Sales and Marketing Expert

Weekday AI· AI Training
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🌍 Remote📍 TELECOMMUTE📍 United StatesContract💰 USD 60–70

About this role

This role is for one of our clients

Compensation: $60-$70 per hour

We are seeking experienced senior sales and marketing professionals to contribute to an AI evaluation initiative focused on real-world Fortune 500 go-to-market environments.

The work is designed around the deal complexity, stakeholder dynamics, commercial processes, and brand considerations found within Fortune 500 and large public companies. Contributors will create realistic enterprise GTM scenarios, develop high-quality reference outputs, and build evaluation rubrics that capture how experienced sales and marketing leaders make decisions.

Key Responsibilities

  • Develop enterprise sales scenarios involving $1M+ ACV opportunities, complex buying committees, multiple stakeholders, and lengthy procurement cycles within Fortune 500 accounts.
  • Create marketing scenarios covering enterprise brand strategy, account-based marketing (ABM), demand generation, lifecycle marketing, and category positioning.
  • Develop Revenue Operations and GTM scenarios using enterprise platforms such as Salesforce, Marketo, 6sense, Gong, and Outreach.
  • Apply established enterprise sales methodologies, including MEDDIC, Challenger, and Force Management, to develop realistic deal strategies and account plans.
  • Create executive-level sales narratives, customer engagement strategies, and go-to-market recommendations.
  • Develop detailed evaluation rubrics that distinguish genuine enterprise GTM expertise from generic sales or marketing playbook knowledge.
  • Review and refine scenarios and reference outputs to ensure they accurately reflect real-world enterprise practices.
  • Incorporate reviewer feedback and continuously improve the quality, consistency, and relevance of evaluation criteria.

Ideal Qualifications

  • 5+ years of professional experience in enterprise sales, marketing, or Revenue Operations.
  • Experience working for a Fortune 500 enterprise technology company, major SaaS organization, or large public-company sales or marketing organization.
  • Direct experience managing Fortune 500 accounts, enterprise sales cycles, major brand initiatives, or large-scale demand-generation programs.
  • Strong understanding of enterprise buying processes, procurement, budgeting, legal review, stakeholder management, and complex commercial negotiations.
  • Hands-on familiarity with enterprise GTM technologies and platforms, including CRM, marketing automation, sales engagement, conversation intelligence, and account-intelligence tools.
  • Strong knowledge of enterprise sales methodologies such as MEDDIC, Challenger, or Force Management.
  • Excellent written communication and analytical skills, with the ability to clearly explain strategic decisions and commercial reasoning.
  • Experience creating sales enablement materials, evaluation frameworks, training content, or professional development programs is a plus.
  • Prior experience with AI training, evaluation, rubric development, or human-data projects is advantageous.

Application Process

  • Submit your resume or relevant professional background to get started.
  • Qualified applicants may be asked to complete a brief assessment or provide additional information about their enterprise sales or marketing experience.
  • Selected contributors may receive onboarding and calibration guidance before beginning project work.

Engagement Details

  • Remote, flexible engagement.
  • Work is structured around project-based AI evaluation and research initiatives.
  • Project scope and duration may vary based on business and research requirements.
  • Strong contributors may have opportunities to participate in additional evaluation, reviewer, or subject-matter-expert projects.

Equal Opportunity

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.

Contract and Payment Terms

  • You will be engaged as an independent contractor.
  • This is a fully remote role that can be completed on your own schedule.
  • Projects may be extended, shortened, or concluded early depending on project requirements and performance.
  • Your work will not involve access to confidential or proprietary information from any current or former employer, client, or institution.
  • Payments are made weekly through Stripe or Wise based on services rendered.
  • H-1B and STEM OPT candidates are not currently supported for this opportunity.

Frequently Asked Questions

What is the salary for the Sales and Marketing Expert role at Weekday AI?
The listed salary for this Sales and Marketing Expert position at Weekday AI is USD 60–70. This is a remote Contract role.
Is the Sales and Marketing Expert job at Weekday AI remote?
Yes, this Sales and Marketing Expert position at Weekday AI is remote, with team members based in TELECOMMUTE, United States. You can work from home or anywhere in the supported regions.
Is the Sales and Marketing Expert role at Weekday AI full-time or part-time?
This is listed as a Contract position. It is posted as a Sales and Marketing Expert role in the AI Training department at Weekday AI.
Which team or department does the Sales and Marketing Expert at Weekday AI belong to?
This Sales and Marketing Expert position is part of the AI Training department at Weekday AI. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Sales and Marketing Expert position at Weekday AI?
Click the "Apply Now" button on this page. You will be redirected to Weekday AI's official application portal hosted on workable where you can submit your application directly.
When was the Sales and Marketing Expert job at Weekday AI posted?
This Sales and Marketing Expert position at Weekday AI was posted on Aug 17, 2026. Apply as soon as possible — early applications are often reviewed first.
Sales and Marketing Expert
Weekday AI · 💰 USD 60–70
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You'll be redirected to Weekday AI's official application page on workable.