Head of Risk

Fragile•San Francisco, CA

1d•$160,000 - $225,000•Onsite

About The Position

The Head of Risk owns the full back half of the customer lifecycle: from the moment a customer starts to look shaky, through every layer of our recovery stack, all the way to a returned asset or a paid judgment. This is not a compliance role. This is a builder's role: you'll architect a layered recovery organization, work with engineers to make our AI recovery engine sharper every week, partner with legal on escalations that actually scale, tie underwriting and risk together.

Requirements

Resourceful and scrappy; ability to build from nothing without waiting for headcount, tooling, or permission.
Operator's instinct; think in unit economics and measure your own work.
Comfortable with the uncomfortable nature of recovery and risk, finding the intellectual problem interesting, treating every customer with dignity, and being firm without being aggressive.

Nice To Haves

Direct experience with AI/LLM-based ops workflows.
Litigation or legal-ops background.
Hardware, leasing, lending, or subscription business model experience.
Fraud investigations, trust & safety, or asset recovery background.

Responsibilities

Layered recovery org: Take ownership of the recovery operation, sharpen every layer, decide what scales and what doesn't, and build out the pieces that are missing. Own the cost per dollar recovered across the entire stack.
AI recovery engine: Partner directly with engineers to improve the model and the workflow around it: what it says, when it says it, who it escalates to, how it learns from outcomes. Be in the loop on prompts, policies, retry logic, and the data feedback loop.
Legal & escalations flow: Partner with legal to own the escalations path from first notice to resolution.
Brand-safe deterrence: Build systems that protect the business through risk and recovery efforts.
Creative pipeline: Bring new ideas for recovery channels, deterrence levers, and product mechanics that prevent loss before it happens. Write the playbook.