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At Gifthealth, we're revolutionizing the way people experience healthcare by simplifying the process of managing prescriptions and health services. Our mission is to provide a seamless, personalized, and efficient healthcare experience for all our customers. We're a dynamic, innovative, and customer-centric company dedicated to making a positive impact on people's lives.

Reporting to the Director of AI Engineering, the Senior Software Engineer – Automation designs, builds, and maintains the internal automation systems that support pharmacy operations across Gifthealth’s business lines. This position establishes and upholds engineering standards for logging, alerting, and self-service configuration so that automation failures surface internally and can be resolved without external vendor involvement. The work performed spans the two distinct technical surfaces of backend automations that integrate with internal APIs and the core OS, and UI automations that interact with third-party pharmacy management systems where APIs are not available.

We are seeking a Senior Software Engineer – Automation to own the full lifecycle of automation development from operational discovery and requirements through production deployment, observability, and ongoing support. This position plays a key role in supporting AI engineering team, ensuring alignment with organizational goals, operational excellence, and compliance standards.

• 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

• Education: Bachelor’s degree in computer science, engineering, or a related technical field; OR equivalent practical experience demonstrated through professional work. (Required)
• Licensure/Certification: AWS, security, or healthcare technology certifications (Preferred)
• Experience:
• 5+ years of professional software engineering experience, including 2+ years building and operating automation systems in production (Required)
• Experience across both API integration work and browser-based UI automation (Required)
• Healthcare, pharmacy, or PBM domain experience (Preferred)
• Experience replacing legacy or vendor-built automation systems while maintaining operational continuity (Preferred)
• Experience working alongside an ML or AI platform team (Preferred)
• Experience replacing or migrating off third-party automation vendors with active production workloads (Preferred)
• Experience designing alerting strategies that minimize false positives while catching silent failures (Preferred)
• Experience working directly with operations or business stakeholders to refine automation behavior over time (Preferred)
• Knowledge, Skills, & Abilities:
• 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) (Required)
• 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 (Preferred)
• Strong programming skills in Ruby and / or Python (Required)
• Excellent written, verbal, and interpersonal communication skills (Required)
• Ability to designing and building reliable, fault-tolerant production systems with clear failure modes and recovery paths (Required)
• Ability to write maintainable, well-tested code that other engineers can extend (Required)
• Ability to diagnosing and resolve production incidents under time pressure (Required)
• Ability to translating business process requirements into technical specifications without losing operational nuance (Required)
• Ability to operate independently on technical decisions with minimal direction (Required)
• Ability to communicate technical concepts clearly to non-technical operations stakeholders (Required)
• Ability to balance pragmatism (ship working automation quickly) with engineering rigor (build it correctly the first time) (Required)
• Ability to prioritize effectively across competing requests, new builds, and incident response (Required)
• Ability to mentos or coach less senior engineers on automation patterns and operational thinking (Preferred)
• Ability to lead cross-functional discovery sessions with operations stakeholders to scope new automation work (Preferred)

Work Environment

• Location: Remote
• Schedule: 8:00 A.M. to 5:00 P.M. Monday through Friday with night and weekend hours on occasion as determined by the needs of the business.
• Regular meetings with internal Prompt Engineering, ML Engineering, Software Engineering, ML Ops Engineering, and product management teams. This role may also have meetings with vendor and consultant partner representatives.

Key Essential Functions

• Must be able to remain in a stationary position for extended periods while writing or reviewing documentation
• Must be able to work on a computer for the entire shift
• Must be able to attend virtual meetings with cross-functional teams

Employment Classification

Status: Full-time
FLSA: Exempt

Gifthealth is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. All employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity, transgender status, national origin, age, disability, veteran status, or any other legally protected status.

We celebrate diversity and are committed to creating an inclusive environment for all employees. If you do not meet every requirement but still feel you would be a great fit for this role, we encourage you to apply!

This job description is intended to describe the general nature and level of work being performed. It is not intended to be an exhaustive list of all responsibilities, duties, or skills required of personnel. Gifthealth reserves the right to modify job duties or descriptions at any time.