Senior / Staff Engineer & Engineering Leader

Jake Gaylor

I make good teams ship like great ones.

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: autonomous agents at Cloaked, the framework behind Block Party's internal coding bots, and Ravi, a funded agent-native SaaS.

jhgaylor@gmail.com 720.453.3994 jakegaylor.com github.com/jhgaylor linkedin.com/in/jhgaylor Boston, MA · will relocate ai.jakegaylor.com · for your AI assistant

Work

Co-Founder

Jan 2026 – May 2026 · 4 mos

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

May 2025 – Jan 2026 · 8 mos

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

Sep 2022 – May 2025 · 2 yrs 8 mos

Cloaked Inc

Started in platform engineering (AWS EKS migration, GitOps 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 GitOps-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 LangChain 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

Oct 2021 – Jan 2024 · 2 yrs 3 mos

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.

  • Led a team of 7 employees, handling recruitment, training, scheduling, and performance management.
  • Directed all facets of business operations, achieving $500K in annual revenue through strategic inventory management and cost control.
  • Designed and implemented operational processes for facility maintenance, vendor partnerships, and quality assurance, driving consistent customer satisfaction.
  • Managed P&L, budgets, and financial reporting, optimizing expenses and improving profit margins.
  • Executed marketing and community engagement initiatives to increase local brand awareness and repeat patronage.

Staff SWE in Developer Experience

Jun 2020 – Jun 2022 · 2 yrs

Inception Health

Architected AWS CDK infrastructure and tooling for HIPAA-compliant patient care microservices

  • Led delivery of AWS CDK infrastructure for patient care microservices platform, ensuring HIPAA compliance and deep AWS integration
  • Collaborated with AWS and partner teams to integrate managed services and accelerate platform development
  • Championed CDK usage across application tiers, designing IaC patterns for teams to consume and interact with the platform
  • Implemented CI/CD pipelines for mobile apps, automating TestFlight and App Store releases through Git, enabling self-serve deployments
  • Trained and mentored product and mobile development teams on CDK, serverless architectures, and CI/CD workflows, fostering autonomy

Senior Platform Engineer

Dec 2018 – Jun 2020 · 1 yr 6 mos

CyberGRX (now ProcessUnity)

Led cloud-native CI/CD vision and implementation for AWS and Kubernetes

  • Led vision on cloud-native CI/CD pipelines for AWS and Kubernetes
  • Developed custom resource using CoreOS operator SDK for orchestrating blue/green deployments
  • Redesigned build and deploy process that dramatically improved team productivity
  • Mentored software engineers in best practices for building and deploying software
  • Grew into Staff Engineer role by owning large-scope initiatives, collaborating with the Tech Lead to drive interactions across the organization and unblock progress

Senior Cloud Platform Engineer

Jan 2018 – Dec 2018 · 11 mos

Cardfree

Managed large-scale PCI-compliant C# installation in AWS

  • Managed a large-scale PCI-compliant C# installation in AWS
  • Architected hybrid AMI build and deploy platform using Packer and Vagrant, enabling consistent Windows and Linux EC2 deployments for C# and Ruby services
  • Standardized infrastructure-as-code practices to pave the way for open-source .NET migration
  • Developed and launched a structured PCI-compliant incident response program, replacing ad-hoc Slack alerts with a streamlined IR workflow without excessive paperwork

Senior DevOps Engineer

Aug 2016 – Jan 2018 · 1 yr 5 mos

Protectwise, Inc (Acquired by Verizon)

Operated SRE for petabyte-scale data ingestion platform

  • Managed SRE for massive scale data ingestion platform with thousands of Cassandra nodes and petabytes in S3
  • Administered $10M+/yr production AWS environment using Infrastructure as Code

DevOps Engineer

Jun 2015 – Mar 2016 · 9 mos

Food Service Warehouse

Built Kubernetes clusters on vSphere using CoreOS technologies

  • Implemented Kubernetes clusters on vSphere using CoreOS, fleet, etcd, and flannel
  • Accelerated release cycles for Node.js services with container orchestration

Software Developer

Jun 2010 – Jun 2014 · 4 yrs

Mississippi State University

Created grant proposals and custom software for research initiatives

  • Created grant proposals to fund custom software for university research initiatives
  • Developed software for tracking 'human sensors' through natural disasters including Hurricane Sandy

Projects

Full project pages

Production-Grade Homelab

A three-node k3s cluster on M4 Mac minis serving production traffic from home — GitOps-managed, fully observable, photo tour included

  • Flux CD reconciles every manifest from git; secrets live encrypted in-repo with SOPS + age
  • Tailscale WireGuard mesh between Lima VMs with direct LAN paths; Traefik, cert-manager, and oauth2-proxy at the edge
  • Longhorn replicated block storage, Garage S3, CloudNativePG, and Prometheus/Grafana/Loki with alerts pushed to my phone

MCP Working Group Contributions

Active participant in Model Context Protocol (MCP) community development

  • Member of the MCP Hosting Working Group
  • Developed strategies for deploying and running MCP servers at scale
  • Contributed to Dart SDK, Express tool for binding to MCP servers
  • Developed various MCP servers (Hirebase, Candidate Job Search, Text Extraction)
  • Created GitOps tool for MCP deployments
  • Operate publicly available MCP servers for community testing

CareerFlick LLM-Driven Mobile App

Developed a mobile application with a Tinder-like LLM interface

  • Built intuitive swipe-based interface for interacting with LLMs
  • Implemented AI-driven content generation and response system
  • Created responsive mobile-first user experience

Hirebase MCP Server

A Python MCP server for Hirebase.org's API

  • Built a Python-based Model Context Protocol (MCP) server for searching jobs on Hirebase.org
  • Dockerized the service and set up GitOps CI/CD pipelines for automated builds and releases

Express MCP Handler

Package to simplify MCP handling in Express.js

  • Developed Express middleware in TypeScript to streamline MCP request handling
  • Authored full type definitions and robust error handling for production-grade reliability
  • Configured CI/CD pipelines to automate code validation and package publishing

Node Candidate MCP Server

A TypeScript library to build customizable candidate MCP servers

  • Authored a reusable library enabling developers to integrate their own candidate data into MCP flows
  • Published as an npm package for easy adoption and extension by other teams

mcp_dart

Dart SDK implementation of the Model Context Protocol (MCP)

  • Contributed stream based support for in-process MCP servers
  • Add support for running MCP servers in flutter apps
  • Authored Dart examples to accelerate SDK adoption

Skills

AI & Agent Engineering

MCP Servers & SDKs Agent Orchestration & Sandboxing LLM Integration Agent-Native Product Design Agent Memory LangChain

Cloud Infrastructure

AWS Kubernetes (EKS, GKE, k3s) Terraform Tailscale Cloudflare Infrastructure as Code

GitOps & CI/CD

Flux CD ArgoCD Argo Workflows Github Actions SOPS Continuous Deployment

Programming Languages

TypeScript Javascript Python Go Bash Dart

Data & Storage

PostgreSQL Redis Cassandra DynamoDB S3-compatible Object Storage MongoDB

Distributed Systems

Kafka RabbitMQ AWS IoT Event-Driven Architecture

Observability

Prometheus Grafana Loki Pagerduty CloudWatch Product Analytics

Product Engineering

Data-driven Iteration Feature Development User Feedback Loops MVP Development Product Analytics

Product & Business

Roadmapping Customer Discovery P&L Management Go-to-Market Strategy Fundraising

Languages: English (native speaker)

What coworkers say

“Jake is a force for good unlike any other. He migrated our infra to a cheaper and more scalable system, crafted a CI pipeline that accelerated deploys by 30x, and taught the whole company how to make data-driven decisions by building and showcasing an entire product analytics stack. And that was just his first 6 months.”

Aaron Biller, Director of Platform Engineering, Cloaked

“I watched Jake redo a build and deploy process over the span of 3 days, whip up a presentation, and get every engineer in the org up to speed using it to deploy new services, a moment I'll never forget because our productivity EXPLODED afterwards.”

Stephen Bapple, Software Engineer, CyberGRX

“I also wanted to second (third? Fourth?) Jake's skills here. I don't have anything unique to add as everyone else has already covered it, but this man will help you achieve what you need.”

Senior Platform Engineer, Inception Health

“Jake worked in the pit with [the operations team] and everyday came in with killer energy. Everyone else told us how to work around problems. Jake built us better tools.”

Magician, Magic

“Jake was instrumental in building our cloud-native security platform. His technical leadership helped shape our architecture and team practices.”

DevOps Engineer, Protectwise

Sound like your next hire?

I’m open to senior, staff, and engineering leadership roles. The fastest way to find out is a conversation.

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