# Brian Greenbaum - Portfolio

> Lead UX Designer & Product Manager | For 20 years I've straddled design and product management at companies like Pendo, Square, Zendesk, Sakara, Weebly, and Intuit. This dual background is a core strength: I bring product judgment to design work and pair UX craft with an understanding of business goals, analytics, and a passion for AI. Currently leading design for AI products at Pendo.

## About

I'm a Senior Staff Product Designer at Pendo based in New York City, where I lead design for AI agent initiatives. I apply 20 years of UX design, product management, and engineering to building AI products.

My work covers discovery, prototyping, UX pattern development, and end-to-end delivery. I work closely with designers, engineers, and product teams to ship AI capabilities. I also shape design direction across teams and help maintain our design system.

I use AI throughout my design process—exploring ideas, testing directions, and building working prototypes. This means I can test ideas in code before hand-off—catching problems earlier and moving faster.

At Pendo, I'm the lead designer for our AI agents and launched AI agent analytics. I also founded and lead our internal AI enablement initiative, helping PMs and designers use AI effectively in their daily work.

I write about AI, product, and design. I post on LinkedIn and publish on my Substack, focusing on real-world AI applications for product teams. I've been featured on Figma's Shortcut, contributed to Pendo's blog, and appeared on the How I AI podcast to discuss AI enablement and how I work with design teams.

I've designed products for Sakara, NakedPoppy, Intuit, and Homestead. I also managed web and mobile products at Square, Zendesk, and Weebly. This dual background is a core strength—I bring product judgment to design work and pair UX craft with an understanding of business goals, analytics, and technical constraints.

I also build personal AI projects to explore ideas and stay close to new AI technology. Where's Maya? is an interactive children's game built with Gemini 3, Meta Segment Anything Model, and Cursor. Clef is a music player that lets me play albums without scrolling through Spotify—something physical in a streaming world. These projects are creative outlets and testing grounds for new AI capabilities.

Outside of work, I enjoy time with my daughter, photography, international travel, learning Spanish, and going to indie rock shows.

## Projects

### Professional Projects

#### Agent Mode (2025)
Company: Pendo | Role: Lead Designer
Tags: AI, Agents, MCP

An AI chat interface that lets teams ask natural-language questions of their product data and move directly from insight to action.

**Overview:**
- Problem: Pendo's existing analytics and reporting capabilities are powerful, but often require a learning curve and a basic understanding of how the subscription is configured. While this works well for experienced users, it can introduce friction for less frequent users and adjacent roles.
- Solution: Agent Mode combines generative AI with Pendo's first-party product usage data and action tools to help teams answer questions faster, explore data more flexibly, and take immediate next steps within a single conversational flow.

Instead of translating questions into report builders or UI constraints, users can ask what they already have in mind and receive grounded, explainable answers represented as interactive charts, tables, and rich text.
- Role: Design lead, covering 6 teams and 3 other designers.
- Status: In active development. Currently in closed beta.

---

#### Agent Analytics (2025)
Company: Pendo | Role: Lead Designer
Tags: AI, Analytics

Defining a new category of analytics for AI agents that shows what users prompt, how well the agent performs, and which use cases drive retention.

**Overview:**
- Challenge: Teams deploying AI agents lack visibility into how those agents are being used, what users are asking, and whether the responses were effective, making it nearly impossible to measure impact or identify product opportunities.
- Solution: Agent Analytics solves this by giving teams prompt-level insights, theme clustering, and key engagement metrics—all integrated within Pendo's existing analytics platform.
- Role: UX Designer, AI Prototyper, User Researcher (with PM)
- Duration: January 2025 - June 2025

---

#### Product x AI (2025)
Company: Pendo | Role: Founder / Leader
Tags: AI, Enablement

Leading internal AI transformation of Pendo's product organization.

**Overview:**
- Goal: Level up AI skills across our product org spanning PMs, designers, and content writers, so folks could confidently use AI in their daily work and apply it thoughtfully in Pendo's products.
            
Help transition Pendo into an AI-forward organization and become a thought-leader in the AI Product space.
- My Responsibilities: - Facilitate bi-weekly one-hour meetings focused on an AI topic with hands-on activities
- Create well-researched presentations on AI topics that are relevant to Pendo's product organization
- Maintain the #product-ai Slack channel to share personal demos, news, new product explorations, and ideas on how AI can be applied to our own product
- Participate in company-wide OKRs to measure AI sentiment across the organization and increase AI's leverage in day-to-day jobs
- Champion AI use outside of the product organization
- Host an AI-focused user group with Pendo's customers where we share our use of AI as well as previews and demos of Pendo's AI products
- Role: Founder and and leader
- Status: Active program launched January 2025

**Story:**
Alongside using AI day to day as a designer—and leading design for Pendo's AI agent features—I also founded and lead our internal "Product × AI" enablement initiative.

It all started while on paternity leave in late 2024. I had a profound experience using Cursor for the first time to build a complex hobby app that I had no business creating. It was immediately clear to me how this was going to change how product teams work, especially how designers and product managers prototype and communicate their ideas.

I sent a Slack message to product & design leadership to get buy-in to lead a formal enablement program when I returned in January. They threw their support behind me right away and it's been one of the most rewarding and impactful things I've done at Pendo.

I was also fortunate to appear on the How I AI podcast to talk in depth about my efforts to enable AI at Pendo.

---

#### Workflow & Journey Analytics (2023)
Company: Pendo | Role: Lead Product Designer
Tags: Analytics

Visibility into multi-step process completion rates, how users move through them, and where friction slows them down.

**Overview:**
- Challenge: Process owners need to understand if users are completing multi-step processes accurately and efficiently. They also need visibility into user paths to identify where friction occurs and how to remove it.
- Solution: Workflows give process owners clear visibility into completion, incompletion, and which users have not started a process, along with time-to-complete metrics and detailed, segmentable visitor data.

Journeys visualize the different paths users take between a workflow's start and end steps, making it easy to identify the most common and most efficient routes—so process owners can spot friction, uncover better paths, and guide users toward faster, more successful completion.
- Role: UX Designer, AI Prototyper, User Researcher (with PM)
- Duration: 2023

---

#### PDP Redesign (2021)
Company: Sakara | Role: Lead Designer
Tags: E-commerce

A comprehensive redesign of the e-commerce product detail page (PDP) experience to improve conversion and showcase Sakara's premium wellness products.

**Overview:**
- Challenge: The original Product Detail Page (PDP) template was basic, inflexible, and offered limited design options to sufficiently market each product.
- Solution: Redesign Sakara’s PDPs, resulting in a modular system for e-commerce managers to publish beautiful, detailed, and higher-converting pages that tell the story of each of the 30+ diverse wellness products.
- Role: Lead Product Designer, User Researcher
- Duration: 2021

---

### Personal Projects

#### Where's Maya? (2025)
Role: Creator
Tags: AI, Children's game

An illustrated, interactive find-and-point web game designed for toddlers, built with loads of AI.

**Story:**
I spent Thanksgiving break 2025 building a cute educational game for my daughter, and it became a great way to test a bunch of new AI tools. 
    
Where's Maya? is a simple game: find and tap three animals in an illustrated scene. It's like "Where's Waldo," but for toddlers.

What made this project especially fun was how many AI models and tools I got to experiment with:

- Nano Banana Pro (Gemini 3 Image Pro) for animal and scene-set images. It's surprisingly easy to steer toward consistent, detailed illustrations.
- Gemini 2.5 TTS for sound effects.
- Meta Segment Anything Model 3 for near–pixel-perfect masking. This was essential for detecting animals in each scene and creating delightful reveal moments when my toddler taps the right spot.
- Gemini 3 Pro (vision) to automatically verify that generated scenes follow the guidelines I set. This saved time and improved quality.

I started the project in Gemini AI Studio. While it's a developer-focused tool, it's incredibly easy to bootstrap applications with built-in Google AI functionality. 

I quickly graduated to Google Antigravity, Google's new agentic IDE. It's still young, but it introduced some welcome features that helped me plan, test, and verify medium-to-large tasks. 

Finally, I refined the app in Cursor using Claude Opus 4.5, which some say is the new king of coding models. I tend to agree, although Gemini 3 Pro was consistently reliable throughout the project.

The visual design was art directed by me, but Gemini AI Studio did a fantastic job of nailing the aesthetic I was going for on the first prompt that I just leaned into it.

The whole process was extremely rewarding and a clear indication of how far the AI ecosystem has evolved since I built my first app in Cursor a little over a year ago.

Link: https://wheres-maya.vercel.app

---

#### 1 to 2, 3 (2025)
Role: Creator
Tags: AI, Claude Code

A subway timing app that helps me decide whether to stay on the local or transfer to the express—built entirely from my phone.

**Story:**
I live on the west side of NYC and ride the 1/2/3 trains daily. The 1 runs local. The 2 and 3 are express. Every day I face the same decision: should I stay on the local or hop off and catch an express to save time?

The catch: you only find out when the next express is coming once you've left your train for the platform. By then it's too late.

I've been thinking about this problem for years. It's minor—a few minutes either way—but it's a decision I make almost every day. When I realized I could probably solve it by vibe-coding something, I decided to scratch the itch.

I built the entire app during a single spin bike session, tested and debugged it on the subway, and refined it while walking my daughter home—all using Claude Code running on my phone.

The workflow was simple: create a GitHub repo, use Claude Code via the iOS app (which runs a sandboxed dev environment in the cloud), connect the repo to Vercel for auto-deploy, and iterate by literally talking changes into my phone using Whisper Flow. The phone-as-dev-environment matched the phone-as-target-device perfectly—I was testing in production conditions by default.

The hardest part wasn't the code, it was testing. Sitting at home with good internet and no time pressure, I couldn't validate the real experience. So the day after I built it, I took my daughter home from the museum via subway instead of bus—specifically to test the app. That's where I discovered what the UX actually needed: immediate feedback when connectivity drops, not a delayed error 30 seconds later when the refresh fails.

The project works and I use it. Honestly, I didn't think I could build anything useful without sitting in front of my computer.

Link: https://1-to-2-3.vercel.app

---

#### Clef (2024)
Role: Creator
Tags: AI, Music

Bringing back the ritual of music discovery while staying compatible with modern streaming.

**Story:**
I wanted a way to play albums without scrolling through Spotify. Something physical, like flipping through album covers, but made for the digital age. That's Clef.

The setup is simple--each album is a printed sheet with artwork on one side and a QR code on the other. Scan the code and the album starts. No search, menus, or recommendations.

I built it during paternity leave in late 2024. It was the first time I used Cursor and leaned on it heavily. It connects to Spotify's API, uses the webcam for QR scanning, and stores everything in Supabase. I also built an admin tool to add albums, pull metadata, and generate sheets cards automatically.

I had never built an app of this scale and wrote such little code by hand. I knew what I wanted the system to do and AI handled most of the implementation. A project like this would've taken me months before... or more likely I would've abandoned it halfway through. Instead, I had something working in a few weeks.

It's also become something for my daughter. She's too young now, but eventually she'll flip through a box of "albums" and pick one herself.

The project works and I use it. Building it changed how I thought about what's possible and inspired me to apply AI to more of my work.

---

## Experience

### Senior Staff Product Designer, AI at Pendo (2022 - Present)
Location: New York, NY

Lead design of Pendo's AI products, formerly focused on Analytics. Pendo ($200M/year B2B SaaS) helps product teams track user behavior, engage customers, and plan product improvements.

- Lead designer of Agent Mode, Pendo's agentic interface for product data. Users ask natural-language questions to quickly answer complex analytics queries or take action by creating Pendo guides.
- Launched Agent Analytics, which shows teams what users prompt, how well agents respond, and which use cases drive retention.
- Drove internal adoption of AI among designers and PMs, including code-gen tools to build prototypes for internal and external feedback.
- Owned design from discovery to high-fidelity Figma hand-offs for several features in the analytics suite including Workflows, Journeys, and SaaS Management.
- Represented design at the Analytics squad level (3 PMs), shaping priorities for feature development, AI integration, and roadmap planning.
- One of the primary contributors and maintainers of Pendo's design system.
- Owned monthly review process, which is the primary way Pendo's 25 designers and researchers share their work, identify common problems, and begin the conversation to align on new patterns for the design system.

### Lead UX Designer at Sakara (2020 - 2022)
Location: New York, NY

Lead UX design & user research of Sakara's website and iOS app, a $150M/year ecom leader in plant-based prepared meal programs and clean consumer products

- Lead design on multiple large web projects including subscription management, product details pages (PDPs), navigation/footer, and homepage
- Conducted multiple rounds of moderated user testing and interviews to validate usability and comprehension of Figma prototypes
- Transitioned organization from Sketch to Figma, trained designers, and rebuilt and expanded on Sakara's standardized styles guide, components, and grid
- Assist in other areas by conducting ad-hoc user data analysis in Amplitude & Google Sheets, collaborate with PMs on project goals & KPIs, and consult with our food preparation operations team on internal-tool designs

### Product Design & Strategy Consultant at Freelance (2018 - 2020)
Location: San Francisco, CA

Help tech startups grow with UX design and product strategy

- Redesigned NakedPoppy's beauty self-assessment and increased completion rates by 40%
- Conducted extensive market & user research for Productboard to help with their go-to-market and product development strategy

### Senior Product Manager, Payments at Square (2016 - 2018)
Location: San Francisco, CA

Lead product for Square's mobile, in-person payments terminal, which drives >$400m in annual adjusted revenue

- Owned the product roadmap for Square's mobile payments terminal with a focus on pricing, hardware ordering, and driving growth of the new seller base via onboarding and early-lifecycle optimization experiments
- Product managed a cross-functional team of analysts, designers, marketers, and software engineers across web, Android and iOS platforms
- Collected customer insights via phone interviews, in-person visits, surveys, A/B tests, product usage and support interactions to inform product prioritization
- Collaborated with key stakeholders, management, and other product managers to achieve company goals and resolve inter-team dependencies
- Grew sales of Square's Contactless and Chip Card Reader by 50% among new sellers
- Mentored junior and recently transitioned product managers

### Senior Product Manager, Growth and International at Weebly (2015 - 2016)
Location: San Francisco, CA

Led cross-functional Growth efforts and International expansion for Weebly's website building service for small businesses

- Increased annual incremental revenue by $10M+ over 40 experiments designed to optimize conversion, packaging, pricing, and retention
- Created dashboards and reports to track, measure, analyze, and share effects of experiments on core KPIs
- Launched Weebly into the UK, German, and French markets by localizing the product and marketing websites, implementing Adyen's payments platform to bill subscription fees in Euros and Pounds, and expanding native domain-name offerings
- Managed the domain name and Google Apps for Work integration products representing 34% of Weebly's annual revenue

### Product Manager at Zendesk (2012 - 2015)
Location: San Francisco, CA

Responsible for trial and feature onboarding, engagement, in-product assistance, and Inbox for Zendesk's customer experience platform for small businesses

- Led cross-functional efforts to deliver a simple trial experience that increased enablement and usage of key features during trial by up to 60%
- Developed a methodology to design for awareness, activation, and usage of all new major features
- Launched Zendesk Inbox, a free standalone product for simple shared-email collaboration in September of 2014 (zendesk.com/inbox)

### Lead Product Designer at Curious.com (2011 - 2012)
Location: Palo Alto, CA

Led product design for a pre-launch startup that is revolutionizing the way people learn and teach online

- Developed wireframes and high-fidelity mockups of core functionality
- Contributed production code in Ruby on Rails, HTML, JS, and CSS
- Managed feature backlog, ran ideation exercises, and promoted agile best practices for project management
- Conducted user testing sessions to validate design assumptions

### Product Manager at Intuit (2010 - 2011)
Location: Menlo Park, CA

Led vision, strategy, roadmap, and implementation of Biz Sites, a tool for small businesses to build and market their website online

- Launched a private alpha in three months and a public beta in six months
- Achieved startup development pace within a large-company by keeping the team small and collaborative, development incremental and agile, design simple, and testing frequent
- Increased 0-day publish rates by 3x over existing website building tool
- Collaborated closely with design and research team on concept tests and usability studies of static and interactive prototypes

### Senior Interaction Designer at Intuit & Homestead.com (2006 - 2010)
Location: Menlo Park, CA

Delivered delightful experiences for small business owners using Homestead and Intuit's website-building products and services

- Managed small and large projects from concept to release
- Led design on projects to market, convert, and retain new and existing customers, which contributed to the 40 percent year-over-year growth
- Conducted needs assessments with management, support, sales, marketing, development, and customers to determine product requirements and scope
- Designed and user tested low- to high-fidelity prototypes to validate and verify design concepts

## Education

### Bachelor of Science in Computer Science
University of Maryland, College Park (2002)
Minor in Economics

## Skills

### Product Management / Project Management / Marketing
Agile/Scrum, Competitor Research & Analysis, Cost/Benefit Analysis, A/B Split Testing, SEO, SEM, Requirements Gathering

### Product Design
User-Centered Design, Usability Testing, Card Sorting, Concept Testing, Contextual Inquiry, Hallway Testing, Visual Design, Prototyping

### Technical
Photoshop, Figma, HTML, CSS, JavaScript, jQuery, Ruby on Rails, Java, SQL

## Writings

- [My AI resources guide](https://briangreenbaum.substack.com/p/my-ai-resources-guide) - A curated list of resources for staying up-to-date with AI news, tools, and techniques.
- [Vibe-coded prototypes can have a second life](https://briangreenbaum.substack.com/p/vibe-coded-prototypes-can-have-a) - Leverage your design artifacts to help sell the product
- [Portable design systems](https://briangreenbaum.substack.com/p/portable-design-systems) - Use rule files to make your prototypes look like your company's app
- [Where's Maya?](https://briangreenbaum.substack.com/p/wheres-maya) - A fun, children's game I made for my daughter over Thanksgiving weekend
- [The best intro to evals I've found](https://briangreenbaum.substack.com/p/the-best-intro-to-evals-ive-found) - And why it's important for PMs & Designers to understand them
- [AI Roundup for Product People - August 3, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-august) - AI is scrambling the traditional design-to-engineering loop.
- [AI Roundup for Product People - July 27, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-july-297) - AI at work: experiments, constraints, and progress
- [AI Roundup for Product People - July 20, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-july-2ce) - Agents for research, design, and weekend plans
- [AI Roundup for Product People - July 13, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-july) - Your data, your docs, your daily tools
- [AI Roundup for Product People - June 29, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-june-006) - Trust, taste, and the future of building with AI
- [AI Roundup for Product People - June 22, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-june) - UIs still matter, multi-agent is messy, and track what's working (hint: we built that)
- [AI Roundup for Product People - Week of June 15, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-week-564) - New design workflows from v0, Windsurf, and Figma
- [AI Roundup for Product People - Week of June 8, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-week-80d) - MCPs, PRDs, and a PM that A/B tests itself
- [AI Roundup for Product People - Week of June 1, 2025](https://briangreenbaum.substack.com/p/ai-roundup-for-product-people-week) - Slack-native dev, manager GPTs, and Rick Rubin's code koans.

## Featured In

- [How I AI Podcast: Interview](https://www.youtube.com/watch?v=yaG70VotukE)
- [Figma's Shortcut: Design Systems](https://www.figma.com/blog/4-ways-for-design-teams-to-chart-new-territory-with-figma-make/#_3-collaborate-and-rev-on-new-interfaces)
- [Pendo Blog: AI Design](https://www.pendo.io/pendo-blog/ai-product-design/)

## Contact

- Website: https://briangreenbaum.com
- Email: briangreenbaum@gmail.com
- LinkedIn: https://www.linkedin.com/in/briangreenbaum/