Redwood Software is hiring a Principal Technical Writer to define the documentation vision and strategy for the RunMyJobs Workload Automation platform. This role leads high-impact initiatives, partners across functions, and pioneers AI-enabled content workflows to deliver a cohesive customer experience.
What You'll Do
- Define and drive the documentation strategy and roadmap for RunMyJobs and related solutions.
- Lead complex documentation initiatives aligned with major product releases and strategic programs.
- Establish scalable content standards, governance frameworks, and quality benchmarks.
- Identify and implement innovative approaches to improve documentation delivery, discoverability, and user experience.
- Mentor and guide other writers, providing editorial oversight and raising overall team capability.
- Champion content design principles to ensure documentation and in-product content are structured, usable, and user-centered.
- Partner closely with UX and Product Design teams to shape customer-facing content, including onboarding experiences, UI text, microcopy, system messaging, and workflow guidance.
- Drive consistency between documentation, in-product experiences, support materials, and customer communications.
- Advocate for the voice of the customer across the product lifecycle.
- Leverage analytics and user research insights to continuously optimize content effectiveness.
- Lead the strategic adoption of AI-enabled documentation workflows, tooling, and experimentation.
- Design and implement AI-assisted content pipelines (e.g., drafting, structured authoring, metadata tagging, content reuse, localization support).
- Evaluate emerging AI technologies and assess their applicability to content operations, customer experience, and knowledge management.
- Establish best practices for responsible AI usage, validation processes, and governance.
- Partner with engineering and product teams to explore AI-driven in-product guidance or automation experiences where relevant.
- Serve as the documentation subject matter expert and strategic partner across Engineering, Product Management, UX, Support, and Customer Success.
- Participate in roadmap planning and ensure documentation is embedded in release planning from early stages.
- Lead cross-department initiatives that improve content alignment across customer touchpoints.
- Drive clarity and alignment during complex product changes, integrations, and technical transformations.
- Represent documentation strategy in executive or stakeholder discussions as needed.
- Modernize and scale documentation practices, including Docs as Code frameworks and structured content approaches.
- Improve tooling, workflows, and automation to increase efficiency and quality.
- Ensure content is aligned with Agile development cycles and enterprise release processes.
- Establish measurable KPIs for documentation performance and user engagement.
What We're Looking For
- Bachelor’s degree in Technical Communication, Computer Science, English, or equivalent experience.
- 7–10+ years of technical writing experience, including significant experience in enterprise or B2B SaaS environments.
- Demonstrated experience operating at a Lead or Principal level, influencing documentation strategy and cross-functional initiatives.
- Proven experience leading cutting-edge or transformational documentation projects, such as implementing Docs as Code frameworks, introducing structured authoring systems, leading large-scale content migrations, redesigning documentation architecture or information models, or driving documentation modernization initiatives.
- Deep understanding of content design principles and their application to technical and in-product content.
- Experience working closely with UX/design teams on customer experience strategy, including microcopy, UI text, onboarding flows, and in-product messaging.
- Ability to align documentation strategy with design systems and broader product experience goals.
- Demonstrated hands-on experience integrating AI tools into documentation workflows at scale.
- Experience evaluating, piloting, or leading AI adoption within content teams.
- Strong understanding of prompt engineering, validation strategies, and responsible AI usage in technical content.
- Strategic perspective on how AI can transform documentation operations, customer guidance, and knowledge management.
- Ongoing personal and professional engagement with AI technologies and emerging trends.
- Strong experience with modern documentation tooling (e.g., MadCap Flare or similar platforms).
- Expertise in Docs as Code methodologies, version control (Git), Markdown, and structured authoring approaches.
- Familiarity with API documentation tools (e.g., Swagger/OpenAPI).
- Experience working within Agile development environments.
- Strong editorial leadership and mentoring capabilities.
- Ability to influence stakeholders and drive alignment across departments.
Nice to Have
- Experience with workload automation or enterprise integration platforms.
- Familiarity with SAP, Docker, or Python scripting.
- Experience contributing to enterprise content governance or design systems.
Technical Stack
- MadCap Flare
- Git
- Markdown
- Swagger/OpenAPI
Team & Environment
You will partner cross-functionally with Product, Engineering, UX, Support, and Customer Success.
Benefits & Compensation
- Salary: CAD $111,000 - $133,000 annually
Work Mode
This role is based locally within Ontario, Canada.
Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws.
