Weekday, Inc. Logo

Weekday, Inc.

B2B Sales Expert

Reposted 11 Days Ago
Be an Early Applicant
Remote
Hiring Remotely in United States
100-150 Hourly
Senior level
Remote
Hiring Remotely in United States
100-150 Hourly
Senior level
Design task-specific grading criteria for B2B sales deliverables and evaluate AI-generated and human work against those rubrics. Provide detailed, evidence-based written justifications, refine rubrics with senior reviewers, and ensure consistent, reproducible evaluations across large volumes of work.
The summary above was generated by AI

This role is for one of our clients

Compensation: $100-$150 per hour

Join an advanced AI evaluation initiative focused on improving how next-generation AI systems understand and perform real-world B2B sales work. We are seeking experienced sales professionals to help establish the standard for high-quality sales execution by designing evaluation criteria and assessing AI-generated and human-created sales deliverables.

Rather than creating sales deliverables yourself, you will define what exceptional work looks like by developing structured grading frameworks and providing thoughtful, evidence-based evaluations.


RequirementsKey Responsibilities
  • 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.
Core Qualifications
  • 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
    • 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 Qualifications
  • Experience evaluating AI-generated content, participating in AI training projects, or working on human evaluation and data annotation initiatives.
  • Experience developing, reviewing, or applying structured scoring rubrics.
  • Ability to provide constructive, well-reasoned feedback while maintaining high evaluation standards.
Application Process
  • Submit your resume or relevant professional background for consideration.
  • Qualified applicants may be invited to complete a brief assessment or provide additional information as part of the selection process.
Equal Opportunity

We are committed to creating an inclusive environment where all qualified applicants receive equal consideration. Reasonable accommodations are available throughout the application and engagement process upon request.

Contract & Payment Terms
  • Independent contractor engagement.
  • Fully remote with flexible working hours.
  • Projects may be extended, shortened, or concluded based on business needs and performance.
  • Weekly payments are processed through supported payment platforms.
  • Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity.

Similar Jobs

3 Hours Ago
Remote
California, USA
131K-177K Annually
Senior level
131K-177K Annually
Senior level
Aerospace • Information Technology • Software • Cybersecurity • Design • Defense • Manufacturing
Lead quality engineering for illumination products: perform internal and AS9100/customer audits, drive corrective/preventive actions, analyze nonconformance trends, develop quality metrics and certification plans, and ensure design and production readiness and compliance.
Top Skills: As9100Faa Part 145Non-Conformance (Ncr) ProcessesQmsRoot Cause Analysis (Rcca)
3 Hours Ago
In-Office or Remote
30-42 Hourly
Mid level
30-42 Hourly
Mid level
Aerospace • Information Technology • Software • Cybersecurity • Design • Defense • Manufacturing
Operate and maintain Insitu unmanned aircraft systems, plan and execute missions, collect/analyze payload and video data, perform pre/post-flight checks and maintenance, support customers in field deployments, and complete inventory and mission reporting. Deployable to remote/austere locations up to 70% travel.
Top Skills: Basic NetworkingIntegratorRq21ScaneagleUas
3 Hours Ago
Remote or Hybrid
United States
55K-70K Annually
Mid level
55K-70K Annually
Mid level
Fintech • Information Technology • Insurance • Financial Services • Big Data Analytics
Provides financial support for group insurance clients through billing management, financial reporting, data analysis, reconciliations, revenue projections, audits, and data integrity oversight. Partners with internal and external stakeholders on implementations, renewals, underwriting, and client presentations. Documents and improves financial processes, supports compliance requirements, monitors financial trends and metrics, and contributes to cross-functional initiatives that improve operational effectiveness.
Top Skills: Ai-Enabled ToolsExcelMS Office

What you need to know about the Boston Tech Scene

Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.

Key Facts About Boston Tech

  • Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
  • Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
  • Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
  • Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account