James Watling

James Watling

Senior Manager, Engineering @ Spring Health

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Core Competencies

Leadership

Strategic Leadership Team Building Product Strategy Startup Scaling M&A Experience

Technical

Ruby on Rails React/React Native Next.js GraphQL AWS/GCP TypeScript

AI & Tools

Claude Code Claude Opus AI/LLM Integration Agentic AI

Process

Agile/Scrum DevOps CI/CD

Open To

Engineering Leadership (CTO/VP/Director)
First Engineering Hire
Technical Due Diligence for Acquisitions
Technical Hiring Consulting

Contact

Interested in discussing technology, development, or potential collaborations?

Executive Summary

Engineering leader with 13+ years of experience in startup growth and technical innovation. Track record of successful exits and fundraising rounds totaling $39M+. Expert in building high-performing remote teams and implementing AI solutions.

Most recently driving AI-powered engagement features and platform transformation at Spring Health. Previously led provider experience transformation at Wonderschool post-acquisition of EarlyDay, where as Founding CTO secured $4M+ in funding. Expert at taking products from zero to one and building and scaling teams to support business goals.

Passionate about leveraging AI and emerging technologies to solve complex business challenges. Active user of Claude Code, Claude Opus, and agentic AI tools to push the boundaries of AI-assisted software development.

Experience Timeline

Senior Manager, Engineering - Spring Health

March 2025 - Present

  • Oversee 15 engineers across two teams, driving platform reliability and feature delivery
  • Led overhaul of video therapy platform, improving stability and patient experience
  • Drove AI-powered engagement features, reducing member ejection rate from 16% to 6%
  • Hiring and mentoring engineers, building a high-performance engineering culture
Team Leadership AI/ML Platform Reliability Video Platform Healthcare

Senior Engineering Manager - Wonderschool (Series B)

February 2024 - March 2025

  • Led multiple engineering teams (14 engineers) across distributed tech stacks and projects
  • Implemented new SDLC improving deployment frequency by 300% and reducing support tickets by 85%
  • Established structured hiring process, successfully scaling team with 8 direct hires
  • Drove technical strategy and platform consolidation post-acquisition
Team Leadership SDLC Rails Next.js GCP

Founding CTO - EarlyDay

Acquired by Wonderschool

February 2022 - February 2024

  • Built product from scratch and scaled to processing 100,000s of job matches and recommendations
  • Led growth from solo founder to team of 6 engineers with 100% retention through acquisition
  • Pioneered AI implementation reducing approval time from 48 hours to <2 minutes
  • Scaled platform to handle 1000s of new users monthly while maintaining performance
  • Secured $4M+ in funding and led technical due diligence for successful acquisition
Technical Leadership Fundraising M&A Rails React

Senior Software Engineer - Hub

December 2018 - February 2022

  • Collaborated with LinkedIn co-founder Eric Ly on revolutionary blockchain-based trust protocol
  • Key contributor to successful $20M token sale through technical leadership and presentations
  • Architected and developed core platform features using Ruby on Rails and React Native
  • Led implementation of blockchain integration for reputation management system
  • Mentored junior developers and established coding standards
Blockchain Rails React Native Token Sale Technical Leadership

Senior Front End Developer - KarmaCheck

$15M Series A

November 2019 - March 2020

  • One of first two developers building MVP for Hub sister company
  • Contributed to successful $15M Series A funding round
  • Set foundation for product architecture and development practices
  • Continued as board advisor after returning to Hub
Frontend Development MVP Development Fundraising Advisory

Team Lead - GuavaPass

Acquired by ClassPass

November 2016 - December 2018

  • Led 5-person development team through successful acquisition by ClassPass
  • Managed product roadmap and technical architecture for fitness marketplace platform
  • Implemented agile methodologies and DevOps practices improving deployment frequency by 300%
  • Conducted technical due diligence during M&A process
  • Mentored team members through career development and technical growth
Team Leadership Rails React Native AWS M&A

Senior Ruby on Rails Developer - Roomorama

September 2014 - October 2015

  • Developed and maintained high-scale property listing platform serving millions of monthly visitors
  • Built robust integrations handling 100,000+ property listings with real-time pricing
  • Improved platform performance and reduced response times by 40%
  • Implemented comprehensive test coverage and documentation standards
  • Collaborated with international team using agile methodologies
Rails API Integration High Scale Performance Testing

Web Developer - Catch Design

September 2013 - October 2014

  • Developed solutions for major NZ companies including KiwiRail and 2degrees
  • Implemented backend systems and third-party integrations
  • Built customer communication management system for 2degrees business customers
  • Integrated ElasticSearch and designed mock backend systems
Rails ElasticSearch System Integration Backend Development

Managing Director - Consilio

January 2013 - October 2014

  • Provided Rails consulting services for small/medium businesses in Wellington region
  • Led requirements analysis, system design and development
  • Managed client relationships and project delivery
Rails PostgreSQL Redis Consulting

Technology Director - Tendersave

September 2012 - January 2014

  • Led team of 4 developers building tender management platform
  • Served as director aligning business goals with technical direction
  • Managed full project lifecycle from conception to deployment
Technical Leadership Rails jQuery Project Management

What I'm Working On Now

AI-Powered Healthcare at Spring Health

Driving AI-powered engagement features and platform transformation. Leading engineering teams to improve mental healthcare delivery through technology.

Claude Code & AI-Assisted Development

Daily user of Claude Code (powered by Claude Opus) for software development. Building with agentic AI workflows to ship faster and explore the frontier of AI-assisted engineering.

Agentic AI & Open Source

Contributing to and experimenting with open-source AI tools like OpenClaw. Building agentic systems and exploring multi-agent orchestration for real-world applications.

Current Tech Stack & Tools

Claude Opus Claude Code OpenAI GPT-4 OpenClaw Agentic AI Cursor.sh Ruby on Rails React TypeScript Next.js GCP AWS GraphQL AI/LLM Integration
old portfolio website