James Watling

Engineering Manager at Wonderschool

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

Process

Agile/Scrum DevOps CI/CD

Open To

Fractional CTO Roles

Technical Due Diligence for Acquisitions

Technical Hiring Consulting (via Tech Talent Vet)

Contact

Interested in discussing technology, development, or potential collaborations?

LinkedIn Calendly Github What I'm doing now

Executive Summary

A seasoned technology leader with over 12 years of experience, specializing in startup growth and technical innovation. Currently leading provider experience transformation at Wonderschool following a successful acquisition of EarlyDay, where as Founding CTO, secured over $4M in funding and built a high-performing remote team.

Proven track record in strategic leadership, having contributed to multiple successful exits and fundraising rounds totaling over $39M across EarlyDay, Hub Token ($20M), and KarmaCheck ($15M). Deep expertise in modern technology stacks including Ruby on Rails, React, and cloud infrastructure.

Passionate about leveraging AI and emerging technologies to solve complex business challenges, with recent focus on integrating Large Language Models and AI agents into production environments.

Experience Timeline

Engineering Manager (Provider Experience) - Wonderschool

February 2024 - Present

Leading technical integration and team alignment post-EarlyDay acquisition
Managing multiple product teams (14 engineers) across distributed tech stacks
Spearheading AI initiatives to enhance provider experience and operational efficiency
Driving architectural decisions for platform consolidation

Team Leadership Product Strategy Rails Next.js GCP

Founding CTO - EarlyDay

Acquired by Wonderschool

February 2022 - February 2024

First employee and technical founder, securing $4M+ in funding
Built and led remote engineering team across US and LatAm
Architected scalable platform serving multiple US metro areas
Established engineering practices and technical vision
Led technical due diligence during acquisition process

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 Integration at Wonderschool

Leveraging OpenAI/Claude to enhance product capabilities and user experience. Building AI-powered features to streamline early childhood education processes.

→

AI Development Tools Exploration

Experimenting with cutting-edge AI tools including Cursor editor and Devin AI agents to enhance development workflows.

→

Agentic AI Research

Building and experimenting with agentic AI systems to understand their potential in software development and automation.

Current Tech Stack & Tools

OpenAI GPT-4 Claude Cursor.sh Devin AI AI Agents Ruby on Rails GCP AWS Ruby Rails React Tailwind Nest GraphQL