Resume Drop

General Interest

Grotto AI | New York City (In-Person, with some travel to customer sites)

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've driven massive increases in conversion with some of the largest apartment owners in the country. 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 is a world where life's most important conversations leave people feeling more connected.

Square Peg, Round hole? Drop Your Resume

We're a small, fast-moving team and we don't always have a role posted for every type of person we'd love to meet. If you're excited about what we're building and think you'd be a great fit—even if there's no open role that matches—we want to hear from you.

What We're Looking For

(Non-Negotiable) 2+ years at an early-stage or growth-stage startup

You build with AI tools (Claude, Copilot, etc.) as a default

Comfort with ambiguity—you thrive when there isn't a clear spec or established process

Excited by prospect of traveling to customers

Strong communication skills

Deeply organized

Based in NYC or willing to relocate

Nice to Have

Strong data analysis and statistics skills

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.