Chief of Staff

CHIEF OF STAFF & AGENTS

New York City HQ ᐧ Full time ᐧ On-site ᐧ GTM ᐧ $150K-$200K + meaningful equity

Prior to Ekho, one of the largest retail segments in the world had no checkout button. If you wanted to buy a vehicle online, the best you could do was fill out an "I'm Interested" form and wait for someone to call you back. Found the bike of your dreams at a dealership two states away? You were mostly on your own. Tax requirements, titling workflows, and registration rules vary by state and county. Most dealers didn't sell across state lines at all, because they had no reliable way to do it.

Now they can. A buyer finds a vehicle, clicks "Buy Now," completes financing and insurance verification online, and gets it delivered to their door in a few days. The whole thing takes as few as ten minutes. And the dealer doesn't have to be at their desk (let alone awake) for any of it.

The first time one of our dealers woke up to a completed overnight sale, they messaged us: "Oh my God, this is crazy. We just fulfilled a transaction while the whole team was asleep."

We get messages like this regularly now, and they're no less exciting than the first one was. What made it possible was 18 months of untangling a combinatorics problem disguised as county-specific titling and registration, and integrating with 50 DMVs that still prefer faxes to APIs. That foundation is built. Now we're putting AI on top of it, expanding into cars, and building the transaction layer that works in-store as well as online.

One thing worth saying directly: Anthropic can't ship something tomorrow that makes this company obsolete. The moat is the foundation beneath the code: the 50-state compliance framework, the DMV relationships, and the legal licenses we've secured. That's not something you can prompt your way around. Unlike most startups right now, we're not racing against the next model update.

WHERE YOU'LL SPEND YOUR TIME

Here's what a typical week might look like (though we can guarantee no two weeks will look the same):

You'll work on whatever the most strategically important problem the company has to solve next. Marketing is first — it'll get the bulk of your time out of the gate. Owning Ekho's marketing function end-to-end: paid spend optimization across channels, the content engine, outbound to dealers, the GTM bets we haven't placed yet. Some days that means jamming with Rowan on GTM strategy in the morning, briefing creative in the afternoon, and rebuilding a HubSpot sequence over dinner. Others it means tearing down what's not working and starting over. You'll have the budget to run real experiments without anyone second-guessing you.

From there it gets cross-functional. You'll tackle whichever critical priorities are in front of the company — often more than one in a given week. RevOps: cleaning up the lead-to-customer handoff, automating renewals, instrumenting the dealer lifecycle. CS Ops: customer-comms quality, health scoring, the agents that ship status updates to dealers automatically. Hiring: building the sourcing engine and the onboarding playbook as we scale. BizOps: the dashboards, the offsite, the systems that hold a fast-growing company together. Some weeks you're heads-down on one. Others you're ping-ponging across three. The role moves with the company's priorities, not any one function's roadmap.

Running in parallel to all of it — and the thread that makes this role compound — is agent orchestration. Every function you take on, you're standing up the agents that run the long tail of it. Marketing is the proving ground: most dealer outbound today is manual, but there's a version where a dealer's first impression of Ekho comes from an agent that already knows what they sell, what their margins look like, what their nearest Ekho-active competitor is doing, and what to say to land the meeting. You'll build that, and in doing so, lay down the agent infrastructure (orchestration patterns, eval loops, internal tooling) that every function downstream will run on too. The more functions you reshape, the more leverage the orchestration layer has — and the more you become the person the rest of the company comes to when they need to ship an agent.

Your mandate is to own the most strategic problems the company has to solve and to build the agent orchestration layer that lets every function you touch scale without always requiring a human in the loop.

WHO YOU'LL WORK WITH

Rowan grew up in South Africa, where his dad owned a used car dealership. Chris grew up in Atlanta, and was close family friends with some of the largest dealer operators in the Southeast. They met at Stanford, went to see what good looked like at scale (Rowan at Duolingo, Chris at Meta), then went through YC determined to find the most overlooked problem in the largest industry they could. This one—a $2 trillion industry that couldn’t complete a sale online—was the one that stuck.

Bongi, our VP of Eng, has known Rowan since high school. He turned down several of Rowan’s ideas before finally saying yes to this one. That kind of conviction from someone who knows the founder well enough to say “no” is its own kind of signal.

Nisarg and Charlie co-lead our Client & Product Success team together. They met at UNC and when they’re not busy rooting on Carolina’s basketball team, they love engaging with our customers to understand what products and experiences will have a profound, lasting impact.

We’re 34 people, mostly in our mid-to-late twenties, with backgrounds across Stanford, YC, BCG, Goldman, and Meta. Nine of us are engineers. We spend four days a week together in our Flatiron office.

Nadim has kept every laptop from every job he’s ever had. They’re now racked in a server farm in his apartment running AI agents (before that it was crypto). David edits a sci-fi publication online and curates the strangest stories you’ve ever read. Alexis is working on becoming a DJ and producer (his genre is deep house). Jon studied film and posts photos to Slack that make everyone else’s iPhone photography look like a crime. Rodrigo can find the Spanish speakers in any room in New York, which is its own kind of superpower.

Mike is our industry vet. He’s in sales, not engineering; but you'd never guess it from the Claude Code usage. He spent decades as an executive at Triumph, Piaggio, and Zero Motorcycles, and recently organized a motorcycle track day for the whole team because he found a free event and figured people would want to go. (They did.)

There’s a gong in the middle of the office that goes off without warning every time a sale closes. Engineering debates here are about architecture decisions, ownership boundaries, and what to name things. The naming convention debates alone have generated Slack polls with 15+ options, many of them so bad they’re good. The founders have never said “my way or the highway.” Engineers define what to build and why, not just how. The whole team has an unlimited Claude Code budget, and it’s not just an engineering thing. People across the company are shipping with AI.

WHO'LL THRIVE HERE

• You came up through cross-functional work that selected for raw horsepower — 3-5+ years of top-tier consulting, IB, product, or a notable startup ops role — and you have some real operating chops behind you. Unfamiliar problem spaces don't intimidate you; they're just puzzles you haven't seen yet.

• Strategy on a slide doesn't count as the work — shipping it does. You'd rather rebuild the broken funnel, run the campaign, or ship the agent than write the deck about any of it.

• Y