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Weekday AI

B2B Sales Expert

RemoteUnited States only
Published
Role
Sales
Experience
Senior
Employment
Contract
$100–$150/hr
Check eligibility

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

No BS summary

Experienced B2B sales professional with 5+ years in quota-carrying enterprise sales roles. Needs full sales lifecycle expertise and strong written judgment to evaluate AI- and human-created sales work. US-based independent contractor; H-1B or STEM OPT sponsorship not available.

What you'll do

  • Design precise, task-specific grading criteria for a wide range of B2B sales deliverables, including prospecting sequences and outreach emails, discovery and demo call plans, account and territory plans, sales proposals, mutual action plans, pipeline reviews and sales forecasting.
  • Evaluate AI-generated and human-created work against established rubrics, providing detailed written justifications for every score.
  • Apply objective, consistent, and evidence-based judgment to ensure evaluations are accurate, reproducible, and defensible.
  • Incorporate structured feedback from senior reviewers and continuously refine evaluation quality.

What they require

  • 5+ years of professional B2B sales experience in quota-carrying roles.
  • Proven experience as an Account Executive, Sales Development Representative (SDR), or similar client-facing sales role selling to enterprise organizations.
  • Strong expertise across the full B2B sales lifecycle, including outbound prospecting and sequencing, discovery and qualification, multi-stakeholder enterprise sales, pipeline management and forecasting, and structured sales methodologies.
  • Exceptional written communication skills with the ability to clearly explain why a sales deliverable would—or would not—resonate with a prospective buyer.
  • Strong attention to detail and the ability to apply evaluation criteria consistently across large volumes of work.
  • Preferred: Experience evaluating AI-generated content, participating in AI training projects, or working on human evaluation and data annotation initiatives.
  • Preferred: Experience developing, reviewing, or applying structured scoring rubrics.
  • Preferred: Ability to provide constructive, well-reasoned feedback while maintaining high evaluation standards.
  • Qualified applicants may be invited to complete a brief assessment or provide additional information as part of the selection process.
  • Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity.

Benefits

  • Fully remote with flexible working hours.
  • Weekly payments are processed through supported payment platforms.
  • Reasonable accommodations are available throughout the application and engagement process upon request.

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

Details

Visa sponsorshipNo
$100–$150/hr