Develop realistic enterprise GTM scenarios and evaluation rubrics for Fortune 500 sales and marketing contexts. Create deal strategies, account plans, marketing and RevOps scenarios using enterprise platforms, apply established sales methodologies, produce executive-level narratives, and refine evaluation outputs through reviewer feedback.
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.
RequirementsKey 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.
- 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.
- 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.
- 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.
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.
Similar Jobs
.png)
3 Minutes Ago
Easy Apply
Easy Apply
Cloud • Information Technology
Leads Wasabi’s AI infrastructure, data factory, and developer partnerships strategy. Hunts and originates new relationships, develops joint go-to-market and co-selling motions, structures revenue-generating deals, and manages executive partner relationships. The role collaborates with Business Development, Sales, Marketing, and Product, builds the developer ecosystem, tracks pipeline and revenue performance, and represents Wasabi at industry events. Candidates need deep AI infrastructure and storage expertise, an established industry network, and a proven record of closing strategic partnerships.
Top Skills:
Ai Developer PlatformsAi InfrastructureAws S3Cloud StorageGpu Computing
Cloud • Security • Software • Cybersecurity • Automation
Coordinates the end-to-end candidate experience across hiring processes, including interview scheduling, candidate communication, applicant tracking system updates, pipeline monitoring, offer contract preparation, and handoffs to People Operations. Partners with recruiters and hiring managers in a high-volume, remote environment while maintaining accurate records, improving workflows, protecting confidentiality, and representing GitLab’s values and culture.
Top Skills:
Applicant Tracking SystemsGitlabGoogle WorkspaceGreenhouseScheduling Tools
Other • Utilities
Hunter-style outside B2B sales role targeting small businesses. Prospect, cold-call, and network to generate leads, recommend wireless solutions, negotiate and close deals, manage sales funnel and forecasts, and grow accounts within an assigned territory.
Top Skills:
Sales Force AutomationSalesforce
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
