James Watling
AI Engineering Leader
Senior Manager, Engineering @ Spring Health
Cofounder & CTO @ Haestus
Core Competencies
Leadership
Technical
AI & Agentic Tooling
Process
Open To
Contact
Interested in discussing technology, development, or potential collaborations?
Executive Summary
Cofounder & CTO of Haestus, where we build bespoke AI solutions for companies — full complex applications end to end, AI phone bots, RAG systems, and agentic pipelines that automate the work a business actually runs on. Not off-the-shelf wrappers: production systems designed around how each company operates, built to be observable, evaluated, and to compound in value over time.
AI engineering leader with 13+ years building products and high-performing teams across startups and scale-ups. Track record of successful exits and fundraising rounds totaling $39M+, with a focus on turning emerging AI capabilities into production systems that move real business metrics.
Currently driving AI-powered engagement and platform transformation at Spring Health, where AI features cut member ejection rates from 16% to 6%.
Previously Founding CTO at EarlyDay (acquired by Wonderschool, $4M+ raised), where I pioneered AI implementations that cut approval times from 48 hours to under 2 minutes. Expert at taking products from zero to one, hiring, and scaling engineering orgs to meet business goals. Daily driver of Claude Code, the Claude Agent SDK, and multi-agent orchestration at the frontier of AI-assisted engineering.
Experience Timeline
Senior Manager, Engineering - Spring Health (Series E)
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
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
Founding CTO - EarlyDay
Acquired by WonderschoolFebruary 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
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
Senior Front End Developer - KarmaCheck
$15M Series ANovember 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
Team Lead - GuavaPass
Acquired by ClassPassNovember 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
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
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
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
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
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
Projects & Ventures
Where I build AI-native products and pipelines beyond the day job.
Haestus
AI ConsultancyAs Cofounder & CTO, I'm building agentic infrastructure for businesses that want to become AI-native. Haestus designs and ships production AI pipelines — agentic workflows, RAG systems, and LLM automation — that wire directly into how a company already operates. The work starts with finding the manual, high-leverage processes hiding in a business, then replacing them with orchestrated agents that are observable, evaluated, and built to compound: each pipeline makes the next one cheaper to ship. Less “chatbot bolted on the side,” more AI woven through the core of the operation.
The Bot Portfolio
AI ProductAn autonomous AI agent that trades a real $1,000 account — with every decision made fully in public. The agent uses MCP servers to execute real trades with real money, running the full pipeline end to end: it researches the market, reasons through a thesis, places the trade through its tools, and documents every step in a public journal. Anyone can follow the complete decision trail. It's my proving ground for the agentic reasoning, tool use, and guardrails I bring into client work at Haestus.
Referrals & Media
What people I've worked with have to say.
Naga shares his experience working with me — on leadership, building strong engineering teams, and shipping AI-driven products. Click the video to hear it in his own words.
Naga
CTO @ Wonderschool