Careers at Sidewalk
Real estate is the largest asset class in the world. It's also the most broken.
Americans spend more on housing than on anything else, and the tools for finding a home haven't meaningfully improved in fifteen years. You still scroll through stale listings. You still get routed to an agent who paid for the privilege of your attention. You still find out the apartment is gone, the price is wrong, or the “listing agent” never actually had it.
The incumbents like it this way. The biggest listings portal doesn't sell you a home. Instead, they sell your attention back to the agents who were supposed to be working for you. The product is a lead-generation toll booth dressed up as a search engine.
We're building the alternative.
What we're building
Sidewalk is the real estate platform built for 2026. A true copilot for buying, selling, and renting, starting in New York City. Not a search box with filters bolted on, but a chat interface that actually understands what you're looking for, knows the market in real time, and works for you instead of whoever paid the most to reach you.
Ask Sidewalk anything you'd ask a great broker who has read every listing in the city. Sidewalk strips the noise out of the process and tells you the truth about every listing, building, block, and price.
We started with NYC because it's the hardest rental and sales market in the country.
Why now
The technology to rebuild this category from scratch finally exists. For the first time, software can reason about a home search the way a brilliant agent does, and do it instantly, for everyone, for free. The incumbents are caught in the middle: their entire business depends on a broken experience where they can charge agents for their own business.
Who we're looking for
We need people who are offended by bad products. People who think “that's just how real estate works” is a challenge, not an explanation. People who want to own a problem end to end and ship it to production yesterday.
We're a small team moving fast in New York. You'll work in person, close to the product and the people using it. The bar is high and there's more to build than you can imagine.
The founders
We've seen this industry from every side: the technology, the capital, and the operations. We're done waiting for it to fix itself.
Atul Ajoy
Second-time founder with a track record of solving hard data problems, and a longtime venture investor. He spent years backing and building the kind of company Sidewalk is becoming, then decided to build this one himself.
Rob Morgenstern
CEO of Canvas Property Group, one of NYC's most scaled real estate investors and managers. He owns, operates, and leases property in this city every day, which means Sidewalk is built on how the market actually works, not how a portal imagines it does.
Al Tylis
Former CEO of NSAM, a $40B real estate investment firm. He has moved capital across real estate at a scale most people will never see, and he knows exactly where the value leaks out of the system.
Open roles
Founding Biz Ops
You'll own a rotating set of problems across go-to-market, operations, marketing, partnerships, and whatever happens to be most broken that week. This is the role for someone who wants to be involved in every part of an early company, move fast across all of it, and grow into whatever the business needs most. You've operated before, you default to action, and you're not afraid to roll up your sleeves.
Founding Growth
You'll figure out how an entire city discovers Sidewalk without buying the same boring ads as everyone else. This role is built for someone who wants to figure out unconventional media and the types of marketing nobody has tried in real estate. You think in narratives and you've made things go viral. We think the most durable growth comes from being genuinely interesting, not from outspending the incumbents. Equal parts creative and operator.
If you think you're a fit for Sidewalk, please reach out:
careers@sidewalkhldgs.com