Part-Time Sales Trainer / Data Labeler

Part-Time Sales Trainer / Data Labeler

Othello is looking for a part-time Sales Trainer / Data Labeler to help train and evaluate our real-time sales coaching model.

This person will review sales calls, transcripts, and Othello-generated suggestions, then provide expert feedback on the quality, timing, and usefulness of those suggestions.

Responsibilities

• Review sales conversations and Othello coaching prompts
• Label and score suggestions for accuracy, timing, and relevance
• Identify where Othello should improve, intervene, or stay silent
• Provide feedback on discovery, qualification, objections, next steps, and value selling
• Help define what great real-time sales coaching looks like

Requirements

• 5+ years as a MIDDLE MARKET - ENTERPRISE Account Executive or similar quota-carrying seller
• No more than 20 years of total sales experience
• Certified in at least one major sales methodology, such as MEDDIC/MEDDPICC, Sandler, Challenger, SPIN, Force Management, Miller Heiman, or GAP Selling
• Strong understanding of B2B sales conversations
• Experience using AI tools
• Clear written communication and strong judgment
• This is not a generic data labeling role. It is an expert feedback role for someone who knows what actually works on live sales calls.