About The Position
This team is on a mission to stress-test the next generation of frontier AI systems to see if they can handle the rigors of real-world sales operations. We are looking for a seasoned Account Executive with deep QuickBooks expertise to serve as a subject matter expert. In this role, you won't just be selling; you will be the "manager" and "adversary" for the world’s most advanced AI models. Your goal is to design complex sales scenarios that challenge these systems and develop the grading rubrics used to evaluate their performance. If you are a sales pro who knows how to spot a mistake in a quote from a mile away, your expertise is needed to shape the future of AI in business.
Requirements
- 5+ years of experience in Sales, Account Management, or Sales Operations with a proven track record of hitting targets.
- 3-4+ years of hands-on experience using QuickBooks (Online or Desktop) for estimates, invoicing, customer records, and sales reporting.
- Precise attention to detail and excellent written English skills.
- Ability to commit to 40 hours per week for a high-intensity 2-week engagement.
- Strong analytical mindset with the ability to break down complex sales workflows into objective, checkable steps.
Nice To Haves
- Prior experience in AI data annotation or prompt engineering.
- Experience in sales coaching or managing junior reps (reviewing their work for accuracy).
- Technical proficiency in spreadsheet modeling and data visualization.
Responsibilities
- Create realistic, high-difficulty sales prompts based on real-world scenarios a sales manager, customer, or business owner would encounter.
- Develop complex tasks including tiered pricing quotes, commission calculations, and converting QuickBooks sales exports into pipeline/forecast reports.
- Run prompts against frontier AI models and perform "manager-level" reviews of the output to identify errors in logic, math, or professional tone.
- Author objective scoring rubrics for each task, ensuring that other reviewers can consistently grade the AI's output based on pass/fail criteria (e.g., "The quote does not exceed the 15% discount cap").
- Produce working deliverables such as spreadsheets, proposals, and email sequences that serve as "Gold Standard" examples for the AI to follow.
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
