when you close your laptop, and scheduled tasks run with no device online. Cloud sessions are marked beta.

Three catches, all on Anthropic’s own pages:

  • Anything on your computer still needs your computer. Local files, your browser and computer use go through the Claude Desktop app, and a scheduled task that needs them only runs locally.
  • Your company may not have cloud sessions on. They are on by default for Team, and off by default for Enterprise until an owner turns them on.
  • It is beta, and some features are not in the cloud yet.
The likely reason
You

“Why did Cowork stop when I closed my laptop?”

The job touched something on your computer, or your organization still runs Cowork on the desktop.

Wall two

“I can’t share it with my team.”

Anthropic’s pages describe Cowork sessions and files as saved to each member’s own Claude account, and every person needs a paid Claude plan to use it.

What Anthropic does offer: on Team and Enterprise, you can share a Cowork project with people in your organization, with view or edit access. The pages we checked do not describe one shared Cowork that anyone on the team hands work to, so we do not assume one.

Anthropic’s agent for team work in Slack is a different product, Claude Tag. We compared it line by line on Bob vs Claude Tag.

In a channel
Teammate

“@Bob same for my accounts.”

Bob runs it again under her access, not yours. Everyone in the channel sees the result.

Your Monday, two ways.

Say the weekly pipeline numbers go to the team every Monday. Here is how that morning goes.

With Cowork

  1. You set a scheduled task: every Monday at 9, pull the numbers and write the summary.
  2. It runs in the cloud, as long as cloud sessions are on and nothing lives on your laptop.
  3. The summary lands in your Claude account.
  4. You copy it into the team channel.
  5. A teammate wants the same cut. That is a task in their own account, on their own paid plan.
  6. Two deals need a follow-up email. You start another task.

Cowork did the hard middle part well. Getting it to the team was still yours.

With Bob

  1. The summary is already in the channel, posted at 9 whether anyone’s laptop was open or not.
  2. A teammate replies, “same for my accounts.” Bob runs it under her access.
  3. Two deals need a follow-up. He drafted both, each waiting on one Approve tap.
  4. Under each post sits a receipt: what it cost, how long it took, what he touched and who approved it.

You told him once, “post the pipeline summary every Monday at 9.” That is the whole setup.

What is different about Bob.

No laptop needed

His own computer

Every job runs on its own computer in the cloud. Schedules and triggers fire on their own, after everyone shuts their laptops.

One hire

The whole team uses him

Anyone asks him in a channel or a direct message, in the HeyBob app or Slack, and everyone sees the finished work. No per-seat fees.

Your access

He works as each person

Gmail, Google Calendar and HubSpot connect per person. A shared account, like a support inbox, reaches only the teammates an admin picks, and every send from it asks first.

Before a change

Nothing goes out without your OK

Changes to your CRM, books or docs wait on Approve or Deny, so the channel can see who approved what.

Every job

A receipt and a cap

What it cost and how long it took, under every job, and a monthly limit he will not cross.

On your calls

Notes with no bot

Hit record on any call. No bot joins. Tap Have Bob do it on an action item and he does the follow-up.

A finished job in a thread showing the answer and its cost: 96 credits, 4 minutes, 3 tool calls

The receipt. Every answer shows what it cost.

Usage page: 31,480 of 50,000 credits used, with a limit per person and a cap for the workspace

The limit. One cap for the team, one per person. He stops there.

Where Cowork is the better fit.

Keep Claude

For the jobs on your own machine.

Cowork on the desktop works directly in the folders on your computer, can reach your desktop apps, and turns out polished spreadsheets, decks and documents. If the job is yours alone, that is a strong fit, on a Claude plan you may already pay for.

Hire Bob

For the team’s repeat work.

The Monday report, the status update, the numbers copied from one app into another, for the whole team, whether your laptop is open or not. Each person’s own access, your OK before anything changes, and a receipt for every job.

Fair questions.

Does Claude Cowork keep working when my laptop is closed?

Partly. Anthropic’s help center says Cowork sessions in the cloud, currently in beta, keep running when you close your laptop, and scheduled tasks run with no device online. Anything using files on your computer, your browser or computer use needs the Claude Desktop app open. On Enterprise plans, cloud sessions are off until an owner turns them on. Bob runs every job on his own computer in the cloud, so nothing waits on anyone’s laptop.

Can my whole team share one Claude Cowork?

Anthropic’s pages describe Cowork sessions and files as saved to each member’s own account, with each person on a paid plan. On Team and Enterprise you can share a Cowork project with view or edit access. Bob is one hire for the whole workspace: anyone asks him, everyone sees the finished work, and there are no per-seat fees.

Which Claude plans include Cowork?

Anthropic lists Cowork on Pro, Max, Team and Enterprise. It is on the desktop app for all of them, and in beta on the web and mobile for Pro, Max and Team, and for Enterprise where an admin has turned it on.

Isn’t Claude Tag Anthropic’s answer for teams in Slack?

It is Anthropic’s own agent inside Slack, in public beta on Team and Enterprise. A thread is one shared session anyone in the channel can steer, and the connections an owner sets up are shared by everyone in that scope. Bob works under each person’s own access instead.

Do I need Slack to use Bob?

No. The HeyBob app for Mac, Windows and Linux works on its own, with team channels and @Bob in a thread. Same Bob either way.

What does Bob cost?

$75 a month per workspace, half price through December 31, 2026, with no per-seat fees and a monthly limit he will not cross. The first $100 of work is free for 14 days. With your own OpenAI or Anthropic key, the plan is $349 a month with 1,000,000 credits included.

Sources.

Every Cowork fact on this page comes from one of these Anthropic pages, checked on September 23, 2026. If one has gone stale, tell us.

Close the laptop. Bob keeps going.

One hire for the whole team. $100 of work, on us.

Claude, Claude Cowork and Claude Tag are trademarks of their respective owner. HeyBob is not affiliated with, sponsored by, or endorsed by them.