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J
James Massa

James Massa

AI Training Expert | Business Operations, SaaS, and Technology Infrastructure

USA flagCincinnati, Usa
$50.00/hrIntermediateAppenScale AILabelbox

Key Skills

Software

AppenAppen
Scale AIScale AI
LabelboxLabelbox
SuperAnnotateSuperAnnotate
RoboflowRoboflow

Top Subject Matter

Prompt Response Writing (SFT) / Text Generation Business operations, go-to-market strategy, digital marketing, and IT/managed services. IT / Managed Services / Technology Business Operations and Strategy Digital Marketing and Demand Generation Legal / Regulatory / Compliance Real Estate and Infrastructure
Evaluation / Rating (RLHF) You can assess quality of AI-generated business, legal, and technology content with a practitioner's eye. IT / Managed Services / Technology Business Operations and Strategy Digital Marketing and Demand Generation Legal / Regulatory / Compliance Real Estate and Infrastructure
Question Answering Strong fit in technology (MSP/IT), business strategy, marketing, and legal/regulatory topics. IT / Managed Services / Technology Business Operations and Strategy Digital Marketing and Demand Generation Legal / Regulatory / Compliance Real Estate and Infrastructure

Top Data Types

TextText
ImageImage
VideoVideo

Top Task Types

ClassificationClassification
Evaluation/RatingEvaluation/Rating
TranscriptionTranscription
Text SummarizationText Summarization
Question AnsweringQuestion Answering
Data CollectionData Collection
Bounding BoxBounding Box
Prompt + Response Writing (SFT)Prompt + Response Writing (SFT)

Freelancer Overview

My experience in AI training data is hands-on and current rather than academic. Over the past 18 months I have been an active daily user of large language models including Claude, ChatGPT, Perplexity, and Gemini, working across research, content generation, agentic workflow design, and technical implementation. Through my work at 10spring and MSP Growth, I have developed a practical working knowledge of how AI engines evaluate, extract, and cite content, which has required me to understand the structural and semantic signals that LLMs use to determine source quality and relevance. I have built multiple Claude Projects with detailed system prompts, custom knowledge bases, and role-specific instructions that shape model behavior across six business workflows, giving me a ground-level understanding of how prompt design, context framing, and instruction clarity affect output quality and consistency. What sets me apart from most subject-matter experts entering AI training work is the combination of domain depth and operational breadth. My primary expertise is in business operations, B2B SaaS scaling, managed services, technology infrastructure, and go-to-market strategy, areas where I have 25 years of practitioner experience rather than theoretical knowledge. I have built companies from zero to $50M, rescued client relationships that were failing due to operational breakdowns, designed QA systems that cut production defects by two-thirds, and managed complex multi-vendor programs across physical and technical environments. That depth means I can evaluate AI-generated business, operations, and technology content not just for factual accuracy but also for whether it reflects how these problems actually present themselves and are solved in practice, which is where most AI models currently fall short.

IntermediateEnglish

Labeling Experience

Founder, 10spring – AI search optimization & generative engine workflow

TextPrompt Response Writing SFT
As founder of 10spring, I led efforts in generative engine optimization and agentic AI workflow development, specifically leveraging large language model (LLM) prompt engineering. My daily activities involved designing, testing, and refining text prompts and schema markup for improved AI-driven search and knowledge extraction. I actively employed and compared leading AI models for content synthesis, evaluation, and performance benchmarking. • Engineered, tested, and tuned AI prompts for structured data extraction and content creation • Managed ongoing optimization for schema markup using prompt-driven feedback cycles • Used Claude, ChatGPT, Perplexity, and Gemini to generate and critique search-driven outputs • Oversaw workflow automation that integrated prompt results into web infrastructure

As founder of 10spring, I led efforts in generative engine optimization and agentic AI workflow development, specifically leveraging large language model (LLM) prompt engineering. My daily activities involved designing, testing, and refining text prompts and schema markup for improved AI-driven search and knowledge extraction. I actively employed and compared leading AI models for content synthesis, evaluation, and performance benchmarking. • Engineered, tested, and tuned AI prompts for structured data extraction and content creation • Managed ongoing optimization for schema markup using prompt-driven feedback cycles • Used Claude, ChatGPT, Perplexity, and Gemini to generate and critique search-driven outputs • Oversaw workflow automation that integrated prompt results into web infrastructure

2026 - Present

Founder and CEO, MSP Growth – Claude LLM prompt & workflow designer

TextPrompt Response Writing SFT
As Founder and CEO of MSP Growth, I developed and deployed multiple Claude Projects to facilitate AI-based outreach intelligence and improved technical SEO via large language model fine-tuning. This work included designing prompt datasets and supervised fine-tuning for meeting preparation, audit delivery, and SEO intelligence generation. I directed the integration of prompt responses into service workflows, enabling automation and real-time optimization. • Designed prompt/response datasets for Claude LLM projects (outreach, audits, SEO tech) • Supervised AI fine-tuning with continual evaluation and workflow improvement • Coordinated integration of AI-generated outputs into technical SEO and marketing automation pipelines • Led prompt engineering for real-time feedback and adjustment in deliverable quality

As Founder and CEO of MSP Growth, I developed and deployed multiple Claude Projects to facilitate AI-based outreach intelligence and improved technical SEO via large language model fine-tuning. This work included designing prompt datasets and supervised fine-tuning for meeting preparation, audit delivery, and SEO intelligence generation. I directed the integration of prompt responses into service workflows, enabling automation and real-time optimization. • Designed prompt/response datasets for Claude LLM projects (outreach, audits, SEO tech) • Supervised AI fine-tuning with continual evaluation and workflow improvement • Coordinated integration of AI-generated outputs into technical SEO and marketing automation pipelines • Led prompt engineering for real-time feedback and adjustment in deliverable quality

2025 - Present

Education

U

University of Denver

Master's Degree, Public Relations

Master's Degree
1997 - 1997
U

University of Denver

Bachelor's Degree, Communications

Bachelor's Degree
1993 - 1993

Work History

1

10spring

Founder

Cincinnati
2026 - Present
M

MSP Growth

Founder and CEO

Cincinnati
2025 - Present