NYC's Affordable Housing Lottery Is Broken. This Startup Aims To Fix It

Red tape keeps New Yorkers out of affordable housing for three times as long as elsewhere in the country, but one startup thinks it has found a pair of scissors.

Pronto Housing, a 6-year-old startup that works with landlords to cut down the time it takes to get tenants into affordable units, started turning a profit this year after raising $12M since its founding in 2020. Its influence is poised to grow as the city looks for ways to get New Yorkers into affordable housing faster. 

“I had overseen lease-ups that had an affordable component,” Pronto co-founder Christine Wendell said in an interview last week. “I was like, ‘Why is this taking so long? This process is terrible.’”

The median affordable building in the five boroughs took 439 days to be leased up between 2022 and 2024, according to an Enterprise Community Partners study — well above the national median of 156 days.

Prospective tenants in NYC apply for affordable units through the city’s Housing Connect lottery system, which selects applications at random. But the process's bureaucratic hurdles cause delays, industry players and tenant advocates say, and Mayor Zohran Mamdani's top housing official said the city wants to overhaul it. 

When Mamdani convened a task force last month to come up with ideas for the city to streamline housing processes, Pronto co-founders Wendell and KC Crosby were among those invited to join the group.

Wendell and Crosby met in 2017, when Wendell was working in real estate asset management and Crosby in private equity. They reconnected in 2020, after Wendell had worked stints at RXR and Megalith Capital Management and after Crosby had bought and sold a boutique hotel on an island in Honduras.

“I came back to the U.S., connected with Christine, just saying, ‘Hey, I'm back, and I don't know what I'm going to do yet,’” Crosby said. “And Christine was like, ‘I have an idea.’”

The pair launched Pronto to make it easier for tenants to get into affordable housing faster and for landlords to lease up the income-restricted units in their buildings. It has grown from three employees when it launched in 2020 to a headcount of 45 today, operating across more than 20 states. 

Pronto's software processes housing applications and helps landlords with initial compliance certifications and annual recertifications. Last year, it added capabilities to list and market vacant units after the Department of Housing Preservation and Development began allowing landlords to market affordable units that needed re-leasing rather than leaving some languishing in the city-run system for more than a year.

Pronto has been slowly building up its client roster, finding new customers from referrals and networking. That is how Crosby met Joy Construction principal Eli Weiss at a Valley National Bank-sponsored event.

“I was in my usual perch position at any networking event, right next to the bar,” Weiss said. “I could say that my relationship [with Pronto is] credited to Valley National Bank and tequila.”

Weiss was partway through leasing up around 500 affordable units at 1164 and 1184 River Ave. in the Bronx at the time and decided to give Pronto a chance.

After the company slashed the time it took to lease those buildings, he hired Pronto again to fill a 611-unit, 100% affordable apartment building at 375 W. 207th St. in Inwood. Weiss had underwritten a 17-to-18-month lease-up period but is now on track to fill the building within around 13 months. 

After seeing its initial results, Weiss decided to invest in the business as well.

Pronto’s steady expansion has happened as affordable developers and landlords across the country sought ways to get tenants into newly delivered units.

NYC developers delivered 85,962 affordable homes between 2023 and 2025, according to HPD.

But those new apartments haven’t made a dent in affordability: High demand and the city’s record-low 1.4% vacancy rate contributed to median rents in Manhattan shooting past $4K a month in 2022. Rents have kept rising since, hitting $5K a month in March for the first time.

All the while, the slow and complex leasing process for affordable units means more eligible New Yorkers are left renting market-rate apartments or living with roommates or family while they wait for their housing applications to be approved.

The process is far more onerous than free-market housing. Applicants may be asked to produce proof of income levels and employment as evidence of residency, citizenship and that they don’t own a home somewhere else. When an applicant’s number is called, an agent hired by the landlord asks for the documentation.

Even if prospective tenants manage to get all their documents together in the time allowed by the city, the majority of applications have historically been done on paper before being sent to HPD for review. 

“There's just a lot of things now that technology reduces that friction, that a manual person going through actual documentation doesn't have to do that anymore,” Crosby said. “You can now evaluate 10,000 people at a time instead of pulling 20 at a time.”

Pronto’s technology has cut in half the time it takes to process applications, said Mildred Flores-Thevenin, the director of affordable housing marketing and compliance at Settlement Housing Fund, another Pronto customer.

“The Pronto system really helped manage the document review process, the calculations, being able to have applicants sign the forms directly on the system as well,” she said. “It really brought everything together.”

But the lottery system is still too slow at getting people into those units. When Wendell and Crosby met with the Mamdani administration alongside marketing agents and property managers as part of a group tasked with improving the process, they said the tenor from City Hall marked a shift.

Previous administrations introduced incremental tweaks like removing credit checks and creating a new user interface, but they failed to meaningfully change the situation facing landlords and tenants, Wendell said. 

“I think that that is a significant change to how the conversation has taken place, where maybe people got a little too stuck in the griping,” Wendell said.