Head of AI & Software

The Engineering Team Lead will direct a distributed software development team executing a portfolio of 50+ concurrent projects across multiple operating companies, including manufacturing, staffing and family office investments. This role is responsible for translating business priorities into a coherent delivery plan, managing developers across application and integration disciplines, maintaining engineering standards, and serving as the senior technical partner to operating-company leaders. The ideal candidate has proven experience leading remote development teams, strong program and project management discipline, and deep technical fluency across modern web, enterprise, and data platforms. Key Responsibilities Team Leadership & Development • Lead, mentor, and develop a distributed team of application and integration developers across multiple time zones. • Set and maintain engineering standards covering code review, branching, testing, release cadence, and incident response. • Conduct regular one-on-ones, performance reviews, and career development planning for each direct report. • Identify gaps on the team and drive recruiting, interviewing, and onboarding of new developers. Project &Portfolio Management • Own a live backlog of 50+ projects across multiple operating companies and prioritize, sequence, and scope work with ruthless clarity. • Translate operator and executive requirements into shippable project scope, milestones, and delivery plans. • Run a transparent weekly delivery cadence with clear status, risks, and next steps visible to leadership. • Make tradeoff calls on cost, speed, and quality across competing business priorities. Technical Delivery & Architecture • Review and approve architecture and major technical decisions across all active projects. • Stay hands-on enough to read any pull request, unblock any developer, and contribute code during crunch or new-domain discovery. • Own the engineering posture around AI-augmented development tools, automation platforms, and modern build patterns. • Ensure security, performance, and reliability standards are met across the portfolio. Cross-Functional Collaboration • Serve as the primary technical point of contact for operating-company leaders across manufacturing, staffing, import/export, family office, and real estate. • Partner with business stakeholders to shape roadmaps, set expectations, and communicate delivery progress. • Coordinate with external vendors, consultants, and enterprise platform partners as needed. • Train and enable business users on new applications, tools, and workflows. Qualifications • Bachelor's degree in Computer Science, Software Engineering, Information Systems, or related field (or equivalent experience). • 10+ years of professional software development experience. • 4+ years leading distributed software development teams of five or more developers. • Demonstrated ownership of a multi-product or multi-domain engineering portfolio. • Strong technical depth across modern web (React, TypeScript, Tailwind) and backend (Node.js, PostgreSQL, Supabase or equivalent). • Working knowledge of at least one major enterprise platform (NetSuite – preferred, Salesforce, SAP, Dynamics, Bullhorn, or equivalent). • Experience running async-first teams with strong written documentation standards. • Hands-on familiarity with AI-assisted development tools (Cursor, Claude Code, GitHub Copilot). • Proven project and program management discipline, including backlog management, estimation, and stakeholder communication. • Experience with automation platforms (n8n, Workato, Zapier, Make) is preferred. • Prior experience in manufacturing, staffing, financial services, or multi-entity holding company environments is a plus. Work Environment + Language Requirements • Global remote position • Requires at least 4 hours of overlap with U.S. Central Time each day • Minimal travel, with occasional U.S. travel for leadership offsites • Fluency in the English language; written and verbal proficiency (B2 level minimum on CEFR scale) • Reports directly to the Owner / CEO This is a remote opportunity.