Jeff Wald, Co-Founder WorkMarket: Future of Work Series

The End of Jobs, The rise of On-Demand Workers and Agile Corporations


Welcome to the podcast version of a Future of Work episode of TotalPicture Media. My name is Peter Clayton. My special guest today is Jeffrey Wald, an Entrepreneur who has started three technology companies the most recent, WorkMarket – sold to ADP in 2018 – for undisclosed millions (or billions) of dollars. He remains with ADP, and is the author of a new book titled, The End of Jobs, The rise of On-Demand Workers and Agile Corporations – and that’s  the topic of our conversation today. I was introduced to Jeff and The End of Jobs by Jessica Miller-Merrell who interviewed Jeff for her Workology podcast, which I edit.


Jeff, thanks for joining me. I’ve been looking forward to our conversation.

  • Here’s a quote: “No More than 52 articles per year.” Let’s start by having you give us a brief background of WorkMarket, and the problem it solves for companies that want to hire freelance talent.
  • In the first chapter of The End of Jobs, I really appreciated the historical aspect of your book: Especially the section on unions and regulations. Would you mind telling our viewers and listeners about the Ludlow Massacre?
  • Why have labor unions all but collapsed in the US?
  • I think there is a correlation between the decline in union i.e. manufacturing jobs, and the long-term trend (as you write), of 25-54 year olds without college degrees dropping out of the labor force. But where are they going?
  • Now there are apps for everything: Taskrabbit, UpWork, Instacart, Uber Eats, Rover (which is dog walking with 1099’s) – how are all of these platforms changing freelance work?
  • You bring up an interesting question: Does someone who drives all day for Uber or Lyft think of themselves as self-employed?
  • Let’s discuss the title of your book: The End of Jobs. It seems that more and more companies are adopting strategies to bring in contract workers. Jeff, has the pandemic accelerated the shift from FTE to an on-demand workforce?
  • Another point you make in The End of Jobs regarding Regulatory: “Many of today’s labor laws and regulations are more than 100 years old and were drafted in response to very different needs.” To add to this mess, Jeff, each state has its own definition of employees vs freelancers. I guess that keeps lawyers busy. But wouldn’t update and streamlining some of this benefit both employers and employees?
  • However, the fact remains that payroll and income taxes make up about 90% of government tax receipts. So the feds (and most states), have a vested interest in keeping as many W2 workers as possible. You write extensively about co-employment claims. Can you unpack this for us?
  • You serve on a lot of boards. Can you please explain the Board Room Friction today between:
  • The CFO
  • The CHRO
  • At first I thought Andrew Yang was crazy with his proposal for a Universal Basic Income. I no longer think this is crazy. What’s your opinion of UBI?
  • The Fair Labor Standards Act’s definition of employee is somewhat Monty Python: “the term employee means any individual that is employed by an employer.” This is the kind of nonsense everyone is faced with.
  • You believe that health care should be decoupled from work. But I don’t see any political will to do so. What needs to happen to make that a reality?
  • Has COVID 19 changed your predictions in the chapter titled What On-Demand Labor Teaches Us?
  • In addition, do you think this not-so-normal-new-normal will speed the adoption of task-based employment?
  • Your suggestion for Alumni Labor Clouds reminded me of a once-great client of TotalPicture Media named Select Minds. I had covered their annual user conference for a couple of years, and produced numerous videos and podcasts with their leadership and clients, which included Swiss Re, JP Morgan Chase, IBM, Lockheed Martin, Deloitte, and EY –. Here’s an excerpt from a podcast with the founder and CEO Anne Berkowitch I recorded way back in 2010:

“We started about 10 years ago.  Launched the idea of a corporate alumni network – this was before the days of social networking – really as a recruiting solution with the idea that in fact the former employees of a company provided a very rich talent pool, as counterintuitive as that is, either to rehire some of the best players or to leverage relationships of the alumni to drive referrals of other talent.”

“Then, over the 10 years we’ve been doing that have found that for many sectors, alumni could be clients.  They go to customer organizations as well.  So maintaining relationships with those alumni was very good for generally maintaining the brand and keeping former employees informed of the brand, but also to drive referrals of new business and of talent.”

Select Minds was acquired by Oracle in September 2012. So yes, I think Alumni Labor Clouds would be a great start-up!

  • Wrapping up here, Jeff, tell us about The Future of Work Prize competition.
  • If you were writing The End of Jobs today, would you change anything?



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