Sales Development Representative (Quickbooks Experience)

About the Role
Are you a sales professional who knows QuickBooks inside and out and wants to shape the future of Artificial Intelligence? This team is seeking experienced Sales Development Representatives and Sales Ops experts to stress-test frontier AI systems. In this role, you will use your real-world expertise to challenge AI models with complex sales scenarios, ensuring they can handle the nuances of pricing, forecasting, and customer communication. Your work will directly influence how the next generation of AI supports global sales teams.

Job Type
2-week Project

Engagement
Independent Contractor

Key Responsibilities

• Develop realistic, high-complexity sales prompts that mimic the daily demands of a Sales Manager or Business Owner.
• Create tasks involving tiered pricing, discount structures, and QuickBooks data exports to test the model’s ability to generate accurate pipelines and forecasts.
• Produce high-quality deliverables including spreadsheets, quotes, proposals, and outbound email sequences.
• Evaluate AI-generated outputs with a critical eye, reviewing them as you would a junior rep’s work before it reaches a client.
• Author objective scoring rubrics with precise, checkable criteria to allow other professionals to grade model performance consistently.

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, and sales reporting.
• Exceptional written English and an uncompromising eye for detail.
• Immediate availability to commit 40 hours per week for a 2-week intensive engagement.
• Ability to work independently as a contractor and deliver high-quality work on a flexible schedule.

Nice-to-Haves

• Prior experience in data annotation or training AI models.
• Deep familiarity with CRM workflows and advanced sales automation tools.