Lessons from Building Charlie Chat — and What’s Next

When I started Charlie Chat, my goal was to learn, experiment, and show how AI could make a resume interactive. The response exceeded what I expected — and the process itself taught me a lot about communication, focus, and shipping something end to end.

That project helped me clarify what kind of work energizes me most, and I’m excited to now bring that same mindset into my new role as Director of Security at JumpCloud.

For anyone working on personal projects during a career transition: build something that stretches you and reflects how you think. Even if it’s small, you’ll come out sharper and with a clearer story to tell.

Charlie Chat is Live

Ask Me Anything About My Career

Today I am excited to launch Charlie Chat, an interactive, resume-aware chatbot that answers interview-style questions about my career. Instead of reading a static PDF, you can now have a conversation with my background.

Building Charlie Chat has been a way to up-skill and get hands-on with AI while showing how I solve problems end to end. The project touches infrastructure, DevOps, security, compliance, UI/UX and analytics, all aimed at creating something clear and useful. In a real-world setting these would be cross-functional teams and I would work to align them toward a shared goal. Doing this project myself gave me a deeper appreciation for each discipline and will help me communicate more effectively with the specialists I would work with in a larger organization.

Charlie Chat is open source and I am happy to share details about how it was built and what I learned along the way.

What’s New Since the MVP

Over the past several days I have gone from "it works!" to "it is ready to share widely." Key improvements since the MVP include:

• Smarter Answers: Tuned prompt engineering for more natural responses and extended the knowledge base of available information
• Safari Support: Deployed CloudFront to support HTTP-to-HTTPS redirects and fix Safari loading issues
• HTML & SEO: Cleaned up layout, ensured URLs are unique for analytics and SEO
• Analytics & Instrumentation: Integrated PostHog and New Relic to track usage, performance and guide improvements
• UI Polish: Refined the chat interface for readability and usability

Why I Built It

I wanted to give recruiters, hiring managers and curious technologists a faster and more engaging way to understand who I am, what I have built and how I lead teams. It is a mix of storytelling and tech demo and a bit of fun.

Try It Out

Try Charlie Chat here

Ask about my work experience, leadership style, cloud architecture projects or even what I like to do for fun. You can also use the feedback form to send your thoughts to me directly.

Thank you for being part of the experiment!

MVP Achieved

🚀 The MVP is ready to share! I focused on building instead of journaling being heads-down coding, shipping and solving problems. The result is something I am proud to put in front of others. I will backfill short entries to capture the journey.

Announcement

The MVP is live and ready for feedback. I still have plenty of TODOs. I will ship improvements in small batches. I want real input before I polish the small stuff, please try it out and tell me what you think.

Costs So Far

Total spend: $1.20 for the entire week.
I kept AWS costs tight with deliberate choices and strict limits. A detailed cost breakdown is coming soon, but interestingly the two biggest costs were:

• DNS Hosting: $0.50/month per zone (I could have left this with my registrar)
• Amazon Lex: Which I ultimately removed in favor of handling all logic in Lambda

Key Milestones

Over the past week I shipped a full end-to-end solution that combines infrastructure, application code and AI-powered interaction. Highlights include:

• Knowledge Base Integration – Wired in resume context, tuned retrieval to keep responses focused.
• Prompt Engineering – Switched to first-person voice, shortened answers and added follow-up prompts.
• Conciseness & Variability – Introduced character-based targets to avoid truncation while keeping answers natural.
• Session Memory – Added light conversation history so the bot remembers context between questions.
• UI & UX Polish – Designed a clean, focused chat interface, improved layout and readability, minimized visual clutter and added voice style controls for a fun user experience.
• Infrastructure-as-Code Deployment – Defined and provisioned AWS resources with Terraform, creating a reproducible and scalable deployment foundation for future growth.
• Architecture Simplification – Consolidated intent handling into a single FastAPI-based Lambda, removing Lex as a dependency for a simpler, faster and fully local development flow.
• Logging & Observability – Added structured logging with timestamps and response timing to improve troubleshooting and performance monitoring.
• Testing Foundation – Set up pytest with coverage and async testing to catch regressions early and prepare for automation.
• Content & Persona Design – Refined Charlie Chat’s tone, voice style options and personality for a recruiter-ready, interactive experience.
• Security & Environment Management – Implemented .env handling and secure secret management for local/prod consistency and safer development.
• Documentation – Updated README and developer notes to make the project reproducible and easy to understand for future contributors or hiring managers.
• Cost Discipline – Logged token usage, setup an AWS Budget, stayed with on-demand models and removed Lex to simplify architecture, have more control and save money.

What's next?

Your fedback matters.

Try the site, click around, ask questions — even try to break it. Tell me what felt smooth and what needs work.

Feel free to either email me or use the feedback form.

Day 1 – A New Challenge Begins

I am an IT leader with deep experience in security, infrastructure and business systems, taking a one-week sprint to build a hands-on project. My goal is to showcase both leadership vision and technical execution to stand out in today’s competitive job market.

After nearly 13 years leading technology teams, I find myself at a professional inflection point. I started in DevOps and grew into leadership roles guiding security, compliance, infrastructure and business systems teams. I have built strategy, scaled organizations and delivered measurable results at enterprise level.

The current job market for IT leaders is competitive and fast moving. There are many talented people looking for fewer senior leadership roles, which makes standing out critical. Rather than immediately flooding the market with more applications, I chose to take a one week break to focus on something different: building a project of my own.

This project lets me step back into hands-on work and flex the skills that originally drew me to technology: programming, architecture and problem solving. The goal is bold yet simple: build something that demonstrates both technical depth and leadership mindset in one cohesive experience.

I am building an interactive site where visitors can explore my experience in a more dynamic way than just reading a résumé. They will be able to ask questions, experiment with the interface and discover a few hidden easter eggs along the way. This project touches multiple layers of technology:

• Front-end & UX: Designing with HTML, HTMX and SCSS for a clean, interactive interface
• Back-end Development: Building with Python and FastAPI
• Infrastructure-as-Code: Provisioning AWS resources with Terraform for reproducibility
• Cloud Architecture: Deploying in a cost-efficient, scalable serverless environment
• AI Integration: Powering contextual, meaningful interaction through LLM-driven responses

I am approaching this as a one-week sprint to sharpen both creativity and execution. I will be writing here along the way to share progress, design choices and lessons learned. This journal is also a way to give readers a sense of my voice and approach, not just what an AI model says about me.

Day 1 is all about laying the foundation: setting up the infrastructure, deciding on tools and creating a clear vision for the final product. Tomorrow I shift from planning to execution - time to build.