Senior Director of Engineering – Technical Strategy & Execution

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

Requirements

• 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
• Hands-on technical background; lead by example and stay close to the code and architecture
• 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

Nice-to-Haves

• Curiosity and willingness to stay current with modern development practices, including emerging approaches such as agentic and AI-assisted coding
• 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

Compensation & 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