Principal Technical Writer

Toast

20h•Hybrid

About The Position

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. 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.

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.

Nice To Haves

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.

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.