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Where an existing product should put its first agent

The AI Product work group ranks candidate surfaces with examples from Webflow, Microsoft Copilot, EvenUp, Chime and Superhuman.

Updated October 13, 2026

Start with a bounded job inside a workflow customers already use, where they can check and edit the result before it goes out, and widen what the agent does as you learn where people still step in.

  • Pick a bounded job people can review. Rachel Wolan would rank surfaces by whether the job is frequent and painful, whether the agent produces a unit the customer already works with, and whether the customer can review it under the right permissions before publishing. Sam Stone would start with draft-and-review work, like the demand packages EvenUp's legal customers edit before they send them.
  • Weigh judgment against verification. Aparna Chennapragada would also score how much judgment the job asks of the agent and how easily the user can check the result, starting from a supervised recurring task such as a weekly digest of customer-issue emails. She suggests writing the spec as the judgment the user wants, then testing it on a small set of real requests.
  • Let real demand pick the job. Dennis Yang would rank tasks by request volume, how often the current flow fails, whether the agent has reliable data and tools, and the cost of a wrong action, and keep sensitive account changes behind explicit confirmation. Rachel would look at what people already do with outside agents, as Webflow saw once it exposed its tools through MCP.
  • Show up at the moment of need. Shishir Mehrotra would build interventions that recognize what the person is doing and bring the context with them, such as Superhuman's Knowledge Checker catching an out-of-date number before someone sends it, ahead of a broad agent that waits for a prompt.
  • Prototype, then give it an owner. Sam would prototype against real inputs and collect 10 to 100 structured evaluations before the final ranking. Rachel would give the first surface a named owner and a decision date, and measure completed jobs, repeat use, human corrections and failed handoffs.

Group chat with Dennis, Sam, Rachel, Aparna, Shishir — the AI Product work group

Question:

Which parts of an existing product should become agentic first?

Rachel Wolan
Rachel WolanFormer CPO of Webflow and VP and GM of Dropbox Core and AI
Start with a bounded job inside the workflow customers already use, where they can inspect and edit the result before it reaches production. At Webflow, our AI Site Builder gave customers a useful first step: describe a site and get a draft. We later learned the agent needed to stay with them as they edited in the Designer. Our separate App Gen product taught a sharper lesson: customers asked for reusable components inside their existing sites, so we redirected that work toward components they could place on a page.rachelwolan
I’d rank candidate surfaces by three questions: Is the job frequent and painful? Can the agent produce a bounded unit the customer already works with? Can the customer review the change under the right permissions before publishing? The Webflow AI Assistant had real tool access, but enterprise customers wanted brand rules, roles, and granular review before trusting it with production sites. Those controls belong in the first release plan, right alongside the agent’s capability.rachelwolan
Aparna Chennapragada
Aparna ChennapragadaVP of Wearables at Meta. Former CPO at Microsoft
I’d score the first surface on a second axis beyond workflow fit: how much judgment it asks the agent to exercise, and how easily the user can verify the answer. In Copilot, I’ve used the example of a weekly request to gather customer-issue emails and send me a digest. It starts with a supervised recurring task; broader skills and more delegation can come as model ability and checks improve.emergingtechbrew
The spec should describe the judgment the user wants, not merely a tool operation. For a meeting, I’d ask for the important points, key risks, and how sentiment changed; “summarize the transcript in five bullets” sets a much lower bar, while “handle all my email” gives the agent too much scope. Build a small set of these real requests, test the outputs with users, and revise the boundaries before expanding delegation.Substack
Sam Stone
Sam StoneSVP of Product at EvenUp. Former Head of Product at Tome
I'd start where users already assemble information, draft an artifact, and review it before sending. At EvenUp, we launched early access to Express Demands so legal professionals could generate and edit demand packages with AI in minutes. The editing step matters: the lawyer has a clear deliverable and a natural chance to catch errors before the package leaves the product.LinkedIn
For each candidate surface, I'd ask three things: Does the work take several steps that the product can help complete? Can the user see the source material and correct the result? Can we observe whether they accept, edit, or discard the output? I wrote about using those natural actions as feedback, rather than asking users to rate every response.Medium Start with a bounded draft-and-review workflow, then expand what the agent can do as you learn where users still have to intervene.
Dennis Yang
Dennis YangPrincipal Product Manager, Generative AI at Chime. Co-founder and former CPO of Dashbot
Support conversations are a useful map of where to begin. They expose the requests people cannot complete through the current flow. In my work on conversational analytics at Dashbot, the raw language was more useful than a clickstream because it showed what users were trying to do. I also argued for keeping buttons where they work and using conversation where users need to express a more specific request.Medium
For an existing product, I’d rank candidate tasks by observed request volume, how often the current flow fails, whether the agent has reliable data and tools to finish the task, and the cost of a wrong action. Start with grounded support tasks such as explaining an account event or guiding a member through a known process. Keep sensitive account changes behind explicit confirmation and a clear handoff. At Chime, we’ve shared that 70% of support interactions are AI-powered, alongside a 60% reduction in cost to serve and more than doubled member satisfaction. Those are results for support as a whole, not proof that every financial action should run autonomously.LinkedIn
Rachel Wolan
Rachel WolanFormer CPO of Webflow and VP and GM of Dropbox Core and AI
Aparna’s verification test makes the rollout decision much clearer. I’d give the first agentic surface a named owner and a decision date, then measure completed jobs, repeat use, human corrections, and failed handoffs. A feature can get plenty of prompts while quietly making people clean up its work. In my framework for AI distribution, I also count maintenance cost per successful retained workflow, because permissions, evals, and support keep accumulating after launch.rachelwolan
Shishir Mehrotra
Shishir MehrotraCEO of Superhuman (formerly Grammarly). Co-founder of Coda and former Chief Product Officer of YouTube
I think distribution changes the ranking. A task can be frequent and easy to verify, yet still fail if the user has to stop working, open a separate chat, explain the context, and paste the result back. We’ve built Superhuman Go to appear alongside a doc, inbox, or tab and bring in an agent based on what the person is doing.X
So I’d add one question to the framework: Can the product recognize the moment of need and bring the right context without making the user ask? Our Knowledge Checker, for example, catches an out-of-date number before someone sends it; the Email Assistant helps sort mail and draft replies in the inbox. Both meet a person inside an existing task. I’d prioritize those timely, contextual interventions before building a broad agent that waits for a prompt.X
Sam Stone
Sam StoneSVP of Product at EvenUp. Former Head of Product at Tome
I'd put a small prototype before the final surface ranking. A task can be frequent, bounded, and easy to review, then fail because the product lacks the context needed to produce a useful result. At Tome, I found it useful to prototype against real inputs and ask colleagues or users for 10 to 100 structured evaluations, with notes on the failures. That often gave us a clearer next build decision than an early automated score.Medium
For each candidate, give evaluators the same user request and available product context. Have them judge whether the output is usable, where it needs correction, and whether the needed correction can happen inside the existing workflow. The first surface should earn its place through those examples before we commit to building the full agent.
Rachel Wolan
Rachel WolanFormer CPO of Webflow and VP and GM of Dropbox Core and AI
Shishir’s moment-of-need test also changes how I’d research the first surface. When we exposed Webflow capabilities through MCP, people used outside agents for landing pages, bulk CMS work, asset management, and content workflows. That behavior gave our team a much better map of demand than a brainstorm of possible AI features. But the same tool access did not make our in-Designer Assistant ready for broad use; we still needed the review and permission controls enterprise teams had asked for. I’d use observed agent workarounds to choose the job, then test whether the native product can complete it safely.rachelwolan

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In This Conversation

  • Dennis Yang
    Dennis Yang

    Principal Product Manager, Generative AI at Chime. Co-founder and former CPO of Dashbot

  • Sam Stone
    Sam Stone

    SVP of Product at EvenUp. Former Head of Product at Tome

  • Rachel Wolan
    Rachel Wolan

    Former CPO of Webflow and VP and GM of Dropbox Core and AI

  • Aparna Chennapragada
    Aparna Chennapragada

    VP of Wearables at Meta. Former CPO at Microsoft

  • Shishir Mehrotra
    Shishir Mehrotra

    CEO of Superhuman (formerly Grammarly). Co-founder of Coda and former Chief Product Officer of YouTube

See all

Frequently Asked Questions

  • What should a first eval setup for an LLM product include?

    A sheet of 50 to 100 real outputs graded by people with notes, a rubric checked against customer evidence, a fixed bug set and rule checks in code, and an agreed list of failures that block a launch.

  • How do you know your LLM evals measure what users care about?

    Build eval cases from failures users hit on real tasks, then compare scores with what people do next: rephrasing the question, editing heavily, abandoning the answer or spending time checking it.

  • How can a working professional build AI skills that last?

    Practice on one recurring task: write down what good looks like, let AI draft while you review, and track rework and review time to see whether the whole task gets better.

  • How is AI changing the product manager's job?

    Execution and coordination get cheaper, so more of the job is choosing the problem, judging output and supervising agents. Sachin Rekhi still wants PMs talking to customers themselves, and Ami Vora wants them close to those conversations.

  • Which operations work can AI agents handle today?

    High-volume work where the answer is written down, the action can be undone and checking is quick: triage, documented support answers, first drafts and summaries. Money, policy exceptions and context nobody wrote down still need a person to approve.

  • How will AI change services businesses?

    The group expects AI to take on more drafting and preparation while firms sell judgment and accountable delivery. Shishir Mehrotra would price an accepted deliverable with a defined scope, and count review, revisions and client setup in its cost.

  • Why doesn't AI adoption show up in business results more often?

    Usage is an input. Results come from changing one workflow and measuring its outcome, including the time spent checking and fixing AI output and whether a decision changed.

  • How should engineering teams work when AI coding agents write much of the code?

    The group would set review by area of the codebase and type of task, keep PRs small enough to read, prove the tests fail when something breaks, and have newer engineers plan and debug by hand.

  • Where does AI speed up design and content work?

    Design variations, throwaway prototypes, first drafts and one-prompt sites. Judging which draft is good, matching the product and keeping scope in check stay slow.

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