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Added 8 mins ago
UH
Clinical Study and Regulatory Assistant
University Health Network
Toronto, ON
- Contract
As a Clinical Study and Regulatory Assistant, under the supervision of the program managers and other team members, you will be responsible for:
Added 8 mins ago
Alternatives, Operational Due Diligence Analyst - Assistant Vice President
iCapital
Toronto, ON
iCapital is looking to hire an Assistant Vice President to join the Research and Education team. The individual will be responsible for overseeing and conducting operational due diligence…
Added 23 mins ago
OV
Personal Support Assistant (CUPE) – Medicine and Transitional Bed Unit (3) - Part Time - Markham Stouffville Hospital
Oak Valley Health
Markham, ON
- Part-time
As a Patient Support Assistant, you will work in partnership with a Registered Nurse/Registered Practical Nurse, to provide patient care and will become an integral member of the…
Added 23 mins ago
Rehabilitation Assistant – Nursing, OT, PT - Surrey Memorial Hospital
Fraser Health
Surrey, BC
In accordance with the Mission and Values of Fraser Health, the Rehabilitation Assistant works under the direction of a professional nurse (Registered Nurse (RN), Registered Psychiatric…
Added 37 mins ago
BH
Medical Assistant
BayCare Health System
BC · Cariboo B, BC
- Full-time
BayCare is currently in search of our newest Medical Assistant or LPN who is passionate about providing outstanding customer service to our community. BayCare’s top priority is the health…
Added 37 mins ago
BH
Medical Assistant
BayCare Health System
BC · Cariboo B, BC
- Full-time
BayCare is currently in search of our newest Medical Assistant or LPN who is passionate about providing outstanding customer service to our community. BayCare’s top priority is the health…
Added 52 mins ago
OT
Assistant Superintendent (Night Shift)
Ontario Transit Group - Ontario Line - Southern Civil, Stations & Tunnel
Toronto, ON
- Full-time
The Assistant Superintendent supports the General Superintendent or Superintendent in coordinating daily on‑site construction activities, ensuring the project runs safely, efficiently, and…
Added 52 mins ago
SM
Registered Practical Nurse - Med/Surg
Stevenson Memorial Hospital
Alliston, ON
- Full-time
Added 52 mins ago
SM
Unit Assistant, Emergency
Stevenson Memorial Hospital
Alliston, ON
- Internship
The Unit Assistant ensures clear concise communication and facilitates the flow of information with other facilities, the health care team, visitors, family members and patients. As part of…
Added 52 mins ago
AV
Client Care Assistant
ARNWOOD VETERINARY CLINICS LIMITED
London, ON
- Full-time
As a Client Care Assistant (CCA) you will be the first point of contact for client phone calls and visits and will be responsible for delivering exceptional care, always there to clients,…
Added 52 mins ago
UO
Research Assistant/Technician: Clinical Research
University of Manitoba
Winnipeg, MB
- Full-time
Collection and recording of data from patient charts and medical records.
Added 52 mins ago
Rehabilitation Assistant - Rehabilitation and Supportive Care Services
Nova Scotia Health and IWK Health
Halifax, NS
Reporting to the Program Manager of the Medical-Surgical and Cancer Care department within the Rehabilitation and Supportive Care Services portfolio, and under the supervision of…
Added 52 mins ago
RS
SaaS Engineer
Redwood Software
ON
- $120,000 to $137,000 CAD / year
Added 1 hour ago
HH
Administrative Assistant
Halton Healthcare
Oakville, ON
- Full-time
…Healthcare requires all new hires to receive pre-employment medical clearance by our Health, Safety & Wellness team, prior to their start date, as a condition of employment. This includes…
Added 1 hour ago
FL
Assistant Gérant / Assistant Manager
Foot Locker
Montreal, QC
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Added 1 hour ago
DU
Prosthodontist
Dalhousie University
Halifax, NS
- Full-time
…tenure-track or tenure-track Prosthodontist at the rank of Assistant or Associate Professor. Following the search process, the position is available to begin as early as January 2027, or at…
Added 1 hour ago
SH
Medical Laboratory Assistant-Repost
Shared Health-Soins Communs
Winkler, MB
- Full-time
Under the general supervision of the Charge Technologist or designate, the Medical Laboratory Assistant (MLA) is responsible for assisting the laboratory in its role of sample triaging,…
Added 1 hour ago
LM
Head of Department – Medical Biology Laboratory
Lacroix Médecine Privée
Quebec, QC
- Full-time
Lacroix Private Lab is seeking a Medical Biology Service Manager to join its team.
Added 1 hour ago
LH
Physiotherapy Assistant
Lifemark Health Group
Wiarton, ON
- $17.6 to $21.17 CAD / hour
- Full-time
Lifemark Seniors Wellness is looking for a Permanent Full-Time Physiotherapy Assistant to join our growing team!
Added 1 hour ago
SI
Personal Injury Legal Assistant
Synectics Inc.
Vaughan, ON
- Full-time
Seeking a Personal Injury Legal Assistant with experience in Ontario accident benefits and tort litigation to support a growing practice in Woodbridge, ON. The ideal candidate will have…
Added 1 hour ago
Medical Secretary, Obstetrics and Gynaecology
Sinai Health
Toronto, ON
Sinai Health is looking for a Medical Secretary, Obstetrics and Gynaecology at Mount Sinai Hospital. As a Medical Secretary you will provide administrative and secretarial support to…
Added 1 hour ago
OV
Registered Practical Nurse (CUPE), Medicine Cardiology - Part-Time - Markham Stouffville Hospital
Oak Valley Health
Markham, ON
- Part-time
…partnership with the Registered Nurse (RN) and a patient support assistant (PSA) responsible for the comprehensive care of medical and cardiac patients including cardiac monitoring. You…
Added 1 hour ago
FH
Client Services Assistant, Home Health - Community South Fraser
Fraser Health
White Rock, BC
- Full-time
We are currently hiring for a Full Time Client Services Assistant to join our Home Health Team at Fraser Health Community South Fraser located in White Rock, B.C.
Added 1 hour ago
H
Medical Laboratory Assistant
HealthCareersInSask.ca
Kindersley, SK
- Full-time
Added 1 hour ago
RS
Senior Agentic Technical Writer
Redwood Software
ON
- $100,000 to $120,000 CAD / year

Redwood Software

Senior Agentic Technical Writer

ON, Canada

$100,000 to $120,000 CAD / year

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Job details

Pay: $100,000 to $120,000 CAD / year
Posting language: English
Posted: Nov 5, 2026

Original job description

Our Mission

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

About Us

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric, with AI embedded across the automation lifecycle, Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what's next.

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 is rebuilding how documentation gets made. Content lives in Git as Markdown, ships through CI/CD, is reviewed by pull request next to product code, and is increasingly drafted by AI agents working from the product requirements, the code, and a structured content model. We are retiring our legacy authoring tool and moving every writer to this way of working.

You will be a senior writer who builds and runs that pipeline. You decide what an agent drafts and what a human must validate, you build the checks that catch failures, and you set the quality bar for AI-generated documentation. You also become a deep subject matter expert on Redwood's products and on the service orchestration and automation platform (SOAP) market they compete in, and you put what you learn back into the content model so every agent and writer inherits it.

This is a senior individual contributor role. You own a program, not a document set: the documentation pipeline and the content for a product area. You choose the approach on new work, guide more junior writers day to day, and have a significant say in documentation decisions for the business area. Not a people manager role.

Build and Run the Agentic Documentation Pipeline

Design, build, and operate AI-assisted and agentic workflows that draft new content and update existing pages from product requirements, merged code, API specifications, Jira tickets, and release information.
Define the handoffs: what the agent drafts, what the writer validates, how failures are detected, and how provenance is recorded. Publish the accuracy and review standards the team follows.
Own the content model and context layer that agents read: structure, terminology, glossary, style rules, reusable components, and product knowledge, so output is consistent and machine-readable for customers, partners, and AI assistants.
Build automated quality gates in CI: style and terminology linting, link checks, code sample and API reference validation, and an evaluation set that measures draft quality as models and prompts change.
Detect drift: flag documentation that no longer matches the product after a code or API change.
Measure the pipeline and report results: cycle time from release to published content, coverage, accuracy defects, reviewer edit effort, and cost per page.
Keep an honest model of where agents fail on Redwood content, and move the human-AI boundary as models improve.

Docs as Code

Own the Git workflow, Markdown/MDX authoring, build, and CI/CD publishing for your product area, with pull-request review alongside engineering.
Lead migration of legacy content into structured, versioned Markdown, including information architecture, redirects, search, and versioning.
Embed documentation in the delivery lifecycle: docs as a release gate, updates triggered by code and API changes, and documentation work that starts when the product definition is approved, in parallel with engineering rather than after it.
Produce OpenAPI-driven API reference and developer guides to the standard expected of a platform product.

Become the Subject Matter Expert on the Product and SOAP

Install, configure, and use the product yourself, and test new features before you document them.
Build working knowledge of how customers use orchestration across ERP, cloud, data, and IT operations, and how competing platforms position and document themselves. Use it to write content that explains how to apply the product to a business need, not only how to click through it.
Partner with product, engineering, support, and customer success to understand complex systems. Raise it early when a feature is hard to document, because that usually means it is hard to use.
Capture what you learn in the content model, so product knowledge compounds in the system and not only in your head.

Lead Through Craft

Teach other writers docs-as-code and agentic drafting through pairing, templates, review checklists, and onboarding material.
Review AI-generated and human-written content to one consistent bar.
Work with a distributed team across time zones, with clear written handoffs.

YOUR EXPERIENCE

8+ years of professional experience (6+ with a master's degree) in technical writing, documentation engineering, developer experience, or technical content for software. Open item: see the open items at the end of this document.
Docs as code in production, which you can show: a documentation repository or platform you built, migrated to, or ran, using Git, Markdown/MDX (or AsciiDoc or reStructuredText), a static site generator or docs platform (for example Mintlify, Docusaurus, MkDocs, Hugo), CI/CD publishing, and pull-request review. You can state the size of the content estate and who contributed.
An AI-assisted documentation pipeline in production. You can describe a specific workflow where AI drafts or updates content from a source such as a code diff, ticket, or API spec; what you validate before publishing; how the tool fails; and how your approach changed in the past six months. You can show the prompts, skills, or agent configuration and the checks around them.
Automated quality checks in CI that you set up, such as a prose linter (Vale or similar), link checking, code sample testing, or spec validation.
Shipped documentation for a technically complex product, and an example of getting to credible documentation in an unfamiliar, dense domain. Describe the process, not only the outcome.
Comfort reading code, API specifications, pull requests, and Jira to verify what you write, and running the product yourself.
Judgment about the trade-off between speed and accuracy in content that customers rely on for mission-critical systems.
Clear writing, and the ability to explain complex technical concepts to technical and business audiences.

Strongly Preferred

Agentic documentation: agents that act on a repository, such as opening pull requests, updating docs on merge, running checks, or looping on review feedback, with human approval gates and evaluations you designed. Experience with tool use or MCP is a plus.
Lead experience: you owned a documentation program, served as the technical lead for a group of writers, or guided other writers' work without a management title.
Content modeling and structured content: taxonomy, reusable components, or migration from a legacy authoring tool or DITA-style content to Markdown.
API documentation with OpenAPI and developer portals.
Enterprise software in automation, ERP, integration, data pipelines, ITSM, or workload automation, or direct familiarity with the SOAP market.
Documentation analytics used to decide what to write, fix, or retire.

Not Required

A long career under the title "technical writer."
Experience with MadCap Flare or any specific legacy authoring tool.
A machine learning background.

What We Will Ask You to Show

A walkthrough of an AI-assisted or agentic documentation workflow you built: the inputs, the human checkpoints, a case where it produced something wrong, and what you changed.
A docs-as-code repository, pipeline, or migration, with its scale and results.
A piece of documentation for a hard technical subject, and how you verified it.

Pay Transparency: The typical base salary range for this position is CAD $100,000- $120,000 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.

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 Privacy@Redwood.com

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More about this job

Responsibilities

Design, build, and operate an AI-assisted documentation pipeline that integrates with product requirements, code, and API specifications. Lead the migration of legacy content to structured Markdown while establishing quality standards and automated gates within the CI/CD process.

Requirements

Requires 8+ years of professional experience in technical writing or documentation engineering with a proven track record in docs-as-code and AI-assisted pipelines. Candidates must demonstrate expertise in Git, Markdown/MDX, and the ability to read code and API specifications to verify technical content.

Skills

Technical writing
Git
Markdown
CI/CD
AI-assisted workflows
API documentation
OpenAPI
Content modeling
Docs-as-code
Software orchestration
Automation
Developer experience
Information architecture
Quality assurance
Subject matter expertise

Visa sponsorship

Not detected in the job text

Keywords

Technical Writing
Agentic AI
Orchestration
SaaS
Git
Markdown
MDX
CI/CD
OpenAPI
API Reference
Jira
Automation
SOAP
ERP
Hybrid Cloud
Content Modeling
Information Architecture
Vale
Static Site Generator
Mintlify
Docusaurus
MkDocs
Hugo
Documentation Engineering
Developer Experience
Data Pipelines
ITSM
Workload Automation
Documentation Analytics
Structured Content

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