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 act as the first responder for issues • Deliver features end to end across the internal operations platform and client-facing portal • Maintain integration health across QuickBooks Online, Microsoft Graph, Bill.com, property management platforms, and CRM systems • Own the security posture of shipped software with explicit 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 application, database, and third-party integration layers • Instrument systems with structured logging, alerting, and monitoring for authentication failures, integrations, queues, and background jobs • Write runbooks for recurring problems • Extend 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 with an existing Philippines-based engineer and an external development partner • Provide consistent coverage from 11:00 AM–7:00 PM ET, Monday through Friday • During the first 90 days, absorb the escalation load, establish alerting and backup verification, and take ownership of a significant workstream

🎯 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/serverless backends • Familiarity with Vite, Tailwind CSS, Vercel Serverless Functions, and Supabase/PostgreSQL highly desirable • Solid SQL/PostgreSQL experience including data modeling, indexing, query performance, and migrations • Experience with REST APIs, webhooks, and third-party integrations • 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 critically review AI-generated code, especially code handling money or sensitive data • Production system ownership, including incident response, rollback or fixes, and follow-up improvements • Experience inheriting and extending another person’s codebase • Experience setting up alerting and logging • Experience with 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 with token refresh, expiry/revocation handling, and encrypted credential storage • Secure document handling, access auditing, and protection against leaked signed URLs • Secure SDLC fundamentals including input validation, IDOR prevention, secrets hygiene, and dependency vulnerability triage • Docker in production, including multi-stage builds, deploys, and rollback strategy • Hands-on experience with Azure, GCP, or AWS • Personal experience restoring PostgreSQL from backup • Ability to read and modify reverse proxy configuration and manage TLS certificate renewal • Consistent availability 11:00 AM–7:00 PM ET, Monday through Friday; schedule is not flexible • Preferred: accounting, bookkeeping, fintech, or property management software experience • Preferred: QuickBooks Online or comparable accounting/ERP integration experience • Preferred: Anthropic Claude API or OpenAI API experience • Preferred: deep Claude Code familiarity • Preferred: Python proficiency • Preferred: scheduled jobs, cron workflows, GitHub Actions, or other background processing systems • Preferred: threat modeling, access logging, or data retention policy experience • Preferred: SOC 2 or similar compliance environment experience • Preferred: distributed remote-team experience across multiple time zones

🏖️ 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 • Meaningful technical problems: multi-tenant financial data, accounting integrations, and AI-assisted workflows that replace genuine manual effort • Ongoing professional development and continuous learning