Caleb Fleming
About Me
I’m Caleb Fleming — a certified Technical Support Specialist in technical troubleshooting, with a decade in customer service at the Senior level. Across my roles, I have always been considered an expert in multiple departments, serving as the ultimate endpoint of Customer Experience for the customers of Apple and Ting.As a troubleshooter, I solve technical problems with patience and a friendly demeanor; I treat my diverse customers like family 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 skills to design web, integration, automation, and payments for the K-P Tech Support CRM.
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. |
| Technical Support Specialist | August, 2025 - Present | Providing Multi-platform support for Ting Smart fire-prevention technology (TingFire.com), troubleshooting hardware and software issues, documenting solutions, and collaborating with engineering and operations to improve service delivery and customer safety. |
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