Evaluate and improve AI-generated enterprise sales workflows, create gold-standard examples for prospecting through proposals, design evaluation rubrics, perform simulated end-to-end sales tasks in modern platforms, produce executive-facing sales materials, and collaborate with researchers and SMEs to enhance AI sales reasoning.
This role is for one of our clients
Compensation: $60-$90 per hour
RequirementsKey Responsibilities
- Evaluate multi-step enterprise sales workflows and determine whether AI-generated outputs reflect real-world best practices.
- Identify gaps, inaccuracies, and missed opportunities in AI-generated sales processes while providing clear, actionable feedback.
- Develop high-quality reference ("gold standard") examples covering activities such as:
- Prospecting
- Lead qualification
- Pipeline management
- CRM maintenance
- Customer communications
- Sales reporting
- Proposal and presentation development
- Help design and refine evaluation frameworks and scoring rubrics that accurately measure AI performance in enterprise sales scenarios.
- Perform end-to-end sales workflows within simulated enterprise environments using modern sales and productivity platforms.
- Produce polished, customer-facing sales materials including presentations, proposals, executive summaries, and account documentation.
- Collaborate with research teams and fellow subject matter experts to improve AI reasoning and decision-making across sales use cases.
- Approximately 10 years of professional experience in enterprise sales with extensive exposure to the complete sales lifecycle.
- Proven history of consistently achieving or exceeding sales quotas.
- Experience as an individual contributor, sales manager, director, or executive overseeing enterprise sales organizations.
- Strong expertise in:
- CRM administration
- Sales operations
- Pipeline management
- Forecasting
- Sales reporting
- Customer relationship management
- Hands-on experience using enterprise sales tools such as:
- Salesforce
- Jira
- Confluence
- Google Workspace
- Microsoft Office
- Comfortable working with additional collaboration and sales platforms including Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams.
- Excellent written communication skills with the ability to produce executive-level customer-facing documents.
- Strong analytical thinking and attention to detail.
- Experience working within AI-powered B2B SaaS organizations, digital marketplaces, or performance-driven enterprise sales environments.
- Familiarity with outcome-based sales campaigns and KPI tracking, including metrics such as customer engagement, conversions, installations, and sign-ups.
- Experience coordinating workflows across integrated business platforms such as Zoho CRM, Freshdesk, Jira, Confluence, Microsoft Teams, and Google Workspace.
- Ability to quickly adapt to new enterprise software platforms and evolving business workflows.
- Full-time remote opportunity within the United States.
- Work closely with AI researchers and domain experts to improve enterprise sales intelligence.
- Contribute to projects that directly influence the development of next-generation AI systems.
- Long-term engagement based on project requirements and performance.
We are committed to creating an inclusive workplace and welcome applications from qualified professionals regardless of legally protected characteristics. Reasonable accommodations are available throughout the application and engagement process upon request.
Similar Jobs
HR Tech • Information Technology • Professional Services • Sales • Software
Own and improve end-to-end payroll and partner operational processes across CX. Design scalable workflows, define SLAs and escalation paths, coordinate incidents, analyze data for trends and risks, and drive cross-functional process standardization using Zendesk, Slack, Asana, and related systems.
Top Skills:
AsanaJIRASalesforceSlackZendesk
Aerospace • Information Technology • Software • Cybersecurity • Design • Defense • Manufacturing
Design, build, test, and maintain web-based enterprise applications across the full stack. Gather requirements, translate to technical solutions, enhance existing software and integrations, troubleshoot issues, participate in Agile ceremonies, write documentation, contribute to code reviews and architecture, and mentor junior team members.
Top Skills:
ColdfusionCSSHTMLJavaScriptJquerySQLSQL Server
Big Data • Information Technology • Software • Analytics • Energy
Handle incoming owner relations inquiries about revenue, land, division orders, JIB, A/R, and A&P. Log and follow up cases in a tracking system, build trusting client relationships, manage difficult situations calmly, provide accurate timely responses, and participate in cross-training.
Top Skills:
MS Office
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



