Summary
Overview
Work History
Education
Skills
Certification
Timeline
Generic
Ashton Fleary

Ashton Fleary

Pompano Beach,FL

Summary

Seasoned IT Professional with over 18 years of comprehensive experience across field support, desktop management, and enterprise infrastructure optimization. Demonstrated expertise in delivering high-quality technical support, managing large-scale hardware deployments, and leading end-to-end IT operations in dynamic, multi-site environments. Proficient in troubleshooting and managing cross-platform systems, including Windows and macOS, with advanced capabilities in Microsoft Intune for device compliance, app deployment, and policy enforcement. Skilled in network diagnostics, endpoint protection, and asset lifecycle management, as well as enabling secure and efficient remote workforce solutions. Recognized for driving operational efficiency, improving service delivery, and fostering collaboration across cross-functional teams to enhance user satisfaction and meet evolving business needs.

Overview

20
20
years of professional experience
1
1
Certification

Work History

IT Field Technician

Conviva Care Center
02.2024 - Current
  • Provided onsite IT support for medical centers and corporate offices, ensuring continuous system functionality and user satisfaction.
  • Supported IT operations during acquisitions, cutovers, center mergers, and site relocations to maintain business continuity.
  • Collaborated with network teams on firewall configurations, TTU and WAP installations, port setups, and MAC address whitelisting using the Cisco Meraki dashboard.
  • Assisted the Information Security team with WinMagic SecureDoc tasks, including software installation, encryption updates, device unlocking with challenge data, and configuring SecureDoc for specialized systems such as GE EchoPAC.
  • Delivered application support for a wide range of platforms, including eClinicalWorks, Microsoft Office Suite, Dragon Dictation, FortiClient, GlobalProtect, DYMO LabelWriter, Starlet, Fujitsu scanners, EasyOne Connect, QuantaFlo, NeuroMetrix DPN, Midmark EKG, and Topaz signature pads.
  • Troubleshot Microsoft Intune issues related to compliance policies, app deployment, and configuration profiles to ensure proper endpoint enrollment and functionality.
  • Maintained VMware ESXi hosts and vCenter, performing VM provisioning, resource management, and snapshot/backups for production and test environments.
  • Managed SSO configurations and troubleshooting for healthcare platforms and internal applications via Okta, Azure AD, and ensuring secure access and HIPAA-compliant authentication processes.
  • Logged, triaged, and resolved incidents and service requests through ticketing systems, ensuring SLA compliance and user satisfaction.
  • Supported users with first-time login, MFA setup, and resolving SSO-related issues with common tools like Microsoft 365, clinical apps, and VPN services.
  • Configured secure Wi-Fi and VPN access for remote staff, ensuring reliable connectivity for EHR access and telehealth systems.

Regional Desktop Manager / IT Technician - Logistics Assistant

Teleperformance USA
Hybrid, Florida
02.2016 - 12.2023
  • Coordinated and directed the activities of staff engaged in computer operations, ensuring tasks were executed efficiently and accurately, either personally or through delegation to subordinates.
  • Managed Okta and Azure Active Directory for identity and access management, supporting SSO, MFA, and automated lifecycle workflows.
  • Oversaw Google Workspace administration, including email, calendar, and shared drive policies for user groups and organizational units.
  • Monitored a problem management database and ensured timely resolution by following up with assigned personnel and implementing accountability measures.
  • Organized and facilitated monthly and quarterly team meetings, contributing to improved communication, alignment, and operational effectiveness.
  • Created a customer feedback program that included personalized correspondence from leadership, leading to a 75% increase in customer satisfaction.
  • Achieved departmental objectives by developing and executing strategic plans aligned with performance metrics and organizational goals.
  • Boosted team productivity by streamlining workflows and fostering effective communication strategies to improve employee performance.
  • Successfully, management initiatives led to organizational transformation while maintaining high employee morale and productivity levels.
  • Assisted with any other duties as directed by the Director of Desktop Support, Desktop Manager, Lead Desktop Engineer, or Regional Lead Desktop Engineer, demonstrating flexibility and adaptability to support the team's needs.
  • Led desktop operations supporting over 5,000 users across regional offices.
  • Shipped and imaged Windows desktops, monitors, and peripherals for 175 agents daily.
  • Managed weekly shipment of 80-90 Apple iMacs using Jamf and Casper.
  • Streamlined logistics and improved hardware deployment readiness.
  • Enhanced billing operations, achieving a 30% increase in on-time payments.
  • Provided hands-on support for network infrastructure, including switches, access points, VPN, and DNS/DHCP, ensuring seamless connectivity and uptime.
  • Led endpoint lifecycle management using Microsoft Intune, Jamf Pro, and ManageEngine, enforcing device compliance, automated patching, and application deployment across distributed environments.
  • Led cross-functional teams to enhance customer experience and operational efficiency.
  • Facilitated communication between departments to streamline project execution and resource allocation.

Desktop Engineer

Teleperformance USA
05.2006 - 02.2016
  • Provided Tier 2 and Tier 3 support for over 2,500 endpoints in a high-volume call center, ensuring minimal downtime and high user productivity.
  • Supported and maintained over 500 Apple iMacs, including hardware repairs, imaging, and deployment to end users.
  • Performed hardware diagnostics, imaging, and deployment of Windows desktops, laptops, and peripheral devices across multiple departments.
  • Responded to service tickets using enterprise ticketing systems, prioritizing incidents and requests to meet SLA timelines.
  • Installed and configured operating systems, application software, network printers, and remote access tools to support business operations.
  • Conducted routine maintenance and performance tuning to optimize desktop environments and prolong hardware lifecycle.
  • Assisted in Active Directory administration, including password resets, user provisioning, group policy enforcement, and profile management.
  • Collaborated with network and server teams to troubleshoot connectivity and authentication issues across LAN/WAN infrastructure.
  • Documented standard operating procedures, technical resolutions, and asset inventory for improved knowledge sharing and compliance.
  • Supported software rollouts and patch deployments to maintain system security and ensure application compatibility.
  • Provided remote support for off-site agents using tools such as Remote Desktop, LogMeIn, or TeamViewer.
  • Participated in on-call rotation and responded to after-hours incidents to support 24/7 operations.
  • Maintained a customer-focused approach, resolving technical issues with patience, clarity, and professionalism.

Network Specialist

Caribbean Businesses
06.2005 - 07.2006
  • Designed and implemented robust network solutions.
  • Monitored network protocols to ensure security and performance.

Customer Support Representatives

Teleperformance USA
12.2005 - 05.2006
  • Delivered exceptional customer service for Xfinity clients across voice, internet, and television platforms.
  • Resolved technical issues promptly while providing clear, step-by-step guidance to non-technical users.
  • Assisted customers with setup and troubleshooting of modems, routers, and cable boxes.
  • Addressed and resolved billing inquiries with professionalism, accuracy, and empathy.
  • Maintained a high standard of service by actively listening, showing patience, and ensuring customer satisfaction.
  • Consistently achieved or exceeded performance metrics, including first-call resolution and customer satisfaction scores.
  • Thrived in a high-volume, fast-paced call center environment while maintaining quality and efficiency.

Customer Service Representative

Geek Squad - Teleperformance USA
Fort Lauderdale, Florida
05.2005 - 12.2005
  • Provided front-line customer support for a wide range of consumer electronics, including computers, home theater systems, mobile devices, and networking equipment.
  • Diagnosed and troubleshot hardware and software issues, guiding customers through effective resolutions or recommending in-store service as needed.
  • Scheduled service appointments, tracked repair orders, and ensured timely communication between customers and technicians.
  • Educated customers on product features, care, and maintenance to improve long-term satisfaction and reduce repeat service calls.
  • Facilitated check-in/check-out of devices for diagnostics, repairs, and upgrades using internal ticketing and inventory systems.
  • Acted as a liaison between customers and technical teams, translating technical jargon into clear, user-friendly language.
  • Assisted in warranty verification and provided options for repairs, replacements, or service plan coverage.
  • Promoted additional Geek Squad services and Best Buy protection plans by identifying customer needs and aligning solutions.
  • Maintained detailed records of customer interactions and transactions while protecting sensitive data and adhering to privacy policies.
  • Delivered a personalized and empathetic service experience, consistently achieving high customer satisfaction ratings and repeat visits.

Education

High School Diploma -

North Miami Senior High
North Miami, FL
05.2006

Skills

  • Systems & Support: Windows OS, macOS, Active Directory, Jamf Pro, Intune (including advanced troubleshooting and policy deployment), Remote Desktop, Imaging & Deployment
  • Tools & Platforms: Casper Suite, ServiceNow, Microsoft 365, WinMagic, VMware, Ticketing Systems
  • Soft Skills: Team Leadership, Process Improvement, Customer Service, Time Management, Problem-Solving
  • Remote support
  • Endpoint security
  • Desktop support
  • Wireless networking
  • IT documentation
  • Software configuration
  • VoIP systems
  • Server management
  • Disaster recovery
  • Virtualization technologies
  • Operating systems
  • Ticketing systems
  • Networking & Security: VPN, VoIP, Firewall Configurations, Patch Management, Endpoint Security, OTDR, SecuredDoc
  • Hardware & Logistics: Desktop Setup, Printer Maintenance, Cabling, Fiber Optics, Inventory Control, Shipping Coordination
  • Network troubleshooting
  • IT asset management
  • Help desk support
  • VPN configuration
  • Hardware installation
  • Hardware diagnostics
  • Network security
  • Patch management
  • Mobile device management
  • System administration
  • Active directory
  • Printer maintenance
  • Network configuration
  • Security protocols
  • Server maintenance
  • Advanced troubleshooting
  • Customer service
  • Problem-solving
  • Attention to detail
  • Microsoft windows and office
  • Multitasking Abilities
  • Organizational skills
  • Team collaboration
  • Effective communication
  • Verbal and written communication
  • Remote technical support
  • Friendly and patient
  • Software installation
  • Technical issues analysis
  • Technical troubleshooting
  • Customer service expert
  • Goal setting
  • Professionalism
  • Interpersonal communication
  • Device installation
  • Application support
  • System testing
  • Adaptability
  • System maintenance
  • Incident management
  • Software deployment
  • Teamwork
  • Teamwork and collaboration
  • Time management
  • Problem-solving abilities
  • Multitasking
  • Reliability
  • Excellent communication
  • Active listening
  • Adaptability and flexibility
  • Decision-making
  • Relationship building
  • Troubleshooting network issues
  • Team building
  • Self motivation
  • Analytical thinking
  • Highly professional
  • System upgrades
  • Customer communication and empathy
  • VPN management
  • Agile methodology
  • Time management abilities
  • Written communication
  • Quality assurance

Certification

Comptia A+ Certified

ID : COMP001022840711

Timeline

IT Field Technician

Conviva Care Center
02.2024 - Current

Regional Desktop Manager / IT Technician - Logistics Assistant

Teleperformance USA
02.2016 - 12.2023

Desktop Engineer

Teleperformance USA
05.2006 - 02.2016

Customer Support Representatives

Teleperformance USA
12.2005 - 05.2006

Network Specialist

Caribbean Businesses
06.2005 - 07.2006

Customer Service Representative

Geek Squad - Teleperformance USA
05.2005 - 12.2005

High School Diploma -

North Miami Senior High

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