Steve Regester
Fractional CTO | Systems Architect | 0→1 Product Builder
15+ years building production platforms from zero
AI/LLM systems, full-stack architecture, cloud infrastructure, and technical leadership
Southwest Washington • Portland Metro Area • Available Remotely
Executive Summary
Founding engineer and systems architect with 15+ years building production platforms from zero. I've been employee #1 at a VC/In-Q-Tel backed cybersecurity startup, directed engineering for a pharmaceutical SaaS company through SOC 2 certification, co-founded a nonprofit crowdfunding platform, and most recently designed an autonomous AI-powered publishing engine with multi-LLM orchestration. I specialize in walking into ambiguity and shipping durable systems — architecture, product, infrastructure, and team — on compressed timelines with minimal overhead.
Core Expertise
Selected Projects
Autonomous AI Publishing Engine | 2025–Present
Designed and built a fully automated local news publication platform. Ingests structured feeds, performs agent-based taxonomy and classification, routes workloads across multiple LLM providers for cost optimization, and publishes to CMS on a controlled schedule with minimal human intervention.
Professional Experience
Founding/Staff Software Engineer
Delphos Labs (VC & In-Q-Tel backed) | June 2024–Present
Employee #1 at a cybersecurity startup using AI to automate binary reverse engineering. Built the company from 0 to 1.
- Designed high-level platform architecture — SaaS product, automation pipelines, database, API layer
- Built cloud infrastructure from scratch using Terraform on AWS
- Engineered distributed task processing with Celery and RabbitMQ for reliable workload distribution
- Developed the user-facing product — React Router v7/Remix v8, isomorphic rendering, real-time dashboards
- Provided engineering and managerial leadership — hiring, mentoring, code review, process design
- Established CI/CD, feature flags, analytics (Hotjar, Sentry), and security-first development practices
Director of Engineering
Studylog Systems, Inc | August 2021–October 2023
Directed all web and cloud engineering for an animal health pharmaceutical SaaS company.
- Led complete rewrite of flagship Windows product into a cloud-native SaaS platform
- Architected infrastructure passing rigorous third-party security audits — achieved SOC 2 Type II certification 3 months ahead of schedule
- Built on AWS with Terraform, Helm, and Kubernetes supporting enterprise clients
- Recruited and mentored engineering team — delivered training that reduced coding errors by 50%+
- Drove agile adoption resulting in 20% reduction in project timelines
Senior Software Engineer II
Synack, Inc | April 2016–March 2021
Lead engineer on a crowdsourced security platform serving enterprise clients.
- Redesigned user interfaces across primary product lines — 60%+ user engagement increase within 12 months
- Built and replaced key product verticals with focus on quality, maintainability, and technical debt reduction
- Established engineering standards through comprehensive testing frameworks and internal coding standards
Founder & CTO
Ultimatum, Inc | September 2015–July 2019
Co-founded a crowd-fundraising platform facilitating automated donations to 501c3 nonprofits based on real-world events.
- Single-handedly architected all interfaces, services, and data flow mechanisms
- Built real-time event processing with Apache NiFi for automated donation triggers
- Established full SDLC with CI/CD on Google Cloud using Docker, Helm, and Kubernetes
Senior Software Engineer, Team Lead
Lookout | April 2013–April 2016
Lead frontend engineer on an enterprise mobile security platform.
- Designed custom security research tooling that doubled research team productivity within 12 months
- Built tools and workflows for internal security research team's Android malware discovery mission
Software Engineer
PBworks | October 2011–March 2013
Engineering generalist on a cloud document and file management platform. Built features, managed MySQL databases, developed RESTful APIs, and implemented responsive interfaces.
Recommendations
"Steve represents the high water mark for me in terms of sheer front-end engineering talent. He is an incredibly gifted engineer, equally passionate about doing things the right way, at a high level of quality."
— Director of Engineering, Lookout
"Steve joined to lead a complete web-based rewrite of our flagship product... architected and developed a cloud-native platform that could meet sophisticated pharmaceutical industry requirements, passing rigorous third-party security audit and achieving SOC 2 certification."
— Head of Product Management, Studylog
"Steve has exceptional ability to lead and inspire his team, setting a high bar for technical excellence... His unwavering commitment to excellence and continuous improvement drives innovation and optimization."
— Full Stack Engineer, Studylog
Available for Engagements
Fractional CTO engagements, architecture consulting, AI/LLM system design, and 0→1 product builds.
Fractional CTO • Architecture Consulting • AI/LLM Systems • 0→1 Builds