Kate Winslet Olesco
Senior Technical Engineer
IT professional specializing in Microsoft 365 support, Azure infrastructure, and IT operations, with experience in technical troubleshooting, cloud administration, and managed services. Focused on solving technical problems, improving processes, and delivering reliable IT support.
Skills & Tools
- IT OperationsIT Operations
- Process ImprovementProcess Improvement
- Microsoft 365 AdministrationMicrosoft 365 Administration
- Microsoft Entra ID / Azure ADMicrosoft Entra ID / Azure AD
- RMM ToolsRMM Tools
- Active DirectoryActive Directory
- Microsoft AzureMicrosoft Azure
About Me
I'm an IT professional with experience spanning Microsoft technical support, managed IT services, and cloud infrastructure operations. My background includes Microsoft 365 administration, tenant migrations, PowerShell, Azure environments, Windows Server maintenance, and troubleshooting across cloud and on-premises systems.
In my current role as a Senior Technical Engineer at TTEC Digital, I support Microsoft cloud and infrastructure operations, including Azure resource maintenance, server patching, SSL/TLS certificate updates, and technical documentation. I also look for opportunities to improve workflows and make technical processes easier for teams to follow.
Throughout my career, I've developed a strong foundation in technical problem-solving, customer communication, and service delivery. I'm interested in opportunities across Microsoft 365, IT support, systems administration, and cloud operations, where I can contribute my experience while continuing to grow my technical expertise.
Work Experience
July 2026 – Present
Senior Technical Engineer
Support Microsoft cloud technologies and infrastructure operations in a CSP/MSP environment.
Assist with the management and maintenance of Azure environments, including virtual machines and cloud resources.
Perform scheduled patching and maintenance of on-premises and cloud servers.
Update and renew SSL/TLS certificates for servers and Azure App Services.
Document technical procedures, maintenance activities, troubleshooting steps, and operational workflows.
Identify process improvement opportunities and present recommendations to improve operational efficiency.
Assist with infrastructure troubleshooting and incident resolution.
April 2025 - July 2026
MSP System Support Analyst
Hi Tech Hui
Provided remote Tier 1–3 technical support for hardware, software, network, and system-related issues.
Supported Windows servers, workstations, firewalls, switches, Microsoft 365, and Azure services.
Used RMM tools, including Datto RMM, NinjaRMM, and ConnectWise, for monitoring, patching, and proactive troubleshooting.
Managed user accounts, groups, and permissions across Active Directory, Azure AD, and Microsoft 365.
Troubleshot VPN, DNS, DHCP, and endpoint security issues.
Assisted with migrations, server upgrades, workstation deployments, and client onboarding.
Maintained technical documentation and communicated with clients to support service quality and SLA requirements.
November 2021 – January 2025
L1 Engineer – Microsoft
Rhipe / Crayon Inc.
Provided Microsoft 365 support to business customers through the Microsoft Admin Center.
Assisted with subscription management, billing inquiries, and license allocation.
Supported Microsoft 365 tenant-to-tenant migrations and troubleshooting.
Used PowerShell for administration across Exchange Online, SharePoint, Microsoft Teams, and OneDrive.
Assisted with MFA configuration, Security Defaults, and Modern Authentication.
Supported email migrations, domain configuration, and DNS record troubleshooting.
Resolved Windows and macOS issues through phone, email, and live chat support.
Documented support cases and guided customers through technical resolutions.
November 2019 – November 2021
Subject Matter Expert – Microsoft
Convergys / Concentrix
Supported team members with technical guidance and Microsoft product knowledge.
Helped coach and train agents on troubleshooting procedures and service standards.
Assisted with escalations and root-cause investigations for complex customer issues.
Reviewed performance indicators and identified opportunities to improve team results.
Shared feedback and recommendations to improve technical support procedures.
Helped maintain service quality, customer satisfaction, and consistent support practices.
Provided technical support for Microsoft Office and Windows software.
Troubleshot installation, activation, account access, and software-related issues.
Assisted customers with product inquiries, purchases, and billing concerns.
Guided users through step-by-step troubleshooting and resolution procedures.
Communicated technical information in a clear, customer-friendly manner.
Worked toward customer satisfaction, service quality, and support performance targets.
Contributed to team knowledge sharing and technical support practices.
October 2018 – November 2019
Billing Customer Service Representative – AT&T U-verse
Convergys Philippines
Assisted customers with billing inquiries, account concerns, and service questions.
Explained charges and helped customers understand their billing statements.
Documented cases and worked toward customer satisfaction.
Education
Undergraduate - Bachelor of Secondary Education Major in English
Undergraduate - Bachelor of Compute Science
Selected Work
Client-Specific Process Organization
Contributed to reorganizing client-specific processes and tools to distinguish them from internal operational workflows. This improvement helped engineers find relevant technical procedures faster and reduced confusion about which process applied to each client.
Certifications
Microsoft Certified: Security, Compliance, and Identity Fundamentals
Microsoft Certified: Azure Fundamentals
Microsoft 365 Certified: Fundamentals
