AI Evaluation Lead

Role Description

Our client is hiring an AI Evaluation Lead to own how we measure the quality of AI-generated financial advice. Getting the advice right matters. A bad output here has real consequences for real people, and this role owns making sure we catch it.

• You will work with an AI-generated test case library and automated scoring infrastructure that is already in place.
• Your job is to make sure we are measuring the right things, interpreting what the results are telling us, and determining what needs to change to keep the system performing well as it scales.
• This is not a monitoring and reporting role. It requires genuine judgment about AI system behavior, advice quality, and what the data is and is not capturing.
• You will report to our Head of Revenue & Compliance, work closely with the AI/ML team and founders, and partner with subject matter experts who provide domain judgment on complex or ambiguous cases.
• You need enough personal finance literacy to make first-pass quality assessments independently and know when to escalate.

Qualifications

• You have worked on AI or ML system quality in a context where outputs had real stakes.
• You think analytically about what data is and is not telling you.
• You are comfortable making judgment calls in ambiguous situations rather than waiting for the answer to be obvious.
• You have enough AI/ML fluency to reason about why a system is producing what it is producing, not just whether the output looks right.
• You bring enough personal finance literacy to read an advice response and have a genuine opinion about whether it is directionally sound.
• You do not need formal credentials or deep expertise across every domain the system covers—you will partner with subject matter experts for the complex judgment calls.
• Your review is substantive rather than mechanical, and you can have an informed conversation with those experts about what you are seeing in the data.
• Fluency with how LLM-based systems behave in production, including output variance, failure modes, and the limits of automated scoring.
• Ability to assess whether an eval framework is measuring the right things, not just whether it is running correctly.
• Comfortable working with behavioral and interaction data to surface patterns and quality signals.
• Familiarity with evaluation and observability tooling.

Requirements

• Model evaluation or QA on a consumer-facing AI product, particularly in a regulated or high-stakes context.
• Model risk or validation with LLM or generative AI exposure.
• Data science or analytics with ownership of production AI system quality.
• Operations quality control built around AI- or ML-generated outputs.
• Financial services or fintech product roles where you developed both analytical depth and personal finance domain familiarity.

Benefits

• Salary: 120-140k, plus early-stage option equity.
• Final compensation will depend on level, experience, location, and scope of responsibility.
• This role is open to candidates based in the United States.

How we work

• We are a fully remote, distributed team.
• Periodic in-person get-togethers will be integral to our operating cadence.
• We prioritize outcomes and output over set schedules.
• We value clear writing, high ownership, fast iteration, direct communication, and thoughtful async collaboration.
• As an early team member, you should expect broad ownership, frequent context shifts, and a high degree of autonomy.
• You will help shape not just the product, but also the technical standards and operating cadence of the company.

AI Interview

We expect a high volume of applications for this role. To help candidates showcase more than what's on their resume, you'll have the opportunity to complete an AI interview as part of the application process.

As an AI-first company, we embrace AI throughout the hiring process and are excited to meet candidates who are equally curious about and enthusiastic about the technology. This interview is your chance to demonstrate your experience, communication skills, and potential beyond your resume.