Oak Tree Software
Revenue Operations Specialist
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Job Title: Senior AI Trainer – Sales Managers / RevOps
Job Type: 100% Remote
Duration: 3 Months + Possible extension.
Employment Type: Freelancing Contract
Pay Rate: $30.00/hr (1099)
Availability: At least 4 hours per day and up to 40 hours per week with 4 hours of overlap with PST.
Locations: US, Albania, Bosnia and Herzegovina, Croatia, Czech Republic, Estonia, Georgia, Hungary, Iceland, Latvia, Lithuania, Moldova, Monaco, Poland, Romania, Serbia, Slovakia, Slovenia, United Kingdom
Role Overview:
We are seeking Senior Sales Management & RevOps Experts to generate, evaluate, and refine high-difficulty tasks for frontier AI initiatives. In this role, experts will build technically accurate, practical tasks that test advanced AI model capabilities in sales forecasting, CRM/CPQ system operations, territory and quota design, compensation plan structuring, and pipeline analytics.
Requirements:
- Professional Experience: ~8–15 years of leadership experience heading sales teams, revenue operations (RevOps), or sales operations functions.
- Core Competencies: Expert fluency in modern CRM and RevOps tech stacks (e.g., Salesforce, CPQ, HubSpot), pipeline analytics, forecasting methodologies, territory planning, quota allocation, and sales compensation plan structuring.
- Deliverable History: Proven track record of producing executive-grade deliverables, such as territory models, variable compensation structures, revenue forecast models, deal desk policies, and pipeline performance dashboards.
- Exceptional Analytical Thinking: Ability to analyze complex sales funnels, diagnose revenue bottlenecks, and evaluate multi-variable commercial strategy models.
- Attention to Detail: Meticulous approach to reviewing high-difficulty task scenarios, ensuring complete operational precision, dataset integrity, and technical accuracy.
- Communication: Superior written communication skills for creating complex corporate scenarios, detailed evaluation criteria, and gold-standard solutions.
- Leadership & Independence: Ability to own day-to-day quality, calibrate peer outputs, and operate independently in a fast-paced environment.
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Responsibilities:
In this role, you will serve as a senior technical authority within a specialized functional pod responsible for creating advanced evaluation and training datasets for AI models. Your day-to-day responsibilities will include:
- Producing high-difficulty expert tasks and gold-standard solutions covering complex RevOps strategies, sales forecasting, CPQ logic, quota architecture, and comp-plan design.
- Reviewing and calibrating team members' outputs to enforce rigorous domain quality standards across all pod deliverables.
- Owning day-to-day quality control and validating that all task scenarios, CRM logic, and analytics datasets are practically realistic and technically sound.
- Applying and enforcing rubric standards set by the Functional SME (Expert) Lead.
- Identifying and escalating genuine edge cases, complex operational paradoxes, and rubric ambiguities directly to the Functional SME Lead.
- Participating in calibration sessions and revision cycles to continuously elevate the complexity and precision of pod outputs.
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Education & Experience:
- Bachelor's degree or equivalent practical experience in any field.
- Experience in AI evaluation, data annotation, content review, quality assurance, or a related analytical role is preferred but not required.
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