Senior Software Engineer
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Job Description
Senior software engineer owning AI-first internal and client-facing tools for Keystone Bookkeepers, an accounting firm serving short-term rental operators. Operating production systems, integrations, and sensitive financial data.
Responsibilities:
- 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
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