Senior Director of Engineering – Technical Strategy & Execution

System1 is looking for a senior engineering leader to serve as a strategic partner to the CTO and provide strong, opinionated technical leadership across multiple businesses and shared platforms. 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. You will work closely with senior engineering leaders, product, data, and business stakeholders to drive clarity, direction, and accountability.

This position is an onsite role requiring you to work in our headquarters located at 4235 Redwood Ave. Los Angeles, CA 90066.

• Provide strong, opinionated technical leadership across multiple engineering organizations and businesses
• Own and evolve System1’s technical strategy and architectural principles
• Act as the final decision-maker for cross‑business and cross‑org architectural initiatives
• Partner closely with the CTO as a trusted thought partner on technical, organizational, and execution decisions
• Represent engineering leadership in executive forums, reviews, and cross‑functional discussions
• Lead and influence senior engineering leaders, architects, and principal engineers
• Set clear standards and expectations that balance speed, quality, scalability, cost, and long‑term optionality
• Drive clarity around decision rights, escalation paths, and accountability
• Partner deeply with Product, Data, and Business leadership to translate strategy into technical execution
• Push back constructively when scope, timelines, or approaches are unrealistic
• Remove ambiguity, unblock execution, and raise the quality of technical decision‑making across the organization

• Engineering leaders have clear technical direction and architectural principles
• Cross‑business technical decisions are faster, more consistent, and higher quality
• The business experiences stronger technical opinions and clearer tradeoffs
• Engineering execution remains stable and predictable as the company scales
• The CTO can delegate with confidence and maintain continuity when unavailable

• 12+ years of experience designing, building, and operating large‑scale, distributed systems
• Deep architectural expertise across cloud infrastructure, data platforms, and application systems
• Strong judgment evaluating tradeoffs across performance, reliability, cost, and complexity
• A hands‑on technical background; while this is not a day‑to‑day coding role, you are expected to lead by example, stay close to the code and architecture, and dive deep when decisions warrant it
• Curiosity and willingness to stay current with modern development practices, including emerging approaches such as agentic and AI‑assisted coding

• Proven experience leading senior engineers, managers, and technical leaders
• Track record of making and defending difficult technical decisions
• High emotional intelligence and strong executive presence
• Ability to influence outcomes through clarity, credibility, and trust

• Strong understanding of how technology decisions impact revenue, margins, and risk
• Experience partnering with product, finance, and business leaders
• Comfortable saying no, explaining tradeoffs, and aligning stakeholders

• Opinionated but pragmatic; decisive without being dogmatic
• Calm under pressure and credible in high‑stakes situations
• Low‑ego, high‑ownership mindset
• Comfortable operating with ambiguity and incomplete information

• Competitive salary + bonus + equity
• Generous PTO + 11 company holidays
• Open sick time
• 100% covered Medical, Dental, Vision for employees
• 401k with match
• Health & Dependent Care Flex Spending Account
• Paid professional development
• Leadership & growth opportunities
• Vi…