--- title: 'Deployments Lead at Grotto AI' canonical: 'https://feeny.ai/job/deployments-lead-grotto-ai-new-york-77ytpn31kzt3' type: 'job' last_seen: '2026-09-11' --- # Deployments Lead at Grotto AI - **Company:** Grotto AI - **Location:** New York, NY - **Employment:** full-time - **Work type:** onsite - **Posted:** 2026-02-19 - **Last confirmed live:** 2026-09-11 - **Apply:** https://jobs.ashbyhq.com/grotto/ec3bdc28-4837-45ff-9696-dfb57941afd7 ## Job description 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 one of the earliest employees 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. ## About Grotto AI ## Company Overview - **One-liner**: Grotto AI provides an AI-powered platform that supercharges leasing teams for multifamily operators by providing real-time guidance, call coaching, and prospect engagement tools to reduce vacancy loss and increase Net Operating Income (NOI). - **Entity Type**: Private (Seed Stage) - **Headquarters**: New York City, New York, United States - **Founded**: 2025 - **Founders**: Nick Deveau (CEO) and Ben Epstein (CTO) ## Core Business - **Primary industry**: Proptech / Multifamily Real Estate Technology / Vertical AI SaaS - **Target customers**: B2B, specifically multifamily property operators, leasing agents, and property management companies - **Mission / Purpose Statement**: "Help humans shine in the moments that matter most" — specifically, transforming the home-finding journey by using AI to enhance human-to-human interactions rather than replace them. ## Products & Services - **Tour & Call Coaching**: An AI-powered tool that analyzes leasing agent calls and tours, providing post-interaction coaching to reinforce best-practices and improve conversion rates. - **Call Guidance**: A real-time AI assistant that provides live guidance to agents during calls, helping them handle objections, ask the right questions, and book tours. - **Emails and Texts**: An AI layer that supercharges written prospect communications, helping agents respond faster and more effectively. - **Leasing Performance Platform**: A full-stack analytics platform that measures ROI and tracks performance improvement across every stage of the prospect lifecycle, with a focus on eliminating "avoidable vacancy loss." ## Market Standing - **Valuation / Market Cap**: Not publicly disclosed for a seed-stage company - **Total Funding**: USD $19.4M across two seed rounds - **Key Investors**: ICONIQ Capital (led the initial seed round); other undisclosed investors in subsequent rounds. - **Growth Signals**: - Employee headcount grew +500% year-over-year (from 2 to 9+ employees). - Founded in 2025 and already raised $19.4M, a very large seed round indicating strong investor confidence. - Co-founders have a track record from EvolutionIQ, which was acquired for $730M in late 2024. - Leadership team includes executives from Procore (PCOR), Bozzuto, Windsor Communities, Bilt Rewards, and Equity Residential, bringing deep domain expertise in both AI and real estate. - **Notable Team**: - Jamie Gorski: CRO, former CRO at Procore (PCOR). - David Dear: Former Sr. Director at Bilt Rewards and First Vice President at Equity Residential. - Dennis Lyandres: Former CMO at Bozzuto / CXO at Windsor Communities. ## Competitive Advantages - **Unique "Human + AI" Philosophy**: Unlike legacy chatbots that automate and depersonalize, Grotto focuses on supercharging human agents in the critical moments (calls, tours) that drive leasing decisions. - **Deep Vertical Expertise**: Built by a team with a proven track record in vertical AI (EvolutionIQ) and direct experience in the multifamily industry (Procore, Equity Residential, Bilt Rewards). - **Measurable ROI Focus**: The platform is built with ROI measurement as a core feature, helping operators directly track NOI and vacancy loss reduction — a critical differentiator in a conservative real estate industry. - **Strong Industry Credibility**: The advisory and leadership team includes C-suite veterans from the top multifamily operators and tech companies in the US. ## Strategic Focus - **Market Penetration**: Rapidly deploying the platform with major multifamily operators across the US. - **Product Expansion**: Likely expanding beyond leasing to cover the full resident lifecycle (renewals, service). - **Scaling the Team**: With $19M in the bank and early traction, Grotto is actively hiring for Deployments, Engineering, Product Marketing, and Client Strategy roles. - **Building the Category**: Establishing "AI-enabled leasing performance" as a must-have category for multifamily operators, moving beyond back-office efficiency to revenue generation. ## Why Work Here - **High-Impact, Small Team**: With <10 employees currently, new hires will have significant ownership and direct impact on product direction and company trajectory. - **Prestigious Backing**: Backed by top-tier VC ICONIQ Capital, providing strong financial stability and network. - **Mission-Driven**: The focus on improving the home-finding experience for renters is a tangible, emotionally resonant mission. - **Hybrid Workspace**: The company operates a hybrid model with an in-office presence in New York City (NYC) combined with remote flexibility. - **World-Class Founding Team**: Opportunity to learn from founders and executives who have previously scaled companies to unicorn status and successful exits (EvolutionIQ, Procore). - **Cutting-Edge Tech Stack**: The company is at the forefront of applying LLMs and generative AI to a real-world, high-value problem. ## Sources 1. [grotto.ai](https://grotto.ai/) 2. [grotto.ai/about-us](https://grotto.ai/about-us) 3. [LinkedIn Company Page](https://www.linkedin.com/company/grottoai) 4. [Built In](https://builtin.com/company/grotto-ai) 5. [Jobs.ashbyhq.com](https://jobs.ashbyhq.com/grotto) ## Other roles at Grotto AI - [Product Marketing](https://feeny.ai/job/product-marketing-grotto-ai-new-york-v635d4vxzjqb) — New York, NY - [Product](https://feeny.ai/job/product-grotto-ai-new-york-82psdt2t78cc) — New York, NY - [Resume Drop](https://feeny.ai/job/resume-drop-grotto-ai-new-york-r74tncq1xpxa) — New York, NY - [Forward Deployed Engineer](https://feeny.ai/job/forward-deployed-engineer-grotto-ai-new-york-2y1fmnf8tqy5) — New York, NY - [Software Engineer, Deployments](https://feeny.ai/job/software-engineer-deployments-grotto-ai-new-york-8a9qnhj27zr7) — New York, NY - [Behavioral Scientist](https://feeny.ai/job/behavioral-scientist-grotto-ai-new-york-yszkkfz125yz) — New York, NY - [Client Strategist](https://feeny.ai/job/client-strategist-grotto-ai-new-york-tgmc99s28caq) — New York, NY