Senior / Staff Engineer & Engineering Leader

Jake Gaylor

I build systems a stranger can run on day one.

15+ years across SaaS, AI, infrastructure, and IoT. At Cloaked I led the move off a legacy PaaS onto AWS EKS, made deploys 30x faster in six months, and ran that platform as its one-person ops team while the product grew from hundreds of users to hundreds of thousands under SOC 2 and ISO 27001. At CyberGRX I rebuilt a quarterly, manual deploy process and had every engineer shipping on it within 3 days. Agents have been in my production systems since LangChain was new, and today a fleet of coding agents builds Fountain, my agent platform, under my review.

Download PDF 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
Verizon acquired Protectwise
Cloaked staff engineer, 2022–2025
DeleteMe acquired Block Party
ProcessUnity when it was CyberGRX
SOUTH PARK COMMONS backed Ravi

Work

Co-Founder

Jan 2026 – May 2026 · 4 mos

Ravi

Cofounded an agent-native SaaS where AI agents manage their own accounts, secrets, and 2FA.

  • Raised a $400K pre-seed from South Park Commons on the usage data from a v1 instrumented from day one
  • Grew to hundreds of users
  • Shipped it end to end, a web SaaS and a Flutter app on the App Store, from 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 until Block Party was acquired by DeleteMe in January 2026.

  • Designed and built the framework behind the company's internal AI coding bots, treating the agent as another consumer of the developer platform

Staff Platform Engineer → Staff Product Engineer

Sep 2022 – May 2025 · 2 yrs 8 mos

Cloaked Inc

Started in platform engineering with the AWS EKS migration, GitOps CI/CD, and compliance, then moved into product to build autonomous AI agents and the ideation portal behind a sticky, AI-powered onboarding experience.

  • Led the migration from a legacy PaaS to AWS EKS with a multi-account model meeting SOC 2, ISO 27001, and ISO 27701 requirements, and it came out cheaper with more headroom than what it replaced
  • Built a GitOps-based CI/CD pipeline that accelerated deployments 30x in my first 6 months
  • Carried that platform from hundreds of users to hundreds of thousands without a rebuild, as its solo ops team
  • Built an end-to-end product-analytics stack that enabled data-driven decisions across the company
  • Built autonomous AI agents with LangChain that log in to user accounts to change passwords and swap the email on file, then made them a core fundraising narrative and an onboarding experience that lifted retention
  • Launched a cross-functional ideation portal nearly the whole org used, one board from idea to usage report for design, product, engineering, and executives

Owner / Co-GM

Oct 2021 – Jan 2024 · 2 yrs 3 mos

The Onward Store Steakhouse

Owned and ran a full-service steakhouse with my wife, 7 staff and $500K a year in business revenue, P&L on me.

  • Ran the full business lifecycle, from spotting the opportunity through acquisition to a $500K/yr operation
  • Hired, trained, and scheduled a team of 7, learning what each person needed instead of running one playbook over all of them
  • Owned the P&L, budgets, and financial reporting, holding margin through inventory management and cost control
  • Built the operating procedures behind maintenance, vendors, and quality assurance that kept service consistent shift to shift
  • Ran marketing and community engagement that grew local awareness and repeat patronage

Staff SWE in Developer Experience

Jun 2020 – Jun 2022 · 2 yrs

Inception Health

Designed the AWS CDK patterns that product and mobile teams used to ship HIPAA-compliant patient-care microservices themselves, and left both teams running their own deploys.

  • Led delivery of the AWS CDK infrastructure behind a HIPAA-compliant patient care microservices platform
  • Designed IaC patterns application teams consumed directly, so a team could ship a compliant service without a platform engineer in the loop
  • Built mobile CI/CD that turned TestFlight and App Store releases into self-serve deploys from git
  • Collaborated with AWS and partner teams to integrate managed services and accelerate platform development
  • Trained and mentored the product and mobile teams on CDK, serverless, and CI/CD until they ran the platform without me

Senior Platform Engineer

Dec 2018 – Jun 2020 · 1 yr 6 mos

CyberGRX (now ProcessUnity)

Rebuilt build and deploy at a company where shipping was a quarterly manual event, and had roughly 50 engineers across several teams deploying on demand within 3 days.

  • Wrote a Go operator on the CoreOS operator SDK that ran blue/green rollouts as a custom resource, keeping the previous version a selector flip away so a bad deploy was undone in under a minute
  • Redesigned the build and deploy process, presented it to the org, and had every engineer shipping with it inside 3 days
  • Led the vision for cloud-native CI/CD pipelines on AWS and Kubernetes
  • Mentored software engineers in best practices for building and deploying software
  • Grew into a 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

Ran a large-scale PCI-compliant C# installation in AWS and took the hand-built hosts out of it, with every Windows and Linux server coming from one Packer build.

  • Architected a hybrid AMI build and deploy platform with Packer and Vagrant, so a drifted host behind the C# and Ruby services got replaced from the image rather than repaired
  • Standardized infrastructure-as-code practices to pave the way for the open-source .NET migration
  • Replaced ad-hoc Slack firefighting with a structured PCI-compliant incident response program, structured enough for the auditors and light enough that engineers actually followed it

Senior DevOps Engineer

Aug 2016 – Jan 2018 · 1 yr 5 mos

Protectwise, Inc (Acquired by Verizon)

SRE for a petabyte-scale ingestion platform, thousands of Cassandra nodes and Kafka pipelines on a $10M+/yr AWS environment run entirely as code.

  • Managed SRE for a massive-scale data ingestion platform with thousands of Cassandra nodes and petabytes in S3
  • Administered a $10M+/yr production AWS environment with Chef and infrastructure as code
  • Held the platform steady under a product that shipped dozens of times a day and could not miss data

DevOps Engineer

Jun 2015 – Mar 2016 · 9 mos

Food Service Warehouse

Ran production Kubernetes on vSphere in 2015, the year it hit 1.0, and put the Node.js services on the fastest release cycle in the company.

  • Implemented Kubernetes clusters on vSphere using CoreOS, fleet, etcd, and flannel
  • Brought Docker and Kubernetes to a C# and vSphere shop and made containers the release path for the first Node.js backend teams

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

Fountain

A multi-tenant developer platform for running fleets of sandboxed coding agents, built by the agents it orchestrates

  • 400+ PRs merged in its first three months, all agent-written; I set the roadmap and review the work
  • Ships under BinaryBourbon, the GitHub identity my agent fleet works as
  • Sandboxes boot holding one short-lived signed identity, so no long-lived secret ever enters the box and teardown invalidates everything it held
  • An inference proxy injects the model key after the request leaves the sandbox and bills every call to the verified identity, with a budget where the open-ended bill used to be
  • Every feature on three surfaces, a web UI for debugging, a REST API for CI/CD, and a Homebrew CLI with manifest-driven fountain apply
  • Speaks ACP, so any ACP client can drive the fleet

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

ai.jakegaylor.com

A live MCP server and A2A agent card that let a screening assistant interview me directly

  • Any MCP client can read my resume, score my fit against a job description, and build the interview
  • The assistant can draft an email to me from the conversation, the human reviews it, and the server sends it
  • Streamable HTTP and SSE transports, an npm package for stdio-only clients, and llms.txt for everyone else
  • Runs on the homelab k3s cluster, deployed by Flux from git like everything else there

MCP Working Group Contributions

Early participant in Model Context Protocol (MCP) community development

  • Was a member of the MCP Hosting Working Group
  • Developed strategies for deploying and running MCP servers at scale
  • Contributed to the Dart SDK and an Express tool for binding to MCP servers
  • Built MCP servers for Hirebase, candidate job search, and text extraction
  • Created a GitOps tool for MCP deployments
  • Still operate a public Echo MCP server 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

Built Cloaked's autonomous LangChain agents and turned them into a fundraising narrative, then cofounded Ravi so agents can run their own accounts and secrets.

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

Cloud Infrastructure

Led Cloaked's migration to AWS EKS under SOC 2 and ISO 27001; administered a $10M+/yr AWS environment at Protectwise, acquired by Verizon.

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

GitOps & CI/CD

Built the GitOps pipeline that accelerated Cloaked's deploys 30x; Flux CD reconciles my homelab from git the same way.

Flux CD ArgoCD Argo Workflows Github Actions SOPS Continuous Deployment

Programming Languages

Shipped Ravi's Flutter app to the App Store in Dart, wrote CyberGRX's blue/green operator in Go, and put Food Service Warehouse's Node.js services on the fastest release cycle in the company in 2015.

TypeScript Javascript Python Go Bash Dart

Data & Storage

Ran thousands of Cassandra nodes and petabytes of S3 on Protectwise's ingestion platform.

PostgreSQL Redis Cassandra DynamoDB S3-compatible Object Storage MongoDB

Distributed Systems

SRE for Protectwise's petabyte-scale event ingestion platform, the largest-scale system I've operated.

Kafka RabbitMQ AWS IoT Event-Driven Architecture

Observability

Built the product-analytics stack that taught Cloaked to make data-driven decisions; my homelab pages my phone through Prometheus and Grafana.

Prometheus Grafana Loki Pagerduty CloudWatch Product Analytics

Product Engineering

Turned Cloaked's AI agents into an AI-powered onboarding experience that lifted adoption and retention; grew Ravi to hundreds of users.

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

Product & Business

Raised Ravi's $400K pre-seed from South Park Commons; ran a $500K/yr steakhouse with my name on the P&L.

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

“Jake and I ran the AWS behind a petabyte-scale security platform. Thousands of Cassandra nodes, Kafka pipelines, a $10M-a-year bill, all of it managed with Chef and deliberately boring tech. I'd sign up to do it with him again tomorrow.”

Alex Artigues, DevOps Engineer, Protectwise

“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

“We were deploying C# on vSphere when Jake joined our first Node.js backend team. He had been using Docker, we identified Kubernetes as our next step, and Jake hit the ground running. Our Node services had the fastest release cycle in the company.”

Architect, Food Service Warehouse, 2015

“Fountain is dope. Jake built one of the most GOATed models for everyone wanting self sovereignty over agent compute while getting the GrokBot like experience using Buzz.”

Akeem Jenkins, Director of Product Engineering, Piedmont Global

“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

“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

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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Or text me at 720.453.3994, or browse my projects & ventures.