4 Ways To Improve Your Contractor Onboarding Flow

Claire Murdough
July 8, 2016
min czytania
4 Ways To Improve Your Contractor Onboarding Flow
ikona wskazówki

Nowy wygląd, ten sam wspaniały produkt! HelloSign to teraz Dropbox Sign.

ikona zamykania

If you’re in charge of hiring a large number of contractors online, then you know it requires a lot of tedious admin work. First, you need to figure out how to handle the logistics of the applications. Then, you need to figure out how you’ll organize documents like start contracts, W-9s, and I-9s. Add frustrations like misplaced documents or incorrectly completed forms, and it’s easy to imagine the kind of challenge you have on your hands.

Yet despite the difficulties, great onboarding remains critical for companies that are powered by contract workers (on-demand services like Lyft, Shyp, TaskRabbit come to mind). In fact, great onboarding can mean the difference between success and failure as you grow your workforce. When you improve the onboarding flow for your employees, you can improve retention rate by 200% (not to mention experience a whole slew of other benefits). 

We’ll be covering how to create an excellent online onboarding program for your contractors.

The Benefits of Great Online Onboarding

Besides increasing retention, online onboarding for contractors has a ton of other benefits for your company. 

Here are just a few:

  • Repeatability for hiring. A well-thought-out onboarding program for contractors acts as a template you can reuse for future hires. This benefit becomes especially valuable when you plan to scale your operations.
  • Admin benefits galore. Most companies suffer administrative bloat and overhead due to old-fashioned paperwork processing. The mere fact that you no longer have to deal with paperwork is a clear pro for a company of any size.
  • Boost to company clout. You don’t hear much about the companies that are onboarding their employees in an inefficient way. You do, however, hear quite a bit about those who are making it absolutely pain free. An online onboarding flow that’s seamless will give you technical prestige as a company.
  • Less confusion and dropoff. If you don’t have the luxury of a face-to-face conversation when onboarding a new team member, you have to be incredibly explicit about what information you share with them, and how you’ll share it. Efficient online onboarding gives you the power to share exactly what needs to be done so contractors aren’t left guessing or frustrated.

On the flipside, when onboarding is done poorly, companies suffer in big ways. 

For example:

  • The admin portion of contractor hiring becomes totally unscalable. If you can’t smoothly transition individuals from the applicant phase to the hired phase, you’re likely dealing with a lot of unnecessary steps that clog up your system. 😡
  • Contractors drop off when onboarding is too painful or cumbersome. This is a waste of time for applicants and for anyone handling the logistics of the application. 😥

How and Where to Begin Improving Your Onboarding

OK so now that you’re ready to improve the onboarding flow, where do you start? There are four critical areas you can focus on to improve your onboarding flow.

1. Start by taking control of expectations.

Not many people like to enter personal information into a box without understanding what’s going to happen with that information. Yet that’s exactly what a lot of contractors are faced with when they begin the application process. Instead of doling out crumbs, lay out the whole cookie at the very beginning. 

Setting expectations can be as simple as laying out what contractors can expect from the onboarding whole flow. You can do this by sending an email, building a special landing page, or creating onboarding packets to share with them early on. 

For example, TaskRabbit has a simple but informative landing page for anyone who is interested in becoming one of their contracted “taskers.” As you can see from the screenshot, not only do they have a clear way to begin the application, but they also share exactly what an applicant should expect from the process.

Another way to set expectations is to take note of common questions and feature answers to them upfront. Lyft does this with an FAQ on their driver application landing page. It includes answers to questions about payment, scheduling, and requirements.

Bonus benefit: When you set clear expectations for what the onboarding process will look like for your contractor (including the application process, the approval process, etc.) you also avoid getting dummy information from people who are curious about the process, but aren’t ready to commit yet.

2. Be ruthless in simplifying the onboarding flow.

Imagine you were applying for a job and were required to jump through hoop after hoop of paperwork before you could even get an interview with the company. No matter how much you wanted the job, at a certain point, you’d simply give up! 

That’s exactly how a contractor might feel if faced with a complicated application flow that seems to span on forever. Simplifying the sign-up flow will help you to decrease drop off and also give the contractor a more pleasant experience. 

Here are couple ways to get started:

  • Decrease the number of steps. Some onboarding flows are super long. For example, you may ask a contractor to fill out an application, and then fill out a survey, and then sign up for a newsletter, and then print out and sign an application. By eliminating or automating even one extra step, you can make the process more digestible.
  • Rearrange the onboarding steps. You can also consider if some steps can be moved to later in the process, rather than front-loading the onboarding with a ton of requirements.
  • Make sure the application process is mobile friendly. With 50% of people using their phones to complete applications, it’s essential to think about application flows that that also fit for mobile devices. Something that feels easy to complete on a desktop might not feel so easy to complete on a phone.

As you’re simplifying, a great way to test out how difficult the flow is to go through the flow yourself, in its entirety. A lot of times we obsess about cogs without actually taking a step back to view the entire machine. 

By putting yourself in the mind of the contractor and experiencing what they might experience, you could very well take on a new view. Maybe what seemed easy enough to you initially will show itself as a really frustrating step.

3. Make it super easy for contractors to sign, store, and access essential paperwork online.

One of the easiest ways to improve your onboarding is to remove “sticky" points in the process. Paperwork is a great example of a sticky spot. Traditional methods would have contractors printing out applications, signing them, and then scanning or faxing them back. This creates a ton of friction and really slows down the momentum. 

You can automate that entire operation by building the signing flow directly into a website or application. Embedding signing flows save you tons of time and energy, and make it much easier for your contractors, too. Take Instacart, an on-demand grocery service. They onboard hundreds of contract “shoppers” each day. If they had each person print and fax a document they’d be up to their necks in administrative work. But they’ve built in a way for their contractors to sign online. 

Instacart uses the Dropbox Sign API to help streamline the application process for their shoppers. That way, documents that require a signature or personal information can be effortlessly completed and signed online. Since the process is embedded in their website, their shoppers never even have to navigate to another page. 

Let's look at what that might look like when signing a w-9 form online as an example. 

This is what a contractor might see as they were filling out the document online:

You can see a real-time demo of what it looks like to embed the contract signing flow. Just schedule a demo here!

4. Provide contractors with an easy way to share feedback.

Feedback is an integral part of any system that wants to improve. Without proper feedback from your audience – and make no mistake, your contractors are your audience – you’re left to guess based on assumptions or guesses. That should make it unsurprising that feedback from your contract hires can help you to improve your online onboarding flow and inform your updates.

To gather feedback, consider adding things like:

  • Follow-up emails that ask for feedback about the experience.
  • Accessible and well-publicized feedback boxes for contractors to use.
  • Built in surveys at the end of your onboarding flow.

The benefits of gathering feedback are twofold: 1) You’ll get insight into how to improve, and 2) you may even get material you can use to attract new contractors. Going back to TaskRabbit, they’ve added a “What Taskers are saying” section that features reviews from past or current hires:


Keep in mind that while we used examples of on-demand services and marketplaces, any company that needs to hire a high volume of contractors can use these tips.

But it doesn't hurt to take a page from companies like Sprig, Doordash, Postmates, Uber, Lyft, WeWork, and Handy. These are all companies that successfully hire large numbers of contractors to support their business ventures.  

As mentioned earlier in the post, if you want to see what an online embedded signing flow might look like for contractor paperwork, we’d love to show you. Schedule a demo here!    

Bądź na bieżąco

Thank you!
Thank you for subscribing!

Lorem ipsum

Lorem ipsum dolor sit amet, consectetur adipiscing elit. Suspendisse varius enim in eros elementum tristique. Duis cursus, mi quis viverra ornare, eros dolor interdum nulla, ut commodo diam libero vitae erat. Aenean faucibus nibh et justo cursus id rutrum lorem imperdiet. Nunc ut sem vitae risus tristique posuere.

Lorem ipsum
ikona strzałki w prawo