resident-engagement
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The Nine-Step Lunch That Became Two
A Belgian software company found its opening in senior living by watching the small frictions of an ordinary day. The lesson was less about teaching older people to tap a screen than giving a meal request somewhere reliable to go.
Enumerate Is Turning the HOA Back Office Into One Big, Boring Advantage
HOA work is a thicket of invoices, late dues, board questions and bounced emails. Enumerate's bet is that the winner will be the company boring enough to connect every last one of them.
LifeLoop Started With One Worried Family. Now It Wants to Be the Operating System for a Better Old Age
A naive plan for a family app became a platform used in more than 4,700 senior living communities. The useful lesson is not the software - it is how LifeLoop followed the paperwork until it found the real problem.
The HOA Software Bet: How CINC Systems Turned Boring Back-Office Work Into an AI Business
CINC Systems spent two decades connecting the unglamorous machinery of HOA management. Now it is using that unusually deep data foundation to automate the invoices, budgets, board packets, and resident requests that make property managers dread Monday morning.
Daisy
Daisy is an AI-native property management company for condos, co-ops and HOAs, founded in 2020 in New York City. It replaces the manual workflows and patchwork of tools legacy managers rely on with a single platform that unifies building finances, maintenance requests, compliance, board decisions and resident communication. Pairing proactive human managers with automation and AI agents, Daisy manages more than 4,000 units across nearly 200 buildings in NYC and has begun expanding into New Jersey, with a stated goal of national and global reach by the end of the decade.
EliseAI
EliseAI is a New York-based artificial intelligence company that builds conversational and agentic AI to automate the routine, high-volume communication work of two administratively heavy industries: rental housing and healthcare. Its assistants answer calls, emails, texts and chats around the clock - scheduling tours, handling maintenance and renewals, collecting rent, and booking patient appointments - so property and clinic teams can focus on people rather than paperwork. Founded in 2017 as MeetElise, the company crossed $100M in annual recurring revenue, serves roughly 70% of the 50 largest U.S. rental housing operators, and reached a $2.2 billion valuation with its 2025 Series E led by Andreessen Horowitz.
Cobu
Cobu is a Boston-based proptech company that turns apartment residents into a real community - and turns that community into occupancy. Its resident-powered, AI-enabled platform runs building-wide chats, interest groups, in-person events, and always-on Google review and referral outreach, backed by a team of virtual community managers. For renters it fights isolation; for owners and operators it drives signed leases, higher renewals, better online reputation, and less busywork for on-site teams. Founded in 2018 as Doorbell, Cobu is used across dozens of U.S. states and by many of the country's largest multifamily operators.
Benjamin Pleat
Benjamin (Ben) Pleat is the CEO and co-founder of Cobu, a Boston-based resident-engagement platform that turns apartment buildings into actual communities. After watching his extroverted mother feel isolated in a well-appointed Manhattan building - and learning that apartment owners bleed money to roughly 50% annual tenant churn - he built a company on a simple bet: a single friend in your building makes you 30%+ more likely to renew your lease. A Harvard economics grad who passed through WeWork's growth team and Goldman Sachs' real estate private equity group, Pleat now leads a company that has powered community in tens of thousands of apartment homes by getting neighbors into the same room for poker nights, potlucks, and chef dinners.