Principal Technical Writer / Technical Writing Lead at Redwood Software

, Ontario, Canada -

Full Time

Start Date

Immediate

Expiry Date

27 May, 26

Salary

133000.0

Posted On

26 Feb, 26

Experience

10 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Technical Writing, Documentation Strategy, Content Design, AI Integration, Cross-Functional Collaboration, Agile Development, Mentoring, User Experience, Content Management, Structured Authoring, Version Control, API Documentation, Editorial Leadership, Workload Automation, SaaS, Enterprise Software

Industry

Software Development

Description

OUR MISSION At Redwood Software, we unleash human potential. We empower our customers with lights-out automation for their mission-critical business processes. Redwood Software is the leader in full-stack automation for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in automation's transformative power. Our unparalleled solutions empower organizations to orchestrate, manage, and monitor their workflows across any application, service, or server—in the cloud or on-premise—with confidence and control. CORE VALUES One Team. One Redwood. Make Your Own Weather Obsess over Customer Success Work the Problem Be Curious Own the Outcome Respect Each Other YOUR IMPACT Redwood Software is seeking an experienced and strategic Principal Technical Writer / Technical Writing Lead to drive the documentation vision and content strategy for Redwood’s RunMyJobs Workload Automation solution. This role goes beyond content creation. As a Principal-level writer, you will lead cutting-edge documentation initiatives, shape AI-enabled content operations, and partner cross-functionally with Product, Engineering, UX, Support, and Customer Success to deliver a cohesive and exceptional customer experience. You will champion content design principles across documentation and in-product experiences while modernizing how we produce, manage, and deliver content. This role is ideal for a forward-thinking documentation leader who understands enterprise software, thrives in fast-moving environments, and actively leverages AI to transform content strategy and operations. Documentation Strategy & Leadership Define and drive the documentation strategy and roadmap for RunMyJobs and related solutions. Lead complex, high-impact 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. Content Design & Customer Experience 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. AI-Driven Content Innovation 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. Cross-Functional Collaboration & Influence 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. Operational Excellence 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. YOUR EXPERIENCE 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 Driving documentation modernization initiatives Content Design & UX Collaboration 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. AI Expertise & Innovation 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. Technical & Operational Skills 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. What Success Looks Like Documentation strategy is aligned with product vision and business objectives. Content is consistent, user-centered, and integrated across documentation and in-product experiences. AI is thoughtfully embedded into content workflows, driving measurable improvements in efficiency and quality. Documentation operations are scalable, modern, and strategically positioned within the organization. Cross-functional teams view documentation as a critical strategic partner in delivering customer value. Pay Transparency: The typical base salary range for this position is CAD $111,000 - $133,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications. The salary ranges provided in this posting are specific to roles based in Ontario, Canada, and reflect the cost of labor and market data unique to this province. These figures are determined based on local economic factors, statutory requirements under the Ontario Employment Standards Act, and regional industry benchmarks. Compensation for similar roles located outside of Ontario may vary based on local market conditions and jurisdictional regulations. Vacancy Status: Existing vacancy AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team. If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us! THE LEGAL BIT 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. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero-tolerance policy applied to it. Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at Recruitment@Redwood.com If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us! THE LEGAL BIT 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. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it. Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at Recruitment@Redwood.com

Responsibilities

Drive the documentation vision and content strategy for Redwood’s RunMyJobs Workload Automation solution. Lead documentation initiatives and collaborate with cross-functional teams to enhance customer experience.