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With over 25 years in the gig economy, Delivery Drivers, Inc. (DDI) has the business experience and unique perspective regarding recruiting and retaining a 1099 independent contractor driver workforce. Given this, we thought it makes sense to share our perspective on how you can work to improve your recruiting efficiency and effectiveness, increase driver engagement and create a pool of high-quality drivers for your firm. Below are 5 ways to retain your workforce by department that you can execute beginning today to get drivers on the road faster and continue a partnership with them.


Recruiting is the linchpin of any company’s effort to build a driver pool, and usually the #1 pain point. A lot of times companies lose out on candidates because the application process isn’t clear enough. Here are 5 recruiting tactics you can do to improve your recruiting process immediately.

  1. Ad placement and information – consider the use of more than one platform or outlet to post advertisements. Make sure to keep your ads up to date by setting start / end dates. Use website analytics to measure the performance of the ad to see what works or not. Then, change them up every quarter. When creating your recruiting ads be direct in what you’re looking for; this means days/ hours, the overall commitment you might need from the worker.
  2. Business information – when workers apply make sure they know you are a legitimate company. Have information about your business, who you are, how long you’ve been in business, company information (website, address, phone or email), companies you partner with, etc.
  3. Workload – In the recruitment process, lay out what kind of activity or workload they may be looking at. Or include compensation averages they might experience on a daily/weekly/monthly basis.
  4. Hidden information – Anticipate and disclose anything a driver might see as a negative, any rental fees they may acquire, any vendors you might work with, and/ or any insurance they may need to obtain. Have a communication plan to mitigate against these perceived negatives.
  5. Being clear on the starting process – Explain to the applicants what they will need to finish before they get started, i.e., paperwork, background checks, MVR checks, linking their bank account, etc. Keep the application process as short as possible. The longer the questionnaire or paperwork, the more likely applicants will stop the process.


This can get very confusing for drivers; sometimes, if some time has passed, an applicant might have even forgotten that they even submitted an application. Make it a goal to have the entire process completed in one meeting. This will reduce your chances of losing them in the process. Here are 5 things you will want to audit when it comes to onboarding.

  1. Schedule shift – Before the worker can leave the meeting make sure you have a shift commitment already in place. Make a schedule of the days/ times for the worker. If they are training with someone, the name of their trainee.
  2. Paperwork – Getting paperwork back from gig workers is a challenge. Make it clear where the paperwork is coming from, when it needs to be done and the specific documents they need on hand to complete it. As soon as a driver has completed paperwork and has the green light to drive you want to get them on the schedule within 24 hrs.  If you can’t achieve this in 24 hours, you are at serious risk of losing the driver to alternatives.
  3. Have an office? – Have the worker complete the paperwork before they leave the meeting, this will insure you have everything and can schedule their training or first shift right away vs. the lag time of follow up emails or phone calls.
  4. Running checks – If you need to run MVRs or Background checks, let the workers who are applying know what they need on hand to complete these. Inform them on the turnaround time for getting these items back.
  5. Document screening – if you have recurring screening checks and fees associated with them, then let the workers know when to expect those fees to be deducted from their settlements. Setting up continuous monitoring is typically more cost effective than running a new report every six months.


Most people are not thrilled when their money is messed with, so putting all the cards out on the table for transparency really goes a long way. Combine these five accounting tactics with the other departments and you’re on your way to successfully retaining a higher percentage of your worker base.

  1. Have perks – let the workers know of any perks, benefits or discount opportunities you may have that they can take advantage of right away.
  2. First payment – we’ve mentioned this a few times and can’t stress this enough. When it comes to the workers first payment, break down what they might see. Be clear with both the positive and negative items. If you charge the worker for screening costs, let them know when that will appear on their settlements, if you charge them for mistakes, let them know how that process works, etc.
  3. Payment help – let them know who they can reach out to if they need help rectifying payment issues or if they have any questions. Include a phone number, email and/or form to fill out for inquiries.
  4. Quick pay/daily pay – if you have a quick pay or daily pay option make sure the workers know how to get signed up and notify them of any holiday pay schedules in advance.
  5. Benefits – offer any accounting benefits or health insurance? Make sure you provide this information to the workers at the time they apply.

The recruiting, onboarding and accounting process, done right, can be quite overwhelming for businesses. This is specially true given exponential recent growth fueled by a global pandemic. DDI is in the business of working with our clients to build and run high quality, engaged driver networks, with the goal being to take this burden off of our clients, and to ensure a fully compliant program as well. Our 25 years of experience in the rapidly growing gig economy means we have the know-how to empower clients across all industries that utilize independent contractors for last-mile deliveries. Check out what sets us apart here.