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Your Next
Technical Cofounder

15+ years of experience helping companies build better tech organizations, launch new products, and grow with confidence.

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Jake Gaylor

How I Accelerate Success

Ship Fast, Learn Fast

Focus on delivering the first quantum of value quickly, then iterate based on real user feedback.

  • MVP in days, not months
  • Data-driven iterations
  • Continuous user feedback loops

Supercharge Your Teams

Deliver faster with proven tools and practices that scale across your organization.

  • Best-in-class development workflows
  • Automated testing and deployment
  • Cost-effective scaling solutions

Find Product Market Fit

Transform engineering teams into product teams that own the full lifecycle from idea to customer value.

  • Data-driven feature development
  • Customer usage insights
  • Value-driven prioritization

Companies I've Helped Grow

I've had the privilege of working with innovative companies to help scale their technology and teams.

Company 1 Logo

Protectwise

Acquired by Verizon

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

- Devops Engineer, Protectwise
Company 2 Logo

Food Service Warehouse

"We were deploying c# on vSphere when Jake joined on our first Nodejs 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
Company 3 Logo

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."

- Director Platform Engineering, Cloaked
Company 4 Logo

CyberGRX

Now ProcessUnity

"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
Company 5 Logo

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."

- Senior Platform Engineer, Inception Health
Company 5 Logo

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."

- Magician, Magic

From Zero to Production

Start with the smallest valuable feature set, then evolve based on real user feedback and data.

Development Philosophy

  • Focus on core user value first
  • Ship early, gather feedback
  • Iterate based on usage data
  • Scale what works

Technical Foundation

  • Production-ready infrastructure
  • Automated testing and deployment
  • Built-in monitoring and analytics
  • Scalable architecture patterns

Development Approach

Quick Starts

From idea to first user value in days

Data-Driven

Every feature backed by usage metrics

Rapid Iteration

Continuous improvement based on feedback

Supercharge Feature Delivery

Stop waiting weeks for features to ship. Eliminate manual tasks. Give your teams the tools and automation they need to go to production with confidence.

Common Pain Points

  • Slow, manual deployment processes
  • Inconsistent environments causing issues
  • Limited visibility into system health
  • Security patches falling behind

The Solution

  • Automated pipelines for instant feedback
  • Infrastructure as code for consistency
  • Real-time monitoring and alerts
  • Automated security updates

Quick Feedback

  • Automated test runs
  • Code quality checks
  • Security scanning

Continuous Delivery

  • One-click deployments
  • Automated rollbacks
  • Environment promotion

Full Visibility

  • Performance metrics
  • Error tracking
  • User analytics

Impact on Your Team

Faster Deployments

Less Manual Work

24/7 System Monitoring

Confidence in Delivery

Build Product Minded Teams

Transform your engineering teams into data driven teams that understand customer needs and deliver measurable business value.

Common Challenges

  • Features built without clear success metrics
  • Limited understanding of customer behavior
  • Disconnect between technical and business goals
  • No feedback loop from production to planning

The Transformation

  • Data-driven feature development and iteration
  • Real user behavior insights inform decisions
  • Clear metrics tied to business outcomes
  • Continuous learning from production data

Analytics That Matter

  • Feature usage tracking
  • User journey mapping
  • Performance impact

Experimentation

  • A/B testing framework
  • Feature flags
  • Controlled rollouts

Customer Feedback

  • In-app surveys
  • Usage analytics
  • Support insights

Results in Teams That

Focus on Customer Value

Make Data-Driven Decisions

Innovate Continuously

Ship with Confidence

Modern Cloud-Native Stack

Leveraging industry-leading tools and practices for rapid, reliable delivery

Platform

  • AWS cloud infrastructure
  • Kubernetes orchestration
  • Cloudflare edge networking
  • Terraform infrastructure as code

Delivery

  • GitOps workflow
  • Continuous Integration pipelines
  • Automated Continuous Deployment
  • Infrastructure automation

Observability

  • Product usage analytics
  • System Telemetry
  • A/B testing
  • Error tracking & Crash Reporting

Are We a Good Fit?

I specialize in modern web technologies and cloud infrastructure. Let's make sure we are a good match.

Great Fits

  • SaaS Applications

    Web applications, APIs, and cloud-native services

  • Infrastructure as Code

    AWS, Kubernetes, Terraform, and modern cloud platforms

  • Developer Experience

    CI/CD pipelines, development workflows, and team productivity

  • Software Delivery

    Deployment automation, monitoring, and operational excellence

  • Technical Leadership

    Architecture decisions, team guidance, and technology strategy

Not Great Fits

  • Design Work

    While I can do a little design work, you dont want me creating your user interfaces.

  • Security Penetration Testing

    While I implement secure practices, I'm not a dedicated security auditor

  • IoT & Firmware Development

    I don't work with embedded systems or hardware-level programming

  • Complex Algorithms

    Deep computer science problems or algorithmic optimization

  • Machine Learning

    While I can integrate ML services, I don't develop ML models