Caleb Fleming
About Me
I’m Caleb Fleming, a senior technical support and customer operations professional with 5+ years of experience across high-sensitivity support, escalation handling, documentation, and systems-driven service delivery.During my time supporting Apple customers, I progressed through multiple senior roles spanning technical troubleshooting, billing and fraud, safety, accessibility, and executive-level escalations.In September 2025, I founded K-P Tech Support, where I apply that same support-first mindset to client service, workflow design, documentation, and business systems improvement.
Connect
Experience
| Role | Org | Dates | Detail |
|---|---|---|---|
| iOS Support Advisor | AppleCare via KellyConnect | June, 2020 - December, 2020 | Provided real-time support for iPhone, iPad, and Apple Watch users, specializing in account recovery, usability coaching, and first-call resolution using screen-sharing guidance. |
| MacOS Support Advisor | AppleCare via KellyConnect | December, 2020 - June, 2021 | Expanded into macOS support while balancing multi-platform issues, specializing in diagnostics, system setup, and secure remote assistance. |
| Senior iOS Support Advisor | AppleCare via KellyConnect | June, 2021 - December, 2021 | Handled complex iOS escalations, coached junior advisors in real time, and exercised discretionary authority for device repairs and engineering coordination. |
| Senior MacOS Support Advisor | AppleCare via KellyConnect | December, 2021 - May, 2022 | Led advanced macOS troubleshooting, advised peers on hardware and software escalations, and exercised elevated discretion for repair approvals and customer goodwill adjustments. |
| Senior Wireless Multimedia Support Advisor | AppleCare via KellyConnect | May, 2022 - October, 2022 | Specialized in advanced support for Apple TV, HomePod, and HomeKit, diagnosing network and smart home issues while maintaining expert-level coverage across prior platforms. |
| Creative Media Support Advisor | AppleCare via KellyConnect | October, 2022 - March, 2023 | Specialized in support for Apple’s creative apps (iMovie, GarageBand, Photos, etc.), resolving media, sync, and compatibility issues while integrating creative workflows into broader platform support. |
| Senior Creative Media Support Advisor | AppleCare via KellyConnect | March, 2023 - June, 2023 | Led senior-level support for Apple’s creative apps, resolving critical data and sync issues, mentoring advisors, and authorizing high-level service exceptions in media-impacting cases. |
| Senior Media Services Support Advisor | AppleCare via KellyConnect | June, 2023 - January, 2024 | Handled senior billing and fraud escalations, resolving complex payment and account access issues with high-level discretion, while contributing to compliance-focused process improvements across the team. |
| Senior Safety Support Advisor | AppleCare via KellyConnect | January, 2024 - February, 2025 | Managed sensitive safety-related support cases involving injury, property, or litigation risk — balancing legal protocols with customer advocacy while coordinating with executive and product safety teams. |
| Senior Support Specialist | AppleCare via KellyConnect | February, 2025 - September, 2025 | Lead advisor across Apple’s core support areas, including accessibility — providing white-glove assistance, peer consultation, and executive-level escalation handling with full operational discretion. |
| Founder & Technical Support Specialist | K-P Tech Support | September, 2025 - Present | Founded and operate a regional technical support business delivering troubleshooting, client support, documentation, and workflow-driven service solutions for households and small organizations across Eastern Kentucky. |
Proficiencies
| Area | Value |
|---|---|
| CRM & Customer Lifecycle Management | Improves customer retention and operational efficiency by organizing interactions, tracking customer journeys, and supporting consistent follow-through across CRM systems. |
| Customer Service Tools & Ticketing Systems | Powers efficient support by organizing issues, tracking resolution, and prioritizing urgent needs across internal teams and client workflows. |
| Data Analysis & Reporting | Turns operational data into usable insights that support reporting, decision-making, and process improvement across support and business workflows. |
| Forms & Conditional Intake | Builds dynamic forms that route clients, trigger workflows, and reduce intake friction — scaling operations without sacrificing personalization. |
| Knowledge Base & SOP Development | Enables consistent, scalable support by documenting processes, reducing ambiguity, and improving onboarding, quality, and client trust. |
| Project & Task Management | Supports organized service delivery, team coordination, and deadline tracking through structured task systems and repeatable workflow management. |
| Workflow Automation & Integration | Streamlines operations by automating tasks, connecting tools, and enabling consistent service experiences across client and internal workflows. |
Certifications
CRM & Support
Business Analysis & Data
Projects & Workflows
Documentation & Collaboration
Web & SEO