Contractor Training In The On-Demand Economy

Contractor Training: What eLearning Professionals Need To Know

The workforce is shifting [1] from traditional 9-to-5 jobs, with increasingly fewer employees becoming “married” to a company that provides a salary and health benefits in exchange for loyalty.

Whether it’s due to the influx of Millennials into the job market [2] or a cultural shift towards a more pleasing work-life balance, statistics show an increase of independent contractors in the workforce. That makes successful contractor training critical to any modern-day company that employs independent contractors.

Who Are The Independent Contractors?

There is a lot of variation on how independent contractors are defined and counted, so it’s not easy to get a definite figure of how many there are.

The surveys that you’ll see quoted about the independent contractor workforce may be including groups that are counted as self-employed by one government agency, as temporary or contingent by staffing agencies or as freelancers by online marketplaces, even if those freelancers work only as a “side hustle” while their primary work is in traditional employment.

For example, a 2015 memo by the U.S. Government Accountability Office looking at the growing number of “contingent workers” says that depending on liberally they define the term, they arrive at figures ranging from 5% to 40% of the U.S. workforce [3].

Much of recent reporting on independent contractors cites a comprehensive survey last year by the Freelancers Union which found that 53 million Americans [4] —or about 34% of the total workforce— engaged in freelance work during the last year. This includes both full-time and occasional independent contractors in a range of professional, creative and service roles. The same study states that the number is expected to climb to 50% by 2020.

A survey conducted by Intuit [5] of 4,622 independent contractors finds that:

  • 33% work for more than one platform.
  • 29% have a full-time job.
  • 14% have a part-time job.
  • 19% care for family members.
  • 11% are full- or part-time students.

On the demand side, according to Deloitte University Press [6], almost half of the executives surveyed (42%) expect to increase or significantly increase the use of independent contractors in the next three to five years.

The On-Demand Economy

The on-demand economy is a large driver of these shifts in the workforce. Uber, for example, employs thousands of contractors worldwide who work a flexible schedule of their choosing.

Uber has inspired a plethora of other on-demand businesses. Handy [7] is a home cleaning service; Instacart [8] delivers groceries; UrbanStem [9] delivers flowers; Fancy Hands [10] act as personal assistants; Wag [11] helps you find a dog sitter; ZocDoc [12] finds you a doctor. At the same time, tech accelerators and SaaS companies are looking to develop the software to allow the next Uber iteration to succeed.

At the heart of a thriving on-demand business is a solid platform for delivering contractor resources. The provider of a service —the person driving a car for Uber, for example— defines the customer experience for an on-demand company, so the success of the business depends on the quality of the provider. Given this reality, on-demand companies must create world-class systems for delivering contractor resources to keep their organizations running smoothly and profitably.

How Contractor Training Is Different

For companies using a dispersed workforce, pulling everyone into the conference room — or even expecting them to log on simultaneously from home — is nearly impossible.

The article How to Train Your Staff in the Gig Economy [13] quotes Yosh C. Beier, co-founder and managing partner of executive coaching company Collaborative Coaching, discussing the new demands of a contractor-focused training model. “What’s increasingly becoming the new delivery mode is training that’s organized in decentralized and on-demand ways”, says Beier, “small chunks accessible anytime, anywhere, based on concrete needs”.

For on-demand companies, that accessibility may mean embedding resources into the platform itself. If an Airbnb host is setting up a listing for the first time, for example, the Airbnb platform should be designed to guide the host and answer questions throughout the process. For SaaS companies using contractors based in four states and three countries, addressing concrete needs may mean accommodating different time zones and local languages.

In the 4 Best Practices in Delivery of Digital Learning Resources, Kate Kalamara helps address some of the challenges posed by a dispersed team of contractors.

  1. Localization.
    If your company is geographically dispersed and contains multiple languages and cultures, create one self-paced eLearning course in English, then supplement it with virtual classes in local languages to address local issues and cultural differences.
  2. Allow downloads.
    Not all learners have access to the Internet all the time. Downloadable content allows learners to work offline.
  3. Social media engagement.
    Additional content can be uploaded to support learners’ personal development. Social media can also be used to “provoke eLearning to user interaction”, which may motivate users to finish courses. And social media may support user-to-user interaction, which will build an engaged online community of learners.
  4. Eliminating the access and understanding gap.
    Not all contractors have the latest devices or software to support such activity. “Businesses should research and acquire what can easily be accessed and used by the majority of their learners.”

Making Contractors Part Of The Team

Whether your contractors are spread throughout multiple time zones or within a five-mile radius, training is an effective way to achieve the competency and loyalty of your employees.

With remote training, the medium is part of the message. A white label training platform embedded into your existing platform —whether it’s an on-demand app or the company’s internal website— can be infused with your branding and messaging to further reinforce the company’s ethos into the contractor’s experience. If your product claims to be user-friendly and available on demand, so should the training for your contractors.

By offering support through the provider’s entire lifecycle —from onboarding the contractor, to guiding them through the early days, to maximizing their earning capabilities and enabling them to share expertise with others— you are acknowledging their importance as part of your company while empowering them to be valuable members of your workforce.

Remember too that your technology should match the modern economy in which your contractors are working. Dated learning management systems weighed down by irrelevant requirements won’t have the agility needed for a nimble workforce. Seek a training platform that can be integrated into your existing systems and in all their digital and mobile forms.

Keep An Eye On What’s Working

As with all training, measuring the ROI on your contractor training is an integral part of ensuring long-term success. A good return on investment means fewer man hours are spent training the contractors, and the contractors are showing growth in their respective objectives.

For example, if you’re still spending time fielding questions from contractors on topics the training was supposed to address, reassess how those topics are covered. Perhaps the materials aren’t easy to access or the content isn’t engaging enough. Or perhaps more content needs to be devoted to a given topic or process.

More importantly, ROI should be measured by the contractor’s performance. Is he or she increasing productivity? If they are consumer-facing contractors, are they well-reviewed by customers? Are they garnering more customers and earning more money?

Training Is Training Is Training

In many ways, contractor training is the same as training for the employees who show up to their cubicles every morning and head home about nine hours later. The training should be accessible, relevant and reflective of the company’s brand. It should cover everything from attracting the contractor to onboarding and optimizing his or her experience. It should be capable of creating metrics that measure how well the training is working and to identify what needs improvement.

But contractor training must also be approached with an understanding of the gig economy. This means training that offers the flexibility and immediacy expected by contractors, and the inclusiveness and comprehensive support that’s characteristic of today’s most successful businesses.

On-demand companies like Airbnb and Lyft rely on SchoolKeep to power their contractor training. Start training your contractors like other top tier companies with SchoolKeep.


  1. How the gig economy is changing employment
  2. 6 Millennials Share Why They Joined The Gig Economy And Ditched Their Day Jobs
  3. Contingent Workforce: Size, Characteristics, Earnings, and  Benefits
  4. Freelancers Make Up 34 Percent of the U.S. Workforce. Here's How to Find, Hire and Manage Them.
  5. Dispatches From The New Economy: The On-Demand Economy And The Future Of Work
  6. The gig economy: Distraction or disruption?
  7. Handy
  8. Instacart
  9. UrbanStems
  10. Fancy Hands
  11. Wag walking
  12. Zocdoc
  13. How to train your staff in the gig economy
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