# Aaron Bailey > Product Design Leader | Building AI-First Products Location: San Francisco Bay Area, United States Profile: https://flows.cv/aaronbailey With 16 years in product design, I've worked across the full range of company stages, from founding designer at a seed-stage AI startup to leading design some of the fastest-growing companies in tech.I've led design at Instacart, Thumbtack, and Wealthfront, and most recently have been working at the frontier of AI as founding designer at a seed-stage AI recruiting startup. In each of these roles, I've operated across product strategy, design, and front-end engineering, and use AI throughout the design process, not just in the products I'm building.I have a strong point of view on how the best AI-first products are built. The interaction model matters as much as the feature set, and the companies that get this right early will have a meaningful advantage. What excites me most right now is figuring out how to design for the moments where AI should lead, where it should support, and where it should get out of the way. My approach to leading design teams is to create the conditions for high-quality, high-trust work. The best design outcomes come from teams that feel safe to challenge assumptions, take real creative risks, and go deep on hard user problems. I invest heavily in cross-functional relationships because the best product work happens when design, product, and engineering are working closely together. Outside the office I spend my time in the workshop, woodworking and ceramics keep me close to making things with my hands. ## Work Experience ### Founding Product Designer @ Tezi AI Jan 2024 – Present | San Francisco, California, United States First design hire at a fast-paced, seed-stage recruiting AI startup, contributing fluidly across product strategy, product design, and front-end code with an AI-first approach at every stage of the process. Led strategy and execution for a product pivot from a chat-only UX to a multi-modal AI experience, dramatically improving users' ability to find and contact high quality candidates. ### Director of Product Design @ Wealthfront Jan 2023 – Jan 2024 | San Francisco Bay Area Led product design and content across our entire Investing platform and design systems team. Led the development and launch of the new Automated Bond Ladder vertical with the VP of product. Grew the new product vertical to $XXXM+ assets under management within the first three months of launch. ### Director Of Product Design - Consumer Experience, Growth, & Ads @ Instacart Jan 2022 – Jan 2023 | San Francisco, California, United States Led the Customers design org in several key launches: the rebrand launch of our Membership experience, strategy and product vision on four of our primary user experiences, and the re-envisioning of our core user journey. ### Director Of Product Design - Ads @ Instacart Jan 2020 – Jan 2022 | San Francisco, California, United States Led the design org to set the vision and build the experience for our zero-to-one Advertiser tooling product and consumer ads experience. Worked closely with VP of Engineering, Sales, and Product to craft a strategy to support quadrupling our product offering. Led design org efforts to: increase equitability and reliability of the interview process and training; grow leadership talent by redefining our manager training and mentorship program; improve visibility of the team's work by architecting org-wide executive design crit. Grew the Ads design team from 2 to 14 while helping establish the content and research functions on Ads. ### Director Of Product Design @ Thumbtack Jan 2020 – Jan 2020 | San Francisco Bay Area Responsible for Product Design, Content, and Design Systems across Thumbtack's Customers business. Managed a team of 18 designers and design leaders. Led designers to craft innovative, high-quality product and brand experiences. Was responsible for the people, processes, and frameworks behind Customer’s design decisions. Directed the team through numerous product launches, including Thumbtack’s rebrand across the product, standing up a new Design System, the alpha launch of Pro calendar and booking system, and Customer’s 2020 product vision. Led recruiting to scale the Design org and helped build our team culture and recognition programs to create one of the most highly engaged teams at Thumbtack. ### Senior Design Manager @ Thumbtack Jan 2019 – Jan 2020 | San Francisco Bay Area - Growth Product Design - Core experience Product Design - Design Systems ### Design Manager @ Thumbtack Jan 2018 – Jan 2019 | San Francisco Bay Area - Product Design - Design Systems ### Senior Product Designer @ Thumbtack Jan 2017 – Jan 2018 | San Francisco Bay Area - Design Systems - Product Design ### Lead Product Designer @ Earnest Inc. Jan 2015 – Jan 2017 Lead Designer on Earnest's flagship student loan refi product, iOS app launch, and expansion of the personal loan product. Led design to scale the app through a phase of 5x user growth via hands-on research, testing, iteration, and vision setting with the c-suite. ### Product Designer @ RelateIQ Jan 2013 – Jan 2015 | Palo Alto, California ### Freelance Product Designer @ Design LLC. Jan 2009 – Jan 2014 Worked with a variety of agencies and clients to spearhead identity, branding, and creative development for online user experiences, e-commerce, touch-screen and mobile interfaces. Managed and creative directed small teams to execute on brand campaign strategies across a portfolio of clients. ### Assistant Teacher for Interactive Web Design @ Colorado State University Jan 2010 – Jan 2010 Created curriculum to teach the first software engineering fundamentals course to design program students. Worked alongside head of design department to establish the new material as an ongoing requirement of the design program. ### Senior Designer @ LSC Marketing Jan 2008 – Jan 2009 I had the opportunity to manage a small team of designers at LSC Marketing. I administered, coordinated, and designed multimedia marketing campaigns, promotional events, and delivered great design work to our clients. ## Education ### BFA in Graphic Design Colorado State University ## Contact & Social - LinkedIn: https://linkedin.com/in/arnbly --- Source: https://flows.cv/aaronbailey JSON Resume: https://flows.cv/aaronbailey/resume.json Last updated: 2026-03-25