With Jack offers peace of mind and protection for UK freelance creatives and SMEs. Friendly, personable and reliable insurance.
The UK has over 7 million freelancers, yet most insurance products treat them like an afterthought. Traditional brokers offer confusing jargon, lengthy forms, and policies that don’t fit how freelancers actually work. Ashley Baxter, founder of With Jack, set out to change that—building an insurance platform designed specifically for creative freelancers.
Add Jam has been With Jack’s technical partner from the ground up, helping transform Ashley’s vision into a full-stack platform that handles everything from quotes to policy documents to ongoing education.
Add Jam worked in partnership with the With Jack team to deliver all software aspects of the insurance platform, this included:
Conversational quote builder Instead of intimidating forms, freelancers get their quote through a friendly chat-style interface. The system guides them through coverage options in plain English, making insurance approachable rather than overwhelming.
Automated PDF policy generation When a freelancer purchases a policy, their documentation is generated instantly. The Rails backend handles complex policy logic and produces accurate PDF documents - no manual intervention required.
Integrated payments Secure payment processing built directly into the quote flow. Freelancers can go from quote to covered in minutes, not days. No manual intervention from the With Jack team.
Policy management dashboard A single place for freelancers to view their coverage, download documents, manage renewals and change their coverage. No more hunting through emails for policy details.
Built-in education platform With Jack isn’t just about selling insurance it also aims to educate and help freelancers understand why they need insurance. The platform includes help articles and courses covering topics like contract disputes, late payments and protecting their business.
The platform runs on a Ruby on Rails API that handles the heavy lifting of policy calculations, PDF generation, payment processing and administrative and reporting functions for the the With Jack team. The backend manages complex business rules while keeping the codebase maintainable and extensible as the product evolves and scales.
The React frontend built with Next.js delivers a fast, responsive experience. The chat-style quote builder required careful attention to UX—making something complex feel simple.
AWS infrastructure provides the reliability and scalability that an insurance platform demands. When freelancers need their policy documents at 2am before a client meeting, the system needs to be there.
Our work with With Jack spans multiple years, operating through sprint-based development with regular releases. As the platform has grown, we’ve helped with technical strategy, infrastructure decisions, and ongoing feature development.
The result is a platform that’s genuinely changed how freelancers think about insurance—making it something they understand, trust and actually use.
This was the most complex project I've worked on and as a small business with no in-house developers I needed a tech partner I could trust and who would be alongside me from start to finish. The tech Add Jam has built has achieved exactly what I needed—it's automated my business so we can scale and freed me up to focus on the parts of the business I'm good at.
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