Open to opportunities

Caleb Fleming

@calebfleming

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Experienced technical support specialist and systems integrator.

United States

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What I'm looking for

I am looking for a role that values innovation, collaboration, and continuous improvement in customer support.

I'm an experienced technical support specialist and systems integrator with over 5 years of experience leading Apple’s most sensitive support teams. My journey has been marked by a commitment to operational excellence, where I have independently developed the infrastructure for K-P Tech Support. I excel at building scalable workflows using web-based tools like Calendly, Tally, and Notion, ensuring seamless scheduling and service fulfillment.

Throughout my career at AppleCare, I have been progressively promoted nine times, culminating in a lead-level specialist role. I have delivered advanced troubleshooting across various platforms, spearheaded mentorship efforts, and designed training materials that have been integral to department-level curriculum. My passion lies in transforming complexity into clarity through documentation, automation, and a human-first approach to support design.

Experience

Work history, roles, and key accomplishments

Current

Founder & Systems Integrator

Current

K-P Tech Support

Mar 2025 - Present (4 months)

Launched and operate a self-sustaining tech support business from the ground up, specializing in integrated client onboarding, ticketing systems, and freelance operational design. Deployed a full client journey using Calendly, Zoom, and Tally, including conditional logic, automated payments, client intake forms, and redirect flows.

Onboarding Ticketing Systems Calendly Zoom)Tally Notion Web Development Signwell

Current

Senior Support Specialist

Current

KellyConnect

May 2020 - Present (5 years 2 months)

Progressively promoted 9 times across AppleCare's highest-sensitivity support domains over five years, culminating in a lead-level specialist role trusted to handle critical escalations and advisor consultations across technical, creative, financial, safety, and accessibility teams. Delivered advanced troubleshooting and real-time peer guidance across iOS, macOS, watchOS, visionOS, tvOS, HomeKit,

iOS MacOS VisionOS HomeKit Troubleshooting Mentorship Customer Advocacy

Education

Degrees, certifications, and relevant coursework

University of Pikeville

Bachelor of Business, Healthcare Administration

Graduated with a Bachelor of Business in Healthcare Administration. This program provided a strong foundation in business principles applied to the healthcare sector.