# Carlos Montoya — resume context > Principal Product Designer and Design Engineer. Park City, Utah. https://losmontoya.com ## Summary Principal product designer and design engineer. I turn ambiguous product questions into working software, then build the evaluation systems that make judgment observable, debuggable, and testable. My current independent practice combines product design, native and web prototyping, design systems, and AI-native workflows. Sole inventor on a patent filing in AI context engineering. ## Highlights - Built a native SwiftUI prototype in roughly two days so Dropbox leadership could judge a mobile AI direction hands-on; iOS engineers asked for the repository and the app circulated internally. - Accounted for 165 Figma files in a taste pipeline; 124 yielded 21,678 candidate nodes, 592 first-run review tiles, and a separate 116-tile labeled gate. - Built four coded onboarding directions that converged on a clear trust model: the system proposes; the human approves. - Brought 25+ Dropbox designers from AI trained to AI native through open working sessions. - Player-coach by preference. Led four senior designers, merged two design orgs after an acquisition, and coach designers daily. Managing is part of the making. ## Flagship evidence map ### 48 Hours to Native - Public case: https://losmontoya.com/work/48-hours-to-native - Product question: define a useful role for AI on Dropbox mobile, then make the remaining state, motion, keyboard, sheet, and reachability questions judgeable in hand. - Working proof: a research-backed companion strategy and installed SwiftUI prototype built over roughly two days, with native navigation and deterministic demo data. - Observable review outcome: leadership reviewed the direction hands-on; iOS engineers asked for the repository; the prototype circulated internally. - Claim boundary: the public evidence is recorded native-runtime footage, not a production service, public app runtime, browser reconstruction, or customer-outcome claim. ### Reimagined Onboarding - Public case: https://losmontoya.com/work/reimagined-onboarding - Product question: help people experience useful AI behavior without blocking the work or acting without consent. - Working proof: multiple coded directions across two rapid research rounds; Round 1 included six participants, and eleven concepts converged to four directions on a shared trust architecture. - Iteration evidence: research synthesis became coded changes between sessions, often within the same day; the final model shows useful work, asks before acting, and leaves a visible trail. - Claim boundary: the footage uses fixture data and demonstrates interaction and decision logic, not a shipped service or achieved activation lift. ## Shipped-scale proof - At Healthy Together, designed the first end-to-end iOS and Android contact-tracing solution for Utah from concept to launched app in 28 days. - Supported a product with a 4.9 App Store rating and 220k+ reviews across iOS and Android, on a platform now serving 5M+ people. - Led four senior designers and merged two design organizations after an acquisition. - At Hamster, helped define and ship an AI-native product workspace from brand identity through MVP product design, design system, and marketing surface; the company shipped to early access. - At Dropbox, mentored and coached 25+ designers through open working sessions, critique loops, and agent-assisted design practice. ## Experience ### Principal, Independent Design Practice — Los Montoya Design Co May 2026 – present · Park City, UT - Built a taste-evaluation pipeline that accounted for 165 Figma files; 124 yielded 21,678 candidate nodes, 592 first-run review tiles, and a separate 116-tile labeled gate. - Benched the calibrated judge against frontier models and kept the disagreement log as the calibration asset. The rubric is versioned like code because it is treated like code. - Rebuilt and shipped production marketing sites for select clients on Next.js and Vercel, migrating them off Webflow for speed and editability. ### Principal Designer — Dropbox Nov 2022 – May 2026 · Virtual First - Built a native SwiftUI prototype in roughly two days because static prototypes could not prove the state and motion model. Leadership reviewed it hands-on, iOS engineers asked for the repository, and the app circulated internally. The public evidence uses deterministic demo data by design. - Built four coded onboarding directions that made an AI-led first-run thesis testable and converged on a clear trust model: the system proposes; the human approves. - Set the bar for what prototyping looks like at Dropbox, moving high-stakes design review from slides to working software. - Mentored and coached 25+ designers from AI trained to AI native through open working sessions, critique loops, and agent-assisted design practice. - Sole inventor on a patent filing in AI context engineering. - Developed principles for AI and workflow systems, covering how users move from search and reading into action, organization, transformation, routing, and automation. - Regular interviewer on the design hiring loop, running Making and Thinking deep dives and portfolio reviews. ### Founding Design Lead (fractional), then Advisor — Hamster · Wheel Go Fast, Inc. Mar 2025 – Oct 2025 · Remote - Helped define and ship an AI-native product workspace for teams building with agents, from brand identity through MVP product design, design system, and marketing surface. - Set up agentic design operations and principles for a team working alongside AI from day one. - Company shipped to early access; I remain an advisor. ### Design Director, Principal Designer — Twenty · Healthy Together Jul 2019 – Jun 2022 · Remote - Designed the first end-to-end iOS and Android contact-tracing solution for the State of Utah, from concept to launched app in 28 days during the COVID-19 pandemic. - Supported a product with a 4.9 App Store rating and 220k+ reviews across iOS and Android, on a platform now serving 5M+ people. Second state in the nation with a COVID app, first to launch on iOS and Android on day one, and the first state app using Bluetooth proximity tracing. - Led a team of four senior designers, hired as the team grew, and merged two design organizations after an acquisition. ### Staff Designer, Creative Director — Juxta Labs · Mappen Aug 2017 – Jul 2019 · San Francisco, CA - Took consumer social products from conception to production and matured design capability across the product team. ### Senior Web Designer — Atlassian Apr 2015 – Aug 2017 · San Francisco Bay Area - Led creation of web design platform systems for marketing at scale. ### Product Designer — Pinger Jan 2013 – Apr 2015 · San Jose, CA - Led product design across iOS, Android, Windows Phone, desktop, and web for Pinger, TextFree, Sideline, and more. ## Skills - **Design:** product design, interaction design, design systems, prototyping, mobile, brand - **AI practice:** agentic workflows, eval design, judge calibration, context engineering, taste rubrics, model-assisted prototyping - **Engineering:** Swift and iOS prototyping, TypeScript, React, Next.js, Figma platform and REST API - **Leadership:** player-coach management, coaching and mentoring, design operations, design hiring ## Recognition - Twenty featured in the Wall Street Journal, TechCrunch, and CNBC. - Healthy Together recognized by GovernmentCIO as a leading contact-tracing solution. - Sole inventor, patent filing in AI context engineering. ## Links - portfolio: https://losmontoya.com - linkedin: https://www.linkedin.com/in/losmontoya - x: https://twitter.com/losmontoya_ - email: los@losmontoya.com