THE BLOG
11/07/2016 04:22 am ET Updated Dec 06, 2017

Women In Business Q&A: Kate Kendall, Founder and CEO, CloudPeeps

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Jennifer Baquing

Kate Kendall is a San Francisco-based, British-Australian entrepreneur and writer. She's the founder and CEO of CloudPeeps - a trusted marketplace, platform and community that empowers freelancers and businesses to do their best work. Kate also created the Freelance Friday offline community and The Fetch event guide. She's serves on the board of the Aussie Founders Network in Silicon Valley, and was ranked the most influential Australian entrepreneur on Twitter by Smart Company. Her work has been featured in Quartz, BuzzFeed, The Next Web, The Australian, the ABC, Marie Claire, Lifehacker and more. General Assembly named her blog in the top 10 startup founder blogs to read in 2014.

How has your life experience made you the leader you are today?
There have been a few life experiences that really shaped who I am...

The first one is around the breadth of places I've lived: I was born in the UK in a small town, then moved to larger town in Australia aged 10 before moving to Melbourne. In 2010, I quit my job as digital director of a magazine publishing company to digital nomad around the world. I sold a lot of my stuff and lived on Airbnb for two years before moving to the US. It's cliché but I strongly believe travel expands people's minds and perspectives, helping them build greater empathy. I was at a meeting recently where a person was saying they love accents and that they didn't have one. Exposure to different parts of the world would have shown them in actual fact they do have an accent! We all do.

Secondly, I think adversity and going through uncomfortable experiences is the best way to build resilience. Around eight years ago, I went through a very challenging time personally. Before this, I was going through what I call 'tick box' living: I had my masters degree, I had the big title business card, a long-term relationship and was even thinking about signing up to the mortgage life. But at the same time, I wasn't fulfilled - I felt like I was in zombie mode. Taking on challenges and taking the 'red pill' made me a better leader. I now think there's a time and a place for ticking certain boxes but don't make the mistake of externalizing happiness, and expected them to be the answer.

Finally, I think time is important. I've gone through different phases in my career where I've been either a manager or a leader - so I'm now trying to combine the two! They are each different things and I believe one can be taught (management), and the other not so much (leadership). I did my Masters of Business and learnt about management tools and practices but as I've had more experiences, I've found my groove more. As time has gone by, I'd like to think I've become calmer, more patient and more consistent while still remaining authentic, energetic and passionate.

How has your previous employment experience aided your tenure at CloudPeeps?
In so many ways! I had my first startup experience in 2010 when I worked for a Y Combinator-backed travel company and it was there that I really got exposed to early-stage dynamics. I then consulted to a few different startups (including a very short stint working with the founders of YouTube!) before founding my first company, The Fetch. This previous startup experience has been crucial for my work at CloudPeeps - each experience helps you to appreciate the everyday challenges that startups face and how to overcome them.

What have been the highlights and challenges been during your tenure at CloudPeeps?
Some of the highlights have included seeing how many freelance Peeps we've been able to help get jobs and follow their dreams. We get notes saying things like: "I've been able to quit my job because of you" and "You've changed my life" - these love letters really make our day. I've also been proud of how much we've accomplished with a small team - how we've evolved our thinking as we've grown. We seem to have been keeping pace with other marketplaces or platforms that have had a lot of funding and big team.

Challenges - well, where do I start? Startups are tough! We are dealing with daily challenges around resources, scale, growth, hiring, tech and so forth.

What advice can you offer to women who want a career in your industry?
I think the first thing is to ask yourself what you really, really want (Spice Girls style!). Startups have been glamorized over the past few years and I think there's a confusion about what they're like to work at day-to-day. If you want freedom, neverending fun and flexibility: a startup isn't going to be the answer. They involve a huge commitment, pressure and responsibility. I'd also look at the stage you're at in your life. It's an age old debate but as women we might not be able to do or have everything at once.

Other advice would be to speak up, be true to you, surround yourself with work that aligns to your values and to have patience. Being a female in tech, or even the workforce, still has its challenges and risks.

What is the most important lesson you've learned in your career to date?
Let go of fear, follow opportunities, be prepared to take a risk, and steer clear of paralysis by analysis.

How do you maintain a work/life balance?
I don't... but I've gotten better at it! When I was running my first company - I worked all the time: evenings, weekends, Monday mornings at 4am - you name it. By the end of 2013, I'd become extremely burnt out. When I started CloudPeeps, things had to change. I now don't work weekends and keep regular business hours. Whether you're a freelancer, CEO, entrepreneur or employee - especially a creative one at that - I find structure, discipline and routine vital to making space for balance.

I also agree with Marissa Mayer's approach to burnout and balance, in that it stems from resentment. For instance, one is more prone to burnout if they don't have or make time for the things they want to do. For me, this might be prioritizing playing soccer on Thursday evenings, or leaving Sundays open and unscheduled so I can write, read or spend quality time with friends.

What do you think is the biggest issue for women in the workplace?
I think the biggest issue for women revolves around if and when we decide we want to start a family. We're the physical bearers of new life, and that comes with additional responsibilities that often don't fit into the workplace as it exists today. We need better support structures - from the government right down to how things are managed at home, to give us greater freedom to pursue our ambitions and dreams.

How has mentorship made a difference in your professional and personal life?
It was quite sad (violins, please!) as for most of my career, I felt alone and that I lacked access to mentors. I think some of that was to do with where I was based (Australia's startup ecosystem was very small back in the day) and being a female doing something new. It was only when I formally established advisors at CloudPeeps, that I truly felt supported and had mentors around me. When we raised an angel round of funding, many of the investors were entrepreneurs themselves so I now feel like I have a great network around me to seek advice from. I've also recently invested in doing some coaching sessions and found it very valuable.

Which other female leaders do you admire and why?
I admire a bunch of folks... there are so many to mention!

I admire tech giants like Marissa Mayer and Sheryl Sandberg for breaking through and leading on a whole other level.

I admire authors like Brené Brown, Elizabeth Gilbert and J. K. Rowling for their contribution to society and would love to walk into their shoes someday.

I admire Tina Roth Eisenberg for her ability to start and build community-driven companies, as well as her creative leadership style.

I admire Danielle Morrill of Mattermark for her ability to shape the conversation around investment.

I admire Payal Kadakia of ClassPass for building a huge company around an important goal (making people move more and feel good) - I am a happy user.

I admire many Rachel Botsman, Maren Donovan, Ligaya Tichy, Jessica Hische, and Emily Castor for various different reasons.

And of course, regardless of politics, I admire Hillary Clinton and Michelle Obama for showing me what's possible.

What do you want CloudPeeps to accomplish in the next year?
We're working on our 2.0 release now, which features more tools for independent professionals to build and manage their freelance business. We've been on the quieter side about what we've built at CloudPeeps to date so I'm excited to share it with the wider freelance community shortly.