VP of Design @rippling. Eventually everything connects.

San Francisco, CA
Joined July 2013
Always has been.
The future belongs to designers who build.
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This, but it’s also very much a Gell-Mann Amnesia effect.
A common dynamic I observe with AI: it feels most impressive when you don’t know much about the subject, don’t care or don’t have a clear idea of what the you want. This applies across design, code, legal, and more. If I don’t know code very well, every piece of code it writes feels very impressive. Once you know what something should feel or look like, it becomes almost impossible to guide AI there. And you definitely can’t one-shot it.
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This is like having a 5-axis CNC mill in your hands and sending your designs to the plotter.
Now you can use AI agents to design directly on the Figma canvas, with our new use_figma MCP tool and skills to teach them. Open beta starts today.
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Fun chat with @BrettBerson from @firstround on Executive Function. We got concrete on what “quality” actually means, scaling design in hypergrowth, and why the best teams blur the lines between design/product/engineering. (Plus I got to slip in a Henry Dreyfuss mention!)
This is Episode 2 of Executive Function with Ryan Lucas, VP of Design at Rippling and former Head of Design at Retool. For Ryan, everything begins with being very clear about what the job of design and a design function really is. In his words, “Useful, usable and desirable are the three things we need to deliver. And I think people often forget about the last bit, but it’s incredibly important to the practice of professional design, whether it’s physical products or software products. Henry Dreyfuss said the designer’s job is not done if the product doesn’t sell, and I’ve always believed that.” We go on to discuss: - Design leaders who "shield" their teams from organizational chaos are doing them a disservice, not a favor. - To truly scale quality, you probably need a benevolent dictator, one opinionated person who sets the bar. - Parker Conrad goes directly to the individual designer when he sees a problem, skipping Ryan entirely, and Ryan thinks that's great. - At Rippling, individual designers sometimes own a Series C company's worth of product by themselves. - Great creative work cannot come from fear because fight-or-flight shuts down the prefrontal cortex, which is where all creative thinking lives. - In the absence of a date, there is no commitment, and that rigor around commitments is what makes Rippling's speed possible. - One-on-ones should be jam sessions on hard problems, not status updates or career development chats. - He'd rather a young designer have opinions he completely disagrees with than no opinions at all. - The hardest skill in the job is knowing which balls are rubber and which are glass, and you only learn by letting some drop. - The most successful use of a design crit is when designers tell you upfront what feedback they actually need, otherwise everyone wastes time on things that have already been decided. - The perfectionism that makes someone a great designer is the same trait that will prevent them from becoming a great design leader. - The best designers steer the business, they see a problem, come out of their lane, and move the tiller without being asked. Timestamps: 03:29 The Useful, usable, desirable — and used — design framework 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 27:53 How to build judgment through pattern matching 34:31 Why Figma is not the source of truth 38:39 The "Do/Try/Consider" framework 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution
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“98% of everything that is built and designed today is pure shit. There's no sense of design, no respect for humanity or for anything else. They are damn buildings and that's it. Once in a while, there's a small group of people who do something special. Very few.”
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Ryan Lucas retweeted
Industrial designers make brilliant software designers. They are wired to put in way more care and intent into what they ship. This is still very underrated.
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“Do you want to sell sugar water for the rest of your life, or do you want to come with me and help enterprises adopt agentic AI to streamline their complex business processes at scale?”
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Justin quietly built one of the best brand teams in Silicon Valley at @retool, and they just dropped a new album. ➡️ retool.com
Today marks a new chapter for @retool. A work forever in progress. Our ode to good software. We have a new brand that I'm beyond excited to finally share. Designed and built in house by a team of the most talented people. Check it out for yourself. 👀 retool.com
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We're hiring AI engineers at Retool as part of a new team we're building. We believe Retool will be the fastest, AI-powered developer inner loop. Our primitives like components, logic, databases, and storage make us positioned to build the future of AI-driven programming. 🧵
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Excited for this to hit the world. LLM-generated code is great, but visually seeing how your prompt gets translated into a workflow is such an unlock. It helps you learn and tweak things, rather than just hoping the output does what you want.
Never build another business automation yourself. Go from prompt to runnable Workflow in seconds with AI ⚡️
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In 2007, a tiny team of hackers built Yahoo! Pipes and immediately changed how we think about the web as a user-programmable surface. Our creative team at Retool decided to retell the story in a long-form visual behind-the-scenes deep dive... incredible. retool.com/pipes
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“I’m completely bowled over by this joy that a pencil leaves on paper when you move it around. And that’s not even art yet, it’s nothing, but it’s leaving a mark, making something that hadn’t existed until then.” artnews.com/art-news/news/ve…
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Rest in peace, Vera Molnar.
1924 – 2023 🖤
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Ryan Lucas retweeted
A few odds and ends made this year for @retool. – at Tulsa, OK
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Ryan Lucas retweeted
How are companies *𝐚𝐜𝐭𝐮𝐚𝐥𝐥𝐲* using AI? We surveyed 1500+ devs, builders, and business leaders to explore production use cases, the models, infrastructure, and tools people are using, and much more. Dig into the new report: retool.com/reports/state-of-…
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I've wanted to write a rich history of Microsoft's Visual Basic for a long time. VB pioneered visual programming and had 3.5M developers(!) at its peak, but was lost to the sands of time. A short 18 months and 5,000 words later, it's finally finished👉 retool.com/visual-basic/
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Supa fresh page design was provided by @camronsackett @justinpervorse and Parker Hutchison on the crack Retool creative team, with a special assist from @ZachSaucier.
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And, of course, many thanks to @MrAlanCooper and @geary for bringing Ruby... er, Tripod... er, Visual Basic into the world—and sharing their time with me to tell the story of a fascinating piece of programming history. Give it a read and let me know what you think. 🧐
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