Director, Engineering

Accountabilities: Engineering strategy and delivery: Own architecture, delivery, and engineering roadmaps across product engineering teams, partnering closely with Product to shape priorities, establish commitments, and deliver measurable value. Predictable delivery: Operate teams on defined monthly delivery cycles with clear scope and cut lines, using evidence and delivery metrics to improve reliability and accountability. Engineering performance: Establish and improve DORA metrics, software quality practices, observability, service levels, testing, trunk-based development, feature flags, and incident management. Organization design: Design effective team boundaries and ownership models so teams can independently complete their work while maintaining clear accountability for every area of delivery. Engineering management: Hire, develop, coach, and calibrate Engineering Managers, maintain a strong hiring bar, and build a capable management bench. Technical leadership: Provide hands-on technical direction without needing to own implementation, reviewing designs and changes and making defensible architectural and engineering decisions. AI-enabled engineering: Drive practical adoption of agentic development tools, specification-first workflows, automated review, reusable engineering skills, and governance around permissions, quotas, security, and cost. Modernization: Lead complex software modernization across long-lived systems, using approaches such as API-based strangler patterns, characterization testing, event-driven architectures, and carefully selected systems of record. Revenue-critical systems: Oversee modernization and consolidation of billing and payment platforms, including dual-run approaches, financial reconciliation, and tested rollback strategies. Hosting platform leadership: Guide engineering across hosting and commerce technologies, including control panels, WordPress, WooCommerce, Magento, Shopware, Linux infrastructure, and major platform migrations. Security: Embed secure development practices into AI-assisted engineering workflows, including secrets management, push protection, static analysis, supply-chain controls, and defenses against prompt injection. Stakeholder leadership: Work with senior stakeholders to reassess scope, timelines, technical trade-offs, and business consequences while maintaining accountability for production availability and delivery outcomes. Remote and distributed teams: Lead engineering teams across time zones, including vendor-supported teams, while establishing clear operating agreements and accountability. Requirements Engineering leadership: 12+ years of software engineering experience, including at least 5 years leading engineering teams and experience managing Engineering Managers. Organizational impact: Demonstrated experience making an engineering organization measurably faster, with hands-on experience instrumenting and improving DORA or equivalent delivery metrics. AI-native engineering: Significant hands-on experience using AI-assisted and agentic coding tools at organizational scale, including designing or operating reusable harnesses, shared skills, repository instructions, tool connectors, permission boundaries, and automated review workflows. Delivery expertise: Strong understanding of modern software delivery practices, including automated testing, coverage gates, trunk-based development, feature flags, observability, service levels, centralized intake, and structured incident management. Technical judgment: Ability to review architecture and code changes, assess technical trade-offs, and establish a defensible technical position without needing to personally implement every solution. Complex systems: Experience leading modernization of large or long-lived software systems, including legacy Perl and PHP environments, API gateways, identity systems, event-driven architectures, and systems-of-record decisions. High-availability operations: Proven experience operating production software with meaningful accountability for availability and reliability. Revenue systems: Experience with billing and payment platforms, including processor consolidation, dual-running systems, reconciliation, and rollback planning. Cloud and hosting: Experience managing a hosting, cloud, or other high-availability service business is required. Platform expertise: Familiarity with technologies such as cPanel, InterWorx, WordPress, WooCommerce, Magento, Shopware, Linux, VMware, and Nutanix is valuable. Security: Strong understanding of secure software development, secrets hygiene, static analysis, tool and connector supply-chain security, and security risks associated with AI-assisted development. People leadership: Demonstrated ability to build teams, establish ownership structures, hire against a clear standard, develop managers, and lead distributed teams across time zones. Business partnership: Strong ability to connect engineering priorities with business objectives and communicate technical risks, trade-offs, and outcomes to senior stakeholders. Benefits Remote work: Fully remote position within the United States. Leadership impact: Opportunity to shape engineering strategy, organizational structure, delivery practices, and AI adoption at scale. Technical scope: Work across high-availability hosting platforms, revenue-critical systems, legacy modernization, cloud infrastructure, and modern AI-assisted engineering. Organizational ownership: Direct influence over engineering roadmaps, team structures, management development, hiring standards, and delivery performance. Collaborative environment: Close partnership with Product and senior business stakeholders to connect engineering execution with organizational priorities. Professional growth: Opportunity to lead complex transformation initiatives while developing engineering managers and distributed teams. Equal opportunity: Commitment to equal employment opportunity without regard to legally protected characteristics.