Principal AI Engineer

About DrFirst For 25 years, DrFirst has empowered providers and patients to achieve better health through intelligent medication management. We improve healthcare workflows and help patients start and stay on therapy with end-to-end solutions that enhance prescription access, affordability, and adherence. Our solutions help 100 million patients a year and are used by more than 420,000 prescribers, 71,000 pharmacies, 270 EHRs and health information systems, and over 2,000 hospitals in the U.S. This is a great opportunity to be a part of a successful Healthcare IT company experiencing significant growth. Here you’ll get to work with some of the smartest and most interesting people around; solving unique and complex challenges in healthcare on a scale matched by a few companies. If you get excited about stretching yourself in new ways, developing yourself to your fullest potential, care about working with smart colleagues; we want to talk to you!

Position Overview DrFirst is building an agentic ecosystem at scale. In the last 90 days we have shipped production AI systems across HR, Finance, Legal, and Marketing, automating hundreds of hours of manual work monthly and delivering measurable business impact.

This is a hands-on technical leadership role. You architect and build production AI automation systems from discovery to deployment. You work directly with department leaders to map workflows and ship tools that augment their work.

The split is 80% individual-contributor engineering and 20% servant leadership and mentorship. You build. You own technical architecture decisions. As the team scales from 2 to 5-6 engineers over 18 months, you mentor through code review and pairing. You also teach non-technical department leaders how to use AI tools, translate technical concepts for executives, and run discovery sessions that extract workflows from stakeholders. Building stays your primary focus.

**Who Will Love This Job**

• You are a senior IC who loves shipping code daily. You have been a Staff or Principal Engineer or led small teams, but you miss hands-on building.
• You can architect multi-agent systems and run discovery sessions with department VPs to map their workflows.
• You can debug OAuth2 flows through enterprise proxies and explain security requirements to non-technical stakeholders.
• You are a servant leader. You remove blockers for others, teach through pairing rather than directives, and make stakeholders successful.
• You organize chaos: 15 stakeholders, 6 systems, 3 sprints in flight. You ask “How can I help?” before “Here is what you should do.”

What You Will Work On **Build Production AI Automation (80%)** You own the technical implementation of department sprints. Example: an HR sprint delivered resume screening (40-candidate PDF extraction with table-of-contents parsing and fuzzy name matching), OKR coaching (Leapsome API integration with performance rating analytics), performance ratings (calibration detection across 328 employees), and milestone email automation in 4 weeks.

• Architecture and Implementation: Design and build Python/FastAPI backends connecting to enterprise APIs (HRIS, ERP, CRM, finance systems, project management).
• Frontend Development: Build Next.js/React frontends with Okta SSO, role-based access control, and audit trails.
• Multi-Agent Systems: Design agent coordination systems, skill discovery hubs, agent registries, and workflow orchestration.
• Enterprise Integration: Navigate Zscaler proxies, VPNs, SSL certificates, Kubernetes pod networking, DynamoDB, and AWS Bedrock.
• Testing and Quality: Write Playwright end-to-end tests before production deploy and maintain a 1000+ test suite with visual regression baselines.
• Deployment: Ship via GitLab CI/CD to AWS EKS (Kubernetes, ArgoCD, Helm, Secrets Manager) and diagnose pod restarts and liveness probe issues.
• Async and Performance: Debug event loop blocking, convert synchronous I/O to async, and optimize CPU-bound operations.
• Security: Partner with the CISO on PII/PHI de-identification, least privilege, and per-user OAuth2.
• Production Support: Debug authentication flows, token expiration, API rate limits, and health check failures.

You will ship 3-5 production tools in parallel within each sprint, deploying multiple times per day based on stakeholder feedback.

**Servant Leadership and Mentorship (20%)** Guide 2-3 engineers through code reviews and pairing….