Chief of Staff

Consumers are using AI models to help them buy things. First AI models were information aggregators: tools people used to search and summarize. Now they're trusted advisors: what people consult before making a decision. Increasingly, they're becoming trusted buyers: agents that shop, evaluate, and transact on behalf of humans. When AI makes the ultimate buying decision, then it becomes more important for brands to win over AI than for them to win over the human consumer. In that world, understanding how AI perceives a company's value proposition becomes one of the most consequential things that company can understand about itself. We apply the principles of AI interpretability research to study how models actually think about companies, and underneath the surface noise we find remarkably stable beliefs, formed from the proof points a company has put into the world (often inadvertently). Companies starting to take this seriously are realizing something uncomfortable: in an AI-evaluated market, marketing claims without substance to back them up don’t work anymore. Conversely, companies that deliver on their value proposition have unbounded opportunity to reach and acquire new buyers. AI agents are judging every brand's value promise, and are teaching humans how to do the same. About our team Unusual is the AI interpretability platform for marketing and GTM teams. We help companies shape how AI models actually think about their brand and value proposition. We're backed by Y Combinator and the first investors in SpaceX, Uber, Stripe, Clay, and Notion, and we already work with Big Five agencies and Fortune 100 brands. Demand is outpacing our capacity to serve it. Our cofounder, Will, is a second-time, venture-backed founder (Khosla and Greylock backed Remedy Health). Will started AI interpretability research in 2014 at MIT, where he applied black-box interpretability techniques to language modeling built on recurrent neural networks. He also built an early prototype of Starlink at SpaceX. Prior to MIT, at sixteen, Will earned international acclaim for having successfully retrofitted his family microwave into a Farnsworth nuclear fusion reactor. Our cofounder, Keller, was previously Chief of Staff and Head of Growth at 8VC-backed Gatsby. He has made 15,000 cold phone calls as part of the Biden presidential campaign in Pennsylvania; he coauthored, “America, Unite or Die” with statistician and inventor of overnight polling, Douglas Schoen; he studied Econometrics at Princeton, where he was the youngest Div. 1 water polo captain in program history. Our Head of GTM, Sarah, has scaled two startups from to eight figure-ARR: she drove 10X growth at Circle Medical (YC W17), then was Chief of Staff at Ambience Healthcare, where she developed the marketing and sales motions from pre-revenue, to closing the first 7-figure ARR deals that led to a $1.3B valuation (backed by Oak HC/FT, Kleiner Perkins, OpenAI, and a16z). Prior to that, she advised startups and scaleups at Google, implementing strategies that drove 2-5X revenue growth. Why this role exists We've grown fast with a very small team force-multiplied by Claude Code and unlimited token budgets. Our constraint today is time. There are always more high-value things worth doing than the exec team can personally carry: a product surface that needs an owner for a week, a customer relationship that needs attention, a hiring loop that should be run well, a new market worth testing. This role exists to take any of those, get up to speed fast, and carry it to a successful outcome with little oversight, and to build the systems that make the next version of that work take a fraction of the time. You're the person the executive team relies on to create leverage on the most important initiatives at the business. Who You are You're a high-agency generalist who's at your best when you're handed something ambiguous and important and left to run with it. With little instruction, you take projects from ideation to over the finish line. You are diligent, obsessed with the details, and you can identify what tasks are worthwhile without being told. You are a team player, and you’re eager to do whatever job is required to give your team leverage. You can hold your own in a product discussion, a sales call, and a hiring debrief in the same afternoon, and your reaction is to create structure where there wasn't any. You learn quickly, both by listening and by doing. Ideally, you're already using tools like Claude Code to do your work better, and you want a role where building the systems that multiply you is part of the work itself. You have good judgment, you can be trusted with sensitive context. You might have been the most capable employee on every team you’ve ever worked on. That will not be true at Unusual. We’re looking for people that are hungry to work with the best possible people. What you'd own Whatever is most important and least owned. It shifts month to month. Here are some of the things we could see you taking up immediately: Client Success: helping our clients (executives at Fortune 500 companies, “Big Five” agencies, and scaleups) plan through their brand strategy in a world where AI is a new audience. Product: systematizing client engagement work so that it’s scalable with software or agentic workflows Sales: taking sales calls, demos, and preparing the materials for live deals and partnerships Recruiting: we are hiring like crazy. Initial screens with candidates, optimizing our hiring funnel, organizing recruiting events. Marketing: testing new growth channels, writing content, and exploring positioning Operations: doing the work and setting up systems that run the company. Fundraising: prepping materials in the lead-up to our next fundraising round. Overall, your goal is to take things off the founders’ plates. Capabilities we look for High agency, reliable. With little instruction, you take projects from ideation to over the finish line. Sharp prioritization. You can tell what's worth doing without being told, and you're diligent and detail-obsessed about getting it right. Generalist range. You hold your own in a product discussion, a sales call, and a hiring debrief in the same afternoon, and you ramp on an unfamiliar domain fast, learning by listening and by doing. Build for leverage. You instinctively turn repetitive work into systems. Claude Code, MCPs, and prototyping with agents are already part of how you work, or you're eager to get there. Low ego, team first. You're eager to do whatever the moment requires to give the team leverage, glamorous or not. If you haven't gone deep on Claude Code yet but you're a fast learner who wants to build that fluency, we still want to hear from you. What we offer Our founders both have experience in quant finance, so we think about talent the way an investor thinks about an asset. A young person with high merit and little experience is an undervalued asset, and the best return they can earn is betting on themselves early. So we hire the way we'd invest. We give high-merit people real range and real ownership long before the market would, and we bet on the team over any one idea. If that's the kind of bet you want to make on yourself, this is the seat for it. Specifically: $130–170K base + meaningful equity Direct, daily work with both founders, and a seat where you see every part of the company A research team that's done the work to make this approach possible, and a platform already producing insights no one else can A small team of people who care deeply about their craft and about each other A front-row seat to a shift in how every brand thinks about strategy over the next decade of agentic commerce The chance to build the playbook for a number of new functions, and a natural path toward owning a function (or founding something of your own) as we grow #J-18808-Ljbffr