Looking for a job

Caleb Fleming

@calebfleming

Working daily to catalyze successes by translating technology for everyone to efficiently use and effectively understand.

United States

Message

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, Make, Zapier, Airtable, Softr, Glide, Notion, and more.

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, Architect, and Consultant

Current

K-P Tech Support

Sep 2025 - Present (6 months)

Launched and operate a self sustaining consulting-style practice, specializing in technical support for all home and small business technology. Operate a full customer relationship journey using no code web applications including my own lite-CRM ticketing system and database based in Notion, Stripe, and Make automations, Tally forms, and an email-distributed booking calendar via TidyCal.

Current

Founder & Consultant

Current

K-P Tech Support

Sep 2025 - Present (6 months)

Launched and operate a consulting practice providing technical support and no-code business systems for consumers and small businesses, designing automated CRM, booking, and payment workflows that streamline client journeys.

Tidycal No Code Systems Notion Stripe Tally CRM Website Development

Senior Support Specialist

KellyConnect

May 2020 - Sep 2025 (5 years 4 months)

Progressively promoted 9 times across Apple’s technical support lines of business over five
years, culminating in a role trusted to handle critical escalations and advisor consultations
across multiple departments. Delivered advanced troubleshooting, spearheaded live mentorships, collaborated on training curriculum, composed and curated knowledge resources, and lead escalations to engineering.

iOS MacOS VisionOS HomeKit Troubleshooting Mentorship Customer Advocacy CX Customer Experience CX Customer Experience Microsoft Teams Technical Support Technical Troubleshooting Customer Service Customer Support Customer Success Customer Experience Customer Relationship Management Team Leadership Team Lead Team Leader Cross Functional Team Leadership Remote Team Leadership Remote Work Remote Support Customer Support Management Customer Support & Success Technical Customer Support Online Customer Support Experience Customer Support Tools Customer Service SLA’S Customer service management Customer Service Skills Customer Service Operations Customer Service Excellence Customer Service Principles Customer Service Leadership Customer Service Representative Customer Experience Management Customer Experience Tools Customer Care Probing Questions Analytical Skills Analytical Thinking Analysis Conflict Resolution Dispute Resolution Call Resolution Critical Issue Resolution Issue Tracking Issue Triaging Processes Issue Tracking Systems Escalations Escalation Pathways Customer Escalation Escalation To Product Development

Education

Degrees, certifications, and relevant coursework

University of Pikeville

Bachelor of Business Administration, Healthcare Management

Graduated with a Bachelor of Business Administration, emphasizing Healthcare Management on May 4, 2019.

University of Pikeville

Bachelor of Business Administration (B.B.A.), Healthcare Management

2015 - 2019

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