Product Manager, Documentation Systems

Accountabilities:: You will own the documentation ecosystem end to end, combining product management, automation, technical knowledge, and customer empathy to improve how product information is created, maintained, and consumed. Own the full documentation surface, including in-product Help, implementation guides, support runbooks, and release notes across the platform and embedded applications. Determine what should be documented, rewritten, updated, or retired. Build information architecture based on customer search behavior, friction points, and support needs. Define and monitor documentation metrics such as release coverage, page freshness, unsuccessful Help searches, and support volume for documented topics. Design and build an AI-assisted pipeline that drafts documentation from tickets, pull requests, release artifacts, recorded demos, and other reliable sources. Develop evaluation processes that identify inaccurate or misleading AI-generated content before it reaches customers. Automate change detection, terminology and style enforcement, screenshot capture, and publishing workflows. Own and evolve the documentation toolchain, currently including MadCap Flare and repository-based publishing. Partner with Product and Engineering to establish a definition of done that captures navigation, permissions, configuration, error states, and impacts on existing users. Develop terminology and style standards that promote consistency across multiple ERP surfaces. Design processes for detecting documentation that has become outdated as external ERP interfaces evolve. Own documentation revalidation processes and related service-level expectations. Learn products through hands-on use to understand actual behavior rather than relying only on specifications. Create high-value human-authored content such as migration guides, error taxonomies, and integration behavior documentation. Influence product managers and engineers across teams to improve the quality and availability of product knowledge. Prioritize documentation initiatives and confidently make trade-offs across a broad documentation surface. Requirements: The ideal candidate is a hands-on product or technical professional who can automate workflows, understand complex products, work directly with customers, and influence technical stakeholders without relying on formal authority. 5+ years owning outcomes in product management, implementation or solutions consulting, technical program management, support engineering, developer experience, technical enablement, or a related field. Demonstrated experience automating your own work and building practical solutions. Comfortable working with Git, command-line tools, and codebases you did not write. Ability to build and automate without necessarily being a professional software engineer. Practical experience shipping a real-world solution using an LLM, including evaluating its outputs and identifying incorrect results. Direct customer-facing experience through implementation, support escalation, solution consulting, professional services, training, or similar work. Ability to understand why technically accurate documentation can still fail to meet a customer's needs. Strong ability to learn complex products without relying entirely on formal specifications. Ability to retain and apply insights from your own learning and customer experiences. Proven ability to influence product managers and engineers without direct management responsibility. Strong prioritization skills and the confidence to make difficult scope decisions. Experience with MadCap Flare is an asset. Familiarity with a complex enterprise system, such as an ERP or accounting platform, is preferred. Experience with docs-as-code or CI-driven publishing is a plus. Exposure to B2B fintech, payments, or accounts receivable is an advantage. Experience building an internal tool that became relied upon by other teams is a plus. Benefits: Remote contractor opportunity based in Canada. Compensation of CAD $60–$70 per hour . Opportunity to own documentation as a strategic product and influence how customers access product knowledge. Hands-on opportunity to build and improve AI-assisted documentation workflows. Access to modern LLM tooling connected to internal systems. Collaboration with Product and Engineering teams across complex platform and ERP environments. Opportunity to develop automation, information architecture, documentation standards, and evaluation systems. Exposure to enterprise software, documentation technology, and customer-facing product challenges. Opportunity to shape scalable processes for maintaining accurate, current product documentation. Diverse and inclusive working environment.