Chris Rickard

Founder & CEO at Userdoc – Better Software Requirements for AI coding.

Greater Melbourne Area

About

I believe the next big shift in software delivery is not just AI writing code faster. It is AI helping teams understand what they should build in the first place. For 20+ years I’ve worked across software teams in Australia, Canada, and the U.S. as a developer, product leader, and founder. Again and again, I’ve seen the same pattern: projects rarely fail because teams cannot write code. They fail because the requirements are unclear, incomplete, outdated, or misaligned. That is why I founded Userdoc. Userdoc is an AI-powered requirements platform that helps teams create, manage, and maintain living software documentation. It helps businesses generate user stories, acceptance criteria, personas, journeys, and system documentation, and can also reverse engineer existing software into structured product knowledge. My focus is on helping teams connect the dots between business intent, product requirements, engineering execution, and AI-assisted development. Today, I spend most of my time working on: - AI-powered requirements and documentation - Requirements-to-code workflows - Living documentation for complex software systems - Developer and product team alignment - Practical AI adoption inside software delivery Userdoc has helped teams reduce the time spent creating requirements and improve the quality of their software planning. “Userdoc helped is go from a six-week requirements cycle to roughly 3 hours of focused work - our business users can literally shape applications in real time.” - Matt Griffiths, CTO, Stanley Black & Decker “Userdoc's AI cut down the time to create our requirementw, and sped up our software development. Saving Infosys a lot of work.” - Lakshmi Narayana, Technical Manager, Infosys If you’re building software and want your requirements, documentation, and delivery process to keep up with the pace of AI, I’d love to connect. https://userdoc.fyi

Experience

  • Founder & CEO at Userdoc
    Dec 2023 - Present · 2 yrs 8 mos

    Userdoc is an AI workspace for defining and understanding software systems. Teams use it to create clear, structured specs for new software and to make sense of existing or legacy systems - all in one place. Userdoc helps you: • Turn ideas into user stories, acceptance criteria, and detailed specs • Manage requirements through your entire project - before, during, and after delivery • Reverse-engineer existing codebases into human-readable documentation • Understand screens, behaviours, business rules, and interactions • Give AI coding tools the clarity they need to generate reliable software Userdoc is used by Fortune 500s, product teams, consultancies, and enterprises needing fast, accurate definition across the full software lifecycle. “We went from a six-week requirements cycle to roughly three hours of focused work - our business users can literally shape applications in real time.” Matt Griffiths, CTO, Stanley Black & Decker

  • City Lead, Advisor and Community Fellow at Build Club
    Nov 2023 - Present · 2 yrs 9 mos

    AI training campus for top AI learners, experts, builders. Backed by Google, AWS, Github and Microsoft. I help AI builders and startups, lead the bi-weekly co-working.

  • Travel at Career Break
    Oct 2021 - Mar 2023 · 1 yr 6 mos

    🏝️ After selling my software development consultancy, and nearly 20 years in the software business - my wife and I jumped in our motorhome and took off see all the parts of Australia I've never seen. One of the best things I've ever done, gave me a chance to think about what I want for my next adventure.

  • Technical Lead (Acquisition handover) at Portable
    Oct 2020 - Sep 2021 · 1 yr

    🚀 Post-acquisition transition, I oversaw the successful handover and integration of my team and customers into the business. ‣ Lead my technical team through the transition ‣ Documented systems and processes acquired ‣ Trained staff in existing systems and processes ‣ Helped a successful transition of clients into Portable ‣ Aided in business development opportunities ‣ Oversaw the delivery of ongoing software projects

  • Co-founder & Director at inoutput
    Jan 2013 - Oct 2020 · 7 yrs 10 mos

    🛠️ Inoutput is a software development consultancy based in Melbourne. We create clever software, solving complex and challenging business problems. We specialise in creating web and mobile applications, business automation software and systems development. Founded at the start of 2013, inoutput grew from a 2 person agency to a 7-figure business in a very short time. As the founder and director, my role changed as the company evolved, but my core responsibilities included ‣ Business strategy ‣ Business development ‣ Technical team management ‣ Software architecture and development ‣ Sales & marketing ‣ Client relations ‣ Project scoping and facilitating client workshops ‣ Ensuring high-quality project delivery, and long-lasting relationships Project highlights include: ‣ Logistics management and scheduling system (Private transport) ‣ Large-scale data collection, monitoring, and warehousing system (Public transport) ‣ Notification system for real-time vehicle disruptions (Public transport) ‣ Vehicle Scheduling and timetable conversion tool (Public transport) ‣ Incident management and reporting system (Public transport) ‣ Large-scale surveying and data reporting system (Healthcare) ‣ Risk management and resolution system (Healthcare) ‣ Online portal for collaboration between healthcare exports (Healthcare) ‣ Stock trading management system (Financial services)