Client Strategist

Grotto AI • New York City, NY

4d • Onsite

About The Position

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. 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.

Requirements

• Unreasonably Organized: You notice when a font is inconsistent, when a follow-up is 12 hours late, or when a deck has a typo on slide 47. You have systems for everything.
• AI-Native: You use AI tools instinctively and have integrated AI into how you work.
• Warm: You embody human connection and are genuinely curious about people.
• Communicate Crisply: You organize your thoughts before you speak and can convey information concisely.
• Customer-Obsessed: You talk about customers as people and understand that every customer relationship is existential in a startup.
• High Agency: You don't wait to be told what to do; you fix what's broken and figure out what's unclear, biasing toward action.

Responsibilities

• Own the customer relationship from signed contract to long-term success.
• Implementations & Onboarding: Getting new customers live—configuring the platform, training their teams, ensuring nothing falls through the cracks.
• Training: Running sessions that get leasing teams genuinely excited to use Grotto.
• 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.
• Acting as the bridge between customers and our Product and Sales teams.
• Feeding real insights back so we build the right things.
• Defining how customer deployments are done at Grotto and setting the standard for how we scale.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed