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.

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.

• You came up through cross-functional work that selected for raw horsepower — 3-5+ years of top-tier consulting, 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.

• You're AI-native in practice — and you build agents, not just use them. Claude terminals open, MCPs wired up, evals you actually look at. You move faster than people who aren't, and you have opinions about which tools are actually good.

• You don't mind long hours when the work is worth it. The team is in at 8:30; dinner gets ordered at 7 for whoever's still here, and most days, most people are.

• You're looking for a place to build, not a place to settle. Two years from now, you could be running one of the strategic functions you reshaped, owning Ekho's agent infrastructure as its own discipline, or carving out a role we don't have a name for yet. All three are real paths.

• To start, you'll have a call with Nisarg or Charlie to learn more about the role and all-things Ekho. Bonus points if you come with your favorite joke.

• From there, you'll chat with Rowan to hear about how the founders are thinking about the strategic roadmap ahead and what it'll take to execute against it. You'll also use that time to share more about your experience and what fires you up the most.

• The onsite is where it gets really interesting. Before arriving, you'll be asked to prepare a case study to show us how you've created real, tangible impact in your prior role. From there, we'll have an interesting (and hopefully fun) live case ready for you once you arrive. This case will be tailored and representative of the types of problems you'll start to tackle from Day 1 at Ekho.

• After that, lunch with the whole team, and a presentation sharing both cases to our team.

• We move fast when we find the right person. And we respect your time enough to be honest if it's not a fit.