Five Women Shaping the Future of Work: Kate Kendall, CloudPeeps

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I was fortunate enough to interview five female entrepreneurs who are actively building the future of work. For a quick introduction to these inspiring women, you can read, Pioneers of the Better Way: 5 Women Blaze a Trail Toward the Future of Work.

Now I am taking a closer look at each of the women and sharing a snapshot of their insights. Today I’ll focus on Kate Kendall, founder of CloudPeeps, a talent marketplace that matches businesses with the world’s top freelance marketing, content and community management professionals. I asked Kate about the barriers she faced while building her career and what she considers to be the largest trends in the future of work.

Kate Kendall and the Future of Work

Kate Kendall

From Kate’s Instagram

 When I asked Kate what she believed were the top two trends in the future of work, she pointed out that by 2020, 43% of the workforce will be freelancers. This means we’ll be seeing more freelancers and micro-entrepreneurs, who she believes are more likely to work on things they are passionate about. She pointed out that Generation Y (those born between 1981-2001) wants purpose and access to learning opportunities, so switching to freelancing gives them the freedom to pursue both of those priorities. That is what she thinks is the most exciting shift happening in the future of work.

Career Opportunities No Longer Tied to Large Cities

Kate also considers the remote work movement a large trend in the future of work. Using technology to communicate and collaborate online means people no longer have to be based in large cities for great career opportunities. In addition, she points out you can’t hide when you’re working online; you have to be extremely accountable because others can see when you’re connected online and when you’re not. In her experience, women who work from home, even with families to care for, are some of the most productive people ever!


I agree there has historically been a misconception that “working from home” meant waking up at noon, working a little, going out for a two hour lunch, working a little more, and calling it a day. In other words, working from home wasn’t really working at all. Those who have experience working from home, or experience managing remote workers, sing a different tune. They know productivity can soar in remote positions. Eliminating the droning time-suck of a commute is just one example of how remote working allows people the time and space to get things done.

Digital Nomad Movement

I found it interesting when Kate mentioned the digital nomad movement, where professionals work on the road globally via a laptop, allowing them to live and work around the world. She experienced this first hand in 2012 when she worked from Bali. She sold all of her things, went on a minimalism spree, and lived for years without a fixed address in Berlin, China, and Canada. She even ended up saving money by working remotely. This type of work-life was unfathomable in the past. Imagine explaining what a digital nomad is to a 9-to-5 company-man even as late as the 1980s. He would think you were explaining a science fiction movie!

Barriers Faced by Kate

Kate Kendall

I asked Kate what barriers she faced while building her career. She said, “When people saw us, they saw ‘female’ first”, explaining that, “You get questions that you can tell are coming from a place where they don’t think you are competent.” She had to fight her way through proving competency. When pitching to investors, they were called “girls” and referred to awards rather than direct funding. They weren’t looking for awards; they were looking for funding!

Yet even after receiving funding, or getting on the board, she stresses that women face a second set of issues that continually require them to prove themselves in different ways than men have to.

In addition, Kate talked about leading in a way that is authentic to you. She explained that we have expectations for how a CEO should behave, how extroverted they should be, whether they should be a 40 year-old American male, yet none of that matters. What matters is that you trust yourself and be yourself. That’s what attracts people to the company and community.

What questions would you like to ask trailblazing female entrepreneurs? Leave a comment below, send me an email, or find me on Twitter and I’ll try to get an answer for you!

Want to meet other inspiring female entrepreneurs? Here’s my interview with Sara Sutton Fell and my interview with Rhiannon Ruff.


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  1. 5 Women Shaping the Future of Work: Maria Simon
    March 5, 2016

    […] Want to meet other inspiring female entrepreneurs? Here’s my interview with Sara Sutton Fell, my interview with Rhiannon Ruff, and my interview with Kate Kendall. […]

  2. This Week’s Links « Timothy Siburg
    March 8, 2016

    […] about “Five Women Shaping the Future of Work,” including profiles focusing on “Kate Kendall, CloudPeeps” and “Maria Simon, Geller Law […]


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