AI Technical Lead (Principal Engineer)
About The Position
EverQuote is hiring an AI Technical Lead to design and build an insurance marketplace that AI agents use to shop on a person’s behalf. This is a hands-on senior role on a small team, with end-to-end ownership of the technical architecture—from models and model serving to the MCP server and tools used by other AI platforms. The early technical decisions made in this role will shape the product and the team’s engineering patterns. The role owns where model reasoning runs, how open-weight models are tuned and served, and how the system maintains reliability while controlling cost and speed. The Technical Lead will own the MCP server, tools, and agent data, choose implementation approaches backed by testing, and build the system. The position is based in Cambridge, Massachusetts, and requires working in the office three days per week: Tuesday, Wednesday, and Thursday.
Requirements
- At least 8 years of engineering experience, including senior or lead ownership of complex technical systems and hands-on work in machine learning or LLMs.
- Hands-on experience fine-tuning open-weight or open-source models, such as with LoRA, QLoRA, SFT, DPO, or similar methods, and running those models rather than relying only on hosted APIs.
- Production experience owning and reliably serving an LLM system, including version pinning, rollbacks, and understanding inference costs.
- Enterprise design and architecture experience for complex, high-reliability systems.
- Strong Python and Rust skills and fluency with modern LLM serving, retrieval, evaluation, and monitoring.
- Strong grasp of evaluation and guardrails, including building evaluation sets, identifying failure modes, and monitoring quality, drift, cost, and speed.
- Experience with model serving, containers and orchestration, and monitoring on at least one major cloud.
- A track record of leading and delivering large, ambitious projects, including with a small team.
- Strong strategic thinking and methodical execution, with the ability to set technical direction and deliver it.
- Excellent communication with technical and non-technical audiences across organizational levels.
- Teamwork, comfort with ambiguity, and a bias for action.
Responsibilities
- Own the agent architecture, including where reasoning runs, model selection and packaging, and how AI platforms connect to the product; support decisions with testing.
- Fine-tune open-weight models and determine when tuning, retrieval, or prompting is appropriate.
- Deploy and operate the agent and MCP server with reliability, speed, affordability, versioning, and rollback capabilities.
- Build programmatic evaluation sets, guardrails, and monitoring for quality, drift, cost, and speed.
- Work with the AI product lead to design the data model and tools, including request and response payloads, exposed reasoning, and trust signals.
- Set engineering patterns and standards for the team and document code and architecture.
- Monitor inference costs and make trade-offs to keep the system sustainable as volume grows.
- Help publish the company’s code, architecture, and findings.
- Mentor team engineers and provide leadership with regular visibility into technical progress and risks.
Benefits
- Variable cash bonus programs may be included in the total compensation package.
- Equity may be included in the total compensation package.
- A comprehensive range of health, welfare, and wellbeing benefits, based on eligibility and designated by role.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
