Sales and Marketing Expert
Weekday AI
•$60 - $70•Remote
About The Position
This role is for one of our clients. 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
- 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.
Nice To Haves
- 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.
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.
Benefits
- Remote, flexible engagement.
- Payments are made weekly through Stripe or Wise based on services rendered.
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What This Job Offers
Career Level
Senior
Education Level
No Education Listed
