Ramp’s Second Era: The Return to Zero-to-One

Simon Corry is Senior Director of Product Design at Ramp, where he leads design for a company that’s rediscovering its startup DNA while operating at scale. Before Ramp, Simon spent 25 years navigating every evolution of digital design, from the pre-iPhone world through the app store explosion to today’s AI inflection point. He’s built teams, shipped products, and watched design transform from a scrappy creative pursuit into a strategic discipline and back again. Now he’s helping Ramp make a bet that financial automation powered by intelligence could reshape an entire industry.

At a glance

* Simon explains why Ramp is entering a second zero-to-one era six years in.

* Simon describes how AI tools are buying back time without replacing designers.

* Simon shares how Ramp Labs is building an industry-defining AI R&D team.

* Simon traces design’s generational shift back toward curiosity and creativity.

* Simon outlines what he hires for: velocity, autonomy, and natural curiosity over polished portfolios.

* Simon lays out Ramp’s vision: context-aware software that’s proactive instead of reactive.

Topics

Ramp’s second era: why Ramp is 0-to-1 again

Simon thinks curious designers look for moments of maximum impact, usually at the beginning when every decision shapes the foundation—but Ramp is different. Six years in, they’ve already made the enterprise transition and now they’re on the other side, entering a second zero-to-one era driven by AI and financial automation. Some areas have strong product-market fit and need careful stewardship, but premium features without deep validation become testing grounds where designers can take real risks with startup energy inside a well-funded company. Simon is clear: “We could play it safe and Ramp will continue to be a very successful company, no doubt. Or we can lean in to the opportunity we’re seeing in front of us and really take that bet on AI automation.”

Velocity as DNA: maintaining Ramp’s competitive edge at scale

Simon divides Ramp’s work into two mental models: PMF areas that get attention to detail and rigorous process, and pre-PMF areas that get looser constraints and faster iteration—but the core principle stays the same across both, saving customers time and money. The real test is whether Ramp can maintain velocity in the PMF areas while taking bigger swings in the pre-PMF spaces, a balance that separates sustained success from companies that either slow to a crawl or break what’s working while chasing the new thing. Simon is direct about the stakes: “We absolutely want to take care of all of our existing customers. So you have to balance the velocity that we’re known for with that care, that attention to detail that we’re also pretty well known for.”

AI tools are buying back more time for the work that matters

Simon doesn’t see designers prompting their way to the app store—instead, he sees AI replacing tedious kickoff sprint meetings that used to burn days on alignment, letting small groups prompt ideas in real time and iterate before investing serious cycles. What used to take a month of red tape and sprints now takes days, and that recovered time goes into work that actually matters: accessibility, design systems, refining details that get brushed aside when teams are rushed. Simon puts it simply: “If all you were doing was drawing wireframes, you’ve probably done something wrong. You got into product design to go develop the end-to-end journey. What we’ve done with AI is giving you more time to go explore the end-to-end journey.”

What designers are responsible for knowing now

Simon draws a parallel to the old “should designers code” debate—the answer is the same: you don’t need to become an engineer, but you need enough understanding to be empathetic about the technology, the customers, and the people you’re working with. Simon thinks curiosity is the baseline, and while understanding models deeply is optional, the real challenge is designing for non-deterministic interfaces where intelligence means designers can’t predict exactly what users will see. At Ramp, Simon’s building around the idea that different customers want different levels of exposure to AI, so the answer is meeting people where they are, showing the work through suggestions and previews, and letting confidence build over time.

Ramp’s vision: context-aware, proactive software

Simon describes Ramp’s dream as no more cold starts—the insight is that Ramp already knows a lot about your business because they’re embedded in your policy, spend, and workflows, so why build a product with a thousand sections and fifteen clicks when you already know the user is an accountant whose main job is closing the books? Simon compares it to Apple versus Microsoft: Microsoft exposed everything, Apple had an opinion about what to surface but kept complexity under the hood for those who wanted it. Simon thinks traditional left-hand navigation with fifteen clicks can now disappear—tailor the experience to the user, surface the jobs that need doing, learn from interactions, and keep automating until the goal is calm, proactive oversight instead of reactive firefighting.

Ramp Labs: building an industry-defining AI R&D team

Simon gives credit to Alex Stauffer for founding Ramp Labs on the insight that most companies have trapped value—experiments that almost became products but didn’t fit the roadmap—and with AI, those experiments can spin up in hours instead of months, which means trapped value can actually ship. Labs serves a second purpose: engaging the broader community thinking about AI in interesting ways, putting experiments out in public with a fun spin, and attracting like-minded builders, which has worked exactly as hoped with DMs blowing up from founders and AI talent. Simon is clear that Labs has already created huge impact across the core product because it’s not restricted by roadmap or existing engineering stack, so it exposes what’s possible and other teams learn from both the mistakes and wins without taking those risks themselves.

Hiring super ICs: velocity, autonomy, and curiosity

Simon hires very differently at Ramp because the culture values velocity above almost everything else, which means being super comfortable with ambiguity, living in it, and thriving on autonomy—Ramp doesn’t want designers who need to be led into problem spaces, they want designers who embrace AI tooling to move faster and go face-to-face with customers using prototypes. Simon looks for natural curiosity in candidates, which shows up in how they ask probing questions and engage in back-and-forth conversation, and he has strong opinions about portfolios: make case studies optional, show the narrative and personality, tell the fun anecdotes instead of boring him with data, and please stop making black and white websites. Simon is direct: metrics are table stakes, not what makes you distinctive—”Show me the unvarnished truth and let that come out on the page.”

Design’s generational shift: rediscovering curiosity and creativity

Simon traces how design went from a scrappy creative pursuit in the 90s to a six-figure career accessible through boot camps in the last 10 years, which changed the culture dramatically—indie software companies that built for fun died out, natural curiosity faded, and UI became sterile because success metrics drove everything toward hero treatments and rectangles. Simon is sympathetic to mid-weight designers who started 5-10 years ago because they have no relationship to the scrappy fun of the early 2000s and just know how to build patterns and design systems, which is why everything from Notion to OpenAI to Anthropic feels sterile despite new technology. But Simon is bullish about what’s next because the sea change with AI is forcing a rethink, playfulness is returning, and he encourages everyone to live a little: take photographs, study color theory, travel to countries where you don’t speak the language, and if you’re in your 20s, leave your hometown unless there’s a family reason keeping you there.

Why we’ll stop calling ourselves designers

Simon doesn’t think rigid role labels will last because there are diminishing returns to overspecializing—instead, he expects more hybrids where designers jump into Cursor and get 80% of the way there while working with someone from a PM background who’s transitioned into building cloud-based architecture through AI tools. Tool sets have always evolved from Photoshop to Sketch to Figma, and the job is solving communication problems, not protecting a title—Simon’s hope is that this allows more people to spin up ideas, work collaboratively, and kill off middle management. Simon says it plainly: “I basically think you’re going to start seeing a lot of these labels kind of drop away. And I think it’s clear from a design perspective that to be successful, even in the era that we’re living right now, you need to embrace this new paradigm with AI or you will get left behind.”

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Simon Corry - Senior Director of Product Design at Ramp

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