With Jack Reviews 

I've been with With Jack since 2021 & luckily never had to claim, but they have been INCREDIBLY useful recently helping me chase payment from 2025. I couldn't even get a reply, and with their help, we're now looking at a repayment plan. The service they provide is human and personal, which feels so novel these days.
I've just renewed my cover for another year, as I'm sure I will every year as I continue to freelance. The new dashboard looks great too, so looking forward to using that! Thanks WJ team!

I emailed Ashley after a client failed to pay and stopped communicating. I was delighted to discover that our insurance policy included the Timely credit control service. Ashley guided me through every step. She requested invoices, answered all my questions, communicated with the client on my behalf, and checked in with me at each stage of the process. Ashley's experience here took all the stress out of the process. And best of all, the client paid within the deadline laid out by Timely's process. I would recommend the service to any solopreneur. Ashley's got your back!

I contacted With Jack to help resolve a late payment from a client which was massively impacting my cashflow. Ashley removed all my worries by handling the client communications on my behalf and kept me updated at regular intervals so I could understand what would happen at each stage. It didn't take long before I received full payment and I am massively grateful to their incredible commitment to service quality and customer satisfaction. A no-brainer option for freelancing.

I'm so happy with the helpful, personal, and professional support from Ashley and her team. This is our sixth year With Jack and I want to personally thank you Ashley for your patience with me in getting our insurance renewed. I had lots of questions and left things to the last minute again. Thank you for your patience and for explaining things to me.

With Jack recently helped me recover unpaid invoices from a bad client who was trying to worm out of paying for services that had already been delivered. The team were extremely responsive at all times and led an informal process to demand payment. When the client stalled and ignored requests, With Jack helped me to claim on the insurance to get legal support and the client settled - I managed to get 82% of the fees and would have nothing without their support. Ultimately I am confident we could have gotten 100% but for personal reasons I wanted to close the chapter.

I have been a very happy customer of With Jack for years and in that time they have been extremely responsive, helpful, and helped explain all the nuances and offer cross-services to provide the right level of cover. The insurance policy itself is very comprehensive which gives peace of mind for small business owners, priced competitively to major players - and with a much more human touch!

If I was running a small business again I would without a doubt return to With Jack.

Ashley is just a dream - so responsive, plenty of helpful advice and signposting, I wouldn't go anywhere else for insurance as a freelancer!

Super responsive, friendly service. I recommend With Jack to any freelancers I know that are looking for Insurance as they just make it so easy.

I always thought of insurance as a necessary evil - but having been insured by WithJack for several years now, it's become a really positive element of my business.

They understand freelancers and small businesses, the customer service is amazing and the products they have are exactly what you need. I was grateful this year to have had the legal cover and late payment option - I was able to use it to recover several thousand pounds from a non paying client.

All in all, a brilliant experience - using WithJack makes my business better.

I've had With Jack cover for several years now, which is essential for me as a Freelance Designer. Unlike most insurance providers, this is not an anonymous organisation, but one with a name and a face (Ashley) who is readily available, and understands what's involved working in the Creative Industries. They now also offer an extra (currently free) service, Timely, which provides assistance in getting unpaid invoices paid. This resulted in me getting some money I was owed, so am very thankful for this.

I have purchased my business insurance through With Jack for the last 6 years. Thankfully I have only needed to use them to provide my Public Liability Insurance certificate when clients or venues required it. However recently I had an accidental damage claim to make. Ashley responded to me quickly with all of the information that I needed to make a claim. I followed her instructions and within 48 hours the matter was settled and I could continue with the repair to my laptop. The whole process was stress free and reassuring that there would be a resolution to the situation. It was really nice to know as someone who is self employed and making business decisions in isolation that I wasn't alone in sorting this out.

I am with WithJack since 2022 and I'm very pleased with them. Not only they are very competitive in terms of price, but from the very start the communication and onboarding has been a breeze - which should be the norm for any insurance company.

However the reason for the 5 star is based on a recent unfortunate event where a client refused to pay us. Ashley has been super helpful with the entire process since my policy was covering unpaid invoices. She has strategically presented me the options and guided me through the process which resulted in the invoice getting paid eventually.

Can't express enough how happy we are with WithJack

going with With Jack for my insurance has been one of the best decisions for my business in 2024. They helped me at the start of the year quickly adding an item to my insurance to protect it with travel, I called them at the airport and they had it added and protected by the time I got through security, that's how quick and simple they made it. Then finished the year helping me with a particular tricky client that was being elusive for payment. Fantastic and caring service.

Truly fast at responding, helpful to talk too and looking into new solutions for me today. Huge thankyou and fingers crossed

Recently I had issues with a supplier not paying their invoice. So I reached out to the guys to see if I had any financial cover (I couldn’t remember) but I only had professional indemnity insurance. However, a member of the team Ashley quickly reassured me and explained a course of action that they could do to help me get paid faster. I expected to pay extra for this service but they explained that it was a value added service that you receive free as a customer. Since Ashley took action on my part I have been paid! I’m delighted with the outcome and so grateful for the support I received from With Jack.

I've used With Jack for PI insurance (and more) for years. Ashley is always helpful and offers guidance and support as to the types of insurance I need. She understands the products but also my industry and I feel 100% confident in the cover she organises for me.

Dealing with a complaint from a client as a wedding photographer can be very challenging and it's those times that make you appreciate having insurance and being able to action it. Ashley at With Jack was a life saver in a dark and difficult time as a business owner. She was there with professional guidance, knowledge, and support. Ashley was responsive to questions I had about the process and gave me the professional and emotional support to make it through. Please, if you are looking for insurance as an independent business owner or freelancer, seriously consider Ashley and With Jack.

With jack have been excellent over the 6+ years I've been with them. When I had to claim for some stolen camera equipment I did feel pretty anxious that it could get difficult quickly, especially after all the nightmare stories you hear about insurance! But it was probably one of the best customer experiences I've had. Ashley and her team approached the claim with a level of care and professionalism that was well deserving of 5 stars. It turned what was a very frustrating and negative experience into a positive and enjoyable one. My claim was quickly dealt with, I was able to provide a record of everything that was stolen and replace it quickly so I could get back to work!

Excellent customer service, quick, honest and helpful. Their documentation is clear and easy to understand. I would definitely recommend them.

From my initial enquiry, I received a fast, personalised service from Ashley that made it obvious With Jack was the right choice for me as a freelancer. When I needed to add extra cover to my insurance, a quote was arranged and the cover added within hours. Nothing ever seems too much trouble and all the hard work is done for you! I would recommend With Jack to anyone.