Senior Director of Engineering - Technical Strategy & Execution

Company: System1
Location: Los Angeles
Posted on: February 27, 2026

Job Description:

Job Description Job Description 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 Have: 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 What Success Looks Like Within The First 6 - 12 Months: 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 What You Will Bring - Technical Experience: 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 What You Will Bring - Leadership & Influence: 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 What You Will Bring - Business & Product Acumen: 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 What You Will Bring - Personal Attributes: 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 What We Have To Offer: 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 Virtual company and team building events The 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 Opportunity: System1 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.

Keywords: System1, Ventura , Senior Director of Engineering - Technical Strategy & Execution, Engineering , Los Angeles, California