[Hiring] Sales and Marketing Expert @Weekday AI

Role Description

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.

• 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.

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.