Senior Director of Engineering – Technical Strategy & Execution

This role will shape technical strategy, guide architectural decisions, and ensure engineering execution aligns tightly with business priorities in an environment with real scale, real tradeoffs, and meaningful complexity.The ideal candidate is deeply technical, comfortable operating at executive altitude, and energized by making high‑quality decisions in complex, ambiguous environments where data is incomplete and tradeoffs are real. Los Angeles, CA 90066.The Role You Will HaveProvide strong, opinionated technical leadership across multiple engineering organizations and businessesOwn and evolve System1’s technical strategy and architectural principlesAct as the final decision-maker for cross‑business and cross‑org architectural initiativesPartner closely with the CTO as a trusted thought partner on technical, organizational, and execution decisionsRepresent engineering leadership in executive forums, reviews, and cross‑functional discussionsLead and influence senior engineering leaders, architects, and principal engineersSet clear standards and expectations that balance speed, quality, scalability, cost, and long‑term optionalityDrive clarity around decision rights, escalation paths, and accountabilityPartner deeply with Product, Data, and Business leadership to translate strategy into technical executionPush back constructively when scope, timelines, or approaches are unrealisticRemove ambiguity, unblock execution, and raise the quality of technical decision‑making across the organizationWhat Success Looks Like Within The First 6 - 12 Months:Engineering leaders have clear technical direction and architectural principlesCross‑business technical decisions are faster, more consistent, and higher qualityThe business experiences stronger technical opinions and clearer tradeoffsEngineering execution remains stable and predictable as the company scalesThe CTO can delegate with confidence and...