Retail Finance Director
About the role
Opportunity Overview
Handshake is looking for experienced senior retail finance professionals to support AI research through flexible, part-time contract work. This is not a traditional job - you'll draw on your hands-on expertise in long-range financial planning and budget management to evaluate AI-generated content and provide feedback that helps AI better understand real-world retail finance and strategic planning workflows.
This is an ongoing, project-based opportunity you can take on alongside your current work.
What You'll Do
- Use your domain expertise to create expert-level training questions and scenarios based on real retail finance and strategic planning workflows
- Review and evaluate AI-generated responses for accuracy and relevance to real-world financial planning and analysis practices
- Provide structured written feedback to help improve AI model performance
- Complete tasks at your own pace with no set schedule or minimum hour requirement
Qualifications
- 5+ years of professional experience in senior retail finance leadership, in a role such as Finance Director, VP of Finance, or CFO
- Hands-on experience with workflows such as long-range financial planning and budget variance analysis
- Strong written communication skills and attention to detail
- Ability to work independently in a remote, asynchronous environment
Where you can work
This role is 100% remote, for applicants located in United States.
From Handshake AI's job posting, checked Oct 18, 2026.
About Handshake AI
Degree-holding US trainers, with hourly contract roles on its live board.
How it pays: Weekly through Stripe (set up in Handshake AI): Handshake sends each Monday-to-Sunday week's pay to its pay partners by Wednesday afternoon; a W-9 or W-8BEN is required (Handshake AI support, read 2026-10-14).
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