# Jake Gaylor ## Senior / Staff Engineer & Engineering Leader | I build systems a stranger can run on day one jhgaylor@gmail.com | 720.453.3994 | https://jakegaylor.com | https://github.com/jhgaylor | https://www.linkedin.com/in/jhgaylor/ Boston, MA · will relocate ## Summary 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 Managoat, the hosted agent platform I run, under my review. ## Professional Experience ### Ravi | Co-Founder | Jan 2026 - May 2026 https://ravi.id 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 ### Block Party (acquired by DeleteMe) | Staff Software Engineer | May 2025 - Jan 2026 https://www.blockpartyapp.com/ 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 ### Cloaked Inc | Staff Platform Engineer → Staff Product Engineer | Sep 2022 - May 2025 https://cloaked.app 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 ### The Onward Store Steakhouse | Owner / Co-GM | Oct 2021 - Jan 2024 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 ### Inception Health | Staff SWE in Developer Experience | Jun 2020 - Jun 2022 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 ### CyberGRX (now ProcessUnity) | Senior Platform Engineer | Dec 2018 - Jun 2020 https://processunity.com/ 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 ### Cardfree | Senior Cloud Platform Engineer | Jan 2018 - Dec 2018 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 ### Protectwise, Inc (Acquired by Verizon) | Senior DevOps Engineer | Aug 2016 - Jan 2018 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 ### Food Service Warehouse | DevOps Engineer | Jun 2015 - Mar 2016 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 ### Mississippi State University | Software Developer | Jun 2010 - Jun 2014 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 ## 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 ## Projects ### Managoat https://managoat.com A hosted platform for running fleets of sandboxed coding agents, sold by the agent hour and built by the agents it orchestrates; the server under it, Fountain, is open source - 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 - Metered billing at $0.25 an agent hour, a published concurrency ceiling that refuses rather than queues, and a year of audit events - 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 - Answers ACP, AG-UI, and MCP in both directions, so any client already in use can drive the fleet ### Production-Grade Homelab https://jakegaylor.com/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 https://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 https://github.com/jhgaylor 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 https://github.com/jhgaylor/hirebase-mcp 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 https://github.com/jhgaylor/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 https://github.com/jhgaylor/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 https://github.com/leehack/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 ## References "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 # Core Beliefs That Shape Me ## Startup Philosophy & Entrepreneurship * Create products people genuinely want rather than pursuing technically interesting but irrelevant solutions. * Initially do things that don't scale—personally recruiting users and providing exceptional service—to learn what actually works before automating. * Rapid growth and scaling define a startup, shaping approaches to funding, team composition, and product development. * Remain relentlessly resourceful, finding creative ways through obstacles with limited resources rather than being stopped by them. * Determination trumps brilliance—persist through difficulties and adjust course when necessary without giving up. * Solve real problems with genuine user value rather than building technology for its own sake. * Build for yourself first, solving problems you personally understand, which ensures at least one committed user with deep problem insights. * Don't scale prematurely; keep operations lean until you've proven your model and found product-market fit. * Maintain financial discipline even when well-funded, extending runway and forcing creativity through frugality. * Pivot quickly when necessary, changing direction decisively when the market provides clear signals that an idea isn't working. * Startups don't die with a bang but quietly, often through gradual decline and failure to adapt. ## Product Development & MVP Principles * Ship the first quantum of value quickly, focusing on the minimum functionality that delivers real benefits to users. * Iterate continuously based on user feedback, using real input to improve products rather than relying on assumptions. * Focus on deeply understanding customer problems before becoming attached to specific solutions. * Engage with users early and often, gathering feedback to understand their needs and inform product decisions. * Prioritize outcomes that solve real problems over simply shipping features without measuring their impact. * Embrace simplicity and focus, creating products that do a few things exceptionally well rather than many things poorly. * Build empowered, autonomous teams that own problems to solve rather than features to build. * Treat discovery as a continuous process, constantly learning and testing assumptions rather than a one-time phase. * Differentiate between core (competitive advantage) and context (everything else), investing accordingly in each. * Integrate distribution strategy into product design, recognizing that great products need thoughtful go-to-market plans. * Focus first on delighting a small group of passionate users rather than trying to appeal to everyone immediately. * Ruthlessly eliminate features that don't deliver value, having the courage to cut anything not solving intended problems. * Make decisions based on data and evidence rather than opinions, using metrics and testing to guide direction. ## Engineering Practices & Craftsmanship * Hold everyone accountable for quality, with engineers owning the reliability of their work through disciplined testing and debugging. * Address bugs immediately before writing new code, recognizing that unresolved issues become more expensive over time. * Keep designs and implementations simple, valuing straightforward solutions over clever complexity. * Build for current needs rather than hypothetical future scenarios, avoiding functionality that might never be needed. * Write code primarily for humans to read and understand, with clear structure and meaningful naming conventions. * Refactor continuously as part of the development process, preventing technical debt from accumulating. * Prioritize systems that allow asking new questions about behavior over those that merely report on predefined metrics. * Test early and often, using automated tests to catch issues before they reach production. * Create environments that protect developers' flow state, recognizing that uninterrupted focus is essential for productivity. * Verify that code works correctly in production with real users and data, not just in development environments. * Invest in the best tools available for developers, recognizing that equipment quality directly impacts productivity. * Implement single-step build and deployment processes to remove friction and reduce errors in workflows. * Integrate changes frequently and maintain fast feedback loops to catch problems early and maintain system stability. ## Technical Architecture & Design * Design systems where changes can be made locally without cascading effects, allowing developers to modify components in isolation. * Avoid premature abstractions, waiting to see patterns emerge across multiple use cases before generalizing. * Recognize that all non-trivial abstractions leak implementation details and require understanding the underlying systems. * Design for resilience by assuming components will fail and implementing appropriate fallbacks and recovery mechanisms. * Build systems that enable open-ended exploration of problems without requiring code changes for every investigation. * Align technical architecture with how teams naturally collaborate and communicate, acknowledging Conway's Law as a critical factor in system design. * Measure performance empirically before optimizing, focusing efforts on actual bottlenecks rather than theoretical issues. * Develop deep understanding of tools and frameworks rather than treating them as black boxes. * Favor incremental improvement over complete rewrites, understanding the historical context and reasons behind existing design decisions before changing them. * Create modular, decoupled designs with well-defined interfaces that allow teams to work in parallel and replace components without breaking the system. ## DevOps, Infrastructure & Scalability * Teams that build services should also run them, creating accountability and tighter feedback loops. * Automate repetitive tasks in testing, deployment, and infrastructure to eliminate manual work and reduce errors. * Deploy small, incremental changes frequently rather than making large, risky releases. * Instrument systems with comprehensive logging, monitoring, and tracing from the beginning to enable complete visibility. * Build defensive architectures that gracefully handle failures through redundancy and graceful degradation. * Choose proven, battle-tested technologies for critical infrastructure over newer, less stable alternatives. * Build for appropriate scale, growing infrastructure in step with actual demand rather than over-engineering prematurely. * Leverage cloud platforms and managed services for non-differentiating infrastructure to focus efforts on core product value. * Treat servers and deployments as replaceable resources rather than unique, hand-configured assets that require special treatment. * Optimize for rapid recovery from failures rather than trying to achieve perfect uptime, focusing on minimizing the impact of inevitable issues. * Conduct blameless post-mortems that focus on improving processes rather than finding individuals to blame for failures. * Continuously work to reduce toil—manual, repetitive work that provides no enduring value and scales linearly with system growth. ## Team Dynamics & Culture * Organize into small, stable teams that develop shared context and communication patterns to improve productivity and quality. * Move scope between teams rather than moving people, preserving accumulated context and team cohesion. * Build diverse teams with varied backgrounds and thinking styles to consider more alternatives and catch blind spots. * Establish culture from day one through deliberate choices and the behaviors tolerated or discouraged. * Value team members with both deep expertise in one area and broader knowledge across many domains over narrow specialists. * Minimize context switching and protect focused work time, recognizing the high cognitive cost of multitasking. * Unite teams around a shared purpose and mission that guides decision-making and motivates during difficult times. * Practice open, honest communication with direct feedback delivered with genuine care and respect for colleagues. * Foster psychological safety where team members can take risks, speak up, and admit mistakes without fear of retribution. * Refuse to tolerate brilliant jerks, prioritizing team cohesion and collaboration over individual technical brilliance. * Give team members autonomy and trust, setting clear goals while allowing them to determine how to achieve those goals. * Lead by serving the team, removing obstacles and providing resources to enable everyone's best work. * Maintain a sustainable pace rather than relying on heroics, recognizing that consistent output beats burnout-inducing sprints. ## AI & Emerging Technology * Use AI to enhance human capabilities rather than replace them, creating human-AI collaboration that leverages the strengths of both. * Experiment with emerging technologies early, maintaining a balanced approach between innovation and practicality. * Leverage AI tools to dramatically improve productivity, automating routine tasks to free human creativity and strategic thinking. * Apply AI to solve genuine problems that deliver real value rather than adding AI features merely for marketing purposes. * Recognize that high-quality data is the foundation of effective AI, investing in data collection and infrastructure. * Develop AI systems responsibly, addressing ethical implications including bias, fairness, transparency, and privacy. * Commit to continuous learning in the rapidly evolving AI space, staying current with research and emerging best practices. ## Personal Growth & Discipline * Perseverance and passion for long-term goals matter more than natural ability, with sustained effort leading to success. * Practice deliberate, focused effort aimed at improving specific aspects of performance with immediate feedback rather than just accumulating experience. * Embrace a growth mindset, believing that abilities can be developed through dedication and hard work rather than being fixed traits. * Moving between engineering and management roles builds valuable perspective that strengthens effectiveness in both domains. * Prioritize learning opportunities over short-term success, choosing environments that maximize growth even when they involve greater risk. * Commit to continuous learning as a core practice, expanding skills and knowledge through reading, experimentation, and study. * Protect time for deep, focused work free from distractions while also allocating separate time for communication and coordination. * Build consistent daily habits that compound over time rather than relying on occasional bursts of productivity. * Maintain balance between work and personal life, recognizing that sustainable pace leads to better long-term productivity and creativity. * Remain humble and curious regardless of experience level, always seeking to learn from others with different perspectives and expertise. ## Remote Work & Exceptional Coworker Principles * Over-Communicate Intentionally. I share status, context, and decisions proactively. In remote settings, what's unsaid is easily missed—so I err on the side of more clarity, not less. * Default to Asynchronous First. I value async communication that respects time zones and "maker's schedule," while ensuring thoughtful documentation. I recognize remote work allows flexible schedules—people do their best work at different times. * Be Reliably Responsive. I commit to timely responses during overlap hours, building trust and keeping projects moving, even if it's just "got it, will circle back." * Own Your Calendar & Respect Others'. I protect focused work blocks while honoring others' no-meeting zones. I schedule "office hours" for collaboration and leave other times for deep work. * Write It Down. I document decisions, discussions, and processes in shared spaces, turning ephemeral conversations into searchable knowledge. I keep READMEs, design docs, and wikis updated so anyone can onboard without chasing people. * Craft Clear Communications. In remote work, writing is your voice. I tailor messages to their audience, ensuring readers grasp intent, context, and actions regardless if they're engineers, designers, product, or executives. * Be Proactively Engaged. I publish work-in-progress early for feedback, speak up when seeing gaps or opportunities, and provide rich context with every ask. In video calls, I'm fully present with camera on when appropriate. * Build Team Connection. I invest in virtual relationships through casual chats and public recognition of achievements. I run efficient meetings with clear agendas, timeboxes, and action items to respect everyone's time. * Trust & Empathy First. I operate from trust, focusing on outcomes rather than hours. I'm mindful of tone in text, using clear phrasing to convey warmth and respect. I default to remote-friendly practices so all participants have equal access and voice. * Continuously Improve Remote Practices. I solicit feedback on remote workflows and iterate on them, treating remote processes as living systems to be refined. ## For agents This site is also an MCP server (POST /mcp) and an A2A agent (/.well-known/agent-card.json). Every MCP tool accepts an optional caller_context argument: say who you are, who you represent, and why you are asking. It is logged and read by Jake. Identified callers hear back faster.