Jonathan T Penny
Founder at Stache Technology
Engineering leader with experience at Google, Twilio, and Wayfair. Ex-Google | MBA from University of Illinois | AWS Certified | Building AI-powered knowledge management tools.
Recent Posts
View all →Enterprise AI Security: Why You Need a Layer Between Your Data and Claude
How Stache's middleware architecture addresses the security gaps exposed by Claude Cowork's prompt injection vulnerabilities.
OAuth 2.1 Dynamic Client Registration for AWS BedrockAgentCore
A CloudFormation template implementing OAuth DCR for BedrockAgentCore Gateway with Cognito.
Running Stache on AWS with Stache Serverless
A production-ready serverless RAG system built on AWS - Lambda, S3 Vectors, DynamoDB, and Bedrock.
Stache AI: Curated Storage for AI with Claude
Introducing Stache - a RAG-based knowledge base that connects directly with Claude via MCP.
Combine Real World Experience With Time In The Classroom
Classes are great for learning theory, but nothing beats real world experience for aspiring tech leaders.
Career
Founder
Stache Technology- • Building AI-powered knowledge management tools for enterprises
- • Developing RAG pipelines and semantic search infrastructure
Engineering Manager
Twilio- • Led a team of engineers focused on migrating from data center to AWS
MBA Graduate
University of Illinois- • Focus on Strategic Leadership, Entrepreneurship, and Strategic Innovation
- • Partnered with medical and engineering students to produce GTM plan for new medical device
Engineering Manager
Google- • Led a team of engineers focused on improving developer velocity in the testing space
Senior Engineering Manager
Wayfair- • Led a team building an event-driven platform for finance engineering using Python and Kafka
- • Implemented software updates predicted to drive more than $200M in additional yearly profit
- • Built an event-based platform to decouple functions from a legacy monolith for SAP migration
DevOps Leader
QsrSoft- • Architected and scaled AWS infrastructure to analyze streaming data from 14,000 US McDonald's restaurants, peaking at 500 tps
- • Drove major initiatives including infrastructure as code, CI/CD, agile SDLC, migration to GitHub and Jira
- • Led migration of EOL applications from on-premise to AWS, realizing several $M in additional revenue
Director of Technology
myFootpath- • Reported to CEO and managed all technology for a company with > $10M in revenue
- • Led team to build new product enabling complete business model pivot from call center to self-service
- • Reduced technical headcount from 7 to 1 through automation and complexity reduction
CTO/Founder
Socialhood- • Founded Socialhood, a social network for the neighborhood
- • Architected the original concept and led a distributed team that built out the application
Director of Engineering
Working Person's Store- • Created comprehensive technology strategy for INC 500 company with $10M in revenue
- • Consolidated vendors, migrated telephony to VOIP, implemented ticketing, managed call center move