Kayla Holliday
@kaylaholliday
I evaluate AI outputs for accuracy, safety, and real-world usefulness.
What I'm looking for
I currently work as a Remote AI Trainer for DataAnnotation, evaluating AI responses to human prompts for accuracy, safety, and usefulness. I combine research and fact checking with intellectual reasoning to help ensure each AI-generated response delivers the best possible output.
I’ve also built a strong track record of supporting people in high-trust, fast-moving environments—substitute teaching Pre-K through 12, coordinating scholarship operations, and handling client support and advertising sales. I’m detail oriented and organized, adapt quickly to new routines, and consistently communicate clearly to maintain continuity and achieve goals.
Experience
Work history, roles, and key accomplishments
Remote AI Trainer
DataAnnotation
May 2026 - Present (3 months)
Evaluates AI responses to human prompts to ensure accuracy, safety, and usefulness. Uses research and fact checking along with intellectual reasoning to produce the best possible outputs.
Substitute Teacher
Union & Broken Arrow Public Schools
Jan 2019 - Present (7 years 7 months)
Managed classrooms of 20–30 students by maintaining order and continuity of instruction. Adapted quickly to new environments by learning lesson plans and routines each day and supporting classroom management across grade levels and subjects.
Scholarship Coordinator
Tulsa Community College
Jan 2012 - Jan 2015 (3 years)
Managed three tuition programs totaling over $2M per semester in accordance with state and private funding. Coordinated with students and multiple stakeholders to ensure scholarship operations, maintained accurate records, and ensured compliance with state regulations.
Advertising Sales
Tulsa Kids Magazine
Mar 2010 - Oct 2011 (1 year 7 months)
Built and maintained client relationships through face-to-face and phone communication. Developed sales strategies to overcome objections and achieve revenue goals, learning new sales techniques quickly with initiative and persistence.
Client Services
Williams & Williams Real Estate Auctions
Jul 2008 - Sep 2009 (1 year 2 months)
Partnered with colleagues to deliver high-quality client support under tight deadlines. Adapted to multiple roles as business needs evolved and strengthened teamwork and communication in a fast-paced environment.
Office Support
OU Women’s Health Care Specialists
Jan 2007 - Jan 2008 (1 year)
Answered phones and supported patient check-in and assistance. Documented and handled filing clerk tasks.
Education
Degrees, certifications, and relevant coursework
University of Tulsa
Bachelor of Communication and Women’s Studies, Women’s Studies and Communication
Earned a Bachelor of Communication and Women’s Studies, with coursework including public relations, interorganizational communication, and interpersonal communication.
Availability
Location
Authorized to work in
Job categories
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