Jordan Schilling | Technologist, Software Builder, and Engineer
Software engineer focused on automation systems, experimental tools, and developer productivity. Projects, dev logs, and technical writing.
About Jordan Schilling
Introduction
I’m a technologist and software engineer driven by a deep curiosity for how systems work and a relentless desire to build tools that make a difference. From the earliest days of tinkering with computers to building production-grade automation frameworks, I’ve always approached technology with an engineer’s mindset: understand the problem, design the solution, build it, test it, and iterate.
My work sits at the intersection of software engineering, DevOps thinking, and hands-on experimentation. Rather than specializing narrowly, I’ve pursued a breadth-first approach to engineering — building competence across the full software development lifecycle (SDLC) while going deep on automation, testing infrastructure, and developer tooling.
The philosophy behind my approach is simple: the best way to learn a technology is to build something real with it. Every project documented on this site reflects that belief. Whether it’s a CLI tool for tracking deep-work sessions, a Playwright automation framework for end-to-end testing, or a civic technology experiment, each project is an opportunity to push engineering skills further.
Career Path
My career path is defined by a commitment to continuous growth and a willingness to tackle unfamiliar territory. Rather than following a traditional linear progression, I’ve taken an intentional, self-directed path through software engineering — one built on practical experience, open-source contributions, and an engineering-first mindset.
I began building technical skills through hands-on exploration of operating systems, networking, and command-line tooling. This foundational work — understanding how DNS works, configuring SSH, navigating Linux environments — gave me a systems-level perspective that informs every project today.
From there, I moved into web technologies and infrastructure. Setting up Nginx, deploying to AWS EC2, and managing CI/CD pipelines with GitHub Actions became the building blocks for more ambitious projects. I didn’t just learn these tools in isolation — each skill was applied to real projects with real users.
Today, I operate as a software engineer and SDET-minded builder focused on automation engineering. The technical work spans test automation frameworks, CLI developer tools, infrastructure scripting, and experimental software projects. My career trajectory is aimed squarely at DevOps engineering, backend systems, and the kind of reliability engineering that keeps production systems running smoothly.
My structured learning roadmap reflects this intentional career design:
| Stage | Focus Areas | Status |
|---|---|---|
| Foundations | CLI, SSH, DNS, networking | ✅ Complete |
| Infrastructure | Nginx, AWS EC2, deployment | ✅ Complete |
| CI/CD | GitHub Pages, Node.js pipelines | ✅ Complete |
| Intermediate | Ansible, Docker, containerization | In Progress |
| Advanced | Prometheus, Grafana, observability | Upcoming |
Technical Interests
My technical interests span several domains, all connected by a common thread: building reliable, automated systems that solve real problems.
Test Automation & SDET Engineering
I’m deeply invested in test automation as a discipline. This isn’t just about writing test scripts — it’s about designing automation architectures that scale, integrate with CI/CD pipelines, and provide genuine confidence in software quality. I build automation frameworks using Python, TypeScript, and Playwright, following patterns like the Page Object Model (POM) and object-oriented design principles.
CI/CD & DevOps Engineering
I view CI/CD not as a buzzword but as a core engineering practice. Every project I build includes automated pipelines, environment configuration, and deployment automation. The goal is to make every code change automatically tested, validated, and deployable — with minimal human intervention.
CLI & System-Level Tooling
I have a particular affinity for command-line tools and system-level software. The FocusBuddy project exemplifies this interest: a terminal-based productivity tracker that monitors application usage and tracks deep-work sessions. The command line is where engineers do their most focused work, and building tools for that environment is both technically rewarding and practically useful.
AI & Experimental Software
I’m actively exploring the intersection of AI and workflow automation. I use N8N to build production automations — including a Congress.gov scraper, a PDF generator, and a comparison operator. From LLM-assisted development workflows to prompt engineering experiments, I approach AI as a practical tool to be understood and integrated — not a magic solution, but a powerful capability to be wielded with engineering discipline.
Projects and Experiments
I maintain an active portfolio of projects that reflect a commitment to learning through building. Each project is documented extensively, with development logs that capture every technical decision, obstacle, and iteration.
Key projects include:
- Python & Playwright Automation Framework — A production-quality test automation framework using OOP and the Page Object Model. I use this framework to smoketest a personal business website on every PR.
- Gaming / PC Quality Playability Harness — A system-level quality engineering case study demonstrating reliability diagnostics and reproducible execution.
- TypeScript & Playwright Framework — An automation framework for testing NotetasticOS, demonstrating cross-language testing capabilities.
- FocusBuddy CLI — A terminal-based deep-work tracker and process monitor built to master CLI development and system-level engineering.
- Portfolio Site — This very site, built using Jekyll, GitHub Pages, and custom theme modifications.
Future Work
My roadmap for the future is ambitious and focused. The next phase of work includes:
- Docker & Containerization — Actively learning container orchestration, Dockerfile authoring, and container-based CI/CD pipelines.
- Infrastructure as Code — Ansible playbooks and Terraform configurations are on my immediate learning path.
- Observability & Monitoring — Prometheus, Grafana, and structured logging are the next frontier for my DevOps skill set.
- Backend API Development — Planning to build RESTful and event-driven backend services to complement the automation and tooling work.
- Open Source Contributions — Committed to contributing to open-source projects in the automation and DevOps ecosystem.
The goal is clear: become a complete engineer who can design, build, test, deploy, and monitor software systems end to end. Every project, every log entry, and every experiment documented on this site moves toward that goal.
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