Founding Lead Engineer
About the role
Lead engineering role reporting to the CTO at an early-stage AI startup (Toothy AI) focused on automating dental clinic back-office operations using Python-based infrastructure, NLP/LLM workflows, and RPA. Key emphasis on building scalable product, engineering leadership, and cross-functional collaboration to enable growth to 140k clinics.
Responsibilities
- Be a cracked 10x engineer: deliver high-impact engineering work.
- Work with CTO to manage engineering operations: coordinate with partners, process insurance documents, communicate with engineers.
- Architect and build: rapidly deploy new product features in Python, ensure robust APIs, data flows, and scalable back-end services.
- Maintain operational stability: troubleshoot high-priority issues across on-prem/cloud-hybrid environments (Windows bots, remote workstations).
- Data modeling & version control: design and maintain data pipelines for patient eligibility, claims, and healthcare data with rigorous version tracking.
- Infrastructure & DevOps: manage multi-region networking, CI/CD, logging/monitoring pipelines.
- Windows RPA: evolve in-house screen-scraping/automation bots to scale to tens of thousands of clinics.
- Healthcare EDI: integrate X12 standards (270/271, 837/277) and parse/store data in a standardized format.
- LLM / NLP workflows: build multi-stage pipelines converting structured EDI data to English and back; oversee logging/observability.
- AI Phone calls: build agents for insurance payer calls.
- Security & compliance: implement HIPAA practices, MFA across remote desktops/jumphosts, SOC2/HITRUST.
- Internal dashboards & tooling: create dashboards and admin tools for claims, eligibility, usage metrics with secure RBAC.
- Collaborate cross-functionally: work with founders, engineers, designers, and sales to deliver iterative features.
Qualifications
- 4+ years of software engineering experience across various domains and technologies.
- Proficiency in Python (core backend).
- Healthcare/EDI knowledge a huge plus (270/271, 837/277, payer integration).
- DevOps & Networking: multi-cloud, NAT traversal, containerization, CI/CD, logging/monitoring, security.
- Data Engineering: experience with data pipelines for dashboards and large batch jobs is a plus.
- Experience building scalable systems from scratch and scaling to high volume workloads.
- Windows automation / RPA experience desirable.
- LLM / NLP familiarity: prompt engineering, model fine-tuning, multi-stage pipelines.
- AI Voice calls: experience with speech-to-text, text-to-speech, IVR tooling (e.g., VAPI, LiveKit, Twilio) or equivalent NLP for payer trees.
- EHR/PMS experience a plus.
- Security & Compliance: knowledge of HIPAA; exposure to SOC2/HITRUST beneficial.
- Strong communication skills and startup grit.
Skills
About Toothy AI
AI for insurance verification & billing at dental clinics
We’re Toothy.ai. We’re building AI agents for dental practices that handle everything related to patient insurance. The average dental clinic spends over 160 hours a month on insurance tasks like verifying patient policies, billing, and claims processing. Our AI agents automate this entire workflow—including making insurance calls with voice AI—saving clinics time, reducing costs, and ensuring faster reimbursements.