Sales and Marketing Expert

Weekday 1; United States; Remote; USD 83,000 - 96,000; Full time

Job summary

Weekday 1 is seeking experienced senior sales and marketing professionals to contribute to an AI evaluation initiative focused on Fortune 500 GTM environments. This remote, project-based engagement creates enterprise scenarios, reference outputs, and evaluation rubrics that reflect real-world decisionmaking.

You will develop $1M+ ACV scenarios, support ABM and demand programs, and apply MEDDIC, Challenger, and Force Management with platforms like Salesforce, Marketo, 6sense, Gong, and Outreach.

Qualifications

• 5+ years of enterprise sales, marketing, or Revenue Operations experience.
• Experience with Fortune 500 or large enterprise technology environments.
• Direct experience managing Fortune 500 accounts or large-scale programs.
• Strong understanding of procurement, budgeting, and complex negotiations.
• Hands-on familiarity with GTM platforms and related tools.

Responsibilities

• Develop enterprise sales scenarios with $1M+ ACV opportunities.
• Create marketing scenarios including ABM, demand gen, lifecycle marketing.
• Develop Revenue Operations and GTM scenarios with Salesforce, Marketo, 6sense, Gong, Outreach.
• Apply MEDDIC, Challenger, and Force Management to build deal strategies.
• Create executive-level sales narratives and go-to-market recommendations.
• Develop evaluation rubrics reflecting enterprise GTM expertise.
• Review and refine scenarios based on reviewer feedback.
• Incorporate feedback to improve quality and relevance.

Skills

Enterprise sales

Marketing

Revenue Operations

CRM

Marketing automation

Sales engagement

Conversation intelligence

Account intelligence

MEDDIC

Challenger

Force Management

Stakeholder management

Analytical skills

Written communication

AI training experience

Tools

Salesforce

Marketo

6sense

Gong

Outreach

Job description

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.

Requirements

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.

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.