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.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 maintain continuity when unavailableWhat You Will Bring - Technical Experience12+ years of experience designing, building, and operating large‑scale, distributed systemsDeep architectural expertise across cloud infrastructure, data platforms, and application systemsStrong judgment evaluating tradeoffs across performance, reliability, cost, and complexityA 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 itCuriosity and willingness to stay current with modern development practices, including emerging approaches such as agentic and AI‑assisted codingWhat You Will Bring - Leadership & InfluenceProven experience leading senior engineers, managers, and technical leadersTrack record of making and defending difficult technical decisionsHigh emotional intelligence and strong executive presenceAbility to influence outcomes through clarity, credibility, and trustWhat You Will Bring - Business & Product AcumenStrong understanding of how technology decisions impact revenue, margins, and riskExperience partnering with product, finance, and business leadersComfortable saying no, explaining tradeoffs, and aligning stakeholdersWhat You Will Bring - Personal AttributesOpinionated but pragmatic; decisive without being dogmaticCalm under pressure and credible in high‑stakes situationsLow‑ego, high‑ownership mindsetComfortable operating with ambiguity and incomplete informationWhat We Have To OfferCompetitive salary + bonus + equityGenerous PTO + 11 company holidaysOpen sick time100% covered Medical, Dental, Vision for employees401k with matchHealth & Dependent Care Flex Spending Account Paid professional developmentLeadership & growth opportunitiesVirtual company and team building eventsThe U.S. base salary range for this full-time position is $197,000 - $246,000 + bonus + equity + benefits. Our salary ranges are determined by role, level, and location. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific salary range for your preferred location during the hiring process. Please note that the compensation details listed in U.S. role postings reflect the base salary only, and do not include bonus, equity, or benefits.System1’s headquarters is located in Marina del Rey, CA with an additional office in Bellevue, WA.Employees near office locations are returning to the office.Equal Employment OpportunitySystem1 provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.