Matthew Sessions

Matthew
Sessions

Developer experience & AI enablement
Developer tooling & automation

I untangle difficult technical problems and build tools teams can use.

I'm a software engineer and architect with more than 10 years of experience across healthcare, local government, and insurance, with a strong C#/.NET background.

I research tools, work through technical constraints, and turn what I learn into practical workflows that make other people's work easier. My work includes configurable migrations, delivery automation, and demos that help colleagues adopt developer tools and AI workflows.

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Technical expertise, practical guidance, and mentoring.
Interested in fully remote roles.

Selected work

Tools, migrations, and ways of working.

HealthTrust Performance Group

Moving teams from Rally to Azure DevOps

C# / JSON / Azure DevOps

Teams used Rally differently. A single migration setup needed to accommodate those workflows without making every team work the same way.

I led the technical planning and team-by-team migration, and built a custom C# CLI with JSON configuration for each team's requirements. I also demonstrated Azure DevOps and helped colleagues learn the tool.

The completed migration let the company cancel Rally and eliminate its licensing costs.

More migration experience

At Local Government Corporation, I also led project migrations to Azure DevOps and configured task automation and deployment pipelines for cloud and on-premises applications.

HealthTrust Performance Group

Automating versioning and deployment

Bash / jq / YAML / CI/CD

Corporate runner constraints shaped the solution. I built a custom YAML action primarily in Bash, with jq, to calculate the next semantic version from the previous version tag and pull request labels.

The action automated version tagging and deployment of pull request code to lower environments.

HealthTrust Performance Group

Automating local developer setup

IIS / HTTPS / Local development

I built a tool to automate setup of a complex application development environment in IIS on developers' local machines.

The tool also created a local HTTPS certificate for authentication.

Evaluation and adoption

Helping colleagues use new tools

I participated in HealthTrust's GitHub Copilot pilot, helped evaluate it for engineering work, and gave colleagues guidance on using it within AI credit limits.

I've also delivered demos on LaunchDarkly feature flags, Azure DevOps, and AI workflows, and led a LinearB proof of concept.

Experimental work at HealthTrust

Planning changes across repositories

I developed a workflow that takes a feature or user story and uses a parent model to coordinate analysis across other models and repositories.

I tested it on real user stories to identify repositories that may need changes and propose plans for human approval. The goal was to keep the work focused and make better use of AI credits.

This work remained experimental.

Experience

Word resume

HealthTrust
Performance Group

Consulting Application Engineer / Architect

Oct 2024 to present

Led technical delivery of the Rally migration, built configurable migration tooling and Bash/jq delivery automation, supported tool adoption, and developed and tested experimental AI planning workflows.

Senior Application Engineer, Lead

Apr 2023 to Oct 2024

Led application development and support, continuing the HCA/HealthTrust assignment begun through Insight Global. Built a tool to automate local IIS setup for a complex application development environment, including creation of a local HTTPS certificate for authentication.

Insight Global

Senior Application Engineer, Lead

Sep 2022 to Apr 2023

Lead developer for a new HCA/HealthTrust team in a contract-to-hire assignment. Delivered implementations and support for Procurement and Supply Chain software.

Local Government Corporation

Software Developer

Sep 2019 to Aug 2022

Developed municipal applications with .NET, SQL, Azure, and Vue.js. Led Azure DevOps migrations and configured automation and deployment pipelines, including certificate updates across customer servers.

Avanade

Senior Analyst

Dec 2017 to Sep 2019

Technical leadership and support during Duck Creek Policy retirement. Automated policy data migration with C# for handoff to another team.

Analyst, ERP Software Development

Nov 2016 to Dec 2017

Completed the initial Duck Creek Claims implementation, then served as Tech Lead for Duck Creek Policy retirement, integrations, and application support.

ASR, Associate Software Engineering

Jan 2016 to Nov 2016

Delivered Duck Creek Claims client work from design through development and defect fixes using C#, .NET, JavaScript, and SQL.

Tools & technical background

My background is in C# and .NET, with experience across application development, delivery pipelines, and infrastructure.

I also evaluate and experiment with AI tools, including local models.

Development
C#, .NET, SQL, JavaScript, Python, Go, HTML/CSS, Vue.js, React, WPF, WinForms
Tooling & delivery
Azure DevOps, GitHub, Rally, LaunchDarkly, LinearB, TFS, Jenkins, UCD, Visual Studio, JetBrains
Automation & platforms
PowerShell, Bash, jq, JSON, YAML, Azure, Google Cloud, SQL Server, IIS, Windows, Active Directory, Azure AD
AI tools I've used
GitHub Copilot, OpenAI and Anthropic tools, OpenCode, Pi, LM Studio, skills and agents

Education & certifications

Bachelor of Science in Information Technology

University of Phoenix, 2015 to 2017

Advanced Software Developer Certificate included in the degree program.

Associate of Arts in Computer Programming

University of Phoenix, 2013 to 2015

Certifications

HDI CSR, issued January 2015
ITILv3, issued December 2014

Let's talk about
the work.

I'm interested in roles focused on developer experience, internal tooling, automation, and AI enablement. I enjoy leading through technical expertise and helping colleagues learn.

Fully remote roles preferred.

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