Learning & Knowledge Systems Lead

About the Company

Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance — we're rebuilding the entire business as software, turning expert human judgment into compute.

Responsibilities

• Build the operating memory by embedding with sales, intake, service, placements, and renewals to document undocumented processes.
• Turn transcripts, Slack threads, and Looms into source-of-truth docs, decision logs, playbooks, and process maps.
• Graduate stabilized rules into skills that AI agents can call and partner with engineering on refresh automations.
• Distill AI-generated playbooks into executable plans with named owners and rollout cadences.
• Build onboarding paths and setup scripts to get new hires up to speed with AI tools quickly.
• Drive adoption of new playbooks and make activity visible across the organization.
• Shape meetings to produce useful artifacts like decisions, owners, and edge cases.

Requirements

• 3–8 years of experience in a relevant field (e.g., knowledge management, product ops, technical writing, or startup operations).
• Exceptional written communication and information-architecture instincts.
• Real AI-tool fluency including Cursor, Claude Code, MCP servers, and structured prompting.
• Demonstrated ability to interview stakeholders and turn messy conversations into clear documentation.
• Proven track record of running adoption rollouts that change team behavior.
• Ability to work on-site in San Francisco in a fast-moving, high-standard startup environment.

Preferred Qualifications

• Experience at an AI-native or dev-tools company.
• Experience authoring Claude/agent skills or capability modules.
• Knowledge of RAG/search systems, data labeling, or human-in-the-loop QA.
• Experience in insurance, fintech, or high-volume operational environments.