About Jayson Lindsley
(JL)Technology Leader & Software Architect
Technology leader and hands-on software architect with 15+ years across engineering, cloud infrastructure, cybersecurity, GRC, and IT operations.
Background
How I got here
Ever since I was little I've been obsessed with computers, and with getting past whatever was telling me "no." Poking around in the BIOS, decompiling software, bypassing security checks, breaking things just to see how they worked.
One early lesson: I wanted to install Red Alert 2 on our Windows 95 machine, and it needed more hard drive space. The solution seemed easy enough. Find space. So I went looking, and I deleted the drivers folder in System32. New problem: a machine with no audio that couldn't get online. New quest: fix it. I made friends with the middle school tech, who loaned me a Windows 98 install disc. It wouldn't install, so he handed me a floppy with instructions on a sticky note to kick-start the installation. It worked.
It didn't stop there. I was constantly tinkering, trying to do things I had no business doing, and it eventually landed me a job in tech repair. I got hired because I could answer a question about Winsock repair in Windows XP. I only knew the answer because I'd broken my own Winsock installing a patch to raise the max number of TCP connections I was allowed.
I crawled my way up to decompiling malware: isolating it, tearing it apart with IDA Pro, OllyDbg, and Process Monitor, and writing custom scripts to unroll the modifications adware had made. I learned to read the raw bytes off a Windows drive to figure out why the MBR was corrupted by TDSS, a popular rootkit at the time.
Somewhere along the way I started building tools for the machines I was fixing, and somehow that turned into web development. I've been using Laravel since 2015.
I joined MyOutDesk as a DevOps Engineer in January 2015, fixing a large codebase and two native applications, and became Director of Information Technology & Chief Architect in June 2017. Today I lead 4 software developers and 9 IT personnel, with responsibility for the applications we ship, the infrastructure they run on, our security programs, and the technology budget. I still work directly on architecture and code.
And my curiosity, just like back then, keeps me deeply involved at every layer. I cannot help but get involved. It's who I am. That's the wildcard part. I just can't help it.
Experience
What I own and what I've delivered
Director of Information Technology & Chief Architect at MyOutDesk | June 2017 to present
- Technology & vendor ownership
- I lead 4 software developers and 9 IT personnel, with ownership of engineering, cloud infrastructure, cybersecurity, IT operations, and technology budgets. I manage vendor evaluations, security reviews, procurement, and cost negotiations. For third-party application development, I oversee timelines, technical specifications, budgets, and quality before bringing the software into internal ownership and support.
- GRC & enterprise security
- I architected and own our enterprise GRC program in Drata, covering controls, policies, personnel compliance, and evidence. I owned the SOC 2 audit from readiness and auditor coordination through successful completion, and led device compliance across 1,000+ endpoints. I also design solutions for prospects and enterprise customers, balancing their security policies with our controls and operational needs, with exposure to CMMC, HIPAA, and ISO 27001 requirements.
- Cloud infrastructure
- I reduced AWS infrastructure spend by 75%+ through targeted optimization while aligning security baselines with CIS AWS Foundations Benchmark and AWS Foundational Security controls.
- Workforce applications & AI
- I architected and delivered MyTimeIn and led modernization from Electron to Rust/Tauri. Our Windows and macOS desktop software supports 2,000+ concurrent users with device compliance, live chat, and productivity tracking. I've also built AI systems for talent matching, skill extraction, candidate-to-job matching, and productivity scoring, plus an internal EOS Level 10 meeting platform adopted organization-wide.
- Marketing data
- I built an end-to-end marketing data pipeline and BigQuery warehouse that enabled a 50% reduction in social media spend while maintaining lead volume and quality.
- Salesforce & delivery
- I managed the Salesforce Lightning migration and large-scale object model migrations, directly managing Salesforce developers and administrators. I also managed CRM security with Salesforce Shield and transaction security policies, and established engineering, QA, deployment, and marketing automation standards across teams.
- DevOps foundations
- As a DevOps Engineer from January 2015 to June 2017, I stabilized a legacy PHP platform for 1,500+ concurrent users and maintained its REST API. My delivery work has included AWS CI/CD with CircleCI and GitHub Actions, deployment automation, branching strategies, pull requests, and code reviews across C#, Objective-C, and PHP applications.
Core Skills
- PHP / Laravel
- Reactive frontends (Vue, Inertia.js)
- Node (serverless, Electron)
- TypeScript
- MySQL / BigQuery
- Rust (Tauri)
- Salesforce (administration, Apex, Shield)
- C# / REST APIs / Astro / Tailwind CSS
- WordPress
- AWS (most services)
- Digital Ocean
- Netlify
- Cloudflare (Workers, R2, Pages)
- Docker
- IaC (Terraform)
- Linux / PowerShell
- CI/CD (CircleCI, GitHub Actions)
Leadership & Business
- Team leadership (4 developers, 9 IT personnel)
- Salesforce migrations & developer/admin management
- Web and desktop app delivery (Electron, Tauri)
- Infrastructure cleanup, migrations, upgrades
- Version control & CI/CD adoption
- SOPs for projects and features
- Pair programming & code review
- Ventana Research 2017 Digital Leadership Award finalist
- GRC architecture & SOC 2 audit ownership (Drata)
- Device compliance & enterprise security reviews
- Technology budgets & cloud cost optimization
- Vendor reviews, procurement & cost negotiations
- Third-party development oversight
- Google Workspace administration
- Salesforce administration
- Marketing data pipelines & analytics (BigQuery)
- Workflow automation (n8n)
Other Experience
- WordPress
- Chrome extensions
- JetBrains IDE extensions (Kotlin)
- Marketo
- Lead funnel management (technical)
- Analytics tooling (GA4, Tag Manager, etc.)
- TOFU assets and PDFs with LaTeX
- Working with external vendors (marketing, artists)
- Technical diligence for investment/acquisition
- Physical network planning (Ubiquiti)
- Hunter - an IP infringement domain investigation tool
Current Work
- MyOutDesk, LLC — Director of Information Technology & Chief Architect
Education
Bachelor of Science in Computer Science
Emphasis in Software Engineering
California State University, Sacramento | 2015
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Summary
| Name | Jayson Lindsley |
|---|---|
| Also Known As | JL |
| Photo | |
| Summary | Jayson Lindsley (JL) is Director of Information Technology & Chief Architect at MyOutDesk, leading 4 software developers and 9 IT personnel. He owns engineering, infrastructure, security, technology budgets, and the enterprise GRC program, and owned the SOC 2 audit from readiness through completion. |
| Occupation | Director of Information Technology & Chief Architect |
| Availability | Available for select work |
| Location | Remote / PST |
| Skills |
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| Current Work |
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| Featured In | |
| GitHub | github.com/WalrusSoup |
| Entity Home | jaysonlindsley.dev |