Deployments Lead

Grotto AI | New York City (In-Person) | 2-10 Years Experience

In Brief:

We're looking for someone both unreasonably organized and deeply warm to own our customer relationships: implementations, training, ongoing support, and everything in between. You'll be employee #3 at a vertical AI company that just raised $10M to solve a $500B problem in rental housing: the money lost due to apartments sitting vacant.

What We Do

Grotto is the AI platform that supercharges multifamily apartment teams during the moments that matter most. We're starting with leasing conversations, one of the most important decisions most of us make every year.

Our data from millions of prospect interactions shows that the #1 predictor of whether someone signs a lease isn't product knowledge or perfect scripts. It's agents who are genuinely curious and who laugh—things that AI alone struggles at today.

So we built a platform that guides leasing agents in real-time during calls and tours—helping them build rapport, handle objections, and convert more prospects into signed leases.

It's working. We drove an 80%+ increase in conversion at Weidner Apartment Homes (72,000+ units). We've been told by customers that we're "the best vendor they've ever worked with."

And this is just the start. Our vision for the world is one where life's most important conversations leave people feeling more connected.

The Role

You'll own the customer relationship from signed contract to long-term success. That means:

Implementations & Onboarding: Getting new customers live—configuring the platform, training their teams, ensuring nothing falls through the cracks. Our customers are used to vendors who disappear after the sale. We're the opposite: being a customer of Grotto should feel like checking into a world-class hotel—proactive, attentive, and frictionless.

Training: Running sessions that get leasing teams genuinely excited to use Grotto. Not reading from a script—actually connecting with people, understanding their workflows, and helping them see how this makes their jobs better.

Ongoing Support: Being the person our customers text when something feels off—and often fixing it before they even notice. Tracking usage and engagement signals to catch drop-offs early. Making sure every customer feels like our only customer.

Voice of the Customer: Acting as the bridge between customers and our Product and Sales teams. Feeding real insights back so we build the right things. We're early—you'll be defining how customer deployments are done at Grotto and setting the standard for how we scale.

What We're Looking For

The Non-Negotiable: Unreasonably Organized

This is the single most important quality for this role.

You're the person who notices when a font is inconsistent. When a follow-up is 12 hours late. When a deck has a typo on slide 47. You have systems for everything—not because someone told you to, but because chaos bothers you on a visceral level.

You're AI-Native

You use AI tools instinctively—not because it's trendy, but because you've found they make you better at your job. You're curious about what's possible and you've already integrated AI into how you work.

You're Warm

Our whole thesis is that human connection drives results. You need to embody that. Customers should feel like talking to you is the best part of their day. You're genuinely curious about people.

You Communicate Crisply

You say it in 30 seconds, not 3 minutes. You organize your thoughts before you speak. This matters because you'll be the voice of Grotto to our customers.

You're Customer-Obsessed

You talk about customers as people, not accounts. You've gone above and beyond for someone and you remember how it felt. You understand that in a startup, every customer relationship is existential.

You Have High Agency

You don't wait to be told what to do. When something's broken, you fix it. When something's unclear, you figure it out. You bias toward action.

About Us

GrottoAI’s mission is to help humans shine in the moments that matter most.

We’re starting with the process of finding a home—one of life's most important moments—where we drive bottom-line impact by helping leasing teams shine in key prospect interactions and convert more leads to leases.

GrottoAI was founded by Nick Deveau and Ben Epstein—we met at EvolutionIQ, an insurance AI company acquired for $730M in 2024. We've spent the last decade building vertical AI products in hiring, healthcare, and insurance. Now we're bringing that playbook to real estate.

We just closed a $10M seed round led by ICONIQ. We're working with some of the largest apartment owners in the country. We're lean, we're moving fast, and we're building a world where, in life's most important moments, people leave every conversation feeling more connected.