About the role:As Principal Technical Writer, you will work with customer-facing technical teams to design and deliver product information that enables enterprise customers to self-implement and self-support. You'll understand business operations goals, identify jobs-to-be-done, develop AI frameworks, and write documentation and enablement materials that enterprise customers need to succeed. This role combines audience research with strategic building: setting documentation standards, designing AI-driven content generation infrastructure, and creating evaluation frameworks that ensure quality at scale. You will have product coverage responsibility for a broad set of functionality areas, selected based on customer needs and your discovery work. For example, product coverage areas might include menu configuration, multi-location management, or enterprise configuration controls.
A day in the life (Responsibilities):- Remove obstacles to self-implementation and self-support for complex customer businesses by designing and writing cross-cutting enablement documentation. Write for enterprise customer technical leadership and support teams, producing implementation guides, architecture overviews, integration patterns, and best practices. Use research, interviews, and collaboration with Toast customer-facing teams to understand business objectives, pain points, and implementation barriers.
- Build and implement AI documentation generation infrastructure, establish evaluation frameworks to verify content quality, and advocate for AI tool adoption to accelerate discovery and shape how we document at scale.
- Collaborate as a strategic leader in developing documentation practice, focused on business enablement writing and AI-driven product documentation infrastructure.
- Cover multiple product functionality areas as a domain expert, using AI tooling for routine documentation updates and focusing your writing on strategic enablement content. For example, topic areas might include menu configuration, multi-location management, and enterprise configuration controls.
- Partner with peer product development leaders to incorporate documentation requirements into product development planning from the start.
- Test complex technical features, write and validate code examples, and advocate for enterprise developer experience.
- Measure and communicate documentation impact on enterprise customer implementation time, support ticket volume, and adoption metrics.
- Mentor technical writers in adopting AI tools, balancing strategic thinking with execution, and establishing documentation quality standards.
What you'll need to thrive (Requirements):- 8+ years of technical writing experience for enterprise products, with demonstrated ownership of major documentation domains or platforms.
- Deep expertise in developer documentation: REST APIs, OpenAPI/Swagger, authentication protocols, integration patterns, webhooks, data models.
- Experience writing for technical decision-makers (engineering leaders, CTOs, enterprise architects) and complex implementation scenarios.
- Proven ability to design cross-cutting documentation strategies that solve problems affecting multiple audiences (developers, integrators, support teams, customers), with effective management of ambiguity in problem definition.
- Hands-on experience with AI documentation tools or demonstrated ability to evaluate AI-generated content for accuracy, completeness, and usefulness.
- Strong technical fluency: comfortable testing APIs, writing code examples, understanding system architecture, and partnering with engineering teams as a technical peer.
- Demonstrated expertise in information architecture for complex product ecosystems-designing maintainable documentation structures.
- Strong systems thinking: ability to balance short-term documentation delivery with long-term architectural integrity and scalability.
- Excellent stakeholder management and ability to influence product development teams to include product information and communication as part of the definition of done.
Special Sauce:- Track record of influencing product development culture to treat documentation as a product quality requirement.
- Experience mentoring technical writers or contributing to documentation practice development across teams.
- Familiarity with documentation-as-code workflows, CI/CD for documentation, and docs infrastructure (static site generators, version control, automated testing).
- Experience with docs analytics and measuring documentation effectiveness (search analytics, page performance, user feedback).
- Experience in fast-growing SaaS companies navigating enterprise market expansion.
- Experience with restaurant technology, POS systems, hospitality software, or similar physical-world operational technology.
- Experience with change management, enterprise customer onboarding, or field enablement.
