About Us

Circle is building the world’s leading AI-powered, all-in-one platform for digital businesses. We empower creators, coaches, educators, and businesses to engage their audience through discussions, live streams, events, chat, courses, and payments—all within their own brand.

We’re a fully remote company with around 270 team members from 30+ countries. We value exceptional individuals and create an environment where you can do the best work of your life, making a meaningful impact.

About The Role

Join our AI Quality engineering team to measure, diagnose, and improve Circle's AI-powered features. We're looking for a Lead Engineer to build evaluation frameworks, observability tooling, and diagnostic infrastructure to enhance our AI Agents' performance.

What You'll Be Doing

• Design and build evaluation infrastructure, including CI/CD pipelines and datasets.
• Diagnose quality issues across the AI agent pipeline.
• Expand datasets for evaluation through annotation and AI-generated conversations.
• Run experiments to evaluate new models and optimize performance.
• Lead and manage the AI Quality engineering team.
• Collaborate with AI Core engineering for quality assurance.

What You'll Need To Be Successful

• 7+ years of experience in production software, particularly with LLM-powered agents.
• Proficiency in Ruby on Rails and Python.
• Experience with evaluation or observability infrastructure for AI systems.
• Ability to design datasets and annotation workflows.
• A willingness to experiment and adapt in a dynamic environment.
• Strong alignment with our company values.
• Proficient in English (CEFR Level C2).

Compensation & Benefits

Circle offers competitive compensation, equity, 35 days of paid time off annually, and remote work flexibility. We come together for retreats and provide benefits that support health and professional growth.

Learn More

• Candidate Safety & Interview Process Notice
• Diversity, Equity & Inclusion
• How We Use Candidate Data
• Equal Employment Opportunity
• Visit our Candidate Hub for more information about working with us.

Compensation Range: $170K