Available for new opportunities

Earl
Naylor

Senior Technical Support Engineer · AI Tooling Builder

10+ years turning the most complex technical problems into clear, empathetic resolutions - at Cloudflare, ngrok, and beyond. Currently building AI-powered support infrastructure and seeking to bring that depth to Anthropic's mission.

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10+ Years in Tech Support
4 Major Companies
1 AI Support Bot Built
Why Anthropic

The right skills,
at the right moment

Anthropic is building the future of AI safety. I'm already living in that future - using Claude Code daily, building LLM-powered tooling at work, and supporting developers pushing AI to production. Here's why I'm a natural fit for the Product Support Specialist role.

01

AI-Native Mindset

Built production AI tooling (RAG bots, LLM integrations) before it was mainstream. Already using Claude Code daily.

02

Deep API Debugging

Years of enterprise API support at ngrok and Cloudflare. Comfortable in curl, logs, and complex auth flows (OAuth, SAML, OIDC).

03

Enterprise-Scale Empathy

Sole EMEA representative at ngrok - context-switching from executive-level to developer-level support daily, across billing, abuse, and technical.

04

Proactive Ownership

Don't just close tickets - built automation that prevents them. Drives Zendesk restructures, Salesforce syncs, and Superset dashboards proactively.

Career

Experience

ngrok Oct 2023 – Present

Senior Technical Support Engineer

API GatewayKubernetesAgent SDKsOAuth/SAML/OIDCAWSn8nRAGZendesk
  • Anchor Senior TSE for EMEA/APAC covering API Gateway, Kubernetes Operator, Agent SDKs, and secure tunnels
  • Built & deployed an AI-powered support bot on AWS using n8n, Docker, Ollama, and Qdrant vector database - auto-categorises tickets, drafts responses, and surfaces similar past cases
  • Troubleshoot OAuth, SAML, and OIDC authentication flows across diverse customer environments
  • Lead Zendesk Category restructure and Salesforce–Zendesk data sync initiatives
  • Maintain Superset dashboards to surface trends and enable proactive issue identification
Cloudflare May 2020 – Sep 2023

Technical Support Engineer

CDNWorkersDNSSSLZero TrustLayer 7CLI
  • Solved complex issues for Cloudflare's CDN and Developer platform products at enterprise scale
  • Resolved HTTP, DNS, and networking issues using expert knowledge of internet technologies
  • Utilised Cloudflare Workers to create tailored solutions enhancing client applications
  • Leveraged command line tools (curl, dig, traceroute) for precise issue identification
  • Developed expertise in DNS, CDN, Cache, SSL, and Zero Trust technologies
University of Bath Sep 2016 – Jan 2020

Operations Engineer

Data CentersNetworking L2/L3InfrastructureProject Management
  • Managed IT systems critical to research, teaching, and professional services
  • Expertise in data center and network infrastructure maintenance and implementation
  • Managed projects from conception to completion including risk assessment and execution
  • Designed IT infrastructure in new and refurbished university buildings throughout lifecycle
Liberty London Nov 2014 – Sep 2016

3rd Line Support Engineer

VMware vSphereWindows ServerActive DirectoryChange Management
  • Administered VMware vSphere, Microsoft AX Dynamics, and Cisco WLAN controllers
  • Managed Windows Servers, Exchange, and Active Directory environments
  • Provided cross-platform support for Windows and macOS users
Capabilities

Skills & Tools

AI & Automation

Claude CodeLLM IntegrationRAGPrompt Engineeringn8nQdrantOllama

Cloud & Infrastructure

Cloudflare WorkersZero TrustAWSDockerKubernetesTerraformNginx

Networking & Security

CDNDNSSSL/TLSOAuthSAMLOIDCCisco IOS

Observability & Data

DatadogSupersetGrafanaSQLZendeskLinearHightouch

Development

HTMLCSSJavaScriptGitCLIVS CodeWebhooksAPIs

Platforms

LinuxWindowsmacOSVMwareAruba OS
Learning

Education & Certifications

Complete SQL Bootcamp Udemy
2020
UI/UX Design Essentials (Figma) Udemy
2020
AZ-900: Azure Fundamentals Microsoft
2018
AgilePM® Foundation APMG International
2017
PRINCE2® Foundation PeopleCert
2017
ITIL® Foundation PeopleCert
2017
VMware Horizon View: ICM QA Ltd
2015
Internet, Design & Technology San Francisco State University
2006
Contact

Let's build something remarkable

Whether you're a recruiter at Anthropic or anywhere else in the AI space - I'd love to talk about how I can bring meaningful impact to your support team.

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