Jill C. Flanagan

Technical Writing / AI Evaluation / Content

I make complicated things easier to understand.

From software manuals to model evaluation, I document how things work, question what doesn't, and turn the results into something people can actually use.

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/About

A writer who tests what she documents

I began my career writing software manuals, help files, training materials, procedures, and step-by-step instructions for technical and non-technical users. That work involved learning unfamiliar systems, asking useful questions, testing software, reporting defects, and revising documentation to match verified product behaviour.

My later work has included website and social-media management, chatbot and automated-response content, fiction writing, editing, formatting, metadata, and self-publishing.

More recently, I created a self-directed AI evaluation and documentation project to develop practical experience with rubric-based evaluation, human-approved test cases, grader agreement, disagreement review, and regression testing.

I’m looking for remote work where careful research, clear writing, sound judgment, and independent problem-solving are valued.

/Writing

Selected work

A cross-section of the writing and documentation I produce. Links are added as samples become available to share.

  • 01Link to be added

    Technical Documentation

    Writing and editing software manuals, help files, training materials, procedures, FAQs, and step-by-step instructions.

  • 02Link to be added

    AI Evaluation Documentation

    Project overview, rubric, case documentation, disagreement records, and regression-testing notes.

  • 03Link to be added

    Digital Content

    Website content, social-media content, chatbot conversations, FAQ sequences, lead-capture flows, and automated customer-response content.

  • 04Link to be added

    Independent Publishing

    Character-centred fiction managed from drafting and editing through formatting, metadata, and publication.

/AI Evals

Self-Directed AI Evaluation and Documentation Project

I created and maintained the technical documentation for a version-controlled AI evaluation project. The documentation included the evaluation rubric, grader setup, case records, disagreement decisions, and regression tests.

Run log

  • Wrote and maintained 18 human-approved evaluation cases.
  • Completed two practice runs using the documented grader setup.
  • Measured 17 out of 18 agreement for sentiment labels and review statuses.
  • Reviewed five disagreements instead of treating grader output as automatically correct.
  • Retained one grader miss as a regression test.
  • Documented decisions so the evaluation process could be understood, repeated, and reviewed.

Skills

  • Rubric-based AI-response evaluation
  • Test-case writing and maintenance
  • Evaluation documentation
  • Grader-result review
  • Disagreement analysis
  • Regression testing
  • Version-controlled documentation
  • Clear written reasoning
/Services

Ways to work together

Available for remote employment and contract projects. A few of the things I can take on:

  • Technical writing and editing
  • Help content, procedures, and instructional materials
  • AI-response evaluation and rubric-based review
  • Evaluation test cases and supporting documentation
  • Knowledge-base and FAQ content
  • Website and digital-content writing
  • Content review, organization, and quality checking
  • Chatbot and automated-response content
/Contact

Start a conversation

If you need documentation people finish reading, or evaluation work you can trust, tell me a little about the project and I'll get back to you.

Elsewhere

British Columbia, Canada
Available for remote work in Canada