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
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.
