Simon Corry on How to Hire in the AI Era
Simon Corry, Sr. Director of Design at Ramp, shares practical advice on how to find and attract top designers and builders in this fiercely competitive AI boom.
At Liftoff, we have a front row seat to the talent war happening for top product designers. Companies are throwing serious money at designers, and the pressure to find great designers has never been fiercer. What worked to hire top designers a few months ago, no longer works today.
Simon Corry, Sr. Director of Design at Ramp, has been figuring this out in real time. Ramp has been on a tear: they recently crossed $1B in revenue in the last year and raised $800M to embed AI deeply across the product. But as Simon puts it, fintech is not always the obvious choice for top design talent. Since joining from Antimetal six months ago, his entire charter has been to change that.
His solution: Fundamentally change how the Ramp design team hires and operates. He’s hunting for “spiky” builders on Discord instead of LinkedIn. He’s pitching candidates on building their own “mini startups” within Ramp. He’s creating protected teams where designers can experiment with AI and ship products without strict roadmaps or revenue targets.
And it’s working. Top AI-native startup founders and designers are joining the Ramp team. During our conversation, he shares the tactics he’s used from his two interview questions that separate depth from buzzwords, to how he sources talent through public work, to why builder-managers are the new super-ICs of the AI era.
Plus: after Simon’s interview, we preview some of the latest searches on Liftoff.
– Eleanor
Q: How has your approach to hiring changed in the last few months as a result of the AI boom happening?
Before I joined the team six months ago, the design team was all generalists. Now, I’m hiring for spiky people who make you a little uncomfortable – in a good way – because they are challenging your defaults and pushing the boundaries of how you work.
In a matter of months, Ramp has gone from “it would be cool if more designers knew about AI” to “you must be using AI in your process to get a job here on the design team.”
Companies are realizing you can’t just bolt AI features onto existing products. We’ve raised $800M to go AI-native because we are in this really rare window where the pace of change is insanely fast, and the teams that learn the fastest will win.
And to be a truly AI-native company, you need people who aren’t just comfortable with AI, you need people who are already fluently building with it. And because we’re still in the wild west of AI where no one knows which toolsets will survive or which models to back, you need people who love building and are comfortable charting their own course.
To be successful in this new paradigm, you need to be cross-disciplinary and have no lanes. When you’re rebuilding from scratch, you need people who can challenge assumptions and work outside traditional boundaries.
Q: How are you actually finding the best talent given the competitive environment right now?
I’ve had to turn recruitment on its head. Most of the time, the people who are cold applying are not the people I’m looking for.
I’ve started to actively seek people out who are doing amazing things – turning up in conversations in Discord servers, Telegram chats, Twitter. Meeting people in those channels, where they’re actually building and sharing their work, gives you signal you’d never get from a polished portfolio or resume.
I’m looking at the projects they’re building, the conversations they’re starting, the problems they’re solving publicly. Often these are people who are a bit disruptive and passionate about building in public.
For example, I recently hired a former founder who was building a creator economy platform. I found him because of the work he was putting out into the world.
Q: I’m curious if you’ve changed how you evaluate talent given the impact of AI, especially as it’s making portfolios look better and helping people sound more relevant. How do you cut through that reality distortion to evaluate real capability?
Every few years there’s a popular change in title. With Web3, everyone suddenly became a crypto expert. Now with AI, everyone’s changed their title to “principal designer of AI” at such-and-such company. Then you speak to them and you realize they haven’t given it much thought.
I ask two questions to assess whether they understand AI deeply and are actually building meaningfully with it.
The first question is: How has AI tooling affected your design process? Where does it show up? What are you doing differently?
This is a self-reflection question. A great answer sounds like: “I realized that when I looked at how much time I spend in each stage of the design process, I could use this tooling to move faster. Instead of sketching in Figma for hours to whittle down ideas, I can spin up actual prototypes. I can prompt my way into something interactive and take it straight to a customer. I don’t need a two-week design sprint anymore.”
The second question is: How has your understanding of the AI landscape changed? How is this superpower affecting the way you build product?
This is about depth. A great answer sounds like: “I’ve gone into understanding how agent orchestration works — not because I want to build another chatbot, but because I want to understand what the power of these agents actually is for my company. So I worked out all the jobs to be done, built an agent orchestrator that fires off different agents to solve the problem, and shipped a prototype to customers.”
If the response to the second question is “Well, I designed a chatbot within my product,” then I know it’s pretty superficial and there’s not enough depth.
Q: Right now, the most well-known designers can choose to work anywhere they want. How do you pitch joining your team at Ramp over joining leading AI companies like OpenAI or Anthropic?
Even when we need specific roles filled, I focus on what the person wants to build. So I figure out what excites them most and work that into their job at Ramp.
This is important because I am seeking out entrepreneurial folks – people who have started their own thing already or want to in the future. During the interview process I’ll ask them to write me a document of their perfect role. Then I will figure out how to get that into Ramp.
I basically pitch it this way: you’re working on something super interesting right now. Why don’t you bring that into Ramp and build your own mini startup, and we’ll fund it? When you leave the door open for that, it’s a lot easier to attract amazing people.
And then there’s what I call the anti-sell. I tell people if they enjoy being told what problems to solve, they’re not going to enjoy it here. This attracts people who want to set their own cadence and seek out problems.
Someone who just started on our team discovered that finding conference rooms in our new office setup was really challenging for everyone, so he just went ahead and built a wayfinding app for the company. This is a small example but that pattern of finding a problem and quickly shipping a solution is what makes people successful here.
Q: One way you’ve made sure you’re at the leading edge is by creating a specific team focused specifically on AI solutions, while the rest of the team is focused on core product development. What can other companies learn from this, especially earlier stage startups?
We think about it this way: we have products that have product-market fit and products that are pre-PMF. For our PMF products, we want rigor – PMs, established pods, structured teams.
For everything pre-PMF, we say: go nuts. There’s no organized team structure. You find the problem and you build the solution.
For example, we built Ramp Sheets – an AI spreadsheet on steroids – out of this protected environment. It became one of Ramp Lab’s biggest launches to-date and fed interesting ideas back to the rest of the company.
For early-stage startups, the takeaway is: don’t put all your eggs in one basket. Give your team dedicated days – not hours, days – to experiment with AI and explore different approaches simultaneously.
And this has to be top-down. Most startups get too laser-focused on one approach, don’t validate it, and then can’t pivot. The best stuff comes from giving people room to explore.
Q: Ramp has led the conversation over the last few years around the concept of super-ICs and has been vocal about hiring super-ICs vs. people managers. How is that view changing in this new AI era?
At Ramp, we think of super-ICs as deeply talented people who spike in specific areas and are exceptionally productive. You still need super-ICs, but the evolution that I’m seeing is that the ability to lead others is no longer a nice-to-have.
Web 2.0 made it too easy where you could build a SaaS company out of the box with all the tools available. You didn’t actually have to be a builder and you could hire professional managers.
Now, with AI, it’s an entirely new frontier and you can’t just hire someone who knows “best practices.” You need people who love building, who want to get their hands dirty – and who can also grow others. That’s the builder-manager.
This shift is already happening. Builders are being celebrated again. Being nerdy is cool again.
We’re going back to garage-style, Steve Jobs startups. In the ‘80s and ‘90s, leaders had their hands in the code, in the product, in the design. They were builders first, managers second.
Thank you, Simon, for sharing your insights with us.
Highlighted searches on Liftoff
On Liftoff, hiring teams create and share role searches and get suggestions of who could be a good fit. We feature some of those searches here so that readers who have someone great in mind can request access and suggest them.
Chris Wyman is looking for a Founding Operations Lead at Deeptune. Deeptune is on the frontier of AI research, building AI training gyms that simulate real-world tasks for AI learning. Their founding team comes from companies like Glean, Uber, Retool, and Hebbia and they’ve raised $40M+ and reached 8-figure ARR within their first six months. As they grow their team from 7 to 30 people by early next year, they’re looking for a Founding Operations Lead to build and scale their data team operations during this critical growth phase. Request Access.
Vikram Bhaskaran is looking for a Senior Design Lead/Head of Design at Roon. Vikram Bhaskaran is the co-founder and CEO of Roon, a community platform where doctors can connect, collaborate, and advance clinical knowledge. The team has raised a $15M Series A from Firstmark, Forerunner, TMV, and Sequoia. They are looking for a Senior Design Lead/Head of Design to take ownership of end-to-end product design for the company. Request Access.
Radhika Delfosse is looking for a Chief Product Officer at Joy 101. Founded by Hoda Kotb and Radhika Delfosse, Joy 101 is an app that helps people unlock joy with daily wellness practices, check-ins from Hoda, and a library of expert-led content. They launched in May and are growing quickly with nearly 100,000 downloads, and have an impressive bench of advisors that include Joanna Gaines and Maria Shriver. They’re looking for a Chief Product Officer to help build a category-defining wellness platform. Request Access.
Previously on Warm Intro:
Tanay Kothari on the counter-trend practices behind building a high-velocity team
How Redscout found their CMO through people, not a job title
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