CTO / Head of Platform Engineering — Pre-Launch SaaS (AWS Serverless, TypeScript, Python)

CTO / Head of Platform Engineering — Pre-Launch SaaS (AWS Serverless, TypeScript, Python) Budget: Expert Tier (Hourly or Milestone-based for initial evaluation phase). Potential for permanent corporate conversion and equity incentives based on milestone performance. About the Role We are an enterprise-grade, multi-tenant B2B SaaS platform preparing to execute our first production deployment. The entire ecosystem is already built—fully implemented across web, mobile, and cloud infrastructure—and we are seeking a technical co-leader to own our production readiness journey. This is not a "build from scratch" role. The architecture is fully implemented, rigorously tested, and spec'd. We need an execution-focused leader to take the platform from "works in development" to "bulletproof in production under sustained load." What Is Built (The Infrastructure You'll Inherit): - Multi-Tenant Architecture: Scalable platform serving complex business verticals with multi-repository governance. - 5 Active Deployment Surfaces: Next.js web application, React Native mobile application, AWS CDK infrastructure, isolated backend computation modules, and a dedicated administrative portal. - Serverless-First Core: 40+ serverless functions (AWS Lambda), 10+ CDK stacks, and a fully decoupled, event-driven architecture. - Persistence Layer: Optimized hybrid relational and NoSQL storage infrastructure (PostgreSQL + DynamoDB + Redis caching layer). - Real-Time Data Engine: High-throughput WebSocket infrastructure engineered to target 10K+ concurrent connections. - ML Pipeline: Production-ready machine learning inference orchestrations (AWS SageMaker). - Advanced Security Perimeter: Privacy-preserving computation via isolated secure enclaves and an enterprise-grade zero-trust device authentication architecture. - Quality & Specifications: Comprehensive test coverage (including unit and property-based testing) driven entirely by formal requirement specifications (IEEE 830 format). What You'll Own: - Production Deployment Pipeline: Perfecting CI/CD pipelines (Main - Staging - Prod) with automated canary releases and rollback protocols. - Observability Stack: Structuring distributed tracing, centralized logging, alerts, and system health dashboards (CloudWatch, X-Ray, or equivalent). - Reliability Engineering: Defining SLOs, managing error budgets, capacity planning, and auto-scaling boundary configurations. - Security Operations: WAF tuning, automated secrets rotation, IAM least-privilege auditing, and penetration test coordination. - Launch Execution: Formulating the tactical playbook for going live with real enterprise data and payment flows. - Cost Optimization: Serverless cost modeling, reserved capacity scheduling, and compute right-sizing ahead of our launch. What You Won't Do: - Rewrite the Architecture: The platform is serverless-native by design and will remain that way. - Manage a Team (Yet): This is an elite, highly technical, hands-on role. Through the initial launch phase, you and the founder are the engineering team. - Define the Product: The founder owns product vision, domain modeling, and feature specifications. You own the infrastructure pipeline to get it to market safely. Required Experience: - 7+ years of software engineering experience, with 3+ years actively operating production systems at scale. - Deep, hands-on AWS mastery (Lambda, DynamoDB, AppSync/API Gateway, EventBridge, SES/SNS, CDK). - TypeScript utilized as your primary development language. - Python proficiency (core machine learning pipelines and isolated backend computation modules are Python-based). - A proven track record of personally transitioning a product from pre-production to live, active users (not just inheriting a running system). - Deep familiarity with event-driven architectures and eventual consistency patterns. - A strict security mindset—mastery of IAM least-privilege, encryption at rest/in transit, and environment secrets management. - Experience handling on-call rotations and debugging complex production incidents under pressure. Strong Signals: - Active AWS Certified Solutions Architect – Professional or AWS Certified DevOps Engineer – Professional credentials. - Previous startup experience (Series A or earlier) navigating a scaling inflection point. - Real-time systems experience (WebSockets, high-throughput pub/sub architectures). - Deploying and monitoring production ML models. - Privacy engineering experience (data residency optimization, advanced encryption key management). Not a Fit If: - You want to replace our serverless architecture with Kubernetes or traditional container orchestration. - You haven't written production-grade code in the last 2 years. - You prefer redesigning codebases over shipping optimized software. - You require a large team reporting to you to be effective. The Offer & Structure Phase 1 (Initial Sandbox Trial): Hourly or milestone-based engagement executed via Upwork. This serves as our practical pilot to evaluate delivery speed, architectural alignment, and communication chemistry. Phase 2 (Long-Term Conversion): Upon successful execution of pre-launch milestones, this position is structured for a long-term corporate position transition including potential equity assignment, evaluated in full accordance with platform contract-to-hire guidelines. Leadership: Full technical co-leadership. Your fingerprint will be on the production infrastructure and every critical deployment choice. Note: A comprehensive Non-Disclosure Agreement (NDA) and Proprietary Information and Inventions Agreement (PIIA) are strictly required before a technical deep-dive or repository access is granted. About the Founder You will be partnering with a technical CEO who holds a deep certification stack—including AWS Cloud Practitioner (CCP), Solutions Architect Associate (SAA), Machine Learning Engineer Associate, and CTFL (testing discipline). The entire platform was built solo to formal specifications. I am looking for a true production partner, not a replacement. You will be working alongside a founder who understands technology—not a business-only founder handing you a napkin sketch. To Apply: Please submit a brief proposal addressing the following three prompts: 1. Describe a complex system you personally transitioned from pre-production to live users. What broke under real load, and what did you learn? 2. What is your systematic approach during your first 30 days when inheriting an existing, highly structured codebase you did not write? 3. In your experience, what AWS serverless anti-pattern causes the most catastrophic failure or cost bottleneck when scaling?