Say hello to Hagerty

Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us!

As an AI Agent Developer, you will design, build, and continuously improve AI agents that handle real member interactions across the full customer lifecycle: from quoting and binding coverage, to policy service, to first notice of loss and claims. You will own the end-to-end agent development lifecycle on the Sierra platform, scoping agent behavior, designing conversation flows, integrating with Hagerty's systems, evaluating quality, and iterating relentlessly in production until each agent is the best version of itself. This is a senior individual contributor role. You are expected to operate with autonomy, partner directly with business and technology stakeholders, bring engineering discipline to everything you ship, and drive outcomes that are measurable in member satisfaction, resolution rates, and reduced manual effort.

What you’ll do

Own the Agent Development Lifecycle

Take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production.
Translate business goals and member needs into agent behaviors that handle complex, high-volume interactions across quoting, policy service, and claims.
Define evaluation criteria for each agent, then use those metrics to drive improvement in resolution rates and member satisfaction.
Coordinate across technical and non-technical stakeholders throughout the full build-and-launch process.

Design and Build High-Quality Agents

Design and build conversational AI agents on the Sierra platform — expressing goals, procedural knowledge, and deterministic guardrails for regulated or high-stakes interactions.
Develop and refine conversational flows, rewrite prompts, and run simulations to tune agent behavior against real member scenarios — edge cases, tone, brand voice, and accuracy all matter.
Integrate agents with Hagerty's internal systems and APIs (policy administration, quoting engines, claims platforms) using appropriate authentication patterns and service accounts.
Build and maintain immutable agent release snapshots — including model version dependencies, knowledge bases, and prompts — following established release and engineering standards.
Apply engineering discipline in a no-code/low-code and declarative platforms: practical logging, error handling, monitoring, automated testing, and regression coverage for critical agent workflows.
Validate data accuracy in agent outputs, build reconciliation and anomaly checks where outcomes touch financial or policy data, and raise issues early.

Drive Continuous Quality and Improvement

Establish and run structured quality assurance processes — regularly auditing live conversations, annotating agent behavior, and converting findings into regression tests.
Use annotated conversations to build a growing test suite that prevents regressions across model upgrades, prompt changes, and platform updates.
Monitor agent performance in production, respond to incidents, and iterate rapidly based on usage signals, member feedback, and business outcomes.
Participate in on-call production support, sharing responsibility for incident response and agent reliability.

Shape How Hagerty Builds with AI

Act as a trusted internal advisor on AI agent strategy — contributing data-driven insights on what's working, where agents can expand, and how to push the platform further.
Identify and champion new agent use cases across the member lifecycle as the technology and Hagerty's capabilities evolve.
Contribute to team engineering standards, reusable integration patterns, and secure-by-default guardrails for agent development.

AI Agent Developer at Hagerty