Caleb Fleming
About Me
I’m Caleb Fleming — a certified Senior Support Specialist in technical troubleshooting, with over five years of experience at Apple. In my role, I am considered an expert in iOS, macOS, iPadOS, WatchOS, Wireless Multimedia, Media Services (billing and fraud), Creative Media, Accessibility, and Safety. I serve as the ultimate endpoint of technical support cases over these matters.As a troubleshooter, I solve technical hardware and software problems with patience and a friendly demeanor; I treat my diverse customers like I would want my own family to be treated: with kindness and inclusivity.In April of 2025, I founded K-P Tech Support, and, through it, I both serve customers with patience and expertise, as well as develop my skills with all the tools needed to build this website, it's internal processes, and integrated systems involving customer intake, case triage, scheduling, and payments.
Connections
Experience
| Title | Timeline | Detail |
|---|---|---|
| B.S. Healthcare Administration | Fall 2015 - Spring 2019 | Focus in systems operations, client service, and cross-functional communication — foundation for future support leadership. |
| iOS Support Advisor | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | February, 2025 - August, 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. |
Proficiencies
| Area | Level | Value |
|---|---|---|
| CRM Platforms & Customer Lifecycle Management | Expert | Improves customer retention and team efficiency by managing interactions, automating workflows, and scaling lifecycle strategies with CRM tools. |
| Customer Service Tools & Ticketing Systems | Expert | Powers efficient support by organizing issues, tracking resolution, and prioritizing urgent needs across internal teams and client workflows. |
| Data Analysis & Reporting | Trained | Translates raw data into insights that drive decisions across support, marketing, and operations using tools like Excel and HubSpot. |
| Digital Office Suites & Collaboration Tools | Expert | Supports business operations through tools like Microsoft 365 and Google Workspace — essential for communication, onboarding, and documentation. |
| Forms & Conditional Intake | Experienced | Builds dynamic forms that route clients, trigger workflows, and reduce intake friction — scaling operations without sacrificing personalization. |
| Infrastructure as a Service (IaaS) | Trained | Provides foundational cloud knowledge to support SaaS, hosting, automation, and infrastructure conversations with clients and teams. |
| Knowledge Base & SOP Development | Experienced | Enables consistent, scalable support by documenting processes, reducing ambiguity, and improving onboarding, quality, and client trust. |
| Marketing | Trained | Helps businesses attract and convert the right audience using SEO, content strategy, and lifecycle marketing tools like HubSpot. |
| Project & Task Management Tools | Expert | Enables scalable service delivery, team coordination, and deadline tracking across both enterprise and client-facing environments through structured task systems. |
| Software as a Service (SaaS) | Expert | Supports scalable, cloud-based business solutions by leveraging SaaS platforms like HubSpot, Salesforce, and Microsoft 365. |
| Workflow Automation & Integration | Experienced | Streamlines operations by automating tasks, connecting tools, and enabling consistent, hands-off client experiences. |
Certifications