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Weekday AI

Retail Specialist

RemoteUnited States only
Published
Role
Content
Experience
Lead
Employment
Full-time
$60–$80/hr
Check eligibility

Open to US only. Set where you work from to check your eligibility.

No BS summary

Seasoned retail professional (8+ yrs in merchandising, category management, buying, planning, or operations) who evaluates AI-generated outputs against rubrics. Must have hands-on LLM/AI output evaluation experience. Fully remote (US-based), ~35 hrs/week, $60-80/hr.

What you'll do

  • Work with research and engineering teams to identify and address knowledge gaps related to retail merchandising, category management, buying, planning, and operations
  • Design challenging, realistic retail tasks that reflect real-world business scenarios and decision-making
  • Develop accurate, well-reasoned solutions based on established retail practices and professional experience
  • Evaluate AI-generated responses using structured rubrics, assessing accuracy, reasoning, judgment, relevance, and completeness
  • Provide clear and actionable written feedback explaining strengths, weaknesses, and areas for improvement
  • Develop and refine evaluation guidelines and scoring frameworks specifically for retail-related tasks
  • Collaborate with other subject-matter experts to maintain consistency, accuracy, and quality across AI training and evaluation datasets
  • Help translate practical retail knowledge and decision-making processes into structured guidance that can be used to improve AI systems

What they require

  • 8+ years of professional retail experience in merchandising, category management, buying, retail planning, retail operations, or related functions
  • Experience working within a recognized large-scale retail, consumer, e-commerce, or omnichannel organization is strongly preferred
  • Prior hands-on experience evaluating LLM or AI-generated outputs against rubrics or structured scoring criteria is mandatory
  • Demonstrated career progression and increasing responsibility, such as Category Manager → Senior Manager → Director of Merchandising
  • Strong understanding of retail strategy, merchandising processes, category performance, inventory considerations, customer behavior, and operational decision-making
  • Ability to assess complex business scenarios and determine whether recommendations are practical and commercially sound
  • Strong written and verbal communication skills
  • Excellent problem-solving and analytical abilities
  • High attention to detail and consistency when applying evaluation criteria
  • Comfortable collaborating with cross-functional teams and other subject-matter experts
  • Ability to commit reliably to approximately 35 hours per week during weekdays

Benefits

  • Fully remote role

Weekday AI is a Y Combinator-backed startup transforming the hiring landscape with outreach tools and a database of white-collar talent, delivering recruitment solutions.

RecruitmentStartup
$60–$80/hr