Greg Olmstead, Developer in New York, NY, United States
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Greg Olmstead

Verified Expert  in Engineering

Security Developer

New York, NY, United States
Toptal Member Since
January 3, 2017

Greg is an experienced, multi-faceted technical leader with a successful track record in the investment banking, energy, InfoSec, and fintech industries. He is well-versed in solutions architecture and product ownership in global, multi-year initiatives. Greg is highly skilled in cloud and on-premise environments, leveraging container and serverless technologies. A leader in innovation, he holds one awarded patent and one pending in the machine learning and NLP fields.


Security, Architecture, Amazon Web Services (AWS), Google Cloud Platform (GCP)...
SparkIT Solutions
Windows PowerShell, Bash, Python, Perl, HTML5...
Amazon Web Services (AWS), Kubernetes, Amazon EKS, AWS Lambda, Terraform...




Preferred Environment


The most amazing...

...project I've worked on was a machine learning/NLP-powered relationship-strength mapping engine based on an organization's email content.

Work Experience

CTO Security Architect

2021 - PRESENT
  • Implemented infrastructure-as-code (IaC) enforcement aligned with CIS benchmarks for a landscape of 240+ cloud accounts. Led engineering teams organization-wide to rectify compliance issues, establishing a secure-by-default framework.
  • Created an endpoint/workload security workstream to build golden cloud images with CIS level 1 hardening and security tooling baked in, rolled out across the organization's 7,500+ cloud virtual machine (VM) compute infrastructure.
  • Developed a guardrails-based cloud role architecture model to empower developers to iterate and ideate on cloud projects while ensuring adherence to security best practices and organizational rules.
  • Built a hybrid encryption helper to allow platforms to encrypt/decrypt data, baking in industry-standard mechanisms such as envelope encryption, authenticated encryption, payload/envelope signing, M of N decryption, and multi-master decryption.
  • Wrote multiple design patterns adopted by the organization, e.g., message queues in hybrid environments, secrets in the public cloud, remote access to cloud computing, and more.
Technologies: Security, Architecture, Amazon Web Services (AWS), Google Cloud Platform (GCP), Azure, Python 3, Python, Terraform, Product Owner, Product Ownership, Kubernetes, Amazon EKS, Azure Kubernetes Service (AKS), Google Kubernetes Engine (GKE), Jenkins, Go, Agile Product Management, Linux, Agile Software Development

Principal Developer

2007 - PRESENT
SparkIT Solutions
  • Created Cetus, a Kubernetes-based threat processing and alerting platform for processing and matching alerts to Certstream feeds and other data. Analyzed 21 million domains daily using Kubernetes, Kafka, Python, Terraform, and Elasticsearch.
  • Developed Phoenix, a next-generation Cuckoo-based malware analysis platform using Python, Django, and Docker.
  • Created a Raspberry Pi based long-term data logging device for UV filters leveraging Modbus over serial communications and built it as an embedded device.
  • Built an appliance for ingesting, retrieving, transforming, consolidating, and transmitting logs, audits, and other data types from multiple systems to send to the RSA enVision platform.
  • Performed reverse-engineering on Windows-based malware using IDA Pro, OllyDbg, Reflector, and Cuckoo.
  • Designed and built multiple small business turn-key solutions, including domain, accounting, file, mail, and client management servers, as well as network and user devices and full integration.
  • Organized and managed community engineering projects.
  • Created a web application that uses SpreadsheetGear and a complex Excel-based model (the Buy to Rent model) to perform analysis on data to determine whether to buy a piece of property as a rental.
Technologies: Windows PowerShell, Bash, Python, Perl, HTML5, Windows Presentation Foundation (WPF), C#, Git, C#.NET, Amazon Web Services (AWS), Kubernetes, Containers, Apache Kafka, Terraform, Security, Go, Java, Linux, jQuery

Principal Engineer

2019 - 2021
  • Designed and implemented a Terraform-based JupyterHub deployment on AWS EKS leveraging AWS App Mesh, AWS Cloud Map, Amazon Cognito, and multiple other AWS services, integrated with Refinitiv Data Platform (RDP).
  • Architected a dynamic, distributed system based on AWS Fargate and Lambda using AWS CDK to publish and host back ends for apps running in our flagship desktop product, saving developers over 90% of their time obtaining resources.
  • Modernized our toolchain and acted as SME for most cloud and security-related issues.
  • Built continuous integration and delivery systems for multiple technologies for delivery into AWS.
Technologies: Amazon Web Services (AWS), Kubernetes, Amazon EKS, AWS Lambda, Terraform, AWS Cloud Development Kit (CDK), C#, C#.NET, Python 3, Python, Apache Kafka, Jupyter, Jupyter Notebook, AWS Fargate, Security, Linux, jQuery, Agile Software Development

Lead Engineer

2017 - 2019
Thomson Reuters
  • Created a re-platforming plan to break a legacy 12-service WCF monolith into microservices running in Amazon ECS and Lambda using Docker and .NET Core/Standard 2.0.
  • Built a clustered and federated RabbitMQ platform for cache distribution and production-development synchronization.
  • Built a continuous integration system for automated deployments to AWS and Docker.
  • Created dockerized staging environment for end-to-end testing in Microsoft Azure.
  • Built a snack detection camera leveraging OpenCV, AWS, and Python on Raspberry Pi.
  • Developed a meeting room presence detection and booking system with ultrasonic detectors, AWS, Angular, and Python on Raspberry Pi.
Technologies: Amazon Web Services (AWS), C#, C#.NET, .NET Core, Terraform, RabbitMQ, Reuters Eikon, Python, Python 3, Python 2, AWS Lambda, Serverless Framework, Serverless Architecture, Microservices, Microservices Architecture, Azure, ASP.NET Web API, Linux, jQuery, Windows, Agile Software Development

Technical Lead

2012 - 2017
RBC Capital Markets
  • Led a team of seven professionals to develop primary institutional credit sales and trading applications, as well as a debt capital market management application to be deployed and utilized globally.
  • Developed a credit and rates trading application using C# and WPF, which has become an integral tool for all RBC traders worldwide to facilitate handling millions of dollars per day in institutional trading transactions.
  • Built a machine learning and natural language processing-powered relationship strength mapping engine. This innovative system analyzed online communications such as email and instant messaging to compute optimal paths between individuals.
  • Developed an in-house WPF-based application framework that managed the creation of business controls and data retrieval and transformation to enable developers to rapidly create highly configurable applications.
  • Worked as an in-house innovation team leader, winning multiple hackathons and producing three applications in the pipeline to become production apps.
  • Managed projects' entire lifecycle from concept to production.
Technologies: Node.js, Angular, JavaScript, HTML5, Windows Presentation Foundation (WPF), C#, .NET, Git, Gang of Four (GOF) Design Patterns, C#.NET, Linux, Microsoft SQL Server, Windows, Agile Software Development, Syncfusion

Software Developer

2010 - 2012
  • Worked as the principal developer on a credit risk aggregation app.
  • Served as the contact point between technical teams and the business users, i.e., traders.
  • Created a WPF-based framework for producing live-data, real-time reports based on Clojure scripts written on the server side.
  • Developed a C# based message bus that allowed remote commands to be sent to applications using C# code.
  • Created the architecture for a unified service platform that serves as the foundation for multiple applications within the credit space.
Technologies: Windows Presentation Foundation (WPF), C#, .NET, Git, Gang of Four (GOF) Design Patterns, C#.NET, Java, Microsoft SQL Server, Windows, Agile Software Development, Syncfusion, Windows Communication Foundation (WCF)


A Kubernetes-based threat processing and alerting platform. It consumes data from disparate feeds, e.g., Certstream, Pastebin, etc., processes it to enrich it with public data, such as DNS, WHOIS, and JA3, and allows organizations to query or set up alerts when data matches.

Various use cases include detecting malicious infrastructure via fraudulent domain names and TLS certificates. It processes 10 million certificates, 21 million domains, and 140 million DNS digs daily on 3-server commodity hardware. Also, it is a fully pluggable framework for ingestion, enrichment, alerting, and output, based on Kafka and backed by Elasticsearch.

I designed and implemented the full implementation along with my business partner.

A next-generation Cuckoo-based malware analysis platform. It leverages Cuckoo under the hood and adds significant functionality like YARA/Suri hunting, advanced search, and network/host indicator matching with added product integration, i.e., Moloch and MISP, and one-button deployment automation to democratize malware analysis and facilitate rapid deployment of sandboxes in incident scenarios. Its commodity hardware processes 7,500 samples daily with 12-15TB of memory dumps per day.

I designed and implemented the entire solution alongside my business partner and presented it at multiple Defensive and Technical Security conferences.

Decision Models

A web application developed in partnership with Jim Leach to calculate and display information about whether purchasing a particular property as a rental property would be a good investment, as well as details about the investment returns.
2008 - 2015

Bachelor of Technology with Honors in Computing & Information Technology

McMaster University - Hamilton, Ontario, Canada

2004 - 2007

Technologist Degree in Network Engineering & Security Analysis

Mohawk College - Hamilton, Ontario, Canada


Infragistics, jQuery, Node.js


Terraform, Git, Syncfusion, Visual Studio 2015, Amazon EKS, Visual Studio, PyCharm, RabbitMQ, Reuters Eikon, AWS Cloud Development Kit (CDK), Jupyter, AWS Fargate, Azure Kubernetes Service (AKS), Google Kubernetes Engine (GKE), Jenkins, Cuckoo Sandbox


Windows Presentation Foundation (WPF), .NET, ASP.NET Web API, ASP.NET MVC, .NET Core, Angular, AngularJS, Windows PowerShell, Serverless Framework


Amazon Web Services (AWS), Linux, Windows, Kubernetes, Apache Kafka, Visual Studio Code (VS Code), AWS Lambda, Azure, Jupyter Notebook, Google Cloud Platform (GCP), Malware Information Sharing Platform (MISP)


C#, Python, C#.NET, Python 3, JavaScript, HTML5, Bash, Perl, Java, PHP, Python 2, Go


Agile Product Management, Agile Software Development, Gang of Four (GOF) Design Patterns, Serverless Architecture, Microservices, Microservices Architecture


Microsoft SQL Server


Windows Communication Foundation (WCF), Telerik Web Controls, Security, Architecture, Product Owner, Product Ownership, Containers, Malware Analysis, Transport Layer Security (TLS), SSL Certificates, DNS

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