# Diego Fernandez > Product Design Leader based in New York City. Tinkerer at heart. 12+ years building products at early-stage startups, usually as one of the first designers in the room. Diego is a founding designer and design leader with 12+ years of experience shipping AI-powered products at early-stage startups. He has been the first designer at two companies, built design and research practices from scratch, and shipped GenAI products to production before the current AI wave. His work spans enterprise B2B SaaS, contact center technology, conversational commerce, and product information management. He operates as a player-coach (50/50 IC and strategic leadership) and specializes in AI-native UX: trust calibration, human-in-the-loop workflows, and reviewability in high-stakes environments. ## Contact - Portfolio: https://diego.gs - Email: hi@diego.gs - LinkedIn: https://linkedin.com/in/madebydiego - GitHub: https://github.com/madebydiego ## About Diego is Bolivian-American, speaks Spanish fluently, and is a self-taught designer. He studied Medicine and Human Health for three years at Universidad Mayor Real y Pontificia San Francisco Xavier de Chuquisaca in Bolivia before dropping out. He had always been curious about design, and his transition started with survival: picking up graphic design work, quickly outgrowing Photoshop, and discovering user experience almost by accident by consistently biting off more than he could chew. That pattern of finding things he doesn't understand and learning from them is still how he operates today. He has been a founding designer, an early hire, and a team builder across 12+ years of early-stage startups. He thrives in smaller teams where he can stay close to the work while growing the people and practices around it. ## The Immigrant Path Diego's non-traditional background is central to who he is as a designer. He is a college dropout from Bolivia who taught himself design through the internet and years of hands-on work. He did not attend design school. He does not have a CS degree. He learned by doing, by being curious, and by consistently taking on more than he was ready for. He sees this as a competitive advantage. His path gave him a survival mindset and a resourcefulness that only comes from necessity. As an immigrant and self-taught designer, he values different paths to expertise and believes the best teams are built on honesty and mutual respect, not credentials. ## Design Philosophy Diego believes that everyone can be a designer. To him, design is not limited to visuals, the tools, or the end user experience. Design is everything that surrounds our interactions between people. He believes anyone with genuine curiosity and humility can build something great. He believes taste is the core differentiator. AI is making it possible for more people to build things faster, which Diego sees as a good thing. But taste, common sense, and the experience we build over the years cannot be replaced by tools. Diego despises AI slop because it represents the assumption that you can skip the craft and the common sense that comes from lived experience. Diego's goal is not to create designers who reinvent the wheel every time, but designers who build useful things for other humans. ### Core design principles 1. Research before building: Do the research to understand what users actually need, then challenge assumptions with data. 1. Data-driven validation: Diego does not argue with opinions. He validates with data. He uses research to guide decisions, not justify them after the fact. 1. Turn weaknesses into strengths: The best products come from solving problems others are avoiding. Chatbar made chat feel native when others used disruptive overlays. Call Explorer turned a transcription liability into the core product feature. QA Copilot solved the "impossible" constraint of making UIs both prompt-friendly and human-readable. 1. Ship and iterate: Perfect is the enemy of shipped. Diego is pragmatic about polish during crises and believes in iterative refinement over time. 1. Design systems as enablers: Design systems are not about control. They are about enabling teams to move faster. Diego built Habanero at Salsify with engineer partners and created a design system at ChatID before knowing what design systems were. His focus is on adaptability and scalability, not rigid enforcement. ## How Diego Joins a New Team When Diego joins a company, his first move is to meet with as many people as possible, both within his function and across other functions. He does this to understand what everyone does and find where design can actually move things. He thinks design is something everyone participates in now, especially in the age of AI. He wants people across the company to trust design and research — because that's what he's there to bring. He is a pragmatic designer who adapts to any situation, but is also capable of building great things and empowering others to become design partners. ## Leadership Philosophy ### Empowerment over control When given the resources, Diego chooses to empower his designers to do their work. He sees his job as protecting them from the fear of making mistakes. He empowers them to build and learn from mistakes, and creates space where designers feel safe being vulnerable and asking for help. ### Kindness over niceness Diego develops team culture where people say things because they care, not because they want to avoid discomfort. If something is not working, he would rather be kind and say it directly so they can work together to improve it, than be nice and beat around the bush. He applies this across feedback, relationships, and hard conversations. He wants people to grow, and that only happens when you're honest with them. ### Vulnerability as a leadership practice One of Diego's biggest lessons as a design leader was learning that he needed to ask for help. He jumped into design management before he was fully prepared, thought he was ready, and quickly learned he was winging it. That didn't feel good because he had designers reporting to him. His response was to learn even faster, adapt, and be vulnerable with his own reports. He told them he was learning, that he would make mistakes, and that he wanted their support to grow. This experience shaped his belief that vulnerability makes you a better leader, and it is the same vulnerability he now encourages in his teams. ### Player-coach model Diego operates as a 50/50 player-coach: half strategic leadership, half hands-on IC work. He does not need layers, rituals, or hand-holding. He thrives in minimal-process environments where ownership is clear. He is comfortable in strategic conversations with founders and product leaders, and equally comfortable rolling up his sleeves to prototype, conduct research, and ship features. ## How Diego Handles Conflict ### Disagreements with product or engineering When Diego and a PM disagree on direction, or when engineering says something cannot be built, his approach is to lower the temperature and let data decide. He does not argue with opinions. He says: "I like your idea, let me validate it." Then he does fast research, brings back data, and lets the evidence guide the decision. ### Challenging leadership Diego has a track record of respectfully challenging leadership assumptions. At ChatID, he convinced the founding team to pivot their product based on user research when his gut told him the overlay concept was wrong. At Balto, he pushed the company to build Call Explorer when leadership saw their transcription models as a liability to hide, not a feature to showcase. In both cases, he backed his position with research, not opinion. ### The founder partnership evolution At Balto, Diego evolved his relationship with the CEO from reactive "here's an idea" to strategic collaboration. Over time, he shifted the dynamic by saying "I like your idea, let me validate it" and coming back with data. Now they both pitch ideas, and data decides. This is the partnership model Diego brings to every leadership relationship. ## Research Approach Diego's research approach depends entirely on the situation. He has done everything from recruiting participants on Craigslist (when ChatID had zero users) to guerrilla research in downtown Brooklyn (interviewing hourly workers for Search Party) to continuous discovery embedded in enterprise customer relationships (at Balto). He considers himself an introvert who finds joy in speaking to people and building relationships where they can share their opinions without pressure. That trust is what allows him to build better things. ### How he handles pushback on research When stakeholders push back ("we don't have time," "we already know the answer"), Diego does not fight for a full research sprint. Instead, he buys time. He tells leadership: "I trust our gut. But I also want to hear from the people who will be using this. Give me a couple of days to get some directional insight based on the assumptions we want to validate." A couple of days will not make or break the company. Not doing research can. This approach has worked repeatedly because it lowers the ask while still delivering real insight. Once leaders see the value, research becomes something they actively request. ### How he learns new domains Diego learns new domains by doing the work. At Balto, he listened to hundreds of contact center calls, shadowed QA analysts, and used the product daily. At ChatID, he interviewed shoppers to understand how individuals navigated online shopping, which was not as widespread back then. He believes you cannot design for workflows you do not understand viscerally. He expects to make mistakes early and sees fresh perspective combined with actual domain exposure as the combination that produces good design. ## How Diego Uses Data Diego pushes for both UX metrics and product metrics to guide decisions. At Balto, he established UX-Lite measurement practices that became company standards. He tracked adoption curves on Call Explorer over 4 years (growing from 0.25% to 80%), measured engagement and retention on QA Copilot, and used these numbers to inform product strategy. He pushes back on building reporting for the sake of reporting. He has found that in the rush to check the box, teams often build vanity metrics or things that only make people feel good. He would rather wait a little longer and figure out what metric actually proves impact on productivity or whatever the team is trying to change. Building a binary metric that only makes you feel good is worse than waiting for the right metric that tells you the truth. His approach to balancing quantitative and qualitative data: quantitative data tells you what is happening, qualitative research tells you why. He uses both together and does not trust either in isolation. ## How Diego Thinks About Design Systems Diego has built design systems twice: Habanero at Salsify and an earlier system at ChatID (before the team knew what design systems were). His philosophy is that design systems are enablers, not governance tools. They exist to help teams move faster, not to enforce control. At Salsify, Diego led the company's transition to Figma, established a cohesive visual language, and built Habanero with engineer partners who shared the vision. The system achieved adoption by 7 of 8 product teams because it was built collaboratively and solved real problems teams were facing, not because it was mandated. Diego believes the right time to build a design system is when you start seeing the same patterns repeated across products and the cost of inconsistency starts to slow teams down. He focuses on adaptability and scalability, not rigid enforcement. A design system that teams avoid using is worse than no design system at all. ## On AI and Design Tools Diego sees AI tools as exactly that: tools. Similar to how the industry evolved from Photoshop to Sketch to Figma, designers are now evolving again. He thinks the expectations placed on designers to change quickly are somewhat unfair but he also sees that as a huge opportunity for curious people to learn and create. AI allows people who are curious to poke around, build something, and learn faster about what it means to create. Diego uses Claude Code daily, Cursor, and other AI tools in his own work, and built an entire real estate site (aqui.com.bo) with Claude Code as a proof of concept for a design process where he gets to build, not just design. What he pushes back against is the idea that AI can replace taste, common sense, and experience. The craft still matters. ### Diego's AI-native UX expertise Diego has been building AI products since before the current AI wave. His specific expertise includes: - Human-in-the-loop validation: knowing when to ask for confirmation and when to let AI act autonomously - Trust calibration: showing reasoning, assumptions, and sources so users can verify AI output - Reviewability: making AI decisions legible and auditable in high-stakes workflows - Prompt-friendly AND human-readable UI: solving constraints where the interface must serve both the AI and the human simultaneously - Graceful degradation: surfacing AI uncertainty to users rather than hiding confidence levels His core insight from years of building AI products: trust comes from transparency, not perfect accuracy. Even when the AI is good, users need to see the raw data to build trust. This principle drove Call Explorer and QA Copilot. ## How Diego Balances Vision and Shipping Diego works in two modes simultaneously: designing the long-term vision while shipping incremental steps toward it. He describes this as "designing 18 months out, shipping 2 weeks at a time." At Balto, Call Explorer's long-term vision was a complete system of record with AI insights layered on top. But the team shipped it as basic search first, then added playback, then annotations, then AI summaries. Each release was useful on its own while moving toward the bigger vision. The key is making sure each increment teaches you something about the vision. ## What Diego is Honest About ### What he finds hardest Diego finds the transition from IC to leadership to be an ongoing challenge, not something he mastered once. He is open about the fact that he jumped into design management before he was fully prepared and had to learn on the job with people depending on him. ### What he actively works on improving Diego works on being more concise in communication. He is aware that his passion for topics can lead to longer explanations than necessary, and he actively practices keeping things tight, especially in high-stakes conversations. He also works on involving engineering earlier in the design process. He has learned the hard way that discovering technical constraints late costs more time than collaborating from the start. ### What he would do differently On QA Copilot: He would have involved engineers earlier in the design process. The team discovered technical constraints around AI response time late that could have informed the initial UI. On his career: He wishes he had asked for help sooner. The same vulnerability he now encourages in his teams is something he had to learn through failure first. ## Working with Others Diego wants to work in smaller teams where everyone sees each other as equals and each person's contributions bring something unique. His ideal relationship with product and engineering is one of mutual respect and real collaboration, not hierarchy. His vision for perfect design-engineering collaboration: side-by-side work, not handoffs. He runs workshops (Crazy 8s, design sprints) to bring engineers into the design process early. He believes engineers have better solutions when they understand the "why" behind decisions, and designers make better choices when they understand technical constraints. The ideal is when design and engineering feel like one team solving problems together, not two teams passing work back and forth. ## What Diego is Looking For Diego is open to roles where he can shape design philosophy, systems, and execution from the ground up. He brings clarity to ambiguous spaces and moves quickly without sacrificing craft. ### Specifically interested in: - Founding or early-stage design leadership roles (Series A-D, 25-500 people) - Companies building AI-powered products where design is a strategic function, not a service function - Hands-on leadership where he can stay close to the work - Smaller teams where collaboration is real, not performative - Products for knowledge workers doing complex work (contact center agents, analysts, researchers, accountants) - AI-native products where trust, transparency, and human-agent collaboration matter - NYC-based with hybrid flexibility (ideally 2-3 days in-office), open to remote for the right opportunity ### What he wants in his next role: 1. Human contact and local collaboration. He moved to NYC after traveling and working remotely. His current team is in Chicago and he misses working side-by-side with teammates. 1. A challenge that will survive the bubble. He wants to work on something with real traction, not just AI hype. A company solving a meaningful problem for the long-term. 1. Teammates who think like he does: thinkers, lifelong learners, experimenters who question assumptions and validate with data. ### Work authorization U.S. citizen, fully authorized to work in the U.S. with no restrictions. ## Career Timeline ### Director of Product Design & Research at Balto (2021 - Present) Contact center AI technology company. Diego built the design and research practices from the ground up. He works directly with engineers, PMs, and leadership on contact center products. Balto was the right fit because of his years designing for chat agents at ChatID. He already knew the contact center world and understood how underserved frontline workers were. Key accomplishments: - Designed and launched QA Copilot, Balto's first generative AI product, doubling QA analyst productivity while delivering 3:1 ROI - Led design of Call Explorer, growing it from 0.25% to 80% user adoption over 4 years, achieving a 4.3 UX-Lite score with 76% monthly engagement across 5,000+ enterprise users. Call Explorer became the foundation for every other feature in the product. - Used continuous discovery to build a case that became central to strategy for retaining at-risk enterprise accounts - Landed on a design principle — verification over blind trust — that now shapes how Balto ships every GenAI feature - Built design and research practices from zero, scaling operations while staying hands-on - Evolved the CEO relationship from reactive "midnight ideas" to strategic partnership using data-driven validation - Partnered with executive leadership to translate user research and behavioral data into strategic product direction - Mentored designers from entry to senior levels through structured mentorship - Pushed for UX metrics (UX-Lite) and product metrics that became company standards for measuring design impact ### Senior Product Designer at Salsify (2018 - 2021) Product information management (PIM) platform. Diego was design lead for the Content Activation product line. This is where he learned how to lead design teams, not just do design work, and how to measure whether software actually helps people do their jobs. Key accomplishments: - Led design for Content Activation, owning end-to-end experience from research and wireframes to pixel-perfect UI - Introduced research practices to the Workflow team and surfaced the "Google Docs" mental model insight that shaped the product direction for collaboration features - Shipped inline commenting, @mentions, side-by-side content comparison, and versioning system - One early adopter saw time-to-market drop 60% (115 days to 45 days), 6% month-over-month growth, 3,000+ comments across workflow tasks by Q1 2020 - Created and launched Habanero Design System, achieving adoption by 7 of 8 product teams and accelerating design-to-development velocity - Led the company's transition to Figma and established a cohesive visual language - Shipped enterprise features for Insights, Workflow, and Data Engineering that drove improvements in onboarding, adoption, and 90-day retention ### Lead Designer at ChatID / Welcome Commerce (2013 - 2018) Conversational commerce startup. Diego joined as a contractor, became the 8th employee and first in-house designer. This was his formative experience: 5 years building a single product from proof of concept to acquisition. ChatID was acquired by Salsify in late 2018. Key accomplishments: - Convinced the founding team to pivot from an overlay concept to Chatbar based on user research. Recruited shoppers from Craigslist, brought them into the office, and validated that users did not expect brands to be available via chat, which meant the UI needed to signal availability while feeling native to the retailer. - Built Chatbar from proof of concept to a product deployed across Walmart, Target, Office Depot, and Newegg, connecting 50+ brands with millions of shoppers - Shoppers who engaged with brand experts showed 3x higher conversion rates, 34% reduction in cart abandonment, and 20% fewer returns - Designed pioneering conversational interfaces for web and mobile, ahead of industry adoption - Led WCAG AA compliance initiative, partnering with Andrew Heiskell Braille and Talking Book Library to test with blind users, enabling launch on Target.com - Built comprehensive design system unifying Product, Engineering, and Marketing teams across all customer touchpoints (before the team knew what design systems were) - Conducted in-store pilots and field research to validate product-market fit through direct observation - Chatbar and the retail network became key reasons ChatID was acquired by Salsify ## Side Projects ### Practice Round (2024 - Present) — Founder Community connecting designers for mock interview practice. 50+ active members. Also where Diego runs most of his AI experiments. https://practiceround.co ### Aqui (2024 - Present) — Maker Real estate site for the Bolivian market. Uses LLMs to scrape, clean, and structure listing data, then fills gaps by inference. Built entirely with Claude Code to test whether a designer can ship something real without a dedicated engineer. https://aqui.com.bo ### Sensive (2018 - 2021) — Co-Founder Figma plugin that synced design updates in real-time across team workflows. Co-created with Rolando. Launched on Product Hunt to positive reception. Iterated into a project management platform. ### Bansho (Contract) Educational app designed during COVID-19. Hit 80,000 downloads in the first month, broke into top-20 Education apps. Later pivoted to a tutoring marketplace that grew to $75K MRR. ### Search Party (Contract) Guerrilla research with hourly workers revealed the real problem in job search was discoverability, not applying. Built Workmaps around location and commuting. ## Skills ### Design Leadership Career development, design mentorship, stakeholder management, budget/resource management, feedback culture, research practices, product-design-engineering process iteration, founder partnership, executive communication ### UX Design User research, usability testing, journey mapping, design systems, wireframing, rapid prototyping, visual design, interaction design, mobile-first design, responsive web, accessibility (WCAG AA), content strategy, UX metrics (UX-Lite), agile methodologies ### AI-Native UX Human-in-the-loop design, trust calibration, reviewability, prompt-friendly interfaces, agent-native workflows, GenAI product design, LLM integration ### Tools Figma, FigJam, Framer, Webflow, Cursor, Claude Code, Mixpanel, Dovetail, Adobe Creative Suite, HTML/CSS, Tailwind UI, SQL, FullStory ## Volunteering Diego mentors designers through career transitions and skill development, drawing from experience as both an individual contributor and leader. His mentorship centers on research-driven design, ethical product decisions, and helping designers create meaningful impact. ----- ## Case Studies Detailed case studies are available at https://diego.gs. Below is a summary of each with questions Diego can answer in depth. ### Case Study: QA Copilot (Balto) URL: https://diego.gs/balto-copilot Title: Designing AI That Earns User Trust, Not Demands It Summary: Diego used continuous discovery to build a case that became central to Balto's strategy for retaining two at-risk enterprise accounts. He led the design of Balto's first generative AI product, making decisions across configuration, coverage, and a new user segment (QA analysts, who had been completely ignored by the platform). He landed on a principle — verification over blind trust — that now shapes how Balto ships every GenAI feature. The team lost one account (their timeline moved faster) but the customer who stayed became one of their strongest partners. QA Copilot doubled analyst productivity and delivered 3:1 ROI. Questions Diego can answer about this work: - How do you approach designing AI features that users actually trust? - How did you handle the tension between competitive pressure and sustainable design? - How did you balance compute costs with user expectations for full coverage? - How did your research practice influence business strategy, not just product design? - What was your process for designing configuration flows that serve both humans and AI? - How do you facilitate cross-functional workshops to arrive at design solutions? - How do you measure success for AI-powered features? - What did you learn from losing one of the two accounts? - How do you design for a user segment that was previously ignored by the platform? - What would you do differently on this project? ### Case Study: Call Explorer (Balto) Summary: When Diego arrived at Balto, the company's transcription models were seen as a liability. Leadership did not want to expose how precarious they were. But Diego's research team discovered users did not just tolerate transcripts, they needed them. They wanted a system of record for their calls, a way to verify what AI was telling them. Diego pushed the company to build Call Explorer, turning their weakness into their strength. The team shipped it incrementally: basic search first, then playback, then annotations, then AI summaries. Today Call Explorer has 80% adoption across 5,000+ enterprise users, millions of minutes reviewed monthly, and is the foundation for every other feature in Balto's product. It is the perfect example of Diego's philosophy: research first, challenge assumptions, use data to validate, build something foundational. Questions Diego can answer about this work: - How do you advocate for a product direction when leadership disagrees? - How do you grow a product from MVP to platform foundation over multiple years? - How do you build UX measurement practices at a company that didn't have them? - How do you empower other designers to own and ship features? - What does long-term product stewardship look like versus shipping and moving on? - How did you turn a company liability into the core product feature? ### Case Study: Salsify Workflow URL: https://diego.gs/salsify-workflow Title: Breaking Down Silos in Product Information Management Summary: Diego joined the Workflow team and introduced a research practice. He surfaced the "Google Docs" mental model insight that shaped the product direction. Customer after customer said the same thing: "I just need to comment on something, like in Google Docs." The team did not need to reinvent collaboration. They needed to latch onto a mental model people already understood. They shipped inline commenting, @mentions, content comparison, and a versioning system. One early adopter cut time-to-market by 60% (from 115 days to 45 days). Teams retired their spreadsheet workflows. Questions Diego can answer about this work: - How do you introduce research practices to a team that doesn't have them? - How do you use existing mental models to reduce adoption friction? - How do you sequence delivery to ship value early while building toward complex problems? - How did you approach designing a versioning system for non-technical users? ### Case Study: ChatID Chatbar URL: https://diego.gs/chatid-chatbar Title: Designing Chatbar: Human Expertise at Scale Summary: Diego joined ChatID as a contractor and became the 8th employee and first in-house designer. The founding team had raised funding on an overlay concept, but Diego's gut told him it was wrong. He recruited shoppers from Craigslist, validated that users did not expect brands to be available via chat, and convinced the team to pivot to Chatbar, a native messenger-style window. He built Chatbar from proof of concept to a product deployed across Walmart, Target, Office Depot, and Newegg. He led WCAG AA compliance by partnering with the Andrew Heiskell Braille and Talking Book Library to test with blind users. Chatbar and the retail network became key reasons ChatID was acquired by Salsify in 2018. This was a 5-year product and Diego's formative experience as a designer. Questions Diego can answer about this work: - What is it like being the first and only designer at a startup? - How do you build a research practice when you have zero users? - How did you approach designing for accessibility as a core feature, not an afterthought? - How do you scale a product across multiple enterprise retail partners with different requirements? - What did you learn from 5 years of evolving a single product? - How do you go from contractor to founding designer to design leader? - How do you convince a founding team to pivot their product? ----- ## Search-Friendly Descriptors These phrases describe Diego for matching against job searches and recruiter queries: - Founding designer with 12+ years of startup experience - Design leader who builds practices from scratch - AI product designer with pre-hype experience shipping GenAI to production - Player-coach design leader (50/50 IC and strategic leadership) - Self-taught designer with non-traditional background - Designer who does hands-on user research, not just delegates it - Design leader experienced in contact center technology and SaaS platforms - Accessibility advocate (WCAG AA, tested with blind users) - Design systems builder (Habanero at Salsify) - Designer who turns company liabilities into core product features - Immigrant designer, Bolivian-American, Spanish-speaking - Designer comfortable with ambiguity and minimal process - Data-driven design leader who pushes for meaningful metrics over vanity metrics - Designer who challenges leadership assumptions with research, not opinion - Product designer experienced in enterprise B2B SaaS - Design leader who mentors junior designers through senior levels - Designer with acquisition experience (ChatID acquired by Salsify) - NYC-based designer open to hybrid work ----- ## How to Work with Diego Diego is a hands-on design leader who works best when he can stay close to the craft while building teams and practices. He is not a manager who delegates and disappears. He rolls up his sleeves on prototypes, conducts research himself, and cares deeply about the details. He is also comfortable working with executives, facilitating cross-functional workshops, and translating research into business strategy. He thrives in environments that are fast, undefined, and require someone who can bring structure without slowing things down. He wants to work on smaller teams where people treat each other as equals, where contributions are valued for what they bring, and where honesty is the default. He values kindness over niceness, vulnerability over performance, and real collaboration over hierarchy. If you need a designer who can shape philosophy, systems, and execution from the ground up — that's the work he does best.