Principal Technical Writer at Toast

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. 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. AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at [Upgrade to PRO to see link] The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy. Zone A$155,000—$248,000 USDZone B$135,000—$216,000 USDZone C$122,000—$195,000 USDHow Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: [Upgrade to PRO to see link] Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: [Upgrade to PRO to see link] Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [Upgrade to PRO to see contact]. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.