# JAKE GAYLOR ## Technical Cofounder | AI/Platform Engineer ## Senior Software Engineer & Product Founder | End-to-End Product Development & Go-to-Market jhgaylor@gmail.com | 720.453.3994 | https://jakegaylor.com | https://github.com/jhgaylor | https://www.linkedin.com/in/jhgaylor/ Remote First, Will Travel ## SUMMARY 15+ years building and shipping products at scale—from founding SaaS ventures to architecting AI-powered platforms. I combine deep SWE expertise with business leadership to drive product vision, go-to-market strategy, and revenue growth. ## PROFESSIONAL PHILOSOPHY - Shipping fast and learning fast - Delivering MVP in days rather than months - Data-driven iterations and continuous user feedback - Supercharging teams with best-in-class development workflows - Automated testing and deployment - Finding product-market fit through data-driven feature development ## PROFESSIONAL EXPERIENCE ### Cloaked Inc | Staff SWE, Office of the CEO | Aug 2023 - Present https://cloaked.app - Driving innovation and technological vision at the executive level - Created a program to ingest ideas from throughout the company with status feedback - Collaborated with executives, product management, and marketing to transform concepts into marketable ideas - Documented roles and ceremonies within the ideation process to facilitate knowledge transfer ### Cloaked Inc | Staff Platform Engineer | Sep 2022 - Aug 2023 https://cloaked.app - Led cloud infrastructure migration and established deployment patterns ensuring compliance and scalability - Migrated all software stacks from various PaaS providers to AWS EKS - Implemented Cloudflare to mask third-party usage and create a control layer for resilience - Migrated single shared AWS account to a spoke and wheel model meeting SOC2 1&2, ISO 27001 and 27701 compliance - Established patterns for Kubernetes and edge network deployments while maintaining compliance requirements - Crafted CI pipeline that accelerated deploys by 30x - Built and showcased product analytics stack to enable data-driven decision-making ### The Onward Store Steakhouse | Owner / Co-GM | Oct 2021 - Jan 2024 - Managed all aspects of restaurant operations from infrastructure to HR and vendor relationships - Managed physical infrastructure including building, grounds, utilities, network, and A/V systems - Handled hiring, firing, HR, taxes, and legal responsibilities - Worked with vendors to maintain fresh selection and food margins - Developed processes and trained staff to serve fresh never frozen food ### Inception Health | Staff SWE in Developer Experience | Jun 2020 - Jun 2022 - Built AWS infrastructure and tooling for HIPAA-compliant software delivery - Created AWS infrastructure and CDK packages to maintain HIPAA Compliance while enabling team autonomy - Trained product teams to work in serverless environments and maintain gRPC contracts despite AWS limitations ### CyberGRX (now ProcessUnity) | Senior Platform Engineer | Dec 2018 - Jun 2020 https://www.cybergrx.com - 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 ### Cardfree | Senior Cloud Platform Engineer | Jan 2018 - Dec 2018 - Managed large-scale PCI-compliant C# installation in AWS - Established best practices for reliably building software and managing incident response ### Protectwise, Inc (Acquired by Verizon) | Senior DevOps Engineer | Aug 2016 - Jan 2018 - 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 ### Food Service Warehouse | DevOps Engineer | Jun 2015 - Mar 2016 - 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 ### Mississippi State University | Software Developer | Jun 2010 - Jun 2014 - Created grant proposals and custom software for research initiatives - Developed software for tracking 'human sensors' through natural disasters including Hurricane Sandy ## SKILLS ### AI Engineering (Advanced) LangChain, Crewai, Custom Agent Framework, MCP Servers, LLM Integration ### Cloud Infrastructure (Expert) AWS, Kubernetes, EKS, GKE, vSphere, Terraform, Infrastructure as Code, Cloudflare, Packer, Vagrant, Linux, Chef ### CI/CD & DevOps (Expert) GitOps, ArgoCD, Argo Workflows, Jenkins, Github Actions, Gitlab CI, Continuous Deployment, Fleet, Docker ### Programming Languages (Advanced) Javascript, Python, Bash, Go, Ruby, Dart ### Databases (Advanced) Neo4j, PostgreSQL, Timestream, MongoDB, Redis, Etcd, Zookeeper, Cassandra, DynamoDB ### Distributed Systems (Expert) Kafka, RabbitMQ, AWS IoT, Big Data, Spark, EMR ### Monitoring (Advanced) Prometheus, CloudWatch, Sensu, Pagerduty, Logstash, Kibana, Grafana, Graphite ### Product Engineering (Expert) Data-driven Iteration, Feature Development, User Feedback Loops, MVP Development, Product Analytics ## LANGUAGES English (Native speaker) ## PROJECTS ### AI Agent Suite https://github.com/jhgaylor - 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 https://github.com/jhgaylor - 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 and experimentation ### LLM-Driven Job Search Mobile App https://jakegaylor.com - Developed a mobile application with a Tinder-like LLM interface without a chat UI - Built intuitive swipe-based like/pass interface for interacting with LLMs - Implemented AI-driven content generation and response system - Created responsive mobile-first user experience ## PERSONAL WEBSITE Jake maintains a professional website at jakegaylor.com where he markets himself as a potential technical co-founder with 15+ years of experience helping companies build better tech organizations, launch products, and grow confidently. ## REFERENCES & CLIENT TESTIMONIALS "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." - Director 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." - 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 Jake has been praised for: - Technical leadership at ProtectWise (acquired by Verizon) - Accelerating deployment cycles at Food Service Warehouse - Infrastructure migration and CI pipeline improvements at Cloaked - Rebuilding deployment processes at CyberGRX (now ProcessUnity) - Energy and tool-building skills at Magic # 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.