Working as an Outside Contractor: How to Get in-House Benefits From Long-Term Clients


Freelancing offers a host of benefits compared to being contractually employed with a business. You can pick and choose your own work, set your own office hours and generally have much more control over your working life. However, this flexibility brings some downsides. Chief among these is that you are not contractually entitled to the perks and benefits that some employers offer to incentivize employees.

These benefits packages often include health insurance, dental benefits, paid time off and retirement plan contributions. This can make being an outside contractor somewhat more stressful in many ways, as you suffer from less security in general. Thankfully, if you have long-term clients who value your work and would like to maintain your services in the future, you may be in a position to negotiate for certain in-house benefits. Here are some ways that you can do this.

The Current Situation

As a general rule, freelancers are not eligible to receive the same benefits of employment that a typical employee would get. This is a primary reason why many companies look to outsource certain jobs to independent contractors. Typically, businesses will offer work with a fixed deadline out for tender, which freelancers can then complete without the employer needing to deal with the hassle of employment contracts.

However, when you have been freelancing for some time, you are likely in a slightly different position to someone who has agreed to do some outsourced, short-term work. In this situation, the company you work for will undoubtedly be aware of your talents and willing to make sacrifices to keep hold of your services. This gives you a great deal of leverage when it comes to negotiating the specifics of your freelance work, including a benefits package.

The Hunt For Talent

With more people than ever before opting to take their skills to the open market and trying their hand at freelance work, there is ever-increasing competition among businesses for talented workers. This has led many employers to get creative when enticing people to work for their company. As mentioned before, freelancers have historically been left out of these conversations, but the landscape may be changing as organizations seek to bring in the best freelancers possible.

Freelance workers often have highly specific skillsets and detailed knowledge of their industry. This is one of the biggest reasons that companies seek their services. However, the lack of consistent income and access to benefits like health insurance has left many independent contractors asking for more from their employers than ever.

The best of the best now expect specific allowances from their long-term clients. They understand that their talents are in demand, and companies have realized they need to offer more to retain their services as talented workers move towards freelancing.

Private Health Insurance

One of the most sought-after perks for independent contractors is private health insurance from their employers. The NHS provides an excellent service for millions of people. While this is adequate for treating some issues, cuts to services and the strain of Covid-19 on the NHS mean that waiting lists are long, with many waiting more than 18 weeks for routine treatment. Medical conditions can be debilitating and impact your ability to work, which can be disastrous for freelancers. Since it’s unlikely that you receive sick pay, it is in your best interest to get conditions seen as quickly as possible so you can get back to work.  This is where private medical insurance could be beneficial, as you can be treated much sooner, helping you reduce the amount of time you take unpaid leave from work.

Group Life Insurance Policy

Another perk you might consider asking your long-term clients for is a life insurance policy. As mentioned above, one of the main downsides to freelance employment is the lack of security it provides. Many companies offer life insurance policies as part of their benefits schemes. Such policies provide support for your loved ones should you pass away while performing your job. Payouts are often scaled depending on your pay to support your family in the worst-case scenario.

If they are not in a position to help but you work through your own limited company you may be able to take advantage of the tax savings with a lesser known plan called a relevant life insurance policy. It’s a company owned policy which can be offset as a business expense and should a claim arise any benefit payment would be paid out to your loved ones tax free. Freelancers can save as much as 50% on their life insurance premiums by opting for relevant life cover over a personal policy

Mental Health Support

There is a growing trend for businesses to offer mental health support services to their full-time employees. In general, the conversation around mental health and working has become a lot more mainstream recently, and for many people, this can be a driving factor for taking up freelance work. However, many people suffered from work-related stress and burnout during the coronavirus pandemic, which has led many to expect more support from their employers. As an independent contractor, it is worth checking whether your long-term clients provide mental health support to their employees. This could take the form of an in-house counsellor or even mindfulness sessions.

There are many other perks that freelancers might typically look for from their long-term clients, so consider what is worth the most to you before negotiating with clients. Having a robust idea of your needs and expectations will help you make a more compelling argument when asking about employment benefits.

How to Get These Perks

The process for getting these benefits from your clients is not particularly straightforward, as you do not operate under an employment contract as a freelancer. However, suppose you are confident in your skillset and are aware of your long-term clients’ reliance on your services. In that case, you will be in a strong negotiating position when discussing potential benefits.

Next is to simply start a conversation with your client. Do some research on the benefits they offer to their full-time employees and consider whether you are looking for anything in the same vein. You must have a clear idea of what you will ask for before meeting with your client, and doing some research on what means the most to you and what they can provide will help you with this.

You do not need to make this a hard sell when negotiating, as it is probably for the best that you don’t jeopardize your long-term business relationships. However, it is essential to remember that much of the balance of power lies in your favor. You are providing a valuable service, and, as a freelancer, you do have the opportunity to walk away. The current shortage of talent in the full-time employment market means that many companies will be willing to make concessions to keep hold of the services of skilled freelancers.


In summary, it is becoming increasingly common for independent contractors to expect more than just money from their long-term clients. Currently, the number of freelancers is at an all-time high, and many businesses are scrambling to secure highly skilled and experienced workers. This has given freelance workers a great deal of power to request more from their clients.

The lack of security involved in freelance work is one of the primary drawbacks of the practice. Now, companies are beginning to make concessions to include contractors in their in-house benefits schemes. Therefore, it is worth researching what benefits you need and starting a conversation with your long-term clients to determine whether getting employment perks is feasible for you as an independent contractor.

The views expressed in this article are those of the authors and do not necessarily reflect the views or policies of The World Financial Review.