Steve Regester

Fractional CTO for Seed-Stage AI Companies — 0-to-1 Architecture and Technical Leadership

Southwest Washington | [email protected] | egeste.net | linkedin.com/in/egeste | github.com/egeste

Professional Summary

Fractional CTO and systems architect who embeds with seed-stage founders to own technical strategy from formation through fundraising readiness. 15+ years defining architecture, hiring first engineers, and shipping production platforms under early-stage constraints. As employee #1 at a VC/In-Q-Tel-backed startup, owned product engineering, cloud infrastructure, and technical delivery end-to-end. As Director of Engineering, set the technical strategy that delivered SOC 2 Type II certification three months ahead of schedule, directly unblocking enterprise revenue. Specialize in standing up investor-ready generative AI systems — cost-controlled LLM orchestration, workflow automation, and engineering foundations designed to survive technical due diligence — so founders avoid the re-architecture that kills post-seed momentum.

Core Competencies

Generative AI: Multi-model orchestration, OpenAI, Anthropic Claude, agentic workflows, RAG (Retrieval-Augmented Generation), prompt engineering, cost-aware inference routing, data pipelines

Architecture: React, TypeScript, Node.js, Python, GraphQL, REST APIs, microservices, server-side rendering (SSR), system design, build vs. buy analysis

Cloud/DevOps: AWS, GCP, Terraform, Kubernetes, Docker, CI/CD, Infrastructure as Code (IaC), auto-scaling, infrastructure cost control

Security Experience: Led teams through SOC 2 Type II certification, worked within OWASP and threat modeling frameworks, secure architecture, third-party audit preparation

Leadership: Fractional CTO, founding engineer, 0-to-1 product strategy, technology roadmap, MVP scoping, early-stage hiring, technical due diligence, Agile/Scrum

Experience

Founding/Staff Software Engineer

Delphos Labs (VC and In-Q-Tel backed) | 06/2024 - Present

  • Employee #1. Owned product engineering, cloud infrastructure, and technical delivery end-to-end for an AI-driven cybersecurity platform
  • Defined platform architecture — SaaS application, data pipelines, PostgreSQL data layer, IaC, API surface — making build vs. buy and speed vs. maintainability tradeoff decisions
  • Set cloud infrastructure strategy on AWS with Terraform; managed IaC for distributed AI workloads
  • Delivered the customer-facing product (React, TypeScript, SSR) and established CI/CD, monitoring (Sentry), and security-first practices — production-ready before first external demo
  • Led early-stage hiring and defined engineering culture, code review standards, and development process as the organization scaled from two cofounders to functioning team

Director of Engineering

Studylog Systems, Inc | 08/2021 - 10/2023

  • Owned technical strategy for a pharmaceutical SaaS company in transition; made the architecture decisions that governed the full rewrite from legacy desktop software to a cloud-native platform
  • Designed AWS infrastructure for compliance from day one — achieved SOC 2 Type II certification 3 months ahead of schedule, directly unblocking enterprise sales pipeline
  • Defined production environment architecture with Terraform, Helm, and Kubernetes; scoped for enterprise client requirements and third-party audit readiness
  • Built and mentored a 5-person engineering team; training programs reduced coding errors by 50%+; Agile adoption cut delivery timelines by 20% within two quarters

Senior Software Engineer II

Synack, Inc | 04/2016 - 03/2021

  • Lead engineer on a crowdsourced penetration testing platform serving Fortune 500 enterprise clients
  • Redesigned core interfaces across 3 product lines, driving 60%+ user engagement increase within 12 months
  • Replaced legacy verticals with maintainable systems; defined testing frameworks and coding standards adopted across the 40+ person engineering org

Founder and CTO

Ultimatum, Inc | 09/2015 - 07/2019

  • Co-founded and sole-architected a crowd-fundraising platform automating 501(c)(3) donations via real-world event triggers — 0-to-1 build as sole technical founder
  • Designed real-time event processing (Apache NiFi) and production CI/CD on Google Cloud Platform (GCP) with Docker, Helm, and Kubernetes

Senior Software Engineer, Team Lead

Lookout | 04/2013 - 04/2016

  • Lead frontend engineer on an enterprise mobile security platform; designed internal tooling that doubled research team productivity within 12 months

Software Engineer

PBworks | 10/2011 - 03/2013

  • Full-stack development on a cloud document management platform — features, MySQL, REST APIs, responsive interfaces

AI and Automation Consulting (Selected Work)