Enterprise Sales Expert for AI Model Training [Remote]

Lead the definition of excellent enterprise selling for a cutting-edge generative AI team by auditing multi-step sales workflows, producing end-to-end expert examples, and shaping the evaluation standards the model learns from. You will apply deep, practical selling experience to create the ground-truth references that guide model behavior and quality.

• Set the standard for excellent selling by reviewing multi-step enterprise sales workflows, identifying where AI outputs diverge from best-practice seller behavior, and explaining why.
• Build "golden trajectories" by executing real sales tasks end-to-end, including prospecting, pipeline management, CRM hygiene, reporting, and customer-facing deliverables to create expert reference examples.
• Design and refine rubrics and evaluation criteria that capture what separates great selling from average performance.
• Work inside realistic test environments that simulate an enterprise sales tech stack, completing and simulating workflows across CRM, communication, and billing tools.
• Produce polished, senior-level artifacts, including pitches, slide decks, and executive summaries, at the quality expected of a senior sales leader.

• About 10 years of hands-on enterprise selling experience, with deep familiarity across the full sales cycle.
• A documented track record of meeting or exceeding sales quotas, with specifics you can discuss.
• Open to quota-carrying individual contributors, sales managers who lead selling teams, and VPs running regional or global sales organizations.
• Day-to-day fluency with core enterprise tools such as Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office, and the ability to learn additional tools like Slack, HubSpot, Notion, Aircall, Intercom, Zoho, and Microsoft Teams.
• Real depth in CRM administration, sales process management, pipeline tracking, and data-driven reporting.
• Strong written communication and attention to polish, able to convert complex situations into clear, customer-facing materials.

• Experience working within or alongside a two-sided, AI-powered B2B SaaS creator marketplace, especially running outcome-based campaigns against contracted performance targets and troubleshooting across a connected stack of CRM, issue tracking, helpdesk, collaboration, and productivity tools.

• This is a full-time, W-2 employment role with Cincinnatus LLC, placed to work as part of an extended workforce at a leading AI lab.
• Position is fully remote, must be based in the United States.
• You will be integrated into the client team and standard enterprise workflows, collaborating closely with internal stakeholders.

• Hourly pay range: 60 to 90 per hour.

• Employment, onboarding, payroll, and benefits for this role are administered by Cincinnatus LLC.
• If you discovered this opportunity through a third-party job channel, apply through that listing or channel; your employment will be with Cincinnatus LLC and you will be placed into the client team for this engagement.
• Cincinnatus is an Equal Employment Opportunity employer, and provides reasonable accommodations for qualified individuals with disabilities during the application process.