On-Demand vs Remote Workers: Regulation, Opportunities, & Skills

October 23, 2020



On-Demand vs Remote Workers: Regulation, Opportunities, & Skills

On-Demand vs Remote Workers: Regulation, Opportunities, & Skills

Jeff Wald, founder and former CEO of WorkMarket, shares his data-rich perspective with authoritative clarity to discuss the evolution of the On-Demand Economy, including the impact of technology, regulation, and the pandemic on its future direction and potential. Jeff considers how new understanding about remote working affects opportunities for on-demand workers, what is the ‘future of the firm’, and the critical issues facing us all with shifting business conditions and labor markets.


[03:44] A lack of systems and processes was holding back the On-Demand economy.

[04:57] The IRS has a 2-factor test to determine if someone should be classified as an employee or not.

[06:02] Each company has a complicated task to decide relevant criteria for their on-demand workers.

[06:55] Labor force regulation needs simplifying, but there’s zero near-term possibility of it happening.

[07:25] The impact (or continuing uncertainty) resulting from California’s Uber lawsuit conclusion.

[08:36] How regulation-related confusion is causing companies to consider hiring fewer freelancers.

[11:00] How much the On-Demand economy has been going over the last 10 years.

[12:20] Regulation has been hindering growth, but software has helped interpret regulations.

[12:39] Jeff guesses that regulation will shrink the on-demand economy over the next 10 years.

[14:48] Are more companies tapping into the ‘total extended workforce’ strategically?

[17:00] The percentage the remote workforce will grow as a result of COVID19.

[17:31] 42% of the US workforce CAN work from home.

[18:03] Moving on from ‘productivity equals presence’ mindsets.

[19:27] How policies, procedures, and infrastructure changed in March 2020, so that everyone possible could work remotely.

[20:11] Humans are social animals—the ‘Hub and Club’ role of offices in the future.

[21:39] The percentage of people wanting flexible work arrangements going forward.

[23:53] Needing to be more responsive, organizations can adapt the employee/freelancer composition of the workforce.

[24:42] One impetus for WorkMarket was the prediction that firms have small fixed cost kernels with everything else done on-demand.

[25:08] Understanding ‘total talent management’ where companies see all their labor resources together.

[26:08] Job versus income security relating to full-time jobs and on-demand work.

[27:12] How the economic environment might affect workers’ attitudes towards full-time positions.

[30:00] The changing social contract and convergence between full-time and on-demand workers.

[32:05] The depletion of training budgets with responsibility shifting to workers.

[32:49] The COVID19 disruption enabling non-incremental change and crafting new work conditions and practices.

[33:50] The rise of robots means displaced workers and re-skilling—but who owns workers’ training?

[34:14] IMMEDIATE ACTION TIP: Jeff’s lingering question—'who should own employees’ retraining?’ Until there is a clear answer, be proactive, keep learning, and keep your skills updated!

[35:15] What the impact of workers getting left behind means for society.

[36:00] Now, the average skill diminishes in four to six years, rather than 30 years.

[38:52] Jeff’s interim full-time gig with the Biden campaign, supporting the democratic process, and the need for Presidential support of the working class and retraining.

[40:31] Jeff’s next entrepreneurial venture—potentially helping companies benefit from staying connected with former employees.


“The tailwind pushing the on-demand economies, people wanting to be more agile. The headwind is regulation pushing the other way.”

“My guess is that regulation wins that fight, and that the on-demand economy shrinks.”

“There is convergence between the part-time or on-demand worker, and the full-time worker.”

“You will see millions of workers that need to be retrained…and as a society we have not done that retraining well, and it’s unclear who should own that training.”

“Everybody has got to constantly be reading and updating and staying in touch with the new stuff, or you will become irrelevant… Everybody’s got to own it in some way on their own.”

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