Senior Software Engineer

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Keystone Bookkeepers

WebsiteLinkedInAll Job Openings

11 - 50 employees

🤝 B2B

🏠 Real Estate

💸 Finance

B2B • Real Estate • Finance

Keystone Bookkeepers is a bookkeeping and accounting services firm focused on short-term rental (STR) property managers, co-hosts and small businesses. They offer month-end owner reports, expense categorization, trust accounting, bill pay, and vacation tax filing, and work with STR management platforms such as Guesty Pro, Hostaway, Hostfully, Hospitable, OwnerRez, and Lodgify. Keystone emphasizes tailored, done-for-you bookkeeping for businesses managing 1–200+ listings, provides case studies and testimonials from STR clients, and positions itself as a B2B service partner that helps property managers scale and streamline financial operations.

📋 Description

• Own production reliability during North American business hours and serve as the first responder for issues • Deliver features end to end across the internal operations platform and client-facing portal • Own integration health across QuickBooks Online, Microsoft Graph, Bill.com, property management platforms, and CRM systems • Own the security posture and define explicit security acceptance criteria • Design, develop, test, deploy, and maintain scalable web applications and backend services • Build AI-enabled features and integrate LLM APIs for document extraction, classification, review workflows, and agent-driven automation • Use AI development tools such as Claude Code as part of the daily engineering workflow • Build and maintain REST APIs, serverless functions, background workers, scheduled jobs, and webhook ingestion pipelines • Own database schema design, migrations with tested rollback paths, and query performance • Triage and resolve production incidents across applications, databases, and third-party integrations • Instrument systems with structured logging, alerting, and monitoring for authentication failures, integration failures, queues, and background jobs • Write and maintain operational runbooks • Extend and modify existing codebases without unnecessary rewrites • Write maintainable, documented code and participate in code reviews • Translate technical risks and tradeoffs into business terms for leadership and operations staff • Work alongside an engineer based in the Philippines and an external development partner • Take ownership of the afternoon issue queue, triage the bug backlog, and document recurring failures during the first 30 days • Implement alerting, verify backup restoration, and establish post-deploy verification during days 31–60 • Own a significant workstream and ship a meaningful feature end to end during days 61–90

🎯 Requirements

• Bachelor's degree in Computer Science, Software Engineering, or equivalent practical experience • Senior-level full-stack experience with a demonstrable record of shipping and operating production software • Strong proficiency in JavaScript/TypeScript and React • Experience developing Node.js and serverless backends • Solid SQL/PostgreSQL experience, including data modeling, indexing, query performance, and migrations • Experience with REST APIs, webhooks, and third-party integrations • Experience handling provider API changes and failure modes • Experience with Git, testing, CI/CD, and collaborative development workflows • Genuine AI-first development experience using Claude Code or comparable AI coding agents on shipped projects • Ability to effectively prompt, intervene in, and critically review AI-generated code, especially code handling money or sensitive data • Production ownership experience, including diagnosing incidents, rolling back or shipping fixes, and closing gaps afterward • Experience inheriting and extending another person's codebase • Experience setting up alerting and logging • Experience building or maintaining software handling sensitive financial or regulated data • Working knowledge of multi-tenant data isolation, PostgreSQL row-level security, scoped request context, and server-side authorization • OAuth 2.0 integration experience, including token refresh, expiry and revocation handling, and encrypted credential storage • Secure document handling experience, including access-controlled storage and access auditing • Knowledge of secure SDLC fundamentals, input validation, IDOR prevention, secrets hygiene, and dependency vulnerability triage • Docker production experience, including multi-stage builds, deployments, and rollback strategy • Hands-on experience with Azure, GCP, or AWS • Experience restoring a PostgreSQL database from backup • Ability to modify reverse proxy configuration and manage TLS certificate renewal • Consistent availability from 11:00 AM–7:00 PM ET Monday through Friday • Familiarity with React, Vite, Tailwind CSS, Vercel Serverless Functions, and Supabase/PostgreSQL is highly desirable • Preferred domain experience in accounting, bookkeeping, fintech, or property management software • Preferred experience with QuickBooks Online or comparable accounting/ERP platforms • Preferred experience with Anthropic Claude API or OpenAI API • Deep familiarity with Claude Code specifically is preferred • Python proficiency for automation, data synchronization, and background processing is preferred • Experience with scheduled jobs, cron workflows, GitHub Actions, or other background processing systems is preferred • Exposure to threat modeling, access logging, or data retention policy work is preferred • SOC 2 or similar compliance-minded environment experience is preferred • Experience working in distributed remote teams across time zones is preferred

🏖️ Benefits

• Competitive salary and benefits • Significant ownership and a direct line to the founder — no layers between you and the decision • A collaborative, remote-first environment across three regions • The opportunity to build modern AI-powered software with current tooling, and to decide how it gets built • Ongoing professional development and continuous learning