Omotolani A.

Key Skills

Software

Other

Internal/Proprietary Tooling

Top Subject Matter

Microsoft 365 technical support

AI-assisted knowledge and response generation

Microsoft ecosystem support

Top Data Types

Text

Document

Image

Top Task Types

Prompt + Response Writing (SFT)

Text Generation

Question Answering

Data Collection

Freelancer Overview

Technical Support Engineer (Concierge) - AI-assisted support and AI knowledge contribution (Upwork via Microsoft). Brings 16+ years of professional experience across complex professional workflows, research, and quality-focused execution. Core strengths include Other, Internal, and Proprietary Tooling. Education includes Master of Science, Federal University of Technology, Akure (2019) and Bachelor of Science, Joseph Ayo Babalola University (2017). AI-training focus includes data types such as Text, Document, and Image and labeling workflows including Prompt + Response Writing (SFT), Evaluation, and Rating.

Labeling Experience

Service Excellence Crew - AI-powered support and AI-generated content (Microsoft via Upwork)

OtherImageText Generation

Created AI-generated images and tailored AI-powered guidance to support over 300 international clients during Microsoft service interactions. Leveraged Microsoft Copilot to anticipate customer needs, refine responses, and improve satisfaction outcomes using feedback loops. • Generated AI images for clients using AI tools as part of support/enablement activities • Used AI-powered tooling (Microsoft Copilot) to tailor responses and anticipate needs • Audited and optimized service workflows using AI-driven analytics for faster resolution • Shared AI-generated content and support guides to digital communities reaching large monthly audiences

2024 - 2025

Customer Support Engineer – Microsoft 365 Business Advisor (Microsoft via Upwork)

OtherTextQuestion Answering

Conducted client consultations and provided tailored technical guidance across Microsoft products while using AI-enabled assistance to improve solution clarity and response tailoring. Translated client needs into recommended Microsoft solution paths and communicated industry trends to support compliance and adoption outcomes. • Delivered structured consultations and recommended solutions for Microsoft 365, Dynamics 365, and Azure • Provided guidance using evolving product ecosystem insights to support client decision-making • Coordinated with technical support and marketing to ensure consistent, accurate client responses • Supported documentation and communication practices that align with future AI-assisted support knowledge

2023 - 2024

Technical Support Engineer (Concierge) - AI-assisted support and AI knowledge contribution (Upwork via Microsoft)

OtherTextPrompt + Response Writing (SFT)

Provided concierge-style technical support using AI-assisted workflows to generate and refine client-facing responses, support guides, and documentation. Used prompt engineering and AI-generated content to improve answer quality and consistency while resolving tickets within SLA constraints. • Created AI-generated support materials and knowledge content for faster customer self-service • Applied prompt+response techniques to tailor explanations for Windows OS, Microsoft 365, Teams, Outlook, and Azure issues • Improved response quality and reduced repeat incidents via root-cause analysis and user education • Contributed content to internal AI knowledge repositories to support downstream automated assistance

2022 - 2023

Technical Support Engineer (Concierge) - Documentation and AI knowledge repository contributions (Tek Expert)

Document

Delivered tier-1 and tier-2 support for Microsoft products while documenting solutions and contributing to AI knowledge repositories. Logged incidents, tracked resolution progress, and supported escalation workflows, enabling improved datasets for team-level AI-driven self-service. • Documented troubleshooting steps and outcomes to strengthen knowledge bases for AI agents • Logged and organized ticket data for subsequent analysis and improved issue resolution patterns • Produced clear client communications and follow-ups to maintain service quality • Contributed curated solution content to support team efficiency and customer self-service

2020 - 2022

IT Support Officer - support and troubleshooting documentation (USA Global Nigeria Ltd.)

OtherDocumentData Collection

Handled first-level IT support inquiries by diagnosing and resolving hardware, software, and network issues while maintaining clear documentation of fixes. Supported user onboarding and reduced support requests through education and improved service processes. • Provided prompt first-level technical assistance and reduced downtime • Performed maintenance, updates, and patching to secure and stabilize systems • Conducted IT orientation and digital onboarding for new staff • Collaborated with administrative teams to align IT service delivery with organizational needs

2018 - 2019

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Education

Work History