With Jack Reviews 

79
TrustScore 5 out of 5

4.9

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Rated 5 out of 5 stars

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, w... See more

Rated 5 out of 5 stars

Insurance should be easy.... And With Jack it absolutely is! Ashley set everything up smoothly, gave me a good premium, and made everything work with minimal effort. I haven't had to claim (fortu... See more

Rated 5 out of 5 stars

WithJack made it easy to sign up and get insured, but most importantly when I stopped trading they made it so very easy to cancel. I called them and was connected within seconds to a wonderful and h... See more

Rated 5 out of 5 stars

Outstanding service from Ashley at With Jack, honestly can’t recommend them enough! I’ve had two issues this year and both times Ashley has gone out of her way to make sure everything is running smoot... See more

Company details

  1. Insurance Agency

Information provided by various external sources

Be a confident freelancer.


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4.9

Excellent

TrustScore 5 out of 5

79 reviews

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4.9

All reviews

(79)

4 reviews in the last 12 months

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Rated 5 out of 5 stars

Best insurance company ever!

I have insured with WithJack for a few years and was recommend them by another start-up. The service from the initial quote, to adding new items to the policy, to most recently claiming for a broken phone, the process has always been simple, smooth and fast.

I had my claim responded to on a Sunday and full completed with funds in my account by the following day.

WithJack makes you feel like an important person and not a number. I would highly recommend them and its the only policy I don't shop about for, as the price is already great and the service is exceptional!

Highly recommend them!

February 23, 2021
Unprompted review
Rated 5 out of 5 stars

Really great customer service

Really great customer service. I am new to the insurance so cannot say for claims, but I had to purchase and make some quick updates on my insurance choices and Ashley helped me greatly and kindly (and right away) through it all. Really appreciated and recommend.

February 5, 2021
Unprompted review
Rated 5 out of 5 stars

Insurance that cares

This is the only insurance I have that I don't shop around for each year. The service is just that good.

I've had to make 2 claims through With Jack. One with a problematic client (extreme scope creep and threats of violence) and another with accidental damage to a laptop. I was so impressed on both occassions with how quickly our problems were dealt with. I never had to wait on hold and was always left feeling reassured that my problems were going to be resolved. It's clear that they genuinely care about their customers.

January 25, 2021
Unprompted review
Rated 5 out of 5 stars

With Jack cares about me.

With Jack cares about me, and my business. That alone is enough to rate 5 stars — and you feel the personal touch from the very first call or email, before you even have a policy.

When you inevitably run into some sort of business-related problem (including broken gear), Ashley is right there to catch you and fight for whatever you need to get back on track as quickly as possible. I filed my first claim last year after some accidental damage (after 3 years of coverage) and it felt like I had someone on my team working to get my gear up and running again — and all in the midst of a pandemic!

Small businesses, especially in the creative industries, need insurance — With Jack not only provides excellent coverage, but Ashley understands how small, creative businesses operate, and she also does a great job of explaining how everything works (including her excellent podcast).

I sleep better at night knowing Ashley and With Jack are on my side.

January 19, 2021
Unprompted review
Rated 5 out of 5 stars

So brilliant!

Ashley at With Jack was so fantastic when my laptop broke during a very busy week. She was so kind and understanding, as well as completely efficient in getting things sorted and the funds into my account so very quickly. Really supportive and compassionate people, and was so impressed with my experience with them.

January 18, 2021
Unprompted review
Rated 5 out of 5 stars

A huge thank you to the wonderful…

A huge thank you to the wonderful Ashley at With Jack. This is an excellent company and we’re so grateful for all the great advice, guidance and support they’ve provided with our various queries! We would highly recommend them.

January 14, 2021
Unprompted review
Rated 5 out of 5 stars

Great service | Quick claim resolution

I've been with With Jack since going fully freelance/ self-employed as a videographer & photographer in 2019. The sign-up was quick and coverage is great; however, I've been most pleased with how quickly my claim was resolved after some of my equipment was stolen during a burglary.

Everyone involved with sorting out the claim was quick to communicate nad sympathetic to the situation. I had funds back in my account to replace kit very quickly without piling on the headache after dealing with being burgled. I have done and continue to recommend them!

January 14, 2021
Unprompted review
Rated 5 out of 5 stars

Highly recommend WithJack

WithJack was fantastic in supporting me in a challenging situation. Very thorough, attention to details, always going above and beyond to support me through this difficult time. If it wasn't for WithJack I wouldn't have won my case so I can't thank them enough. I highly recommend every creative business to get protection with WithJack as you'll never know when you will need it as I found out personally.

January 14, 2021
Unprompted review
Rated 5 out of 5 stars

Ashley is brilliant - go With Jack!

Ashley is brilliant! We are a small, 1 woman creative agency and since signing up With Jack I have been happy to be paying a reasonable fee for a great service. They are really thorough and helpful if you have any questions at any time. Go With Jack!

January 14, 2021
Unprompted review
Rated 5 out of 5 stars

As a freelancer who wears many hats

As a freelancer who wears many hats, I was really struggling to find anyone who was willing to insure me. Then I found With Jack. Female-owned business made for freelancers! Budget-friendly as well and super communicative and friendly :)

December 7, 2020
Unprompted review
Rated 5 out of 5 stars

Great company

Working with "With Jack" has been an absolute pleasure. They're everything and more that they promise. We recommend them to everyone.

Kevin
Client Manager
Friendly

October 19, 2020
Unprompted review
Rated 5 out of 5 stars

Makes insurance feel human

The service by Ashley at With Jack is amazing!

Right from the start, when getting a quote, could get a quote out of hours & right away, rather than the usual "Enter your email" and then getting the hard sell over the phone. With With Jack, got an emailed quote straight through.

Really personable approach that makes it pleasant to deal with insurance rather than going through a load of legalese small print.

Ashley also has a background in freelancing so knows what it's like herself and can pitch information appropriately to you. Number of good add-ons available; again, no hard sell on it, but explained clearly why you might want to go for them and what they offer you.

A really competitive quote (for public liability / professional indemnity), beating all the big names, but still part of Lloyds of London so feel like you're getting that safety net too.

Have and will continue to recommend With Jack to anyone I know who's a contractor or freelancer looking for business insurance.

October 15, 2020
Unprompted review
Rated 5 out of 5 stars

Great

Ashley made the task of sorting out insurance (Everyone’s least favourite task!) so hassle-free and easy, I wouldn’t hesitate to recommend her.

August 19, 2020
Unprompted review
Rated 5 out of 5 stars

Peace of mind as a freelancer

I've been a customer of With Jack for over two years now, and I couldn't recommend them enough. Ashley goes above and beyond to help her customers, providing useful content and advice for all situations as a freelancer. The customer service is next level, and Ashley is so quick to help out no matter how big or small the query. It's so easy to change details or amend your cover with no pesky hidden charges, all for such an affordable premium, unlike other providers.

It makes such a difference to have a business insurance provider that really gets how freelancers work, and can be adaptable to changing business practices across the duration of the cover. I truly believe that you can't get better service, and Ashley brings a much-needed breath of fresh air to the insurance industry!

Being a With Jack customer gives me the peace of mind and confidence to run my business knowing someone has my back if I need it.

April 17, 2020
Unprompted review
Rated 5 out of 5 stars

Highly-Recommended!

I recently contacted With Jack to ask for amendments to my business insurance policy schedule to satisfy a US customer. The whole thing couldn't have gone smoother - With Jack sorted my problem in no time with no fuss.

I feel like my freelancer insurance is in safe and capable hands here and I can recommend With Jack for any freelancers out there wanting to get set up with affordable insurance.

April 17, 2020
Unprompted review
Rated 5 out of 5 stars

I've run a business for over 12 years…

I've run a business for over 12 years and never had any legal issues with my clients.

That changed recently when a client significantly changed the project scope and demanded I complete the work within the original budget. As I'd already completed around 70 hours of design work, I asked the client for a new detailed brief so I could provide a revised cost estimate. The client demanded a refund unless I could stick to their original budget otherwise they would take legal action.

As soon as I was threatened, I contacted Ashely and the With Jack team. I received a response within an hour (on a Saturday) to discuss what to do. By Monday I was speaking with a claims manager. The team talked me through the process step by step and even offered emotional support.

The With Jack team helped me stick to my guns, reviewed my emails back to the client and advised me on how to respond. Thanks to their advice, the client backed down, allowed me to keep the money I had already earned and we went our separate ways.

Thank you for fighting my corner, you rock!

April 16, 2020
Unprompted review
Rated 5 out of 5 stars

6 stars if possible!

6 stars if possible!
After a certain breed of bird decided to pluck my drone out the sky and kindly drop it into a river - one tweet to Ashley and less than 16 hours later everything is sorted.

Unbelievable service, support and transparency.

March 6, 2020
Unprompted review
Rated 5 out of 5 stars

Excellent customer service so far

I have just arranged my business insurance through With Jack. Ashley has been extremely helpful and thorough, and has been patient with all my questions! I obviously haven't had to make a claim yet (and hopefully won't have to!) but my experience with the company so far has been excellent in comparison to everyone else I spoke to and received quotes from.

February 27, 2020
Unprompted review

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