Derek Kupsky
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Derek Kupsky Email & Phone Number

IT Systems and Network Administrator - Managed Service Provider Role at My CFL Tech Solutions
Location: Tavares, Florida, United States 5 work roles 2 schools
1 work email found @reliancefl.com LinkedIn matched
✓ Verified August 2026 4 data sources Profile completeness 100%

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Current company
Role
IT Systems and Network Administrator - Managed Service Provider Role
Location
Tavares, Florida, United States
Company size

Who is Derek Kupsky? Overview

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Quick answer

Derek Kupsky is listed as IT Systems and Network Administrator - Managed Service Provider Role at My CFL Tech Solutions, a with 10 employees, based in Tavares, Florida, United States. AeroLeads shows a work email signal at reliancefl.com and a matched LinkedIn profile for Derek Kupsky.

Derek Kupsky previously worked as Information Technology System Administrator at My Cfl Tech Solutions and Senior IT Network & Systems Administrator at Reliance Construction Company, Llc. Derek Kupsky holds Associate Of Arts And Sciences (A.A.S.), Business Administration And Management, General, 3.8 from Lehigh Carbon Community College.

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*@reliancefl.com
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Profile bio

About Derek Kupsky

With 11+ years of experience in designing, managing, and optimizing IT infrastructures, I specialize in delivering secure, high-performance networks and systems that drive business success. My expertise spans LAN/WAN, TCP/IP, DNS, DHCP, BGP, OSPF, and Wi-Fi protocols, as well as both cloud and on-premises environments, including file, database, web, DNS, and email servers. Proficient in Microsoft 365 administration, I excel at integrating VOIP solutions and troubleshooting complex network issues to enhance functionality and reliability.I bring extensive hands-on experience with Ethernet and fiber cabling, as well as rack-and-stack configurations to optimize network setups. Skilled in Windows Server 2012 R2 through 2022, Active Directory, and Group Policy management, I ensure secure access and seamless collaboration. My technical portfolio includes configuring and troubleshooting Cisco, Dell, and Ubiquiti gateways, routers, switches, firewalls, access points, and VPN solutions ensuring secure and efficient network operations across multiple office locations. I also leverage VMware and Hyper-V for server virtualization, enhancing disaster recovery and ensuring business continuity with 99.99% uptime.In cybersecurity, I’ve deployed solutions to address vulnerabilities and safeguard network integrity using tools such as SentinelOne and Datto. My project management expertise includes leading system upgrades, migrations, and cloud integrations, aligning IT strategies with organizational goals to reduce costs and improve efficiency.Collaboration is at the core of my approach, demonstrated by leading cross-functional teams, streamlining issue resolution with ServiceNow, and managing vendor relationships to ensure optimal service delivery. I’m also skilled in construction-specific IT solutions, having implemented Procore, PlanGrid, PlanSwift, and Prolog software while training end-users for maximum efficiency.As a CompTIA Network+ certified IT professional and Procore Technologies Administrator with Admin Series and Project Manager: Financial Management certifications, I bring a proactive approach to optimizing IT infrastructures, streamlining systems, and managing software implementations and administration. My expertise extends to SolarWinds monitoring, VOIP/PBX systems, and mobile device management across Windows and macOS platforms. Whether configuring networks, managing Microsoft 365 environments, or leading disaster recovery initiatives, I am dedicated to creating scalable, reliable, and efficient IT systems that support operational excellence.

Listed skills include Microsoft Office, Microsoft Excel, Microsoft Word, Customer Service, and 14 others.

Current workplace

Derek Kupsky's current company

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My CFL Tech Solutions
My Cfl Tech Solutions
IT Systems and Network Administrator - Managed Service Provider Role
Tavares, FL, US
Website
Employees
10
AeroLeads page
5 roles

Derek Kupsky work experience

A career timeline built from the work history available for this profile.

It Systems And Network Administrator - Managed Service Provider Role

Tavares, Fl, Us

Senior It Network & Systems Administrator

Delray Beach, Fl

Network Infrastructure & Cloud Management: Managed both cloud and on-premises network infrastructures, specializing in LAN/WAN, TCP/IP, DNS, BGP, WiFi, and OSPF protocols. Implemented and managed file, database, web, DNS, and email servers, including Office 365 and Intermedia. Proficient in VOIP systems and remote connectivity, as well as software installation and troubleshooting for optimal performance.Server Management & Virtualization: Skilled in Windows Server environments (2012 R2, 2016, 2019, 2022) and server virtualization. Managed Active Directory, Office 365, SharePoint, and Group Policy configurations, along with hardware upgrades.Network Optimization & Troubleshooting: Expert in configuring and troubleshooting network components, including Cisco/Dell switches, routers, firewalls, and VPNs, ensuring secure connectivity.Cybersecurity & Disaster Recovery: Developed cybersecurity solutions and disaster recovery plans using tools like Datto and SentinelOne, maintaining data integrity and 99.99% uptime.IT Project Leadership & Strategic Planning: Led network overhauls, server migrations, and cloud integration projects, aligning IT initiatives with business goals to reduce costs.Led the seamless integration and configuration of Procore, PlanGrid, PlanSwift, and Prolog construction software, aligning them with project requirements to enhance efficiency and streamline workflows across all construction phases. CompTIA Network+ Certified and Procore Admin Certification: Series Certified, with a commitment to completing additional Procore certifications, including Project Manager: Financial Management for General, Specialty, and Owner Construction. Vendor & Stakeholder Management: Managed vendor relationships and negotiated contracts to ensure optimal service delivery.Team Leadership & End-User Support: Led teams and provided desktop support for Windows and macOS systems, focusing on user training and productivity.

Network Administrator | It Support Technician

Delray Beach, Florida

As Network Administrator and prior role as an IT Support Technician at PDG IT Solutions, I maintained and secured the network infrastructure, ensuring seamless integration with IT goals and regulatory compliance. Worked closely with system and security teams to integrate network policies with broader IT infrastructure goals, ensuring cohesive system performance and security. Ensured network security policies and configurations met compliance requirements for HIPAA and GDPR regulations. Implemented Cisco ASA firewalls and VPN solutions to secure remote access and protected the network from external threats through proactive vulnerability assessments. Configured and maintained dynamic routing protocols (OSPF, BGP) to optimize network traffic flow across geographically dispersed sites. Automated network device configuration, backups, and log management using PowerShell scripts. Planned and implemented copper and fiber network systems for both wired and wireless environments, ensuring connectivity and security standards.Developed and implemented disaster recovery plans, achieving 100% data backup and ensuring business continuity through efficient systems design.

Jun 2013 - Apr 2016

General Manager

Lilos Restaurant

Delray Beach, Florida

As General Manager, I directed daily operations, financial management, IT solutions, and marketing strategies for Lilos Restaurant, driving consistent growth and operational success. I secured catering contracts with small and medium-sized businesses, increasing monthly sales while enhancing the restaurant's market presence. Managed all IT solutions, including point-of-sale (POS) systems, network infrastructure, and software integration, streamlining operations and improving data accuracy to support catering services for small and medium-sized businesses. Personally secured catering contracts with small and medium-sized businesses, contributing to the restaurant's financial stability and enabling the growth of our catering services. Developed and executed targeted marketing campaigns focused on catering services, resulting in a 15% increase in monthly sales through creative advertising strategies aimed at B2B clients. Led recruitment, training, and staff management to ensure operational excellence, fostering a high-performance work environment that facilitated the successful execution of secured catering contracts.

Mar 2010 - Jun 2013
Team & coworkers

Colleagues at My CFL Tech Solutions

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2 education records

Derek Kupsky education

Certifications, Automotive Engineering Technology/Technician, 3.9

Activities and Societies: Automotive Technology/Electronics/Air Condition licensed/ PA state inspection and emissions licensed/ FORD.

FAQ

Frequently asked questions about Derek Kupsky

Quick answers generated from the profile data available on this page.

What company does Derek Kupsky work for?

Derek Kupsky works for My CFL Tech Solutions.

What is Derek Kupsky's role at My CFL Tech Solutions?

Derek Kupsky is listed as IT Systems and Network Administrator - Managed Service Provider Role at My CFL Tech Solutions.

What is Derek Kupsky's email address?

AeroLeads has found 1 work email signal at @reliancefl.com for Derek Kupsky at My CFL Tech Solutions.

Where is Derek Kupsky based?

Derek Kupsky is based in Tavares, Florida, United States while working with My CFL Tech Solutions.

What companies has Derek Kupsky worked for?

Derek Kupsky has worked for My Cfl Tech Solutions, Reliance Construction Company, Llc, Pdg It Solutions, and Lilos Restaurant.

Who are Derek Kupsky's colleagues at My CFL Tech Solutions?

Derek Kupsky's colleagues at My CFL Tech Solutions include Carol Brancato, Matthew Goldman, Roy Lyons, George Wood, and William Phillips.

How can I contact Derek Kupsky?

You can use AeroLeads to view verified contact signals for Derek Kupsky at My CFL Tech Solutions, including work email, phone, and LinkedIn data when available.

What schools did Derek Kupsky attend?

Derek Kupsky holds Associate Of Arts And Sciences (A.A.S.), Business Administration And Management, General, 3.8 from Lehigh Carbon Community College.

What skills is Derek Kupsky known for?

Derek Kupsky is listed with skills including Microsoft Office, Microsoft Excel, Microsoft Word, Customer Service, Powerpoint, English, Windows, and Research.

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