Product Leader

Hi, I'm Skyler.

I build intelligent products with generative AI, from concept through launch. 8 years shipping SaaS, iOS, and eCommerce. 4 years deeply exploring AI.

Seattle, Washington
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Experience
Technical Program Manager · Amazon
Dec 2025 - Present
Product Manager · Amazon (Contract)
Oct 2024 - Dec 2025
Senior Consultant · Spur Reply (Microsoft)
Jan 2024 - Oct 2024
Head of Product · Connexpert
Jul 2021 - Jun 2023
Co-Founder · OLEO
2016 - 2020
By the Numbers
8
Years building SaaS, iOS,
and eCommerce products
4
Years of hands-on AI
product experience
8
AI products built
and shipped
🥇

1st Place, AI Hackathon

ScamDetect · June 2023
🥉

3rd Place, AI Hackathon

DoppelFlow · December 2023
Selected Projects

These are the ones worth a full write-up. Newer builds usually land on GitHub first. github.com/summerstateofmind

FlaggedLeads map dashboard screenshot
Live · SaaS

FlaggedLeads

Distress-Signal Lead Engine for Real Estate

Pulls Seattle's code-violation records, maps every flagged property, and scores each one by distress signal, so investors spot motivated sellers before the listings ever appear.

What It Does

A code violation is a quiet tell that an owner is checked out. FlaggedLeads reads those public records, ties each one back to its owner, and ranks the property by how likely that owner is to sell. Investors get the lead before anyone else knows it exists.

What I Built

Built solo, end to end. An ingestion pipeline cleans messy municipal records and matches each violation to the right parcel; a scoring engine turns volume, severity, and recency into one sortable number and shows its work. An early-warning layer reads 311 calls and permit filings to flag a property before the violation even lands. Owner enrichment catches absentee landlords, PO-box forwarding, and multi-address portfolios.

Tech Stack
Python Flask PostgreSQL Leaflet.js Socrata API Geocoding Scoring Engine Railway
Live Now

12,000+ active violations across 9,500+ Seattle properties, refreshed continuously. Free map to browse; a paid tier unlocks scores, owner data, and CSV export.

Visit flaggedleads.com
cityparity calculator homepage screenshot
Live Product

cityparity

Relocation Economics Calculator + MCP Server

Compares the true cost of a move across 165 cities, weighing not just rent and salary but childcare, healthcare, vacation, and parental leave. The same engine is open to AI agents over MCP.

What It Does

Most calculators stop at salary and rent. cityparity also prices the social safety net, turning subsidized childcare or universal healthcare into an equivalent salary. The result: "the lower-paying city actually pays more" becomes a number you can show your partner, not a hunch.

What I Built

The financial engine is pure JavaScript. It models progressive tax across 69 countries and runs the same code in the browser and the test suite. Your salary never leaves your device; every calculation is client-side. I also shipped a public MCP server so AI assistants can run the comparisons themselves, plus a programmatic-SEO system that generates a ranked page for every city pair.

Tech Stack
JavaScript Node.js Alpine.js Tailwind CSS Model Context Protocol Cloudflare Workers Programmatic SEO Playwright
Live Now

165 cities across 69 countries. No account, no tracking. Your numbers never leave your browser. AI agents can connect at mcp.cityparity.com.

Visit cityparity.com
resuumi homepage screenshot
Production

resuumi AI

Automated Resume Keyword Optimization

GPT-4 powered tool that ingests a resume and job description, optimizes keyword matching, and outputs an improved, downloadable PDF.

The Problem

Job seekers waste hours manually tailoring resumes for each application, often missing critical keywords that ATS systems filter on. Most don't know which terms matter.

My Role & Approach

Designed the product end-to-end and built the UI in Panel (Python). Integrated GPT-4 for semantic keyword analysis and resume rewriting. Shipped to production as a self-serve web app.

Tech Stack
Python GPT-4 Panel PDF Generation
Status

MVP shipped August 2023

Spellforge homepage screenshot
Production

Spellforge

LLM Quality Evaluation with Synthetic Users

Scalable quality evaluation platform for LLM apps using simulated synthetic users and AI judges.

The Problem

LLM-powered apps are difficult to test at scale. Manual QA is slow and subjective. Teams need automated, repeatable evaluation that simulates real user behavior.

My Role & Approach

Conceived and built the platform. Designed the synthetic user simulation framework and integrated AI judge evaluation. Built the Streamlit interface for team workflows.

Tech Stack
Python Streamlit GPT-4 GPT-3.5
Status

MVP shipped October 2023

DoppelFlow homepage mockup
Hackathon · 3rd Place

DoppelFlow

AI Agents for Desktop & Browser Automation

A repeat-after-me training system for AI agents. Record your task, AI parses the video & DOM input, then replay your Doppel on demand.

The Problem

Automating repetitive desktop and browser tasks typically requires programming knowledge. Non-technical users need a way to teach AI by demonstration, not code.

My Role & Approach

Served as PM on a three-person team. Defined the product vision, designed the user flow, and coordinated between two developers during a hackathon sprint.

Tech Stack
Python GPT-4V HTML/CSS DOM Parsing
Result

Won 3rd place at AI Hackathon, December 2023. Demonstrated the viability of demonstration-based agent training.

Cyber Fort homepage screenshot
Hackathon

Cyber Fort

AI-Simulated Cyber Attacks for LLM Security

Leverages synthetic user knowledge to simulate attack vectors and build a self-improving firewall for AI companies.

The Problem

LLM applications are vulnerable to prompt injection, jailbreaking, and data extraction attacks. Static security rules can't keep pace with evolving threats.

My Role & Approach

Applied learnings from Spellforge's synthetic user framework to simulate adversarial attack patterns. Designed a self-improving defense loop that adapts to new attack vectors.

Tech Stack
GPT-4 Python Red Teaming
Status

Hackathon project, January 2024

Connexpert homepage screenshot
Production

Connexpert

Digital Marketplace for Expert Interviews

A two-sided marketplace connecting subject matter experts with researchers and consultants for paid interviews.

The Problem

Researchers spend excessive time sourcing and vetting domain experts. Experts lack efficient platforms to monetize their knowledge for short consultations.

My Role & Approach

Hired as Head of Product (CEO-level). Led market research, defined the MVP, managed the build with developers, and executed go-to-market strategy.

Tech Stack
Web Platform Marketplace Payments
Status

Production, October 2022

OLEO homepage screenshot
Venture-Backed

OLEO

Dietary Supplement eCommerce Brand

Co-founded a DTC supplement brand. Raised $2.5M in funding and grew revenue to nearly $1M annually.

The Story

Co-founded in 2016 and built from the ground up: product development, branding, supply chain, and a custom-built eCommerce store. Raised a seed round and scaled operations.

My Role

Co-Founder. Oversaw product development, eCommerce operations, fundraising, and brand strategy. Managed the full lifecycle from concept to ~$1M ARR.

Key Metrics
$2.5M Raised ~$1M ARR Custom eComm
Status

Series Seed, founded 2016

I love building things.

Looking for an earnest, AI-forward product leader? Let's talk about what we can build together.

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