Training Data Contributor

Olive Tree Consulting is looking for a Training Data Contributor to help refine the logic and tools we use to support leadership teams. As our advisory work incorporates more data-driven tools, we need accurate, well-labeled information to ensure these systems reflect our principles of clarity and ownership. This is a part-time contract role where you will work fully remote, focusing on the quality and accuracy of the data that informs our management models.

About the Role

This position sits where our advisory practice meets our interest in how language shapes management behavior. We help teams stop repeating the same mistakes by creating clearer records of their work. As a Training Data Contributor, you will review management communications, meeting notes, and project documents to help our systems learn the difference between a vague discussion and a firm decision. The work you do ensures that the tools we build are helpful, plain, and free of the corporate jargon we try to eliminate. This is an entry-level position that offers a window into how organizational habits are analyzed and improved.

What You Will Do

• Review internal and anonymized text to identify key decision points and owner assignments.
• Label and categorize segments of management dialogue based on criteria like clarity and actionable steps.
• Check automated summaries against original transcripts to ensure no critical context or ownership details were lost.
• Write short, clear examples of effective management communication to serve as reference models for our systems.
• Identify and flag instances of ambiguous corporate language that needs to be simplified.
• Collaborate with the advisory team to ensure that the data labeling stays consistent with our core management principles.
• Organize and maintain lists of training examples to keep them accessible and well-structured.
• Participate in remote check-in meetings to discuss nuances in language and how to improve data accuracy.
• Suggest improvements to our internal guidelines when you find management scenarios that are hard to categorize.

What We Are Looking For

• A sharp eye for detail and the ability to notice subtle differences in how people communicate.
• Strong written English skills with a preference for a simple, direct, and effective vocabulary.
• A logical mindset that enjoys categorizing information and finding patterns in text.
• The ability to work independently in a remote setting while staying on track with project timelines.
• Curiosity about how teams work together and how clear writing can improve management.
• A professional and discreet approach to handling internal or client-related technical data.
• Honesty and transparency when tasks are unclear or when data does not fit easily into existing categories.
• Careful reading habits and the patience to review long documents for specific nuances.

Helpful Background

• Interest in organizational psychology, business communication, or linguistics.
• Basic familiarity with data entry, transcription, or content editing.
• Comfort using common remote collaboration tools like shared documents and messaging apps.
• Experience writing for a blog, university publication, or local organization.
• A basic understanding of how software models use training data is helpful but not required.
• Willingness to learn the Olive Tree approach to management and apply it to data tasks.

What We Offer

This is a fully remote position, allowing you to work from wherever you are most productive without the need for travel. The role is a part-time contract, offering fixed hours that provide a predictable schedule for your week. We provide a competitive and attractive pay rate for this entry-level position that reflects your contribution to our work. You will see firsthand how a management advisory firm operates and how modern tools are built to support professional teams. Our work environment is focused and quiet, prioritizing deep work and clear communication over constant meetings.

About Olive Tree

Olive Tree Consulting Group is a focused advisory practice that helps leadership teams solve recurring management issues. We typically work on the space between strategy and daily execution. A team can have very capable people and still find that decisions keep reopening, priorities stall, or responsibility remains unclear. These are rarely personality problems: they are structural habits that have not kept up with the company growth. We favor practical changes over large-scale transformation programs. Our work involves looking at how decisions are made, how meetings are run, and how ownership is recorded. We prefer useful written notes and clear ownership over polished presentations and vague alignment. Good advisory work should make things plainer and leave the team with a rhythm they can continue on their own. The firm is built on the principle that memory is not a management system. We help teams create the smallest possible written record to support their work so that important follow-up does not depend on who was in the room or who has the best memory. The goal is a quieter management pattern that makes the existing work easier to lead.