How AI is changing my job: Kate Kendall, CEO at CloudPeeps

This post is part of’s ‘Future of Jobs’ interviews series. We’re talking to leaders and mavericks to find out how emerging technologies like AI and automation are changing how they do their jobs. You can find all the posts in the series here.


As the founder of freelancer marketplace CloudPeeps, Kate Kendall is well acquainted with the changing nature of work. CloudPeeps is at the forefront of the gig work economy, and she is building the company with a fully remote team—two of the defining trends of the future of work.

We caught up with Kate to get her take on how two other major future of work trends—AI and automation—are reshaping her own job as a startup CEO.

What aspects of your job would you like to see automated? What aspects of your job are already being automated or will be, in your view, over the next few years?

I would like to see the administration and management of work be further automated. Complete automation of project and task management tools, scheduling, and checklist processes will occur. For instance, every Monday morning I prioritize my goals and focus for the week. I map out time to get this done in my calendar, using tools like Google Spreadsheets to manage projects and Asana to add tasks. Once items are completed, I check them off and update files. Rinse and repeat. There is no reason this couldn’t all be put on autopilot!

Having an AI evaluate my business, weekly workload, and priorities using data and predictive modeling could ensure I focus on the most important and creative pieces of work.

What parts of your job are you uniquely qualified to do (vs. AI, machine learning, etc.)?

Automation frees us up to do work that humans do best—and that’s building relationships with other humans. If we spent less time on our laptops managing work, we would have more time to directly connect with other people. We’d have more opportunity to share ideas, feedback, goals, and most importantly, our feelings. This may sound esoteric, and you may have heard the phrase human beings instead of human doings, yet if you get to the heart of what makes us human, it’s our sentience and emotional responses. As mental health issues rise, and technology transforms not only our relationships with others but also ourselves, I’d love more time for us to dedicate to the psychology of work, increasing contentment, and cultivating purpose.

If artificially intelligent assistants could take over the tasks from the first question, what would your day look like? What would you spend that extra time doing?

I’d spend more time out in the world—especially more time experiencing the physical environment. I love travel, architecture, cities, and also being in nature. If I didn’t have to manage work or operate via everyday business tasks, I’d treasure this time and also spend more time on self care and having quality time with friends and family.

What’s the main thing you wish you had more time for?

I touched on this, [but] having more time for self care and self exploration would be great! I love sport (especially soccer and tennis), going for walks, and swimming. I’d love to write more, too. With my current workload, it can be hard to prioritize physical activity and non-work related creative time.  

If AI gave you time back, would you spend it doing the things you just mentioned?


If you accept the premise that AI will fundamentally change your job in some way over the next decade, what will your job look like then? What qualities will drive your success?

I believe with increased automation that my job could be completely run from a smartphone (no desk time!), over a day or two a week, if that. I could get a digest of key metrics, a summary of business health, and even ideas for growth based on market analysis, all without lifting a finger. Recommendation algorithms could connect me with future team members, clients and people near me that I should meet. Success will be based upon understanding trends and change: how the world works then and how it will evolve further in the future. In some ways, humans will need to let go and adjust to having a power dynamic like we’ve never known before.

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