Head of Design Systems & AI Tech (Remote)

CSAA Insurance Group

Vermont

Remote

USD 120,000 - 150,000

Full time

4 days ago

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Job summary

CSAA Insurance Group is seeking a Lead Design Technologist in Design Systems for a remote role in the United States. The candidate will lead the technical structure of the enterprise design system, translating UX decisions into scalable code structures, tokens, APIs, and shared packages, while ensuring assets translate across platforms and AI-enabled experiences.

The role emphasizes collaboration with UX, CX, Engineering, Architecture, and platform teams to extend the system to AI capabilities

Qualifications

Bachelor's degree or equivalent practical experience.
8+ years of progressive experience in design systems, front-end engineering, design technology, or experience architecture, including technical ownership or stewardship of a design system implemented in code.
Strong hands-on front-end engineering experience with a modern component framework, including component structure, composition, and API design.
Experience implementing and governing design tokens, component libraries, and the technical expression of reusable UX patterns at enterprise scale.
Practical experience with design-to-code workflows and the tools that connect design assets to production components.
Working fluency with AI-assisted development tools and a practical understanding of how AI models use context, skills, and tool definitions.
Ability to define the structure and technical direction of a shared system and partner effectively with Engineering and Architecture to bring it to life, rather than needing to build every part personally.
Strong written communication skills, with the ability to create documentation and standards that teams can understand and use.
Demonstrated ability to influence across design and engineering teams without formal authority.
Comfort working through ambiguity, including in areas where the field and standards are still evolving.
Ability to translate between design and engineering audiences, turning design intent into implementable system structures without losing important details in either direction.

Responsibilities

Define and maintain the technical structure of the design system, including how components, tokens, patterns, shared packages, reusable capabilities, and reference implementations are organized and relate to one another.
Partner with UX Design to translate approved patterns, templates, and design decisions into scalable structures in code, including component APIs, design tokens, shared packages, and implementation standards.
Maintain the connection between design tooling and code so approved UX definitions can be implemented accurately and consistently in production.
Define how design-system assets are structured, composed, governed, and versioned in code so they can be reused consistently across products and applications.
Partner with UX and platform teams to resolve how CSAA's design standards and technical system assets translate into third-party platforms such as Pega and Guidewire, where CSAA does not control the underlying design system. Define what can be reused directly, what requires platform-specific implementation, and where documented extensions or exceptions are needed.
Define clear ways to contribute, update, deprecate, and version shared system assets without disrupting the teams that depend on them.
Set clear criteria for what should become a shared system asset versus what should remain specific to one product, platform, or solution.
Extend the Design System to AI: Foundations, Capabilities, Interfaces & contracts, Patterns, Reference implementations, Evaluation, Observability, Make system assets easy to discover, Define guardrails and governance, Keep one coherent system across internal and customer-facing experiences.