[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.

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

Skills

• 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
• 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

Benefits

• Cash compensation (overtime, bonus/commissions if eligible)
• Equity
• Benefits
• Flexibility to meet Toasters’ changing needs
• Reasonable accommodations for persons with disabilities to enable them to access the hiring process

Company Overview

• Toast 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 Bo

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