Senior Software Engineer - Automation

Gifthealth is revolutionizing healthcare by simplifying the management of prescriptions and health services. They are seeking a Senior Software Engineer – Automation to design, build, and maintain internal automation systems that support pharmacy operations, ensuring operational excellence and compliance standards.

Responsibilities:

• Designs, builds, and deploys production automations that integrate with internal APIs and third-party operational systems (browser-based UI automations where APIs are not available)
• Builds and maintains step-level logging, alerting, and observability so automation failures, skips, and anomalies surface in real time rather than via downstream impact
• Maintains, debugs, and enhances existing automations as operational requirements change and triages production incidents and resolve them within the internal fix path
• Partners with operations stakeholders to translate process requirements into technical specifications, validates automation outputs during parallel-run periods, and defines acceptance criteria
• Establishes and documents engineering standards for automation development, logging conventions, error handling patterns, configuration management, deployment processes
• Evaluates, selects, and integrates tooling (including UI automation frameworks, observability platforms, and orchestration systems) that support the long-term automation roadmap
• Documents automation logic, operational runbooks, and architectural decisions so that knowledge transfers cleanly across the engineering team

Requirements:

• Bachelor's degree in computer science, engineering, or a related technical field; OR equivalent practical experience demonstrated through professional work
• 5+ years of professional software engineering experience, including 2+ years building and operating automation systems in production
• Experience across both API integration work and browser-based UI automation
• Knowledge of modern web application architecture; background job processing and scheduled task execution at production scale (Sidekiq, GoodJob, ActiveJob, or equivalent); OCR or document extraction tooling (Textract, Tesseract, or equivalent); browser automation frameworks (Playwright, Puppeteer, Selenium, or similar); RPA platform experience (UiPath, Power Automate, Blue Prism); REST API design, authentication patterns, retry and error handling; production observability concepts (structured logging, metrics, alerting, distributed tracing); source control workflows (Git) and CI/CD pipelines; and database fundamentals (Postgres or similar relational store; familiarity with query performance and migrations)
• Strong programming skills in Ruby and / or Python
• Excellent written, verbal, and interpersonal communication skills
• Ability to designing and building reliable, fault-tolerant production systems with clear failure modes and recovery paths
• Ability to write maintainable, well-tested code that other engineers can extend
• Ability to diagnosing and resolve production incidents under time pressure
• Ability to translating business process requirements into technical specifications without losing operational nuance
• Ability to operate independently on technical decisions with minimal direction
• Ability to communicate technical concepts clearly to non-technical operations stakeholders
• Ability to balance pragmatism (ship working automation quickly) with engineering rigor (build it correctly the first time)
• Ability to prioritize effectively across competing requests, new builds, and incident response
• AWS, security, or healthcare technology certifications
• Healthcare, pharmacy, or PBM domain experience
• Experience replacing legacy or vendor-built automation systems while maintaining operational continuity
• Experience working alongside an ML or AI platform team
• Experience replacing or migrating off third-party automation vendors with active production workloads
• Experience designing alerting strategies that minimize false positives while catching silent failures
• Experience working directly with operations or business stakeholders to refine automation behavior over time
• Knowledge of Ruby on Rails; healthcare or pharmacy operations workflows, including prescription processing, insurance verification, or order fulfillment; HIPAA and PHI handling best practices in production systems; AWS infrastructure (EC2, ECS, Lambda, S3) and infrastructure-as-code (Terraform); Snowflake or similar data warehouse environments
• Ability to mentos or coach less senior engineers on automation patterns and operational thinking
• Ability to lead cross-functional discovery sessions with operations stakeholders to scope new automation work