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Jake Gaylor

Jake Gaylor

Technical Cofounder | AI/Platform Engineer

Remote First, Will Travel, US
720.453.3994
English

Background


About

About

15+ years of experience working across the web stack with recent focus on AI engineering, product engineering, and platform engineering. Expert in Kubernetes, GitOps, cloud infrastructure, and AI agent development. Serial entrepreneur with experience running SaaS, PaaS, physical products, and restaurant businesses. Proven track record of transforming engineering teams into product-minded teams and accelerating software delivery through automation and best practices.

Work Experience

Work Experience

  • Staff SWE, Office of the CEOCloaked Inc

    Aug, 2023 - Present

    Spearheaded executive-level innovation by developing autonomous AI agents and a cross-functional ideation portal—driving a highly sticky, AI-powered onboarding experience that boosted user adoption and retention and defined governance processes

    • Developed autonomous AI agents using LangChain to automate user account management tasks such as auto change password, auto login, and auto change email

    • Leveraged these AI agents as a core fundraising narrative and created a highly sticky, AI-powered onboarding experience that significantly boosted user adoption and retention

    • Designed and launched a cross-functional ideation portal engaging design, customer success, engineering, product development, and executive teams with transparent status tracking

    • Partnered with design, product, engineering, marketing, customer success, and co-founders to validate, refine, and ship concepts into market-ready features

    • Defined and documented cross-functional roles, ceremonies, and governance processes to unify ideation and accelerate product delivery across the organization

  • Staff Platform EngineerCloaked Inc

    Sep, 2022 - Aug, 202311 months

    Oversaw strategic AWS EKS migration and architected enterprise deployment governance, compliance frameworks, and GitOps CI/CD pipelines to enhance security, scalability, and developer productivity

    • Defined and executed a strategic migration roadmap transitioning legacy PaaS platforms to AWS EKS, driving cost reduction and scalability

    • Collaborated with cross-functional leadership to implement a Cloudflare control plane, enhancing security posture and resilience

    • Architected and led adoption of a multi-account AWS hub-and-spoke model, ensuring SOC2, ISO 27001, and 27701 compliance

    • Established enterprise Kubernetes and edge deployment standards, mentoring engineering teams in best practices and governance

    • Spearheaded design and implementation of a GitOps-based CI/CD pipeline, accelerating deployments by 30x

    • Partnered with product and analytics teams to develop an end-to-end analytics stack, enabling data-driven decision-making

  • Owner / Co-GM, The Onward Store Steakhouse

    Oct, 2021 - Jan, 20242 years 3 months

    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, Inception Health

    Jun, 2020 - Jun, 20222 years

    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 EngineerCyberGRX (now ProcessUnity)

    Dec, 2018 - Jun, 20201 year 6 months

    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, Cardfree

    Jan, 2018 - Dec, 201811 months

    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, Protectwise, Inc (Acquired by Verizon)

    Aug, 2016 - Jan, 20181 year 5 months

    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, Food Service Warehouse

    Jun, 2015 - Mar, 20169 months

    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, Mississippi State University

    Jun, 2010 - Jun, 20144 years

    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 Experience

Projects Experience

  • AI Agent Suite

    - Present

    Created a suite of AI agents for automated user account management

    • Developed 'auto change password', 'auto login', and 'auto change email' agents

    • Leveraged LangChain, Crewai, and custom homebrew agent framework

    • Implemented production-ready autonomous agents for real-world tasks

  • MCP Working Group Contributions

    - Present

    Active participant in Model Completion 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

  • LLM-Driven Mobile App

    - Present

    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

Skills

Skills

  • AI Engineering

    LangChain

    Crewai

    Custom Agent Framework

    MCP Servers

    LLM Integration

  • Cloud Infrastructure

    AWS

    Kubernetes

    EKS

    GKE

    vSphere

    Terraform

    Infrastructure as Code

    Cloudflare

  • CI/CD & DevOps

    GitOps

    ArgoCD

    Argo Workflows

    Jenkins

    Github Actions

    Gitlab CI

    Continuous Deployment

  • Programming Languages

    Javascript

    Python

    Bash

    Go

    Ruby

    Dart

  • Databases

    Neo4j

    PostgreSQL

    Timestream

    MongoDB

    Redis

    Etcd

    Zookeeper

    Cassandra

    DynamoDB

  • Distributed Systems

    Kafka

    RabbitMQ

    AWS IoT

    Big Data

    Spark

    EMR

  • Monitoring

    Prometheus

    CloudWatch

    Sensu

    Pagerduty

    Logstash

    Kibana

    Grafana

    Graphite

  • Product Engineering

    Data-driven Iteration

    Feature Development

    User Feedback Loops

    MVP Development

    Product Analytics

References

References

  • Director Platform Engineering, Cloaked

    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.

  • Software Engineer, CyberGRX

    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.

  • Senior Platform Engineer, Inception Health

    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.

  • Magician, Magic

    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.

  • DevOps Engineer, Protectwise

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