[Remote] Principal Technical Writer

Note: The job is a remote job and is open to candidates in USA. Toast creates technology to help restaurants and local businesses succeed in a digital world. As a Principal Technical Writer, you will design and deliver product information for enterprise customers, focusing on enabling self-implementation and self-support through documentation and AI-driven content generation.ResponsibilitiesRemove 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 barriersBuild 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 scaleCollaborate as a strategic leader in developing documentation practice, focused on business enablement writing and AI-driven product documentation infrastructureCover 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 controlsPartner with peer product development leaders to incorporate documentation requirements into product development planning from the startTest complex technical features, write and validate code examples, and advocate for enterprise developer experienceMeasure and communicate documentation impact on enterprise customer implementation time, support ticket volume, and adoption metricsMentor technical writers in adopting AI tools, balancing strategic thinking with execution, and establishing documentation quality standardsSkills8+ years of technical writing experience for enterprise products, with demonstrated ownership of major documentation domains or platformsDeep expertise in developer documentation: REST APIs, OpenAPI/Swagger, authentication protocols, integration patterns, webhooks, data modelsExperience writing for technical decision-makers (engineering leaders, CTOs, enterprise architects) and complex implementation scenariosProven 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 definitionHands-on experience with AI documentation tools or demonstrated ability to evaluate AI-generated content for accuracy, completeness, and usefulnessStrong technical fluency: comfortable testing APIs, writing code examples, understanding system architecture, and partnering with engineering teams as a technical peerDemonstrated expertise in information architecture for complex product ecosystems—designing maintainable documentation structuresStrong systems thinking: ability to balance short-term documentation delivery with long-term architectural integrity and scalabilityExcellent stakeholder management and ability to influence product development teams to include product information and communication as part of the definition of doneTrack record of influencing product development culture to treat documentation as a product quality requirementExperience mentoring technical writers or contributing to documentation practice development across teamsFamiliarity 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 expansionExperience with restaurant technology, POS systems, hospitality software, or similar physical-world operational technologyExperience with change management, enterprise customer onboarding, or field enablementBenefitsCash compensation (overtime, bonus/commissions if eligible)EquityBenefitsFlexibility to meet Toasters’ changing needsReasonable accommodations for persons with disabilities to enable them to access the hiring processCompany OverviewToast is a point-of-sale and restaurant management platform designed for businesses in the food service and hospitality industry. It was founded in 2011, and is headquartered in Boston, Massachusetts, USA, with a workforce of 1001-5000 employees. Its website is https://pos.toasttab.com.Company H1B SponsorshipToast has a track record of offering H1B sponsorships, with 3 in 2026, 26 in 2025, 32 in 2024, 39 in 2023, 66 in 2022, 29 in 2021, 17 in 2020. Please note that this does not guarantee sponsorship for this specific role.