Open to opportunities

Kate Winslet Olesco

@katewinsletolesco

Message

Technical support specialist delivering Microsoft 365 and Azure-driven solutions.

Philippines

Message

What I'm looking for

I seek technical roles in supportive, collaborative MSP or enterprise teams focusing on Microsoft 365/Azure administration, migrations, automation, and opportunities for growth and impact.

I am a technical support specialist with five years of experience delivering Tier 1–3 support across Microsoft 365, Azure, and on-premises environments. I combine deep product knowledge with strong customer-service skills to resolve complex issues and maintain high client satisfaction.

I have led tenant-to-tenant migrations, administered Azure and Microsoft 365 portals, and used PowerShell to automate and optimize administrative tasks. My background includes working with RMM tools, VPNs, DNS/DHCP, VMware, and endpoint security in managed service and corporate settings.

I hold multiple Microsoft and related credentials (MS-900, SC-900, AZ-900) and a Microsoft 365 PowerShell certificate, and I continually focus on improving processes and knowledge sharing to support team performance and successful project outcomes.

Experience

Work history, roles, and key accomplishments

Current

MSP System Support Analyst

Current

Hi Tech Hui - Hawaii U.S

Apr 2025 - Present (9 months)

Delivered Tier 1–3 technical support and maintained client IT infrastructure, improving system reliability and SLA compliance through proactive monitoring and timely incident resolution.

Technical Support Windows Server Azure Active Directory VPN Incident Management

L1 Engineer Microsoft

Rhipe / Crayon Inc

Nov 2021 - Jan 2025 (3 years 2 months)

Supported Microsoft account and Azure administration, executed tenant-to-tenant migrations and automated tasks with PowerShell to reduce downtime and streamline Microsoft 365 operations.

Azure Tenant To Tenant Migrations PowerShell Exchange SharePoint Teams MFA Troubleshooting

Subject Matter Expert

Convergys / Concentrix

Dec 2020 - Nov 2021 (11 months)

Led training and escalation efforts, developed technical procedures, and performed root cause analyses to meet KPIs and improve team performance and customer outcomes.

Training Escalation Management Root Cause Analysis Coaching KPI Tracking Customer Engagement

Software Support Engineer

Convergys / Concentrix

Nov 2015 - Dec 2020 (5 years 1 month)

Provided technical support for Microsoft Office and Windows, diagnosed software issues and maintained an average handle time of 13 minutes while achieving customer satisfaction and sales targets.

Microsoft Office Customer Service Technical Diagnostics

Customer Service Representative

Convergys

Oct 2019 - Nov 2019 (1 month)

Handled customer inquiries for DirecTV services including troubleshooting, repair scheduling, and billing support, using CRM to resolve issues and maintain positive customer interactions.

Customer Support Troubleshooting CRM Scheduling Billing Call Center Operations

Billing Customer Service

Convergys

Oct 2018 - Oct 2019 (1 year)

Resolved high-volume billing and account inquiries for AT&T U-verse customers, conducting investigations and providing timely, fair resolutions to improve customer satisfaction.

Billing Support Account Management Investigation Customer Service