Stessa

Stessa offers a streamlined, finance-first platform designed for real estate investors—both individuals and small businesses—with a strong focus on tracking rental income, expenses, and portfolio performance. It combines property management tools with automated accounting and tax reporting—all delivered via web and mobile apps 

• Founded in 2016 by Heath Silverman and Jonah Schwartz, headquartered in the San Francisco Bay Area, with a team of 11–50 employees by 2023 

   

• In 2021, Stessa was acquired by Roofstock, a major proptech firm, officially announced through Crunchbase and Yodlee sources in March 2021 

   

• As of early 2025, over 300,000+ landlords/investors rely on Stessa for portfolio oversight.

• Before acquisition, Stessa participated in the Envestnet | Yodlee incubator, using Yodlee's API for financial data aggregation

   

• It received non-equity assistance with no public venture capital rounds, but has backing implied via Yodlee incubator and later acquisition by Roofstock

   

• The acquisition by Roofstock likely followed revenue-driven terms, supported by the strong user base and asset tracking milestone (>$100 B AUM)

• Essentials (Free): Unlimited properties, single-entry accounting, auto bank feeds, tax-ready reports (Schedule E), receipt scanning, and mobile access

   

• Manage ($12/mo): Adds automated rent collect, vacancy advertising, custom leasing templates, tenant applications and screening, eSigning, and basic support 

   

• Pro ($28/mo): Includes advanced bookkeeping, full Chart-of-Accounts, CapEx tracking, unlimited receipts, priority support, enhanced banking with higher APY (3.98%), debit cards, and tenant fee waivers 

   

• Core Tools:

   

  • Real-time portfolio dashboards (cash flow, NOI, rent roll)

     

  • Automated banking integration and high-yield FDIC-insured accounts

     

  • Tenant screening via RentPrep

     

  • eSign with DocuSign

     

  • Maintenance tracking, document storage, and tax package prep

     

  • Mobile apps support quick receipt capture, tenant management, and financial insights

• Stessa Cash Management (2022): Banking tools—dedicated checking accounts for each property, rent automation, late fee handling, and debit cards with cash-back and APY (~3.98%) 

   

• Stessa Pro (2024): Premium tier offering advanced financial modeling, unlimited properties, extended report export, and partner/investor access features 

   

• Recognition: Surpassed $100 billion in assets tracked by March 2023, and ranked among the top real estate investor software of 2025 

• Tech-first and user‑centric: Built by investors for investors, emphasizing ease-of-use and reducing manual work with automation 

   

• Security-focused: Employs bank-grade protection and multi-factor authentication, with FDIC insurance for banked deposits 

   

• Efficiency-driven: Claims an average of 100+ hours saved and $4,000 returned to investors annually through automation 

• Over 300,000 landlords/investors, including individuals and small property managers, tracking more than $100 billion in real estate assets 

   

• Rated 4.5/5 on SoftwareAdvice and similar platforms, with strong feedback on financial reporting, mobile experience, and simplicity, though some feature limitations noted for larger-scale PM tasks.