Senior Director of Engineering – Technical Strategy & Execution
About the role
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.
Responsibilities
- 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
Qualifications
- 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
Requirements
- 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
Skills
- 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
Benefits
- 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
Pay
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.
Schedule
This position is an onsite role requiring you to work in our headquarters located at 4235 Redwood Ave. Los Angeles, CA 90066.