Don Sylvester
Cloud & Automation Engineer
Bridging enterprise IT with AI-driven cloud automation
About Me
Hi, I'm Don
I'm a Cloud & Automation Engineer based in Honolulu, HI, skilled in AWS, Infrastructure as Code, and AI-driven automation. I specialize in supporting enterprise migrations, optimizing cloud resources, and integrating modern tools (Python, Power Automate, Prompt Engineering) to improve reliability and reduce costs.
With over 7 years of experience spanning enterprise IT support, AWS cloud infrastructure, and AI systems integration, I've driven innovation across diverse environments—from healthcare to food distribution, corporate real estate to managed service providers. My unique approach bridges traditional IT operations with cutting-edge cloud-native technologies.
Currently serving as a Field Support Specialist at Freshpoint (Sysco), where I delivered infrastructure leadership during a multi-island M&A integration, consolidating systems across 3 islands with minimal downtime on aging equipment. I deployed Cisco networking and Workday ERP while resolving 100+ high-priority incidents in my first 6 months, maintaining 100% audit readiness through effective procurement and compliance management.
👔 For Hiring Managers: While my current title is Field Support Specialist, I function as an infrastructure engineer—leading AWS cloud migrations, designing multi-site network architecture, and building Python automation solutions that reduce deployment time by 60%. I'm actively seeking full-time Cloud/DevOps Engineering roles that leverage my AWS, Infrastructure as Code, and automation expertise.
Willing to relocate to: Maysville, KY • Louisa, VA
Download ResumeMy Journey
Building expertise in cloud infrastructure and IT operations
Field Support Specialist
Freshpoint (Sysco subsidiary) - Oahu Island, HI
- Delivered infrastructure leadership during Sysco M&A integration, consolidating systems across 3 islands with minimal downtime on 12-15 year-old equipment
- Deployed Cisco networking & Workday ERP while resolving 100+ high-priority incidents in first 6 months
- Maintained 100% audit readiness through effective procurement, licensing, and compliance management
- Provided on-site hardware support for desktops, laptops, printers, and mobile devices
IT Systems Specialist II
GSI Service Group Inc - Honolulu, HI
- Administered Microsoft 365 for 200+ users; automated workflows with Power Automate to boost productivity by 25%
- Conducted patch management and security assessments, reducing vulnerabilities by 40%
- Created technical documentation and knowledge base articles, driving 50% increase in self-service ticket resolution
- Managed IT asset tracking and ticketing tools to improve visibility and compliance
Cloud Support Engineer
Cloudnexa - Remote
- Delivered AWS infrastructure support in SLA-driven MSP environment, resolving 200+ incidents across EC2, S3, Lambda, VPC, and IAM configurations
- Monitored AWS resources (CloudWatch, CloudTrail) to prevent outages and identify performance bottlenecks across multi-client environments
- Executed cloud migrations from on-prem to AWS, implementing IAM policies, EC2 provisioning, and VPC network architecture
- Reduced deployment time by 60% through Python automation scripts and Infrastructure as Code implementations
Technical Support Engineer
The Howard Hughes Corporation - Honolulu, HI
- Delivered first-level IT support for 600+ employees across laptops, phones, tablets, and AV equipment
- Supported enterprise systems (O365, VPN, Salesforce, Adobe), reducing repeat support tickets by 25%
- Documented processes and ensured adherence to infrastructure security policies
What I Build
Real-world projects showcasing cloud infrastructure, automation, and AI integration
AI-Powered Portfolio Assistant
Intelligent chatbot built with AWS Bedrock (Claude 3 Haiku), Lambda, and DynamoDB. Features RAG architecture with vector embeddings for contextual portfolio Q&A.
AWS Cloud Cost Optimization
Comprehensive cloud infrastructure review and optimization project. Implemented rightsizing, reserved instances, and automated resource management.
Enterprise Network Integration
Multi-site network consolidation during M&A integration. Deployed Cisco infrastructure, VPN tunnels, and redundant connectivity across 3 islands.
How I Think
Technical skills and expertise areas
Cloud & AWS
90%
- EC2, S3, Lambda
- CloudFormation
- Bedrock AI
- VPC, IAM
IT Support
95%
- Windows 11
- Office 365
- Active Directory
- Troubleshooting
Automation
85%
- Python
- PowerShell
- Power Automate
- Scripting
Networking
80%
- Cisco
- VPN, VLAN
- TCP/IP
- DNS, DHCP
Latest Insights
Technical articles and learning experiences
How I Built an AI-Powered Portfolio Chatbot with AWS Bedrock
A deep dive into building a serverless AI chatbot using AWS Lambda, Bedrock (Claude 3), DynamoDB vector search, and RAG architecture. Learn about prompt engineering, embeddings, and real-time streaming responses.
AWS Cost Optimization: 42% Savings in 90 Days
Practical strategies for reducing AWS costs through rightsizing, reserved instances, and automated resource management.
Prompt Engineering for IT Professionals
How to leverage AI tools like Claude and ChatGPT for IT troubleshooting, documentation, and automation tasks.
Let's Connect
Looking for a Cloud & Automation Engineer who bridges IT operations with AI innovation?
Get in Touch
I'm always interested in hearing about new opportunities, collaborations, or just connecting with fellow tech professionals.
Schedule an Interview
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