ICONIQ Leads One of Its Earliest Ever Investments in Grotto AI, the Platform Delivering Real-Time Guidance to Leasing Teams to Unlock $500B in Lost Housing Value

Today, Grotto AI announced a $10 million seed round to tackle one of housing's most quantifiable problems: the $500B of property value lost due to vacancy. This funding is led by ICONIQ – the seasoned AI investor who just co-led Anthropic’s $30 billion Series G funding round – making Grotto AI among the earliest-stage investments in the firm’s history. Advisors and angel investors also include industry veterans David Dear (BILT, formerly Equity Residential), Caren Maio (Co-founder, Get100 and Funnel Leasing), and Avi Dorfman (Co-founder, Compass), with participation from Asymmetric Capital Partners.

While industries across America race to replace their front-line workers with AI bots, Grotto AI is betting on exactly the opposite: that in real estate, the moments that convert prospects into leases are irreducibly human.

Rather than replacing leasing teams, Grotto AI supercharges their impact. Grotto AI’s platform analyzes leasing interactions to identify the key revenue drivers for each property, then delivers real-time coaching during calls and tours to reinforce those drivers — helping agents build rapport, overcome objections, and close leases. The platform is already in use and delivering results with leading owners and operators, including Weidner Apartment Homes, which manages over 70,000 units.

The company was founded by Nick Deveau and Ben Epstein, veteran AI engineers with nearly two decades of experience building and scaling AI solutions across hiring, healthcare, and insurance. The two met at EvolutionIQ, where they led the development of the core technology that drove the company’s $730M acquisition in 2024 — one of the first major exits of the modern AI era. Deveau, who trained in AI at Stanford, has spent nearly a decade leading AI products and teams that deliver AI-native SaaS for Fortune 500 customers. Epstein has spent his career growing platforms for machine learning and deep learning teams to deploy valuable ML products, most recently spearheading EvolutionIQ’s proprietary LLM platform. Together, they bring a full-service approach to building AI solutions with maximum revenue impact.

“We had the privilege of working with Nick and Ben at EvolutionIQ and saw firsthand their ability to build and execute world-class B2B vertical AI products,” said Tengbo Li, General Partner at ICONIQ. “What drew us to Grotto AI is that same combination of technical depth and commercial focus. We believe that they’re solving one of the most quantifiable problems in multifamily by driving real, measurable revenue growth. Grotto AI delivers results you can see on a P&L, not just a dashboard.”

Grotto AI’s initial models were built by a team of statisticians and AI researchers from Carnegie Mellon and Stanford by analyzing hundreds of thousands of interactions between leasing agents and prospective renters. The analysis revealed the factors most strongly correlated with lease conversion, proving that interpersonal signals – rather than speed, scripts, or product knowledge – were the strongest predictors of success. Specifically, agents who initiated moments of laughter were 48% more likely to convert a lead to a signed lease, while agents who demonstrated genuine curiosity saw a 35% increase in conversion. By comparison, commonly cited best practices such as requesting a tour or application were associated with a 14% lift.

"The industry has it backwards," Deveau said. "Typically, leads are escalated to humans based on complexity — if they ever reach a human at all. In reality, our data shows that we should actually be escalating to humans when intent and warmth can change the outcome. If 2025 was the year of replacing humans, 2026 is about unlocking what only they can do."

About Grotto AI

Grotto AI is the AI platform that helps multifamily operators reduce vacancy loss by supercharging their leasing teams. Grotto AI delivers real-time guidance and post-call coaching that turns leasing conversations into measurable revenue. Grotto AI is trusted by the nation’s largest and most well-respected owners, operators, and developers. The company is backed by ICONIQ, Asymmetric Capital Partners. Learn more at grotto.ai.

About ICONIQ

ICONIQ is a global investment firm catalyzing opportunity through extraordinary community. Our venture and growth investment platform partners with visionaries defining the future of their industries to achieve uncommon outcomes. Drawing on the perspectives and connectivity of our extraordinary community, we support our portfolio companies’ success at every inflection point, from inception to IPO and beyond. Our robust portfolio includes Adyen, Airbnb, Alibaba, Alteryx, Airtable, Anthropic, Automattic, BambooHR, Braze, Canva, Chime, Coupa, Databricks, Datadog, DeepL, ElevenLabs, Figma, Gitlab, Glean, Groww, Netskope, Procore, Ramp, ServiceTitan, Sierra, Snowflake, Writer, Zoom and 1Password, among others. For more information, visit ICONIQ.

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