Principal Technical Writer / Technical Writing Lead (AI, Enterprise Software)

TL;DR

Principal Technical Writer / Technical Writing Lead (AI, Enterprise Software): Leading documentation strategy and content operations for Redwood’s RunMyJobs Workload Automation solution with an accent on AI-enabled content workflows and cross-functional collaboration. Focus on shaping content design principles, modernizing content delivery, and leveraging AI to transform content strategy.

Location: Ontario, Canada

Salary: CAD $111,000–$133,000 annually

Company

hirify.global is a leader in full-stack automation, providing the first SaaS-based composable automation platform for mission-critical business processes.

What you will do

• Define and drive the documentation strategy and roadmap for RunMyJobs, aligning with major product releases and strategic programs.
• Champion content design principles, partnering closely with UX and Product Design teams to shape customer-facing content.
• Lead the strategic adoption of AI-enabled documentation workflows, tooling, and experimentation.
• Serve as the documentation subject matter expert and strategic partner across Engineering, Product Management, UX, Support, and Customer Success.
• Modernize and scale documentation practices, including Docs as Code frameworks and structured content approaches.

Requirements

• 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 documentation projects, such as implementing Docs as Code frameworks or structured authoring systems.
• Deep understanding of content design principles and experience working closely with UX/design teams on customer experience strategy.
• Demonstrated hands-on experience integrating AI tools into documentation workflows at scale.

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.

Culture & Benefits

• Collaborative "One Team. One Redwood." culture with a focus on customer success.
• Emphasis on curiosity, ownership, and working through problems.
• Opportunity for growth and working with enthusiastic colleagues.
• Values respect and a positive work environment.
• Empowers customers with lights-out automation for mission-critical business processes.

Hiring process

• Utilizes an AI-enabled notetaking assistant to help capture and summarize interview discussions.
• All final hiring and selection decisions are made exclusively by individuals on the hiring team.