Robert Sivilli
Principal Software Developer
Chantilly, VA
I build things end-to-end and ship them. A decade across defense research labs, the Pentagon, and DoD startups — growing ideas into funded programs, shipping production infrastructure at scale, and building a dozen side projects in my own time. Now looking for a cofounder to build something real.
I can build the product — end to end, fast. What I'm looking for is someone who brings strong founder instincts: the ability to spot problems worth solving, talk to customers, and push through ambiguity. Domain and role are secondary to mindset.
I'm open on problem space. I'd rather find the right person and figure out the right problem together than lock in a thesis before I know who I'm building with.
Principles
as a founderHumans Stay in the Loop
AI should augment judgment, not replace accountability.
When asked to build an AI system to triage Afghan evacuees, I pushed back and built a decision-support dashboard instead, one that let decision-makers define their own filter criteria and see real-time impact on the people affected. Moral weight belongs with people, not models.
Engineering-First, User-Grounded
The most passionate people are engineers, but only great ones stay close to users.
Technical decisions about implementation belong with those who understand the constraints. But engineers have a habit of thinking they know best. The antidote is staying genuinely engaged with the people you're building for, not ceding product judgment to sales, and not retreating into the assumption that clever code equals a good product.
Automate to Liberate
Automation is progress. But companies owe their people a path forward.
Like agriculture freed our ancestors to pursue new specializations, AI should free us to pursue higher callings. I'm an optimist about this. But companies adopting AI have a responsibility to build cultures that support people through the transition, with training, policy, and clear guardrails, not just automate them out and move on.
Build for Imagination
The best products are sandboxes that spark what could be.
I want to make the world more magical and brighter. Products that give people (especially younger generations) a space to explore, wonder, and eventually build are the ones worth making. The goal isn't just utility. It's inspiration that moves someone to imagine a better world and then go build it.
Respect is Non-Negotiable
Engineers are not order-takers.
I won't work where technical staff are second-class citizens. Creativity, curiosity, and mutual respect aren't perks; they're the foundation of any company worth building. A culture that treats engineers as pure executors of someone else's spec won't ship anything remarkable.
Work is Family
The best teams aren't just colleagues. They're people who genuinely care about each other.
The Air Force didn't just teach me about mission and discipline; it showed me that the line between work, family, and friends can disappear when a team truly commits to each other. That's not a management strategy or a culture deck talking point. I genuinely believe a good company builds something closer to a family: people who invest in one another, show up when it matters, and are better for having worked together.
Live Projects
8 deployedFlutter app for NFC-powered personal item tracking — tag physical belongings and log them across three modes: laundry cycle tracking, location placement, and trip packing lists. Includes an achievement system, streak tracking, and ADHD-friendly onboarding. Currently in closed testing for Android.
Guided moral framework interview platform — walks users through ethical scenario questions and uses LLM scoring to generate a moral profile across 10 dimensions (agency, consent sensitivity, power skepticism, and more), producing an archetype, tension map, and simulation rules for predicting future reasoning.
AI-powered social media management tool for content creators — indexes past interactions and uses RAG to generate contextual reply suggestions with optional automation workflows
Next.js app for planning and managing garden beds, tracking plants, layouts, and seasonal schedules
Product catalog site that uses Gemini to auto-generate daily product drafts for admin review, with careers listings and AdSense feed integration
Flutter app for tarot readings and astrology — AI-generated card interpretations, natal charts, transit reports, daily horoscopes, and a personal journal
Open Source
15 public reposConfigurable RAG chatbot for querying government website content, with a web scraping bot manager and support for both OpenAI and self-hosted LLMs
MCP server exposing SAM.gov contract and entity registration data to AI assistants via the SGS API
Terraform setup to deploy OWASP Juice Shop on GCP's always-free tier — a zero-cost intentionally vulnerable e-commerce app for practicing web security and CTF challenges
Tampermonkey userscript that adds a floating panel to Amazon's Subscribe & Save page showing upcoming deliveries grouped by month with totals, savings, and one-click PDF or plain-text export
Stable Diffusion plugin for generating character portraits and full profiles for tabletop RPGs
Twitch bot that feeds live chat messages as prompts into Stable Diffusion, streaming the generated images back to the channel in real-time via a virtual webcam
Django app that scrapes defense and space news RSS feeds, synthesizes paragraph-level narration with Suno's Bark TTS, generates matching Stable Diffusion XL imagery, and assembles it all into narrated AI news videos
CLI tool for applying AI prompts to source files in bulk — improve comments, generate docstrings, and more using the OpenAI API
Angular SPA proof of concept using the Unified Data Library (UDL) as the primary data and identity source for a space order-of-battle visualization
Reusable pytest fixture that handles the full MFA auth flow for AWS Cognito users in integration tests
Opinionated Python microservice template with batteries included
Exploration of ADS-B drone ID spoofing, emulating the broadcast signals commercial drones use to identify themselves over RF
Experience
Defense Contractor
Principal Software Developer
- Led multiple small teams in art-of-the-possible prototypes to guide company strategic direction — including a grassroots rebuild of the flagship Unified Data Library, AI-driven data standardization tooling, and agentic AI operators built around analyst and operator workflows.
- Spearheaded open-source initiative, including a commercial partnership to auto-deploy SDKs across 4 languages covering 1500+ API endpoints.
- Led initiative for safe use of AI coding assistants, including privacy-agreement review and policy/guidance memo development.
Technology Startup
Lead, Data
- Developed and executed data standardization plan across client, sales, backend, and operations.
- Built and led a team of analysts supporting C-suite decision making and board reporting.
- Designed custom ORM tools for BigQuery with granular, least-privilege security; built centralized schema definitions with testable CI/CD integration across three programming languages.
- Built a generalized inbox listener and parser handling heterogeneous Excel reporting formats from 16 distributors.
U.S. Air Force
Chief of Test, Exercise & Evaluation
- Led Air Force-wide discussions and planning around coordinated test and evaluation of upcoming capabilities.
- Instructed General Officer-level senior officials on how data, software, and cloud capabilities should be exercised and evaluated alongside physical systems.
DoD Startup
Software Engineer
- Designed, built, and deployed a Kubernetes-based configuration service enabling shared scenario development and configuration control across multiple cross-functional teams.
- Created inroads for company involvement in Sprint Advanced Concept Training — a quarterly international space exercise involving 7+ countries and 40+ government agencies.
Defense Digital Service
Digital Service Expert (GS-15)
- Served on 1–2 person engineering teams providing rapid response and advisory support to the highest levels of the Department of Defense.
- During the Afghanistan evacuation, designed and managed tools for real-time situational awareness across disparate data sources, mass communication to evacuees, and streamlined special immigrant visa processing.
- Developed an Android application and Bluetooth-based wearable to assist in identifying potential causes of Havana Syndrome.
- Served on advisory boards for Software, IT, and Data policy across DoD.
U.S. Air Force
Chief, Data Program Management Office (DPMO)
2019 — 2021- From concept to capability — led, prototyped, and deployed the Unified Data Library (UDL), growing the office organically from 4 to 60 people over two years.
- Briefed top senior government and military leadership to shift cultural perspective toward data centricity and valuation.
- Designed system architecture for scalable, resilient, and secure commercial cloud deployments.
Engineer, DR II
2014 — 2019- Led teams of civilians, military, and contractors across multiple research thrust areas.
- Built a cloud-based software development enclave; built mission analytics and hypertime physics/agent-based simulators for satellite missions.
- Built autonomy modules for a satellite to understand and respond to its environment.
Research Engineer, DR I
2013 — 2014- Built software components for autonomous satellite systems focused on deterministic responses to external stimuli.
Education
M.S. Aerospace Engineering — Control Systems
University of Central Florida
B.S. Aerospace Engineering — Control Systems
University of Central Florida
Systems Engineering Certification
Air Force Institute of Technology
Program Management I · Eng & Tech Mgmt III · Test & Evaluation I
Defense Acquisition University