Rupa Chaturvedi

Head of Merchant & Ads Design at Uber, Adjunct Lecturer at Stanford University

I’m a UX Design Leader and AI/GenAI specialist who blends 0→1 invention with platform-scale delivery. I build high-performing global teams, architect systems and information frameworks, and turn ambiguous problems into durable products that move KPIs.Highlights:- 0→1 to v2 at scale: From concept to launch to systematized patterns—GenAI assistants, video discovery, conversational shopping, AR/3D visualization.- Platform UX and IA: Unifying fragmented surfaces into responsive, multi‑platform systems; shaping primitives for workflows, analytics, and monetization.- Design org building: Scaling diverse, distributed teams; codifying operating cadences; partnering with research and content; aligning roadmaps to outcomes.- AI design enablement: Equipping UX orgs to design AI responsibly—expanding influence beyond UI via model evaluation, systems thinking, AI‑first mental models, and AI workflows.Selected outcomes:- Built a 14-person global design org across 3 continents; shipped 80+ features in under 5 months; consolidated a multi‑platform system; meaningful KPI impact.- Incubated 0→1 GenAI initiatives (consumer LLM assistant, Merchant Copilot, AI creative tools, video discovery)—adopted by SMBs and enterprises globally.- Scaled a conversational shopping product from 0→1 to 1M WAUs in under 6 months; 20+ patents granted/published; launched AR “View in Your Room/AR View” with press coverage.- Taught and enabled 1,500+ professionals via a human-centered AI institute; consistent 5/5 ratings; partners include Reforge, Stanford, Maven.Today, I focus on platform UX, AI-assisted experiences, and design org development—bringing product strategy, systems thinking, and responsible AI to enterprise and SMB workflows.

UX Design Manager

Over 4000 people signed up for my talk on Designing for Trust in AI Agents yesterday.

As the industry continues to dig deeper on what AI agents can do, the question of whether users will actually trust them to do it seems to be top of mind for many of us product builders.

I've been experiencing this firsthand. I've tested Claude Cowork, Cora, Manus, and a handful of other agents over the past few months. They're fast. They're thorough. And I keep finding myself unable to use what they produce.

The pattern I keep landing on: we've designed agents to optimize for speed to output instead of speed to understanding. The industry celebrates execution time. Users care about whether they can actually do something with the result. Those metrics have almost nothing to do with each other.

I wrote up the core ideas from the session in this week's newsletter. It goes deeper on where the trust gap actually lives and why the usual mechanisms (transparency, guardrails, reversibility) don't solve the underlying problem.

If you'd like to watch a replay of the talk, comment AIUX and I will send you the recording link.

Design & AI Leader | Stanford Lecturer | AI enablement for UX orgs | ex-Uber, Google, Amazon

This is the AI UX Brief - my weekly newsletter on designing intelligent systems, leadership in the AI era, and navigating the messy reality of AIUX. F

Open article: The Speed Paradox: Why AI Agents Feel Impressive But Unusable by Rupa Chaturvedi • 7 min read

The Speed Paradox: Why AI Agents Feel Impressive But Unusable

I help Product Managers break into AI Leadership - no coding required! Ex-Alexa AI Principal Product Manager | Launched 1st GenAI Answers on Alexa | Top 100 Women of the Future Winner | Reforge Instructor | Speaker

Polly Allen has spent over 20 years building and leading software teams, most recently as a Principal Product Manager at Amazon Alexa, where she guided cross-functional science and engineering groups at the cutting edge of AI. She specializes in natural language applications—search, discovery, understanding, and generation—and in 2020, she led the launch of Alexa’s first automatically generated web content summaries (yes, powered by the same transformer technology behind today’s ChatGPT).

But Polly’s story isn’t just about technology. After years in the deeply technical world, she became convinced that the future of AI shouldn’t be shaped only by coders and data scientists. The biggest breakthroughs will come when product and business leaders—those closest to customers, strategy, and impact—have the tools and confidence to lead AI initiatives. That belief drives everything she does today.

Now, through her company AI Career Boost, Polly helps experienced leaders step into AI roles and lead AI product development with confidence—without needing a computer science degree. She also hosts two podcasts, AI Product Leader and AI Afterhours, where she shares insights, stories, and candid conversations about building the future of AI.

An experienced angel investor and past corporate board member, Polly has advised startups, spoken at global conferences, and earned degrees from MIT, the University of Victoria, and UBC. Above all, she’s on a mission to open the doors of AI leadership to a far wider range of thinkers and builders—and to make sure the next wave of AI innovation is driven by leaders who understand both people and technology.

👉 Join Polly’s AI Career Boost Newsletter to stay connected, get behind-the-scenes insights, and explore how you can lead in the AI era.

Polly M Allen

AI Career Boost turned three years old in December 2025. 🎂

Here are the top 3 AI leadership lessons I’ve learned working with thousands of senior product leaders trying to lead AI initiatives — from early use case selection all the way to production.

A lot of them came in quietly worried about the same thing:
“Am I already behind — or am I just missing something everyone else seems to know?”

Here’s what I’ve seen, watching who actually pulls ahead.
1️⃣ Leaders who get hands-on — even a little — end up years ahead of the ones who don’t.

Not because they’re smarter.
Because firsthand experience collapses confusion faster — especially with AI. More so than any other technology I’ve worked with in 20+ years.

2️⃣ The real difference between ‘technical’ and ‘non-technical’ leaders isn’t skill — it’s permission.
Technical leaders don’t wait to be invited.
They poke, test, break things, and learn reflexively.

3️⃣ When leaders get hands-on and bring their teams along, something shifts.
Shared prototypes.
Shared prompts.
Admin access instead of gatekeeping.

AI stops feeling intimidating — and starts feeling collaborative.
That’s the pattern I see again and again.

For leaders who were starting to feel exposed or sidelined, this is often the moment their credibility snaps back into place.

If you want to learn how to lead this way — without becoming an engineer or starting over — I’m teaching a free masterclass on Jan 20:

How senior leaders stay essential in the age of AI
👉 https://lnkd.in/g64gFChW

Grab your seat quickly - they're going fast!

I help Product and Business Leaders thrive in AI Leadership - no coding required! Ex-Alexa AI Principal Product Manager | Launched 1st GenAI Answers on Alexa | Top 100 Women of the Future

If 2025 was about learning what’s ✨possible✨, 
2026 is about making it 💪real💪.

2026 already feels like a builder’s year - for ICs and leaders alike.

Not a year of demos-for-demos’ sake.

Not a year of “AI strategy” decks that never leave the slide.

A year of:
 – shipping real things
 – testing ideas in the wild
 – turning AI curiosity into actual capability
 – building signal, not noise

The leaders who will stand out this year aren’t the ones who know everything about AI.

They’re the ones who can apply it, evaluate it, and make it useful inside real products and teams in real-world situations.

*That’s the work.*

And it’s the most exciting version of this moment.

✨Happy New Year  ✨. What are YOU building in 2026?

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Product managers & leaders, I'm begging you: DON'T LEARN CLAUDE COWORK.

I'm serious. The most dangerous thing about Cowork is that it will make you feel like you've invested in being on the leading edge - and you'll miss out on the real transformation on how work gets done that underlies the buzz about Claude Code.

As a former developer, I've been obsessed with Claude Code for non-coding tasks for at least 3 months, and I've been trying out my workflows in Cowork. Of course it will grow - but in it's current form, it doesn't change the way you work.

The MENTAL SHIFT you go when using Claude Code, from doing work to designing repeatable workflows and systems, is the most important shift you can make right now to understand how Agentic AI will change the face of digital work. 

I'll be breaking down the important differences and how this work relates concretely to product management and leadership tasks in our next AI Career Boost newsletter. Follow for more! 🔔 

AND we'll be diving into this in my next Masterclass, "The Path to AI Product Leadership", happening tomorrow.

Seats are limited!-> https://lnkd.in/g64gFChW

Claude Cowork vs. Claude Code: Why Product Leaders Shouldn't Get Stuck at Cowork

A lot of senior leaders are quietly terrified they’re about to be forced back into IC work.  Especially because of AI.

I hear this a lot right now:

“If I’m not technical enough, am I going to be sidelined — or worse, cut?”

Here’s what’s real: You don’t need to become an engineer. BUT: you also can’t stay purely high-level anymore. This is counter-intuitive for a lot of leaders: you spent years getting out of the execution weeds, right?

In the AI era, leaders lose credibility when they can’t tell what’s real.

The leaders who stay influential aren’t the most technical — they’re the ones who’ve gotten hands-on just enough to:
• ask better questions
• spot bullshit
• understand real constraints
• and translate tradeoffs for their teams

You don’t need years.
You need the right kind of exposure.

I’m breaking this down live on Jan 20 in a free session for senior leaders on staying essential in the age of AI. If you’re ready to find the right balance between leading and building - grab your seat early! 

Https://https://lnkd.in/g64gFChW

graphical user interface, text, application, chat or text message

Excited to be keynoting at the DataConnect Conference West in May!

Please welcome our first Keynote Speaker for DataConnect Conference West 🎤

Polly M Allen, AI Product Coach and Advisor, Founder of AI Career Boost, and a leading voice in making AI careers more accessible. Polly brings deep expertise at the intersection of AI, product, and career growth, and we can’t wait for her to share insights that will inspire, challenge, and empower our community.

This is just the beginning. Stay tuned for speakers.

Your CEO's teenager shipped a working demo over winter break. 

A year ago, "vibe coding" wasn't even a term. Now Replit, Lovable, and Cursor are baseline. And this month, Claude Cowork put serious AI agent power into a simple chat interface anyone can use. 

When everyone can prototype, the credibility gap moves. It's no longer "can you demo?" It's "can you ship?" 

In this week's newsletter, I break down: 
→ The 4 types of prototypes (and why confusing them kills your credibility) 
→ Which tools to use for each 
→ How to articulate the path from idea to production 

(This is based on my favorite tools & stack. What did I miss? What do you prefer and why?)

Plus insights from Sudha Kumar on why your data probably isn't AI-ready.

A year ago, "vibe coding" wasn't even a term - it wasn't coined until February 2025. Now your CEO's teenager is shipping demos over winter break. Repl

Open article: Everyone Can Build a Prototype Now. That's the Problem. by Polly M Allen • 4 min read

Everyone Can Build a Prototype Now. That's the Problem.

I see senior product leaders make the same AI mistakes over and over — and they’re rarely technical. They’re leadership mistakes.

Here are 5 that quietly erode credibility in the AI era:
• Treating strategy documents as proof of execution
 • Bringing a deck to a demo fight
 • Not knowing what kind of prototype to ask for
 • Delegating too many decisions because AI feels “too technical”
 • Ignoring ROI and total cost of ownership beyond the prototype

AI didn’t make leadership harder.
It made execution visible.

The leaders who are winning funding and trust aren’t coding,
they’re showing teams how they expect work to happen.

Slides explain intent.
Prototypes demonstrate judgment.

I break down why these mistakes keep costing leaders credibility, and how to avoid them in the full video here: https://lnkd.in/gmDAqXgF

👉 Join the free masterclass on leading AI from prototype to production. Link in comments.

#AILeadership #ProductLeadership #ExecutiveLeadership #DigitalTransformation

Attention Senior Product Leaders and Executives!

Reimagine your role and stay ahead in the AI era. FREE Masterclass with an Industry Expert in AI Product Leadership.

Here’s what you'll learn:
• How to lead AI initiatives in 2026 effectively - no coding background required.
• Ways to spot high-impact opportunities and avoid the hype.
• How to stand out as an AI leader in any organization or venture.

📅 Thursday, January 29th at 12PM PDT

Don’t miss this chance to elevate your AI leadership journey. Space is limited. Reserve your spot now!

👉 https://lnkd.in/gbf4yX7x 👈

#AI #ArtificialIntelligence #LearnAI #Free #AIProductLeadership #FREEMasterclass

I see you. You have AI product ideas.

You also have back-to-back meetings, a demanding job, and maybe 2 hours of actual energy left at the end of the day.

So the ideas stay ideas. Another week passes. You watch someone else launch the thing you've been thinking about for months.

Here's what changed for me: I stopped waiting for the "perfect time" and started with a framework that actually works.

Tomorrow, Yuying Chen-Wynn and I are teaching it live — for free.

In 45 minutes, you'll:
→ See real case studies of $100K AI products (built by non-technical people)
→ Validate YOUR best idea using our 3-part framework
→ Watch AI tools build actual products in real-time

The window for this opportunity won't stay open forever. The tools that exist today didn't exist 2 years ago.

Nearly 300 people have already signed up.

Thu, Jan 15 @ 12pm PST | Free | Virtual
Grab your seat -> https://lnkd.in/gbRXsuGc

Product managers & leaders, if you're thinking about investing time to learn Claude Cowork, PLEASE read this first.

I'm begging you: DON'T LEARN CLAUDE COWORK. Invest in trying Claude Code instead.

Cowork is genuinely useful. It's a great executive assistant. But if you stay there, you're missing the bigger shift.

Cowork makes you an AI user. Claude Code makes you an AI builder.

That's not a small difference. That's the difference between delegating a task and delegating a system. It's keeping you in the same mindset that keeps so many aspiring AI enthusiasts in the 'still just using ChatGPT for things' camp.

Cowork will help you work faster. Claude Code will change how you work.

The mental shift from "doing work" to "designing systems that do work" is THE most important shift you can make right now. It's how Agentic AI will change digital work - for everyone.

I broke down 4 scenarios showing exactly where the gaps appear, why they matter for product leaders, and how to get started. 

https://lnkd.in/eEySajBm

I hope you'll believe me, and thank me later. 
I hope you'll share for anyone in your circle who wants to be vastly ahead of the Claude Cowork crowd in 2-3 months' time. 
And I hope you'll help me spread this, because of how much it matters to product leaders trying to stay relevant today. Don't get stuck in the non-builder trap.

(And because it's at least one post today NOT about Moltbot!)

Claude Cowork vs. Claude Code for Product Leaders

I spent years building AI products inside Amazon — and now I help senior product leaders stay indispensable in the age of AI.

You don’t need to become an engineer.
You do need enough hands-on fluency to ask the right questions, challenge bad assumptions, and lead when things get messy.

If you’re feeling sidelined or second-guessed in AI conversations, it’s not because you don’t belong.

It’s because the bar quietly moved — and no one showed you how to cross it without starting over.

I’m teaching exactly how to do that in a free masterclass, “How Senior Product Leaders are Staying Essential in the Age of AI”. Grab your seat now -> link in comments bellow. #ProductManagement #AIcareers #aiproductmanagement #aileadership #executiveeducation

Unlock the full potential of AI in your product management leadership journey. 

Here’s what you'll learn:
🟣 What does it really mean to lead AI initiatives in 2026?
🟣 How do you identify high-impact AI opportunities and avoid overhyped distractions?
🟣 What’s the fastest way to become the go-to AI leader in your organization – or build projects that truly stand out?

Join Polly Allen, the trailblazer behind the first generative AI answers on Amazon Alexa in 2020, for a free webinar.

📅 Thursday, January 29th at 12PM PDT

⏳ Spots are filling fast — grab yours now! ⬇️
🔗 https://lnkd.in/gbf4yX7x

#AI #ArtificialIntelligence #LearnAI #Free #AIProductLeadership #FREEMasterclass

Open article: Registration Page - The Path to AI Product Leadership WEBINAR 2026 by aicareerboost.com

Registration Page - The Path to AI Product Leadership WEBINAR 2026

Claude Cowork is powerful. But it's no Claude Code.

I've been obsessed with using Claude Code for non-software workflows since November. As a former developer, a lot of things just clicked: managing cascading context in folders, overt context clearing/management/compacting, creating repeatable shortcut commands on the fly as you discover you're doing things more than a few times, easy selective sync to git hub for version control for reversions if you go off on a tangent you don't like later.

I like Cowork and frankly, I'm not in love with working in the terminal -  but I miss too many things.

(Also, how much did Microsoft and Apple fumble the ball, if we're all using Claude Cowork to organize our desktop folders instead of something they should have built??)

Agree? Disagree? What's your favorite use case so far for either Claude Code or Claude Cowork?

It’s easy to overlook a prototype. It is hard to guide it to production.

That execution capability is what separates a standard PM from an indispensable AI leader.

You don’t need to code to do it; you need the right strategic framework.

Join Polly Allen (former Amazon Alexa Principal PM behind its first generative AI launch) to learn how to lead this transition.

We’ll cover:
🟣 The "Prototype to Production" Gap: How to guide teams from the sandbox to the market.
🟣 The Right Altitude: How to lead AI initiatives without getting lost in the technical weeds.
🟣 The Indispensable Factor: Moving from managing features to orchestrating AI business value.

📅 Tue., Jan. 20 at 12pm PT | 3pm ET. Space is limited. Reserve your spot now.

🔗https://lnkd.in/gASfwZWc 👈

#AI #AILeadership #ProductLeadership #AICareer #LeadershipDevelopment

If you’re building with AI but not actively shaping how it learns, you’re falling behind faster than you think.

In this clip, Sudha Kumar explains why data definitions, rules, and real-world context matter more than flashy demos. AI reflects the decisions you encode into it — good or bad.

This is how serious product leaders stay competitive: less hype, more intention.

🎬 Watch the full episode here: https://lnkd.in/gqaxD78V

#AIProductManagement #AILeadership #ProductLeadership #EnterpriseAI #DataStrategy

The most dangerous thing in tech right now? A majority of product leaders feel "confident" about AI... while missing the revolution happening under their noses.

I'm seeing too many orgs celebrating their "AI transformation" while shipping chatbots driven by top-down requests and cost-cutting automation. We're optimizing the wrong things, asking the wrong questions, and dangerously overconfident about our readiness to lead in the AI era.

This isn't about learning prompt engineering or keeping up with the latest LLM releases. It's about fundamentally reimagining what it means to create value when AI is a core capability — not just a feature.

Three questions every product leader should be asking:
🤔 What if AI isn't just another tool in our stack, but a complete reinvention of how users interact with technology?
🤔 What if the "product surface" isn't a UI anymore, but an intelligent agent that works alongside users?
🤔 What if our role isn't to define features, but to architect intelligence that augments human capability?

Join Polly Allen, the trailblazer behind the first generative AI answers on Amazon Alexa in 2020, for a free webinar as she guides you through the evolving landscape of AI product leadership. 

📅 Thursday, January 29th at 12PM PDT

Space is limited. Reserve your spot now.
🔗https://lnkd.in/gbf4yX7x 👈

#AI #ArtificialIntelligence #LearnAI #Free #AIProductLeadership #FREEMasterclass

If AI makes you uncomfortable, that’s your signal not to avoid it, but to engage with it.

In this episode, we unpack why fear pushes thoughtful leaders away from the table… and why that’s the real risk. The people shaping AI shouldn’t only be the loudest or fastest movers.

Your perspective matters more than you think.

🎧 Full episode: https://lnkd.in/gs9fRyTJ

#AILeadership
#TechLeaders
#FutureOfWork
#ProductManagement
#AIAtWork

We, collectively, are too quiet about this: your personal data is TOO easily weaponized, against you. Right now. No additional advancements or AI leaps required.

I hope 2026 can be the year consumers finally start valuing trust, good actors and the companies willing to stand up and fight for basic rights. For all of us building software: this article is a great place to start digging in, and asks an important question:
"What are you willing to say no to?"

Thanks Ariba Jahan!

Head of Transformation @ Anomaly ✦ Helping brands build for what’s next ✦ product, tech, design & consumer experience ✦ Creator & Author of Unmissables ✦ Toddler Mom

"Can you do facial?" 
One Border Patrol agent to another, standing over a 16-year-old on a bike near his high school in Aurora. No ID. No warrant. Just a phone pointed at his face. 

That video went viral last year. But here's what the coverage missed: the infrastructure that made that moment possible wasn't built by the government. 

It was built by the apps on your phone. 

I went down a rabbit hole reading FTC enforcement actions, congressional testimony, investigative journalism, and academic research. The picture that emerged: 

→ 750+ data brokers registered in the U.S. (only 4 states even require registration) 
→ LexisNexis holds 282 million identity profiles. ICE searched them 1.2 million times in 7 months. 
→ For $160, journalists bought a week of location data on 600+ Planned Parenthood clinics 
→ Three weeks after the FTC banned Gravy Analytics from selling location data, they got hacked. 17 terabytes stolen. 30 million records exposed. The distance between your period tracker and a prosecutor is maybe 3-4 handoffs. None of them require your permission. 

I've built products that use location data. I've designed experiences that ask about your mood, goals, interests. Used well, this data makes products better. I know what that looks like. 
I also know what it looks like when the same infrastructure gets pointed somewhere else, without consent. 

I wrote this piece for anyone who builds products, designs experiences, or makes decisions about data collection.  

What are you willing to say no to? 

Read here: https://lnkd.in/e9XWEU6V

Most businesses asking “Why don’t I show up in ChatGPT?” are missing one thing: structure.

In this AI Product Leader episode, Maggie Mae breaks down the 3-part schema stack that actually gets businesses cited by AI tools:
• Off-page signals (directories + reviews)
• On-page clarity (classic SEO still matters)
• Technical schema that AI can read

This isn’t theory — it’s showing real results in under an hour for some teams.

If you care about AI visibility, this is required listening.

🎙️ Full episode: https://lnkd.in/gsMP9AWN

#AIProductManagement #AILeadership #GenerativeAI #ProductLeaders #AIStrategy #SearchVisibility

“AI will confidently walk you off a cliff, and that’s how you learn.”

Maggie Mae shares why waiting until you “feel ready” to use AI is the wrong move.

If you’re a PM, founder, or leader:
• Prototyping is low risk
• Curiosity beats credentials
• Breaking things is part of the deal

The fastest learners aren’t perfect — they’re willing to try.

🎧 Full episode: https://lnkd.in/gpgppeE9

#AIProductManagement #AILeadership #GenerativeAI #ProductLeaders #AIStrategy #SearchVisibility

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The Battle

Rupa Chaturvedi

Polly M Allen

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Rupa Chaturvedi's LinkedIn Performance

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