Executive Director, Software & AI Engineering

At TWG Global Holdings, LLC (“TWG Global”), we drive innovation and business transformation across a range of industries—including financial services, insurance, technology, media, and sports—by leveraging data and AI as core assets. Our AI-first, cloud-native approach delivers real-time intelligence and interactive business applications, empowering informed decision-making for both customers and employees.

We prioritize responsible data and AI practices, ensuring ethical standards and regulatory compliance. Our decentralized structure enables each business unit to operate autonomously, supported by a central AI Solutions Group, while strategic partnerships with leading data and AI vendors fuel game-changing efforts in marketing, operations, and product development.

You will collaborate with management to advance our data and analytics transformation, enhance productivity, and enable agile, data-driven decisions. By leveraging relationships with top tech startups and universities, you will help create competitive advantages and drive enterprise innovation.

At TWG Global, your contributions will support our goal of sustained growth and superior returns, as we deliver rare value and impact across our businesses.

The Role:

We are seeking an Executive Director, Software & AI Engineering to serve as a hands-on technical leader and enterprise architect across TWG Global’s AI and software initiatives. This role is responsible for threading architecture, engineering execution, and technical decision-making across multiple concurrent projects, acting as a senior individual contributor and people leader who ensures systems are designed to scale, delivered to completion, and aligned to business outcomes.

Key Responsibilities:

• Lead architecture and hands-on engineering across multiple TWG Global AI and software initiatives, making critical decisions on system design, technology selection, and integration across complex environments.
• Serve as a senior technical owner across projects, providing oversight and guidance while directly contributing to core engineering work in high-impact areas, including AI-driven workflows, digital employee systems, and complex data platforms.
• Manage and mentor a small team of engineers (typically 4–5 at any given time), ensuring high standards of execution, accountability, and delivery in fast-paced, deadline-driven environments across multiple industries.

Requirements

• Hands-on technical experience as a senior software engineer and architect, with demonstrated success designing, building, and finishing complex systems across multiple technology stacks in production environments.
• Hands-on expertise with modern cloud platforms and data ecosystems, including Azure-based architectures, enterprise analytics platforms (for example, Palantir), and core backend technologies such as Java, PostgreSQL, Redis, and distributed systems.
• Strong architectural judgment and technical maturity, with the ability to make high-stakes decisions around system design, scalability, performance, and long-term maintainability across multiple concurrent projects.
• Experience managing and mentoring small, highly skilled engineering teams, while remaining a deeply technical individual contributor.
• Demonstrated ability to operate in high-pressure, deadline-driven environments across multiple industries, including client-facing or consulting-style engagements where execution speed and delivery quality are critical.
• Record of successfully orchestrating and integrating multiple technology stacks and vendors into cohesive, production-ready platforms that support complex workflows and AI-driven decision-making.
• Strong communication skills with the ability to translate complex technical concepts to senior business leaders and non-technical stakeholders, influencing outcomes and driving alignment across the organization.
• Experience evaluating, selecting, and integrating emerging technologies, with a practical, execution-focused mindset that prioritizes shipping durable solutions over experimentation without delivery.
• Master’s degree or PhD in Computer Science, Software Engineering, Artificial Intelligence, Machine Learning, or a closely related technical discipline.

Benefits

Position Location

This position can be based in Santa Monica, CA; New York, NY; or remotely for an exceptional candidate.

Compensation

The base pay for this position is $350,000 - $409,000. A bonus will be provided as part of the compensation package, in addition to a full range of medical, financial, and other benefits.

TWG is an equal opportunity employer. All applicants will be considered for employment without attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.