Senior Software Engineer at Opendoor
Washington, United States
Diana
Cheryba
Council Member
Diana Cheryba is a Senior Software Engineer with over 5 years of experience leading cross-functional teams to build scalable, user-first web applications. She is known for end-to-end ownership and product thinking, and she has delivered high-impact features across healthcare and real estate technology.
Since February 2026, she has worked as a Senior Software Engineer at Opendoor, a technology-driven real estate platform that helps homeowners sell, buy, and transact with greater speed and certainty. She modernized the Cash Now, More Later pricing model to lower seller fees and align resale incentives through weekly carrying costs, which drove a 25% conversion lift, protected 150 bps in gross margin, and influenced $2M-$5M+ in annual transaction margin. She shipped the Final Offer Comps experience, which turned the final offer from a black-box price into a data-backed seller decision flow, lifting conversion by 1-3% and reducing pricing-confidence escalations by 20%. She also architected post-contract repricing infrastructure that replaced manual escalations for late-stage price changes with a repeatable reprice-and-re-sign workflow, projected to save 1,000+ operations and engineering hours annually and protect $1M+ in transaction value. In addition, she created an internal transaction state simulator for seller and closing flows, cutting staging setup from hours to minutes and speeding up QA for contract-signing, dashboard, and closing workflows.
From May 2023 to December 2024, she was a Senior Software Engineer at Oak Street Health, a value-based primary care provider for Medicare-eligible adults. She led a team of four frontend engineers to deliver core Encounter Note features, reducing documentation errors and improving accuracy, which contributed to $18M in annual revenue impact. She built an order management system that generated $11.2M in annual revenue by streamlining care delivery and improving reimbursement compliance, and she established new billing workflows that reduced administrative burden and lowered provider attrition by 15%. She architected and implemented a Diagnosis Modifier Workflow that lets clinicians refine broad diagnoses efficiently. On the engineering side, she developed declarative test utilities that removed boilerplate, cut test code by 30%, and doubled the speed of writing component tests. She also eliminated redundant API calls in Encounter Note, reducing peak server load by 3,000 requests per minute.
Since February 2026, she has worked as a Senior Software Engineer at Opendoor, a technology-driven real estate platform that helps homeowners sell, buy, and transact with greater speed and certainty. She modernized the Cash Now, More Later pricing model to lower seller fees and align resale incentives through weekly carrying costs, which drove a 25% conversion lift, protected 150 bps in gross margin, and influenced $2M-$5M+ in annual transaction margin. She shipped the Final Offer Comps experience, which turned the final offer from a black-box price into a data-backed seller decision flow, lifting conversion by 1-3% and reducing pricing-confidence escalations by 20%. She also architected post-contract repricing infrastructure that replaced manual escalations for late-stage price changes with a repeatable reprice-and-re-sign workflow, projected to save 1,000+ operations and engineering hours annually and protect $1M+ in transaction value. In addition, she created an internal transaction state simulator for seller and closing flows, cutting staging setup from hours to minutes and speeding up QA for contract-signing, dashboard, and closing workflows.
From May 2023 to December 2024, she was a Senior Software Engineer at Oak Street Health, a value-based primary care provider for Medicare-eligible adults. She led a team of four frontend engineers to deliver core Encounter Note features, reducing documentation errors and improving accuracy, which contributed to $18M in annual revenue impact. She built an order management system that generated $11.2M in annual revenue by streamlining care delivery and improving reimbursement compliance, and she established new billing workflows that reduced administrative burden and lowered provider attrition by 15%. She architected and implemented a Diagnosis Modifier Workflow that lets clinicians refine broad diagnoses efficiently. On the engineering side, she developed declarative test utilities that removed boilerplate, cut test code by 30%, and doubled the speed of writing component tests. She also eliminated redundant API calls in Encounter Note, reducing peak server load by 3,000 requests per minute.
Earlier, she spent three years at SAP Signavio, first as a Front-End Engineer from February 2020 to November 2021 and then as a Senior Front-End Engineer from November 2021 to January 2023. In the earlier role, she engineered a feature-rich Workflow Builder for the Build Process Automation platform that enabled nontechnical users to automate processes and decreased IT support requests by 45%. She also developed an internal bike-rental map that saved 20 minutes daily for 30% of the office. As a senior engineer, she designed the architecture and led a team of six engineers to deliver the Process Flows module for Signavio Process Insights, addressing over 1,000 recurring workflow inefficiencies surfaced in customer data. She implemented a custom SSR solution for the SAP client e-commerce platform Flexi, which required minimal codebase changes and reduced loading times by 60%. She also mentored colleagues and delivered recurring presentations to the SAP application engineering department.
Alongside her roles, Diana Cheryba has served since December 2023 as Owner and Lead Engineer at Spectrum Unlimited LLC, where she builds ClientBirthday, a tool for creating and sending personalized greetings to clients, friends, and family. She rebuilt a 29-year-old PHP and MySQL system using React, Express, and MongoDB, migrating all users with zero downtime and adding email scheduling and a template editor. She also architected and developed News of the Past Professional, which replaced a 38-year-old Windows-only Visual FoxPro application with a cross-platform Electron desktop version supporting Mac and Linux. She delivered the full product stack within twelve months, including frontend, backend, authentication, billing, database layer, and desktop software, and she owned design, architecture, and implementation end to end.
Her technical expertise spans JavaScript, TypeScript, HTML, CSS, React, Vue.js, Redux Thunk, Redux Saga, Electron, Node.js, Express, NestJS, Ruby on Rails, REST, GraphQL, gRPC, OAuth, JWT, MongoDB, Mongoose ODM, PostgreSQL, Docker, Nginx, AWS, Azure, GitHub Actions, Vite, Webpack, Babel, OpenTelemetry, Sentry, Datadog, Jest, and Vitest, along with software architecture, test-driven development, Agile methodologies, user-centered design, team management, and mentoring.
Alongside her roles, Diana Cheryba has served since December 2023 as Owner and Lead Engineer at Spectrum Unlimited LLC, where she builds ClientBirthday, a tool for creating and sending personalized greetings to clients, friends, and family. She rebuilt a 29-year-old PHP and MySQL system using React, Express, and MongoDB, migrating all users with zero downtime and adding email scheduling and a template editor. She also architected and developed News of the Past Professional, which replaced a 38-year-old Windows-only Visual FoxPro application with a cross-platform Electron desktop version supporting Mac and Linux. She delivered the full product stack within twelve months, including frontend, backend, authentication, billing, database layer, and desktop software, and she owned design, architecture, and implementation end to end.
Her technical expertise spans JavaScript, TypeScript, HTML, CSS, React, Vue.js, Redux Thunk, Redux Saga, Electron, Node.js, Express, NestJS, Ruby on Rails, REST, GraphQL, gRPC, OAuth, JWT, MongoDB, Mongoose ODM, PostgreSQL, Docker, Nginx, AWS, Azure, GitHub Actions, Vite, Webpack, Babel, OpenTelemetry, Sentry, Datadog, Jest, and Vitest, along with software architecture, test-driven development, Agile methodologies, user-centered design, team management, and mentoring.