Surviving a High-Stakes $40M Federal Live Code Challenge

Earlier this year I led TCG's technical team for a competitive real-time development challenge vying for a $40 million contract with the Department of Treasury. What began as a seemingly simple "one-day code challenge" rapidly devolved into a month-long race to prepare the Release One build needed to just begin the challenge day. Our final solution featured a full DevOps pipeline, Terraform deployment, multi-region failover Kubernetes infrastructure, and a comprehensive web application with AI image processing. This was all delivered under immense pressure within a one month schedule and limited customer access.

This isn't theoretical; it's a raw, honest look at real-world challenges. We'll delve into the critical, sometimes painful, lessons learned about DevOps principles and Agile anti-patterns that surfaced under fire. I believe these in-person live coding and technical assessments will become increasingly common in contract competitions, especially as AI blurs the lines of expertise when presented via written proposals.

Join us for immediate, practical steps your teams can implement, drawn directly from our experience competing in a real-time development challenge vying for a $40 million contract with the Department of Treasury. This isn't theoretical; it's a raw, honest look at real-world challenges. We'll delve into the critical, sometimes painful, lessons learned about DevOps principles and Agile anti-patterns that surfaced under fire:

• Why Continuous Integration from Day One isn't just best practice—it's a survival mechanism. We'll share our practice run panic and how targeting the "perfect CI pipeline" nearly derailed us.
• How to establish an effective customer surrogate when direct stakeholder collaboration is impossible, and why their early feedback is non-negotiable, even in a challenge scenario.
• The unexpected payoff of a production-ready mindset in a demo environment, and how small efforts can save your project during a live presentation.
• Navigating the tricky balance of tooling choice and team familiarity: When powerful tools become bottlenecks, and why a gelled team outperforms a collection of individual experts.
• The often-overlooked secret weapon: realistic team availability. Discover how managing after-hours expectations impacts velocity and team morale.

This talk offers concrete, actionable takeaways for anyone navigating complex software development on a laughably short timeframe, whether you're competing for a new contract or launching your startup MVP. We’ll share the "aha!" moments and the pitfalls, providing practical pro-tips to help you succeed in your next race to release 1.0.

Transcript

1. 7348 GEORGIA AVENUE NW, WASHINGTON, DC 20012 202-986-5533 | WWW.TCG.COM | INFO@TCG.COM 7348 GEORGIA AVENUE NW, WASHINGTON, DC 20012 202-986-5533 | WWW.TCG.COM | INFO@TCG.COM Surviving A High-Stakes 40 Million Dollar Live Code Challenge
2. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. A $40 Million Challenge 2 THE PRIZE A $40 million federal contract. THE PROCESS Final round of a 5-stage competitive down-select. THE TEAM 15 people from multiple companies. THE TWIST New lead and new team chosen 2 weeks before the deadline.
3. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. The Challenge 3 LABEL DATABASE SEARCH WEB APP • Multi-region failover • Terraform IaC Deployments • Scalable microservices • Kubernetes • Hardened Infrastructure • Monitoring • CI/CD Pipeline • Automated Testing • AI Image Analysis
4. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. Prioritize Continuous Integration from Day One 4 PRIORITY #1 Build the shortest possible pipeline first. No Bells. No Whistles. PRO TIP Get a Minimum NON-Viable Product into "production" in the first 10% of your timeline. CRITICAL AGILE PRINCIPAL Working code over comprehensive documentation.
5. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. A strange hammer swings wide of the nail 5 THE TOOLING TRAP Prioritize team familiarity along with raw features. CHOOSING TOOLS The best results right now come from tools you are familiar with. SCALE Build for the scale you have. “Premature optimization is the root of all evil.”
6. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. Tools are good, teams are better 6 THE "ALL-STAR" FALLACY A roster of experts is not a team. PRACTICE EVERYTHING Use quick-repetition of iterations to overcome friction. REPEATABILITY A unified team delivers predictable execution under pressure.
7. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. What Do You Need When the Pager Goes Off at 2am? 7 PRO TIPS Add basic resiliency - e.g. API Limits, Health Check. THE PAYOFF Reduced stress and maybe some surprise victories. PRODUCTION FEATURES ≠ PRODUCTION READY
8. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. Production Readiness 8 IMPLEMENT BEST PRACTICES When you know that something should be done, make sure it happens. BE SMART This isn’t an excuse to gold plate every feature. DON'T FORGET THAT YOU ARE THE EXPERT
9. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. Feedback is a gift 9 IMMEDIATE ACTION Empower an Internal "Customer". CUSTOMER IS KING Live by the requirements. THE METHOD Test Like a Judge, Not a Partner.
10. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. A Proposal is Not a Hobby 10 THE HARD TRUTH Treat it like a project, not after-hours work. PREPARE Every team should be ready to work through unexpected absences THE ASK Secure dedicated time, not "spare" time.
11. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. The Reveal and Debrief 11 OUTCOME We were not selected for the award. • Price was a significant factor • The noted mistakes on challenge day • Long agile ceremonies • Insufficient focus on the “User Centric Design” philosophy used by TTB DEBRIEF NOTES
12. This presentation contains proprietary data that may not be disclosed or released to any individual or party without consent from TCG, Inc. It's a Delivery Challenge, Not a Code Challenge 12 YOUR TEAM IS YOUR MOST CRITICAL TOOL Their cohesion, familiarity with the tools, and dedicated time are paramount. THE FUTURE IS LIVE DEMOS As AI devalues written proposals, the ability to deliver under pressure will become the ultimate differentiator. YOUR PROCESS IS YOUR GREATEST ASSET Prioritizing working systems and a rubric-driven mindset delivers wins.