Jake Gaylor

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

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

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.

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

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

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

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

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

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