For employers

Hire this AI Trainer

Sign in or create an account to invite AI Trainers to your job.

Invite to Job
K
K.j. Ester

K.j. Ester

AI Training Specialist | B2B Sales & GTM Systems

USA flagRemote, Usa
$65.00/hrIntermediateOther

Key Skills

Software

Other

Top Subject Matter

B2B Sales
SaaS / Software
Go-To-Market Strategy

Top Data Types

TextText

Top Task Types

Evaluation/RatingEvaluation/Rating
ClassificationClassification

Freelancer Overview

I specialize in training and evaluating AI systems for B2B sales and go-to-market execution. My background is as a sales and GTM operator, where I’ve built outbound systems, pipeline strategies, and revenue workflows from $0 to $5M+ ARR. I translate that real-world experience into structured frameworks used to assess and improve AI-generated outputs. My work focuses on evaluating reasoning quality, not just surface-level responses. I analyze whether outputs would succeed in real-world execution, identify gaps in logic, and provide clear, structured feedback to improve performance. I have experience working with AI-generated messaging, outbound strategies, and pipeline decision-making, ensuring outputs align with actual buyer behavior and sales dynamics. I specialize in text-based evaluation, ranking, and scenario-based training to improve AI performance in sales and GTM use cases.

IntermediateEnglishSpanish

Labeling Experience

GTM Decision Framework & AI Evaluation

TextEvaluation Rating
Evaluated and improved AI-generated outputs for B2B sales and go-to-market use cases, including outbound messaging, pipeline strategy, and lead prioritization. Assessed responses based on clarity, relevance to target personas, logical consistency, and likelihood of driving real-world outcomes. Performed structured evaluation and rating of AI-generated content, focusing on reasoning quality rather than surface-level correctness. Identified gaps where outputs appeared strong but would fail in execution due to poor prioritization, weak messaging, or lack of contextual awareness. Developed scenario-based training examples to improve model performance in areas such as cold outreach, objection handling, and deal progression strategy. Provided detailed feedback explaining why certain responses were effective or ineffective, helping guide iterative model improvement. Maintained consistent evaluation standards, including clear justification of ratings, alignment with real-world sales workflows, and focus on measurable business outcomes such as response rates and pipeline generation.

Evaluated and improved AI-generated outputs for B2B sales and go-to-market use cases, including outbound messaging, pipeline strategy, and lead prioritization. Assessed responses based on clarity, relevance to target personas, logical consistency, and likelihood of driving real-world outcomes. Performed structured evaluation and rating of AI-generated content, focusing on reasoning quality rather than surface-level correctness. Identified gaps where outputs appeared strong but would fail in execution due to poor prioritization, weak messaging, or lack of contextual awareness. Developed scenario-based training examples to improve model performance in areas such as cold outreach, objection handling, and deal progression strategy. Provided detailed feedback explaining why certain responses were effective or ineffective, helping guide iterative model improvement. Maintained consistent evaluation standards, including clear justification of ratings, alignment with real-world sales workflows, and focus on measurable business outcomes such as response rates and pipeline generation.

2024 - Present

AI Sales & GTM Output Evaluation and Optimization

TextEvaluation Rating
Evaluated and improved AI-generated outbound sales messaging across multiple use cases, including cold email, LinkedIn outreach, and follow-up sequences. Assessed outputs based on clarity, personalization, relevance to ICP, and likelihood of generating responses. Provided structured feedback on messaging effectiveness, tone, and positioning. Reviewed AI-generated GTM strategies and pipeline recommendations, identifying gaps between theoretical outputs and real-world execution. Focused on prioritization logic, sequencing of actions, and alignment with actual sales workflows. Created scenario-based training examples to help models improve decision-making in areas such as lead prioritization, objection handling, and outbound strategy. Provided reasoning-based feedback to guide model improvement beyond surface-level corrections.

Evaluated and improved AI-generated outbound sales messaging across multiple use cases, including cold email, LinkedIn outreach, and follow-up sequences. Assessed outputs based on clarity, personalization, relevance to ICP, and likelihood of generating responses. Provided structured feedback on messaging effectiveness, tone, and positioning. Reviewed AI-generated GTM strategies and pipeline recommendations, identifying gaps between theoretical outputs and real-world execution. Focused on prioritization logic, sequencing of actions, and alignment with actual sales workflows. Created scenario-based training examples to help models improve decision-making in areas such as lead prioritization, objection handling, and outbound strategy. Provided reasoning-based feedback to guide model improvement beyond surface-level corrections.

2024 - Present

Education

F

Florida State University

Master of Science, Sports Management

Master of Science
2015 - 2017
M

Michigan State University

Bachelor of Arts, Economics

Bachelor of Arts
2011 - 2015

Work History

P

Percapita

GTM & Sales Systems Advisor

Remote
2026 - Present
N

NAUTA

GTM & Sales Systems Advisor

Remote
2025 - 2026