Founding Lead Engineer

**Recruiters: we only want to hear from applicants. Emails from recruiters will be marked as spam.** **Here’s the deal:** **We’re building a world where every doctor can run their practice with zero support staff. We do this by building vertical AI agents that automate a clinic’s back office operations.** \ We grew 30x during the W25 batch, just closed our seed round, already have a mature GTM motion in place, but now we need to build our product to be capable of handling 140k dental clinics.  \ As a Lead Founding Engineer, you will work with the CTO in  developing and maintaining the product with a small talented team of other founding employees. There is a lot to build, but you won’t be alone. You will be joined by a team of experienced founders, builders, designers, and dreamers. Amongst us are people who have raised over $100m. Scaled businesses to $12m ARR in 18 months. We have people who were instrumental in the earliest days of some of the largest dental software companies around today.  **What does Toothy offer you?** Toothy is early-stage, and our biggest challenges are all engineering-oriented. You will be instrumental to the success of this company, and those that it serves. We are a small team but we have a lot of resources and connections at our disposal that are atypical of a startup our size. \ \ There is a real opportunity to do something big here, and when we succeed, you will reap the rewards that go with that. This is the most important position that we will hire for at this stage of the company; you will feel that when you work here.  \ **Tech Stack** We’re primarily a Python shop, and thus all our core infrastructure is built in Python. However one of our founders is a fullstack React/Node dev, and thus any app with an interface gets built in JS.  **What we need you to do (or help others do):** * **Be a cracked 10x engineer:** We want Neos not Smiths.  * **Work with CTO to manage engineering operations:** Harass development partners, sift through insurance docs, overcommunicate with engineers, oh my! * **Architect and build**: Rapidly deploy new product features in Python, ensuring robust APIs, data flows, and back-end services that can scale. * **Maintain operational stability**: Troubleshoot and resolve high-priority issues, often in complex on-prem/cloud-hybrid environments (e.g., Windows bots, remote workstations). * **Data modeling & version control**: Design and maintain data pipelines for patient eligibility, claims, and other healthcare data, with rigorous version tracking. * **Infrastructure & DevOps**: Help manage multi-region networking (low-latency requirements, NAT traversal, secure connections to windows environments), CI/CD, and logging/monitoring pipelines. * **Windows RPA**: Evolve our in-house screen-scraping/automation bots, and ensure they can scale to tens of thousands of clinics. * **Healthcare EDI**: Integrate X12 standards (270/271, 837/277) and design solutions to parse, map, and store eligibility data in a standardized LLM-readable format. * **LLM / NLP workflows**: Build multi-stage pipelines that convert structured EDI data to English and back. Oversee logging and observability (LangFuse or similar). * **AI Phone calls:** Build agents that place calls to insurance payers for a wide range of use cases. * **Security & compliance**: Implement best practices for HIPAA, manage MFA across remote desktops/jumphosts, SOC2/HITRUST * **Internal dashboards & tooling**: Create user-facing dashboards and admin tools for claims, eligibility, usage metrics, etc., ensuring secure role-based access. * **Collaborate cross-functionally**: Work with founders, engineers, designers, and sales to deliver features in an iterative, fast-paced environment. --- ### **Relevant Experience** * **4+ years of software engineering** across a variety of domains and technologies. * **Proficiency in Python** (our primary back-end) or a track record of picking up new languages/frameworks rapidly. * **Healthcare / EDI knowledge** is a huge plus (270/271, 837/277, payer integration). * **DevOps & Networking**: Comfortable with multi-cloud, NAT traversal, containerization, CI/CD, logging/monitoring, and infrastructure security. * **Data Engineering:** Experience setting up reliable pipelines for dashboards, tracking, large batch jobs is a plus * **Building scalable systems from scratch:** Experience owning projects where you had to start at nothing and scale to processing work at a large scale is a huge plus * **Windows automation / RPA**: Experience building or maintaining screen-scraping bots or RPA solutions is highly desirable. * **LLM / NLP**: Familiarity with prompt engineering, model fine-tuning, or multi-stage pipeline design. * **AI Voice phone calls:** Speech-to-text, text-to-speech integration with LLM, IVR scripting and automation (VAPI, LiveKit, Amazon Voice Connector, Twilio, or comparable) or custom NLP for payer phone trees. Extra credit for high-volume call handling. * **EHR/PMS:** Any experience interfacing practice managements systems or EHRs is a huge plus * **Security & Compliance**: Understanding of HIPAA or other regulated environments. Any exposure to SOC2/HITRUST is beneficial. * **Strong communication**: Ability to tell compelling stories about your work and present complex ideas to both technical and non-technical stakeholders. * **Startup grit**: You’ve thrived on small, tight-knit teams before. You iterate quickly, learn constantly, and adapt on the fly. **About Toothy** At Toothy, we’re enabling doctors to focus on what’s most important: patient care. We strive to ship the highest quality products while working at the pace that a startup environment demands. As a startup, our team and culture is built around transparency, integrity, and trust with a passion to meet our larger mission and goal. We believe when our employees thrive our service flourishes. Toothy is automating all of the mundane back office work that a dental practice needs to do to deliver patient care. Gathering insurance benefits, submitting & following up on claims, depositing checks, and a whole lot more, we do this so the clinic doesn’t have to. We deliver this through LLMs, AI voice, and a lot of ingenuity.  We believe we are only scratching the service on a vast opportunity in this market, and we are looking for amazing and passionate people to help deliver an outstanding experience for doctors and patients. Visa sponsorship is not available for this role.