Jake Gaylor
I build systems a stranger can run on day one. 15+ years across SaaS, AI, infrastructure, and IoT, with a core of delivery: finding what slows a team down, rebuilding it into tools the whole team uses, and putting real metrics in place so decisions stop being guesses. Lately deep in AI, riding the whole arc: from smart line changes in Cursor, to agentic coding with Claude Code, to building frameworks that operate fleets of coding agents.
Along the way: internal coding bots at Block Party, autonomous agents at Cloaked, and Ravi, a funded agent-native SaaS.
Experience
Founder
Ravi
Cofounded an agent-native SaaS that lets AI agents manage their own accounts and secrets. Raised a $400K pre-seed from South Park Commons. Grew to hundreds of users.
Shipped the product end to end: a web SaaS and a cross-platform Flutter mobile app on the Apple App Store, built on prototypes started in 2024. Designed agent-native account, secret, and 2FA management so AI agents can operate their own identities.
Staff Software Engineer
Block Party (acquired by DeleteMe)
Built internal AI and developer tooling for the engineering org, including the framework behind the company's internal coding bots, until Block Party was acquired by DeleteMe in January 2026. Designed and built the framework behind the company's internal AI coding bots.
Staff Platform Engineer → Staff Product Engineer
Cloaked Inc
Started in platform engineering (AWS EKS migration, Git Ops CI/CD, compliance), then moved into product, building autonomous AI agents and a cross-functional ideation portal that drove a sticky, AI-powered onboarding experience. Built a Git Ops-based CI/CD pipeline that accelerated deployments by 30x. Led the migration from legacy PaaS to AWS EKS, with a multi-account model meeting SOC2, ISO 27001, and 27701 compliance.
Built an end-to-end product-analytics stack that enabled data-driven decisions across the company. Built autonomous AI agents with Lang Chain to automate user account management (auto change password, login, and email). Turned those AI agents into a core fundraising narrative and a sticky, AI-powered onboarding experience that boosted adoption and retention.
Launched a cross-functional ideation portal connecting design, product, engineering, and executives with transparent status tracking.
Owner / Co-GM
The Onward Store Steakhouse Owned and managed a full-service steakhouse with 7 staff, generating $500K in annual revenue and overseeing P&L, operations, and vendor relations.
Staff SWE in Developer Experience
Inception Health
Architected AWS CDK infrastructure and tooling for HIPAA-compliant patient care microservices.
Senior Platform Engineer
CyberGRX (now ProcessUnity)
Led cloud-native CI/CD vision and implementation for AWS and Kubernetes.
Senior Cloud Platform Engineer
Cardfree
Managed large-scale PCI-compliant C# installation in AWS.
Senior DevOps Engineer
Protectwise / Inc (Acquired by Verizon)
Operated SRE for petabyte-scale data ingestion platform.
DevOps Engineer
Food Service Warehouse
Built Kubernetes clusters on vSphere using CoreOS technologies.
Software Developer
Mississippi State University
Created grant proposals and custom software for research initiatives.
Skills
MCP Servers & SDKsAgent Orchestration & SandboxingLLM IntegrationAgent-Native Product DesignLangChainAWSKubernetes(EKSGKEk3s)TerraformTailscaleCloudflareInfrastructure as CodeFlux CDArgoCDSOPSTypeScriptJavascriptPythonGoBashDartSQLPostgreRedisCassandraDynamoDB
Skills
AI & Agent Engineering
Cloud Infrastructure
GitOps & CI/CD
Programming Languages
Data & Storage
Distributed Systems
Observability
Product Engineering
Product & Business
Languages
English (native speaker)