Product Management Jobs 2026 (Now Hiring) – Smart Auto Apply

Product

Grotto AI | New York City (In-Person)

What We Do

Grotto is the AI platform that supercharges multifamily real-estate 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 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.

The Role

The world is changing quickly, and you should be excited by a product role that changes in definition and responsibility just as fast.

As an AI-native company with top-tier engineering talent, we execute impossibly fast. This makes Product that much more important. You'll need taste, judgment, and discretion to ensure our high-horsepower development abilities are always pointed in the right direction.

• Relish in execution. This job does not operate at 30,000 feet. Much of your time will be spent turning vision into concrete reality—working with engineering, thinking deeply about the job to be done, and running projects meticulously. You know that project management is not a function to be delegated away at this stage, and you're excited by this fact.

• Own the doing, share in setting the vision. Product direction comes from many inputs: customer feedback, front-line observations from deployments, rich usage data, and yes—sometimes hunches without hard data. You know that "owning product" doesn't mean singlehandedly defining the vision.

• Go deep with customers. Sit on leasing calls. Shadow apartment tours. Watch training sessions. Understand what a Tuesday afternoon actually looks like for a leasing agent at a 300-unit property in Phoenix. The best product insights don’t come from dashboards—they come from the moment you hear an agent hesitate on a call and realize our UI caused it.

What We're Looking For

• (Non-Negotiable) You've spent at least 2 years in product, design or engineering at an early or growth-stage startup. You’ve been close enough to building that you know what it takes to ship when there's no playbook and few resources.

• You have taste. You have strong, earned opinions about what makes a product good. You relish simplicity and removing unnecessary parts of products and processes.

• You're technical enough to be dangerous. You don't write production code, but you can read a PR, sketch a data model, and argue about architecture tradeoffs without embarrassing yourself. You understand what AI is good at today, what it's bad at, and where the line is moving.

• You're customer-obsessed. You'd rather spend an hour on a Zoom with a leasing manager than in a strategy meeting.

• Ambiguity activates you. You don't ask for permission or resources or clarity. You just start.

• You're a clear thinker and a crisp communicator. You can take a messy problem and find the structure in it. When you make a recommendation, people understand the "why" immediately.

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 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.