Retail Operations AI Training Specialist — Task Creation & Model Evaluation (Contract)

@ Rise Data Labs

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Canada

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Overview

Rise Data Labs is hiring a contract Retail Operations AI Training Specialist to author retail task scenarios and rubrics from their professional experience and to grade AI-generated deliverables against them. The work is remote-style benchmark creation and evaluation, with calibration sessions alongside other evaluators.

Responsibilities:

Create realistic retail task scenarios from professional experience
Write clear rubrics for professional-quality deliverables
Grade AI-generated documents against rubrics
Join calibration sessions with other evaluators

Requirements summary:

Prior hands-on retail operations or merchandising experience
Licensed retail specialty such as pharmacy is a plus
Comfort writing and reviewing operational or client-facing documents
AI training or evaluation experience is a plus

Source and dates

Source type not verified · apify-linkedin

Employer posting date: 2026-10-18
First seen by our source: 2026-11-15
Source record updated: 2026-11-15

These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.

Job details

Seniority	Mid level
Department	Data & analytics
Travel	air: none · ground: none
Work setting	Home
Position	Mostly sitting
Physical demands	physical low · computer high
Languages	English

Summary and details written by AI from the posting; the employer’s posting is the authority.

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Rise Data Labs

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People associated on LinkedIn: 22
Other recorded names: Rise Data Labs

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Field	Value
Industry	Software Development
Headquarters	New York, NY
Open jobs on Jobsy	8
LinkedIn	View page

Job description

About Rise Data Labs Rise Data Labs is a leading AI training and data annotation company that specializes in creating high-quality training data for artificial intelligence systems. We work with top AI companies and research institutions to improve machine learning models through expert human annotation and validation. Our team of domain specialists, subject matter experts, and quality assurance professionals work across various fields including retail operations, merchandising, and store management. We pride ourselves on our attention to detail, domain expertise, and commitment to delivering accurate, high-quality training data.

Job Overview As a Retail Operations AI Training Specialist at Rise Data Labs, you will play a crucial role in training and enhancing AI models specifically tailored for the retail domain. This role centers on benchmark task creation and evaluation: you'll author realistic, economically valuable retail tasks and rubrics based on your own professional experience, then grade AI-generated deliverables against them.

What You'll Do

Create realistic task scenarios based on your professional experience - e.g., writing an operations report, reviewing a merchandising plan, drafting client- or customer-facing communication, or handling a specialized professional task
Write clear rubrics for what a correct, professional-quality deliverable looks like
Grade AI-generated deliverables (often PDFs, Word documents, or short reports) against your rubric
Join calibration sessions with other evaluators to align scoring standards across the benchmark

Preferred Qualifications

Prior hands-on experience in retail operations, store or district management, merchandising, or a licensed retail specialty (e.g., pharmacy)
Comfort writing and reviewing operational or client-facing documents
Prior experience with AI model training, evaluation, or benchmark development is a plus

What We Offer At Rise Data Labs, we value our contributors and strive to create a supportive, flexible working environment. We offer opportunities for professional development in the AI field and the chance to work on innovative projects that directly shape the future of AI in retail work.