The poster boy for common sense insurance.

Insurance how it should be

Insurance how it should be

We know what it’s like to be a business owner. And that’s why we want to make this part of your everyday lives simpler, better and, dare we say, pleasant. That’s why you won’t find any jargon or sales attacks on our site - just one great policy and some pretty excellent customer service.

Less is more

Straight up service

We’re not trying to be everyone’s go-to insurance guy. Jack is all about the freelancers, the designers, developers, illustrators and all round web-pros that haven’t been given the insurance answer they deserve. Making insurance better meant making it simpler, so we champion one policy for one group of professionals. It’s just how we do things.

What you see is what you get with Jack

What you see is what you get

No passing you off to the next department or ugly upsells here. Jack is clean, simple and personal. We’ve pulled out all the stops to make this a no-fuss experience, free from the drama of crazy quotes and fiddly forms.

Our Customers Like Us


"I received my very reasonable quote quickly. We had a few emails back and forth and then boom, I was insured. Insurance is boring but Ashley at With Jack made the process simple and painless, which was delightful."


"Buying insurance through Jack was so simple and smooth, it couldn't be any easier! They were great at answering all my questions and made everything easy to understand."


"Now that I’m insured by Jack, I know that my business is secure and safely insured. I also know I can rely on Ashley at With Jack to help with any issues that crop up - there’s nobody I’d trust more to help me handle such an important part of my business."

We asked ourselves one important question

What do we want out of an insurance provider? Jack is the answer.