Ray Winkelman

Principal Software Architect

Software architect with 12+ years building platforms for Fortune-scale retail, asset management, and security organizations. Now focused on AI systems, agentic architectures, and distributed infrastructure.

Experience

Shadow Software LLC

December 2024 – Present

FounderRemote

Built TERRA — an AI-powered jurisdiction intelligence platform that helps founders and online operators decide where to incorporate, bank, and live. Compares 217 countries across entity structures, tax regimes, financial rails, and risk data to generate practical relocation and structuring plans.

Home Depot Inc.

November 2022 – June 2023

Senior Software Engineer, ContractRemote

Senior Engineer on an Agile team maintaining QuoteCenter — the Pro ordering platform for the world's largest home improvement retailer (Fortune 17, $157B revenue). Led development across 40+ .NET microservices and orchestrations; secondary ownership of Google Cloud, Harness, and CircleCI IaC.

Capital Group Inc.

March 2022 – August 2022

Lead Software Engineer, Scrum Master, ContractRemote

Lead Engineer and Scrum Master at one of the world's largest asset managers ($3.2T AUM). Directed 5–16 engineers on a large-scale data platform, owning planning, execution, cross-team coordination, and technical direction over REST APIs and microservice orchestrations.

Union.dev

March 2022 – May 2022

Principal Software EngineerHalifax, Canada

Helped build the first version of Union.dev's .NET platform alongside another engineer — the operating system for unions, benefit funds, and third-party administrators. Contributed foundational workflows for member records, dues, grievance tracking, dispatch, and pension and benefits administration that the company now runs at enterprise scale across North America on Microsoft Azure.

Kangaroo Solutions Inc.

November 2020 – May 2021

Director of Engineering, ShareholderRemote

Managed a team of 3–5 engineers building the Kangaroo food delivery platform from concept to 30+ regions across Atlantic Canada, and e-commerce applications for global brands including McDonald's, Subway, Dairy Queen, and A&W. Founding architect and delivery lead. .NET REST API on AWS with React and React Native.

Elfster Inc.

March 2018 – November 2019

Senior Software Engineer, ShareholderRemote

Scaled Elfster's gift exchange platform from 6M to 15M users on a bootstrapped, remote-first team. .NET REST API, two Chrome extensions, and Vue.js frontend; secondary AWS infrastructure.

6Joe's Software Inc.

October 2017 – March 2018

Founding Software Engineer, ShareholderHalifax, Canada

Founding architect and development director of the 6Joe's fantasy golf platform, concept to launch. .NET REST API on Azure with Vue.js and Cordova.

Unisys

February 2017 – April 2017

Software Engineer IIIRemote

Worked on a large confidential data migration, system re-architecture, and software development project.

BeyondTrust Software Inc.

September 2015 – February 2017

Software EngineerHalifax, Canada

Cybersecurity engineer at an invite-only, seven-time Gartner Magic Quadrant PAM leader. BeyondTrust is trusted by 75 of the Fortune 100 and ALL US cabinet-level federal agencies for privileged access management, zero-trust security, and identity governance. Contributions under NDA.

HarvestHand Inc.

June 2015 – September 2015

Software DeveloperWolfville, Nova Scotia, Canada

Ground-floor startup built on a multi-tenant Zen framework PHP application. Won the AVCC Agriculture Innovation Accelerator Award and delivered an economic impact of $21 million in the Community Shared Agriculture (CSA) farm space.

Education

Information Technology Diploma, Honours — 4.0 GPA, Computer Programming concentration.

Acadia University

2011 – 2013

Advanced Mathematics, Biology, Psychology, and Sociology coursework.

Recommendations

Afgan Abbasov

Frontend Engineer @PRODATA

Reported to Ray directly · November 2024

I would highly recommend Ray for his leadership. His skills in project management and development make him great at guiding the team and helping everyone succeed.

Kishor Kumawat

Founder & Executive Assistant | Executive Support Specialist | 8+ Years in Remote Operations | Streamlining Productivity for Global Teams | Tech & Digital Marketing Enthusiast

Reported to Ray directly · November 2024

I strongly recommend Ray for his technical skills. His strong leadership skills and dedication to the company's mission make him an invaluable asset.

Justin Bishop

Business Development Associate

Reported to Ray directly · August 2023

Ray and his team built an innovative and complex software system that I was lucky to play a small role in building. Ray has excellent communication skills and 10 years experience in software leadership, business development and software architecture. He was good at letting the Junior developers get some advice while at the same time throwing them to the wolves to figure it out. Great guy. Very good reference for him.

Riki Montgomery

Reliability Engineer at The Home Depot

Worked on the same team · June 2023

Ray joined our team to help us upgrade more than 30 legacy .Net services and their dependencies to the latest versions. It was a daunting task and we wanted it done as quickly as possible, but fortunately for us this was not a stressor for Ray. He quickly whipped up some automation to help him and began knocking out services in record time. It was a huge weight off our shoulders. Ray was a great help and there isn’t a project too big for him.

Taylor Christy

Staff Software Engineer at The Home Depot

Worked on the same team · May 2023

Ray is a passionate and easy-going senior software engineer. I had the pleasure of working with him at The Home Depot, where he easily integrated into our team. During this time, Ray did an amazing job taking on a large project to modernize many of our legacy services. He is always eager to collaborate and is full of great ideas for positive change. He would be an asset to any organization seeking a flexible and experienced software engineer.

Eric Weber

Creative, Proven & Mission-Driven Problem Solver

Worked on the same team · April 2023

Ray has been a fantastic addition to our team! He on-boarded quickly and became comfortable in an extremely complex space in record time. He is always able to effectively tackle his work and finds creative ways to help others. He had a tremendous impact on increasing our sprint velocity and the ability to add value to the business. His work ethic is outstanding and his wit and sense of humor are unmatched! I would not hesitate to recommend Ray to any other organization and I would be honored to have the chance to work with him again.

Cris Llagas

Principal Software Engineer - Agentic AI | Microservices | Distributed Systems | Python | C# | AWS

Worked together at Capital Group · October 2022

Ray and I worked together on a huge team for an enterprise and highly visible project in Capital Group. Ray is a true team leader. He's very technical and knows his craft well and always cognizant of the team's sprint commitments and deliverables. Ray is always full of energy and purpose and that greatly influences and motivates the project team to perform on a high level. It's a pleasure working with him.

Brian Jones

at Capital Group

Managed Ray at Capital Group · October 2022

Ray worked on a team I led and helped make an immediate impact with his drive and dynamic personality. He always strived to get the best out of the developers and was influential in making critical decisions and offering candid feedback. I’d definitely recommend him as a strong team lead and significant contributor to any project.

Cy Ramos

Product Strategy, Analysis, Engineering, and Prototyping

Worked on the same team · August 2022

Ray is a true leader that starts with understanding the people and resources around him -- leveraging them symbiotically: a true team player. He excels as a leader through masterful code, providing expert guidance to junior devs and communicating impactful insight to management. It is much to say about someone when working a short time with them, but that is the talent and work ethic that Ray exemplifies. It is rare to find someone both meaningfully nice and extraordinarily competent. I sincerely hope to work with him in the future, but also know that he is a rare person that is high in-demand.

Russ Ramirez

💼 Product Manager @ CCI |⚙️ .NET & C# Expert | ☁️ Microservices & Event-Driven Architecture | 🧠 Scalable System Design & Integration | 🚀 Driving Innovation Through Cloud-Native Solutions

Worked on the same team · August 2022

I had the pleasure of meeting and working with Ray at Capital Group, San Antonio. Ray is a dynamic leader with a "get it done" attitude. I saw Ray constantly looking for ways to improve our deliveries and dates within the team we worked on together, and was always willing to work to remove blockers for the team. It was routine for Ray to work after hours and generally do whatever it took to complete his own work as well as making our team successful by directly working with stakeholders outside of the organization when needed. Even though I will sincerely miss working with Ray, I know he will continue to be a success in the future.

Randy Ansems

CEO at Union.dev

Managed Ray directly · May 2018

I worked closely with Ray during his tenure at 6Joe's. He was always a pleasure to work with and really knew his tech dev. 6Joe's will miss him, but his contributions are everlasting.

Oleksandr Skazhenyuk

Software Developer at BF&M

Ray mentored at 6Joe's · April 2018

Ray mentored me at 6Joe's. He demonstrated exceptional leadership, knowing when he could skip over unnecessary information or when to focus on the particulars instinctively. The 6Joe's platform that he engineered served as an excellent demonstration of his deep knowledge and understanding of object-oriented programming and RESTful development as well as the needs of the product. The project was designed from the ground up to be easily scale-able and very technologically robust. I had great respect for his style of both leadership and engineering, and trust that the product core that he created will serve for years to come with minimal maintenance.

Lorne Seth Piercey

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Worked at the same company · March 2018

I had the pleasure of working near Ray while at BeyondTrust; Ray has continually shown himself to be knowledgeable and approachable, and he has been a great teacher to me in several situations. Ray is a great leader, and I would jump at the chance to work with him again in the future.

James Ahn

Web Application Developer

Reported to Ray directly · February 2018

Ray is a great leader! I currently work with Ray at 6Joe’s. When solving problems he promptly gives me the right advice. Moreover, he has a positive attitude and is always very energetic. I feel motivated working with Ray, and together we make a strong team.

Jeff Bond

Senior Azure Integration Services Developer

Worked at the same company · January 2017

Ray has a quick wit and a strong aptitude. He's proven to be an expert with both Git and Oracle 12c

Thomas Showers

Software Developer | DevOps Evangelist

Worked at the same company · December 2016

Ray is an ambitious and creative developer with a broad skill set. In the time I've worked with him he has taken responsibility for a number of challenging projects and consistently demonstrated both talent and dedication.

Benjamin Mury

Lead of Front-end Development at InnerLogic

Worked at the same company · December 2016

Ray is very enthusiastic and committed to his work here at BeyondTrust. He has a great aptitude and is always sharing new ideas.