Legal AI Supervisor

Location: Remote. We work across European, US, and APAC time zones, so flexibility on working hours is important.

About Us

Legal teams are drowning in repetitive work. The rest of the business is stuck waiting. Flank is changing that.

We are operating at the cutting edge of AI development, building the future of autonomous agents for the enterprise. We have raised a $10M Series A led by Insight Partners (US), with continued support from Gradient Ventures (Google's AI fund).

We are already deploying Flank agents to multinational enterprises with >100,000 employees, completely automating workflows that were previously impossible to solve.

The Opportunity

We're looking for someone with hands-on contracts experience — a lawyer, paralegal, contracts manager, or similar — to join our Legal AI Alignment team.

As a Legal AI Supervisor, you'll be on the front line of how legal judgment is embedded into autonomous agents. You'll review, test and calibrate live agents across real customer workflows, and provide the precise feedback that makes them better. You'll work closely with AI engineers and product, acting as the bridge between legal reasoning and technical implementation.

This is not a role for the hesitant or those content with the status quo. It's for people who care about getting things right, in an environment that values independence, experimentation, and candid communication.

What You Will Be Doing

• Legal AI Alignment: Ensure agents reflect sound legal reasoning, appropriate risk tolerance, escalation logic, and business-aware judgment across live and evolving use cases.
• Review, Testing & Calibration: Assess agent outputs for accuracy, clarity, tone, and contextual fit across workflows such as contract review, triage, intake, and legal help desks.
• Refinement & Feedback Loops: Provide precise, actionable feedback to improve agent logic, prompts, guardrails, and escalation pathways.
• Documentation & Knowledge Capture: Record learnings, decisions, and observed behaviours in a structured way to support internal alignment and long-term improvement.

Who You Are

• Contracts Experience: You have at least 2 years of hands-on experience working with commercial contracts — drafting, reviewing, negotiating, or managing them. A legal qualification is a plus, not a requirement.
• Strong Judgment: You naturally think in terms of risk, nuance, and escalation — and you know when "it depends" matters and when it doesn't.
• Unreasonably High Standards: You care deeply about quality, are comfortable giving and receiving candid feedback, and push for better outcomes.
• Clear Communicator: You can translate complex legal concepts into clear, structured feedback that non-lawyers can act on.
• Tech-Curious: You're not an engineer, but you're excited by how AI systems work and how legal reasoning translates into product behaviour.
• Time-Zone Flexible: Our team and customers span Europe, North America, and APAC. You're comfortable shaping your working day around a global team, including regular overlap with US hours.

If you don't meet all of these criteria but believe you'd be a strong asset to Flank, please reach out anyway. We're sometimes flexible on scope, or have other roles that might fit.

Nice to Haves (but not required)

• Legal qualification (UK, US, or equivalent).
• Experience in tech-enabled legal services or legal ops.



What's In It for You

• Innovative Work: Be part of a groundbreaking function at the forefront of legal technology and AI integration.
• Autonomy & Impact: Operate with high trust, high expectations, and the chance to shape a completely new category.
• Clarity & Challenge: Join a team that values directness, high standards, and meaningful work.
• Global Team: Remote-first, working with a mission-driven team of smart, candid, and ambitious people across time zones.
• Competitive, Benchmarked Salary.