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
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead and build Headway's payer marketing function: set strategy, craft positioning and narratives, commercialize payer solutions, translate clinical data into commercial proof, enable sales and field teams, run events and competitive intelligence, and measure relationship and commercial impact.
10 Minutes Ago
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Manage investigation, evaluation, and resolution of high-exposure, complex auto and homeowners casualty claims. Assess coverage, liability, and damages; develop settlement strategy; coordinate with trial counsel; attend mediations/trials; prepare litigation reports; supervise reserves and counsel billing; identify subrogation and suspicious activity; mentor colleagues and support regulatory matters. Remote or hybrid role supporting Eastern, Central, and Mountain regions with occasional travel for hearings and mediations.
Software • Defense
Lead integrated communications strategy to advance policy, congressional, and reputational objectives. Manage media engagement, rapid response, external materials, and cross-functional messaging. Build and mentor the communications team and advise senior leadership.
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
