Software Engineer, Deployments

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.

About This Role

This is not a typical product engineering role. You won't be shipping features to a faceless user base and measuring success through dashboards.

As a deployment-focused engineer, you'll work directly with our customers to make Grotto fit like a glove for each one. That means building atomic, customer-specific customizations—features, integrations, workflows—that solve real problems for real property managers. You'll partner with Deployment Leads to understand what each customer actually needs, and then you'll build it. In this specific role, you will be entirely responsible for the technical success of multiple customers.

We're not scared of last-mile customization. We believe that's where the magic happens. If you're the kind of engineer who gets energy from seeing your work in action, from visiting a customer and watching someone use the thing you built yesterday, this role is for you.

What You'll Do

• Build customer-specific features, integrations, and customizations across our Python and VueJS/TypeScript stack

• Work closely with Deployment Leads to translate customer needs into working software

• Ship fast—we operate in short cycles

• Occasionally travel to customer sites (a few days per month) to understand their world firsthand. It’s a lot fun, trust us.

• Collaborate directly with design, product, and founders

• Help define what "delivery engineering" looks like at Grotto—there's no playbook yet

What We're Looking For

• (Non-Negotiable) 3+ years of full-stack experience with Python and VueJS/TypeScript

• (Non-Negotiable) 1+ year at an early-stage or growth-stage startup

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

• Genuine excitement about customer impact over technical elegance for its own sake

• You build with AI tools (Claude, Copilot, etc.) as a default—you relish building, not the art of writing code

• Strong communication skills—you'll interface with customers, Deployment Leads, designers, and founders

• Based in NYC or willing to relocate

What Makes You a Unicorn

• Strong data analysis and statistics skills—being able to measure customer impact and dig into that data makes you a near-unicorn here

• Experience with AI/ML, whether integrating LLM APIs, building AI-powered features, or working with ML pipelines (we love BAML here)

• Background in property management, real estate, or other operationally complex industries

• Experience in early-stage startups or high-ambiguity environments