Caleb Fleming
Technology Support & Solutions Expert
About Me
I’m Caleb Fleming — a certified specialist in technical support, customer operations, and workflow systems, with over five years of experience leading frontline and escalated support across Apple’s most sensitive support teams.I’ve earned a reputation for solving complex problems with clarity, calm, and systems-level thinking — from guiding individual customers through device issues, to managing high-risk business escalations, to collaborating directly with engineers on resolving mission critical software and hardware issues for Apple products. At every level, I focus on building solutions that are sustainable, consistent, and human-centered.In 2025, I founded K-P Tech Support, a freelance operation designed to bring enterprise-quality service to individuals, families, and small businesses — especially those underserved by traditional IT models. Through this brand, I’ve developed pricing structures, onboarding workflows, automated scheduling and intake systems, and tiered support subscriptions. These systems are powered by tools like Calendly, Tally, SignWell, Notion, and integrated platforms like Zoom and PayPal.Alongside my hands-on experience, I’ve earned over 80 certifications across technical support systems, CRM platforms, inbound marketing, workflow automation, and cloud tools like AWS and Azure. This knowledge now powers both my business and my consulting work, where I specialize in designing scalable support infrastructure — including ticketing flows, SOP libraries, customer lifecycle documentation, and self-service intake forms.I’m currently focused on opportunities where support, systems, and strategy intersect — and where empathy, efficiency, and operational excellence are treated as inseparable goals.
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
Click here to view my fully detailed Showcase
| 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
Connection
Want to learn more or get in touch?Click here to view my full LinkedIn profileClick here to download a current version of my résumé (PDF).To discuss potential opportunities or professional collaboration, contact me at [email protected].