Jonathan Waddingham / AI work and prototypes

AI work built to survive real workflows.

I help teams move from AI curiosity to working tools, sharper decisions, and repeatable delivery. The examples here show internal transformation work, rapid prototype sprints, and practical automations tested in real use.

Build First. Learn Fast.

The work here spans professional delivery, internal transformation, and rapid personal prototyping. Some of it was built inside teams. Some of it was built solo. All of it comes from the same belief: the fastest way to learn what AI is actually good for is to build something usable and put it in context.

I care most about AI when it becomes part of a workflow: removing friction, sharpening judgement, speeding up execution, or opening up a genuinely better way of working.

Products That Pressure-Test the Tools.

Alongside structured client and team work, I build products to explore ideas and solve real problems. It keeps me hands-on and keeps the tooling, patterns, and workflows honest.

Featured side project

Hailo

Charity Voice AI Multi-agent

Hailo is a calm, voice-led tool that helps people work out what they actually care about, then shows them the charities already doing that work. Instead of a search box that assumes you can name the cause, it runs a short reflective conversation, draws your answers back to you as a single woven thread, and only then suggests organisations that fit.

It is built as three deliberately separate AI agents, so the part you talk to can never recommend or sell, your voice is processed as you speak and discarded, and every match traces back to a line in your own words. A bigger, more ambitious build than the quick utilities below, made solo with AI-assisted tools.

The Hailo landing page with the headline find the causes you never knew you cared about.
A woven Hailo circle drawn from the user's answers, labelled your Halo.
Charity match cards showing fit labels and quotes from the user's own conversation.
Even Stevens app screenshot
01

Even Stevens

Grassroots football coaching app that tracks players, substitutions, and playing time. Designed for real-time use on the touchline and built solo using AI-assisted tools.

Oxford Cycle Parking Map screenshot
02

Oxford Cycle Parking Map

Simple utility for finding cycle parking in Oxford. Map-based, fast, and mobile-friendly, built to solve a real local problem without unnecessary complexity.

Between Sessions screenshot
03

Between Sessions

Conference planning tool that turns a crowded programme into a usable daily plan, maps sessions across Oxford with walking times, and suggests useful stops between events.

The Hinksey Park FC Summer Party tournament app home screen showing live events
04

HPFC Summer Party

Live tournament app built in a day at a “Dadathon” to run the Hinksey Park FC summer party. Results update instantly, fixtures stay in sync, and parents follow everything live from their phones, across 10 teams and 60+ kids.

“What was different was (Rob and) Jonathan’s amazing tournament app he’s developed that did away with white boards, fixture grids, and maths on the go!” — Tournament coach

How I Pressure-Test AI Ideas.

01

Start with a Real Problem

Begin with something people genuinely experience and would notice being solved.

02

Build Something Usable Quickly

A working prototype creates more learning than a long speculative plan.

03

Test in Real Conditions

Put it in front of the people who would actually use it, inside the constraints they really have.

04

Iterate on What Works

Follow the evidence, keep what proves useful, and strip away what does not.

Talks, Lessons, and Practical Walkthroughs.

I occasionally share how I approach AI in practice, with a bias toward building quickly, testing with real people, and learning in public.

Bring me in to build, test, and ship.

I work either as a senior product leader inside the team or through focused advisory support around AI, product strategy, and delivery.

Full-time

Senior Product Leadership

  • CPO, VP Product, or Head of Product roles
  • Leading product, design, data, and engineering work together
  • Owning strategy, execution, and outcomes rather than just roadmap process
  • Particularly strong in AI-enabled products and mission-driven organisations
Fractional / advisory

AI & product advisory

  • Rapid AI opportunity assessment grounded in real workflows
  • Prototype sprints to test ideas quickly with genuine users
  • Support for embedding AI into team practice, not just tooling demos
  • Hands-on guidance where delivery matters as much as strategy
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