How this PM uses AI for PRDs, JIRA tickets, and replying to coworkers | Dennis Yang (Chime)

How this PM uses AI for PRDs, JIRA tickets, and replying to coworkers | Dennis Yang (Chime)

How I AIOct 27, 202550m

Claire Vo (host), Dennis Yang (guest)

Cursor as PM workflow hub (non-coding use)Markdown-first writing + live previewGit/source control for product artifactsMCP interoperability (Jira, Confluence, Notion, Figma, custom APIs)Publishing docs + round-trip linkingAI-assisted comment triage and repliesPRD-to-Jira ticket generation and status automationMorning briefing systems (ChatGPT memory vs tool-based briefings)“Super MVP” agent prototyping inside Cursor

In this episode of How I AI, featuring Claire Vo and Dennis Yang, How this PM uses AI for PRDs, JIRA tickets, and replying to coworkers | Dennis Yang (Chime) explores a PM’s Cursor-based AI system for docs, Jira, and updates Dennis Yang (Principal PM for GenAI at Chime) walks through using Cursor as an AI “hub” for everyday product-management work, emphasizing speed, multi-model access, and tool interoperability via MCPs.

A PM’s Cursor-based AI system for docs, Jira, and updates

Dennis Yang (Principal PM for GenAI at Chime) walks through using Cursor as an AI “hub” for everyday product-management work, emphasizing speed, multi-model access, and tool interoperability via MCPs.

He drafts PRDs in Markdown inside Cursor (with preview), source-controls them with Git, then publishes to Confluence/Notion and links back to the canonical doc for round-trip workflows.

He uses AI to read and triage stakeholder comments, draft replies for human approval, and then post responses as the authenticated user—keeping the PM “in the loop” while removing toil.

Finally, he shows how to generate high-quality Jira epics/stories directly from PRDs, automate weekly status reports from Jira activity, and prototype an agentic “morning briefing” product in a ‘super MVP’ way using tool-calling and model switching inside Cursor.

Key Takeaways

Cursor is valuable to PMs because it combines models, files, and tools.

Dennis prefers Cursor as an AI UI because it supports multiple LLMs, has native access to a local file system for durable artifacts, and connects to key PM systems through MCPs.

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Markdown + preview turns an IDE into a practical document editor.

Working in Markdown aligns with LLM strengths, and using a Markdown preview extension makes PRDs readable and shareable without living in Google Docs/Confluence while drafting.

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Treat PRDs as versioned artifacts, not static snapshots.

By putting PRDs under Git, PMs get change tracking and can imagine a workflow where docs live adjacent to code—encouraging continuous updates as learning happens during development.

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Interoperability becomes a selection criterion for AI workflows.

Both hosts stress that tools that “lock content away” are less useful; the winning systems will let content move fluidly across repos, docs, and task trackers via standardized interfaces like MCP.

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Close the collaboration loop: publish, collect comments, respond with AI assistance.

Dennis exports early PRDs to Confluence/Notion for broad commenting, then has AI read comments, prioritize them, draft responses, and (after review) post replies—reducing manual communication overhead.

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PRD-to-Jira automation eliminates a major PM toil: translation fatigue.

Cursor reads the PRD and generates an epic plus well-structured story tickets (acceptance criteria/Gherkin/DoD), avoiding the common “just link the PRD” shortcut that shifts burden to engineers.

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Status reporting improves when Jira becomes the “queryable” source of truth.

By generating weekly status reports via JQL from Jira activity, Dennis saves time and increases quality; engineers also add better ticket context because they know it will be surfaced in reports.

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Prototype agentic products without code by using Cursor as a tool-calling runtime.

Dennis drafts a PRD and TDD, then writes “super MVP” instructions that call an MCP (e. ...

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Notable Quotes

The reason why Cursor is my favorite UI for the AI is... it has all the interfaces and interactions and connections into the tools that are critical for my daily product management.

Dennis Yang

The most useful solutions will have interoperability as one of the key things.

Dennis Yang

If that's my content, and I want all my systems to be able to access it when it needs to.

Dennis Yang

Cursor reads the PRD... and then splits the effective tickets. The story tickets in particular are very, very well described.

Dennis Yang

It's really improving communication and reducing the time I'm spending writing status, and at the same time, improving the status content... up to leadership and across the organization.

Dennis Yang

Questions Answered in This Episode

When you publish PRDs to both Confluence and Notion, how do you decide which one is the “source of truth,” and how do you prevent drift between them?

Dennis Yang (Principal PM for GenAI at Chime) walks through using Cursor as an AI “hub” for everyday product-management work, emphasizing speed, multi-model access, and tool interoperability via MCPs.

Get the full analysis with uListen AI

What are the specific Cursor Rules you use for (a) Jira ticket creation and (b) weekly status reports—and what did you learn after iterating on them for two months?

He drafts PRDs in Markdown inside Cursor (with preview), source-controls them with Git, then publishes to Confluence/Notion and links back to the canonical doc for round-trip workflows.

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In the comment-reply workflow, what’s your approval/check process to prevent incorrect or tone-deaf AI responses from being posted as you?

He uses AI to read and triage stakeholder comments, draft replies for human approval, and then post responses as the authenticated user—keeping the PM “in the loop” while removing toil.

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What minimum information must be in a PRD for your PRD→Jira generation to work reliably (scope boundaries, non-goals, acceptance criteria, rollout plan, etc.)?

Finally, he shows how to generate high-quality Jira epics/stories directly from PRDs, automate weekly status reports from Jira activity, and prototype an agentic “morning briefing” product in a ‘super MVP’ way using tool-calling and model switching inside Cursor.

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You mentioned MCPs can be flaky (red/green toggling). What reliability practices (fallbacks, tool scoping, retries, logging) have made this workable day-to-day?

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Transcript Preview

Claire Vo

We've seen so many people use tools like Cursor to write code. We actually haven't seen anybody yet just using Cursor to write, [chuckles] and that's what you're doing.

Dennis Yang

The reason why Cursor is my favorite UI for the AI is it has all the interfaces and interactions and connections into the tools that are critical for my daily product management.

Claire Vo

I think we're at this really interesting place where, because these primitives are being built in the context of software engineering, you're getting these concepts of markdown, Git, commits, change tracking in these tools that used to be very software engineering-centric.

Dennis Yang

The most useful solutions will have interoperability as one of the key things. So any system that if it feels like it's locking that content or data away, I'm not gonna prefer to use that system. I don't care why you have these modes. I'm sure there's a good reason, but if that's my content, and I want all my systems to be able to access it when it needs to. It's really improving communication and reducing the time I'm spending writing status, and at the same time, improving the status content that is being circulated both up to leadership and across the organization. [upbeat music]

Claire Vo

Welcome back to How I AI. I'm Claire Vo, product leader and AI obsessive, here on a mission to help you build better with these new tools. Today, we have a fun conversation with Dennis Yang, Principal Product Manager for Generative AI at Chime. Now, this one makes me sweat a little bit because I thought I was the alpha AI-powered PM, and Dennis shows me his workflows, which are way beyond anything I've seen before. He's gonna show you how to use Cursor to not only write your PRDs, but push them into Confluence or Notion, read comments, reply to comments, prototype AI tools, and more. This is a awesome one for anyone out there who's curious if you can make use of Cursor without writing code, and I think you're gonna learn a lot. Let's get to it. AI is supposed to make work easier, but I've been there: weeks of setup, endless back and forth with engineering, and yet another tool the team never really adopts. That's why I use Zapier's AI orchestration platform. It connects with nearly 8,000 apps, so I can finally put AI to work without the drama, without the delays, and without pulling engineering in every time I want to automate something. With Zapier, you can roll out AI-powered workflows that do real work across your whole company in days, not weeks. I use Zapier every single day. It automatically responds to leads with enriched, personalized data, it checks my calendar weekly and offers smarter ways to manage my time, and it even drafts emails for every new request that lands in my inbox. All of that running quietly in the background, so I can focus on the work that matters. And Zapier's built for scale. With enterprise-grade security, compliance, and governance, it's trusted by teams at Dropbox, Airbnb, Opendoor, and thousands more. Go to try.zapier.com/howiai to learn more about how Zapier can bring the power of AI orchestration to your entire org. Dennis, thanks for joining How I AI. I am really excited about this episode because we've seen so many people use tools like Cursor to write code, but we actually haven't seen anybody yet just using Cursor to write. [chuckles] And that's what you're doing, um, as, as a product manager and somebody who's thinking about strategy all the time. So before we dive in, why Cursor? Why writing? You're not writing a lick of code in here for at least this use case that we're gonna see. So how did you kind of get into this flow with this AI-powered IDE?

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