In Oakland, California, Using Property Ownership to Solve Teacher Retention

Written by:

Alejandra Rodriguez

Date:

08 Jun 2026

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Teacher turnover is one of the more persistent challenges facing urban school districts, and while the causes are complex, housing costs have emerged as a measurable driver. In Oakland, 63% of educators leaving the Oakland Unified School District cited the high cost of housing as a primary reason for departure. One organization has spent the past several years building a practical response – and is now moving into property ownership to make that response last.

Rooted, a program of the Oakland Fund, has been working since 2020 to improve housing affordability for teachers and other school district employees. The organization’s approach has evolved from direct financial assistance into a more durable model centered on building a nonprofit-owned educator housing portfolio, to our knowledge the first of its kind in the country.

From Stipends to Ownership

Rooted’s early programming included housing stipends, which stabilized costs for individual educators but required constant replenishment. The organization found that when housing costs were stabilized, educator retention rose sharply, but the model needed to scale beyond annual grants.

Jack Woodruff, Housing Director at Rooted since 2023, says the organization needed to grow beyond that initial approach. The next step was a housing marketplace that connects educators with private landlords willing to offer discounted rents and other incentives. The platform functions similarly to a standard rental listing site, but with negotiated benefits not available through Zillow or Craigslist. In one example, a unit listed at $2,550 per month is available to educators through the marketplace at $2,380 per month, saving roughly $2,500 over the course of a lease through a landlord-funded concession. Landlords bite this bullet to fill vacancies with great, long-term tenants, Woodruff says.

Rooted also covers security deposits for educators via a revolving fund, and provides one-on-one financial coaching out of a recognition that reducing housing costs is only part of the equation for a workforce that is often stretched thin financially.

The Landlord Value Proposition

For housing providers, the marketplace addresses a different problem: tenant reliability. Educators may earn modest salaries, but their employment tends to be stable, their benefits solid, and their community ties strong. According to Rooted, educators placed through the program renew their leases at a 74% rate annually, compared to roughly 50% in the broader Oakland rental market.

Participation carries little risk for landlords. Rooted scrapes listings daily to mirror them on its own platform, adjusts pricing per agreed terms, and handles the administrative work of connecting educators with available units. Landlords are not required to stop advertising elsewhere or to rent exclusively to Rooted-referred tenants.

Woodruff acknowledges that larger institutional owners and REITs have been harder to bring on board. “Given the lower vacancies and delinquency and the higher renewal rates, I think the math is there for them if they choose to see it, but those institutional clients have been the toughest sell so far,” he notes. Small and medium-sized housing providers have shown considerably more openness. The organization’s recent first property acquisition has also raised its profile, drawing new housing partners to the marketplace program.

A Legislative Push

Beyond direct programming, Rooted has pursued policy changes to expand the supply of housing for educators. The organization spearheaded AB 1021, working with Assembly Member Buffy Wicks and co-sponsors including the California School Boards Association and UCLA CityLab. The legislation aimed to clear regulatory and financial barriers that have made it difficult for school districts to develop workforce housing on their surplus land.

Woodruff notes that many school districts hold surplus land that could support new workforce housing development: 75,000 developable acres, according to a 2022 Terner Center report. While Rooted is not itself a ground-up developer, the organization sees legislative advocacy as necessary to its mission of addressing the affordability gap facing educators.

Owning the Solution

The most significant recent development is Rooted’s first property acquisition, completed in February 2026 with funding support from the City of Oakland and philanthropic contributors including the Crankstart Foundation. The move marks a strategic shift toward long-term ownership as the most sustainable way to deliver affordable housing to educators. The property is a 33-unit development built in 2017, with a purchase price of $12.6M.

Woodruff’s background in fintech, including roles at Unison and Landed, both of which developed equity-based financing tools for homebuyers, informs how he thinks about building durable housing solutions. At Landed, he worked on a down payment assistance model structured as preferred equity, allowing educators to purchase homes with support that tracked alongside the property through appreciation and loss. The common thread, in his view, is applying financial innovation to a housing market that has not kept pace with the needs of middle-income workers. For example, Woodruff and Rooted worked to ensure that the acquisition was in a TCAC high-opportunity area, unusual for a publicly funded project, and forged the legal certainty needed to focus on this specific population.

“Working at Unison and Landed gave me an appreciation for flexibility and innovation that we are applying now at Rooted,” Woodruff says. “We are now benefiting directly from the kind of tenant stability that we’ve provided to other landlords for years.”

The Numbers Behind the Mission

The retention data reinforces why housing support matters for school districts, not just individual educators. Rooted reports that educators who receive housing support through its programs stay in their positions at a 93% rate, compared to an 82% district average. The gap may appear modest in percentage terms, but Woodruff estimates that once the organization reaches its portfolio goal of 150 units,  it will prevent roughly 80 educators from turning over annually in Oakland alone. “Our focus is really on those educators in their first five years, those struggling to make ends meet without the bank of mom and dad at the outset of a tough career,” Woodruff noted. 

That kind of continuity has downstream effects that extend well beyond individual classrooms. Experienced teachers build relationships with students and families over time. High turnover disrupts those relationships and places a recurring burden on districts that must recruit and onboard replacements year after year.

“A little can go a long way in educator housing,” Woodruff says. “It does solve the recruitment and retention challenges for districts, and it just needs our focus.”

Looking Ahead

With property values in the East Bay still at what Woodruff describes as historic lows, Rooted sees the next 18 to 24 months as a meaningful acquisition window. The goal is to expand its owned portfolio while continuing to operate the marketplace and advocate for policy changes that support workforce housing development more broadly.

The organization is also exploring whether its model could extend to accessory dwelling units, potentially offering homeowners a guaranteed educator tenant in exchange for building or renting an ADU, a way to bring more units online while connecting them directly to the workforce housing pipeline.

Rooted’s trajectory suggests that targeted, mission-driven property ownership can address workforce retention in ways that stipends and policy alone cannot. If the model proves replicable, particularly the combination of marketplace partnerships, direct ownership, and legislative advocacy, it may offer a blueprint for other high-cost districts facing similar educator shortages. The next test is whether the organization can scale its portfolio fast enough to meet demand before the acquisition window closes.

About the Expert: Jack Woodruff is the Housing Director at Rooted, a program of the Oakland Fund focused on improving housing affordability for teachers and school district employees in Oakland. His background includes roles at Unison and Landed, both of which developed equity-based financing tools for homebuyers.

This article is based on information provided by the expert source cited above. It is intended for general informational purposes only and does not constitute legal, financial, or real estate advice. Readers should conduct their own research and consult qualified professionals before making any real estate or financial decisions.