System12mo ago

Senior Director of Engineering – Technical Strategy & Execution

Los AngelesFull-timesenior

EngineeringOtherManagement

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Overview

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.

Technical Tools

EngineeringOtherManagement

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