Remote Work At CloudPeeps




Team Members



* As of January 2020

CloudPeeps Team

CloudPeeps Team

CloudPeeps Remote Company Q&A

Kate Kendall, Founder and CEO - Interview with

What does your remote-friendly company do?

CloudPeeps is a talent marketplace that matches businesses with the world’s top freelance marketing, content and community professionals. Our mission is to allow everyone the ability to work the way they want, from wherever they are in the world.

I originally had the idea for CloudPeeps in 2011 when I was managing social media for travel companies while working remotely as a digital nomad. I noticed there was a disconnect between businesses needing help and not knowing where to find quality freelancers, and talented independents looking for opportunities. We launched in beta in 2014 and then as a platform in early 2015.

How important is remote work to your business model?

Remote work is the most important thing in our business model. The entire premise of CloudPeeps is about matching talented individuals with online-based, remote work opportunities. We like to practice what we preach at HQ so we work remotely too.

What do you consider the biggest benefits of a remote workforce?

You are more mindful about the people you recruit and the team you build, which I think is a huge benefit. Remote work suits a certain kind of autonomous individual who is comfortable managing and motivating themselves. Many workers aren’t used to this freedom or level of trust – and take a while to adjust. Some other big benefits are that it makes workers happier, healthier and more productive – while also distributing congestion from high-traffic hubs and regions.

What were the main reasons to integrate remote work into your workforce?

One of our advisors and angel investors is Joel Gascoigne at Buffer. I’ve long been an admirer of how he’s built his company and work culture so it was a big inspiration to me when creating CloudPeeps. Perhaps, selfishly, I also wanted to create a company with an environment I wanted to work in. I like to focus on productivity, creative rhythms and energy management while working – sleep, exercise and non-work relationships are important to me. We still work hard and long as well as smart at CloudPeeps but we have freedom to do it in a format that suits each team member (e.g. hours/location/environment). Another reason is that we’re still an early-staging company and can’t really justify the cost of a large office. I know some companies in the Bay Area spend upwards of $45K each month for their offices and I’d rather put that back into our salaries, benefits or company retreats.

What traits do you look for in candidates for a remote job?

I look to see if a candidate’s freelanced or worked independently in the past. I also look for someone who’s been through a redundancy or period of change and uncertainty. These qualities build up a deep resilience and mature career mindset. Not everything is secure – even long-term employment. Startups are tough – there’s lots of challenges and it’s not always possible to offer a smooth sailing experience. I need someone who thrives with change, and can operate with unknowns.

How do you conduct interviews for remote jobs?

We’ve recruited thousands of remote freelancers now – we do a combination of written applications and Skype/Google Hangout calls. For full-time HQ hires, we often begin things on a contract-to-hire basis. That’s one of the things I love most about what we’re building at CloudPeeps – we’re focused on first testing the suitability of the match between an employer and potential employee, before ramping things up. It is a lot like dating. The traditional recruitment model of doing a few inauthentic interviews then making a decision based on factors like how someone’s suit fit or how nervous they were seems antiquated. The beauty of online reputation is that it’s much more telling and meaningful. I hire many people full-time who I’ve worked with in a freelance-relationship in the past.

How do you convey your remote culture in the recruiting process?

It’s clear in all our hiring collateral, job search descriptions and reiterated throughout the recruitment process.

Do you use third party testing or evaluation services when hiring remote workers?

Not right now – but there are a lot of new services popping up to do this on scale for on demand and talent marketplaces. For us, we’re much more focused on quality and professional skills – so it’s less about volume.

How do you measure the productivity of remote workers?

We look at a lot of different metrics – from crude things like time (it’s remarkably easy to see if someone is “showing up” and giving their all each day when working online), to deliverables, impact and if goals were met. We’re still a small team so things are tight-knit and highly synced. It gets much harder at 50 people, then 100 people and so on.

What elements are key to successful working relationships with remote teams?

We place a strong emphasis on transparency, authenticity and being direct. We do monthly one-on-one feedback sessions, which we call “pair calls” where we run through challenges, positive feedback and constructive areas to improve. These are non-hierarchical where openness and honesty is encouraged. It doesn’t matter if you’re the CEO or the newest member of the team – we share how you can improve coming from a kind place.

What is the hardest part about managing a remote workforce?

For me, it’s to do with setting the pace. When you’re in an office, the fastest person often sets the pace and lifts the energy and momentum of folks around them. I think it’s easy to ‘hustle’ when you’re out and about with your team and have an effect on each other. It’s harder to communicate the speed things need to happen at via Slack or email. You often need to show not tell. I’ve found setting hard deadlines helps us increase our speed and meet milestones faster.

How do you keep remote employees engaged and feeling part of the bigger picture?

Sharing how the company is going and being fully transparent when it comes to growth and financials has allowed our team to be and stay really engaged. We have a clear mission and goals – and in turn, this allows employees to see what impact they’re making to the company. I think it’s really important to share the vision, direction and bigger picture often – the ‘why’ at the heart of what we’re doing so everyone can interact with it. Startups can often be chaotic so having a strong purpose and passion around what you’re building helps with clarity and purpose.

What is your BYOD policy for remote workers?

As a small team, we don’t have an official policy yet. We have a small percentage of the team with company-purchased devices (with a buy-back option indexed over time) and the rest on their own. Even as we scale, I’m unsure if we will provide devices. I’ve spoken to a few people about this and many say they end up with two laptops, one they don’t use. With much of our data being cloud-based with easily editable security permissions, I think providing devices is less relevant as time goes on.

What is your time off policy for remote workers?

In the early days of CloudPeeps, we had a really flexible vacation policy that I called “Aussie-style”. (In Australia, you get four weeks of paid vacation.) We didn’t really monitor it. As we’ve scaled, we’ve become tighter with our operations and more aware of the stage we’re at. We now have two weeks of paid vacation that accrues, and unlimited additional time off that is unpaid.

What were your biggest fears in managing remote workers?

My biggest fear is that remote work becomes too lifestyle-driven where people become complacent, too comfortable and chilled out. I still want us to be ambitious and bold – hungry to achieve!

How did you implement a remote work policy?

It happened both organically and formally. Formally in that it was something we deliberately wanted to champion and structure. Organically in that during 2014, we were struggling to find the balance of remote and non-remote – and it did come to a turning point in the company where we had to decide what we wanted to be. The decision came to the forefront when we’d just hired an incredible team member who was based in a different city than the current team. This meant we had to switch communication to be online versus in-person. Slack was a huge catalyst for making this transition seamless. All in all, I think remote work functions best when a company has committed to it. It doesn’t have to be all or nothing – in that some people might work in a centralized office, and others in satellite locations. It just has to be part of a company’s cultural fabric, processes and communication flow to work best.

What advice would you give to a team considering to go remote?

Start by working on your company culture and having a good look at your founding or executive team’s values. It’s harder to build a remote work company if you don’t have buy-in from management. Ask yourselves what you want to prioritize and how you want to go about prioritizing it. If you want to “move fast and break things” and get a lot out of all-night hackathons like Facebook’s culture, remote work might not suit.

What are the most effective tools for remote team communication?

We organize our communication and company activities around specific actions. So, instead of chatting about something that’s just popped up or sharing more ideas, we ask how we can save it for later or turn it into an action. This means we stay focused on priorities and are all on the same page about deliverables, expectations and deadlines. We do this using Asana, Github, Trello and Slack. Of course, we still banter here and there – we’re just aware of where we’re putting our time and attention!

What is your personal remote work environment?

My personal work environment is very light, white and clean. I’m a bit of a neat freak and fan of the paperless office environment. I have an external display on top of the popular MELLTORP IKEA table with a nice SF-bay window nearby. I often switch it up and work on a couch using a laptop desk too.

How do you personally manage work-life balance?

I’m not sure if I’ll ever manage this perfectly! When I was starting my first company, The Fetch, I was very obsessive about it and worked all the time. I would often be up at 3am doing everything and struggled to move beyond a one-person control center. With CloudPeeps, I went in determined not to burn out and create boundaries. How you manage also has to do with your environment. I was based in New York for the first year of CloudPeeps and was there for the infamous Polar Vortex. I was working remotely in many dimly-lit spaces during that time and found it a challenge. As an Australian, I need my sun, daily nature and outdoor activities for balance and productivity – so I headed back to San Francisco in 2015 for comfort. Now, the most important things for integration are exercise, scheduling and sleep. I use ClassPass for great workouts, run along Crissy Field near my apartment and play indoor soccer via ZogSports. Dan Martell has a great video about how to schedule based on energy versus time management.   

Do you have a favorite quote or bit of business wisdom?

Trust that everything in your career will work out the way it should, and that you can’t stuff it up if it’s meant to be. All roads will lead you where you need to go, it might not be exactly how you imagined it. Quieten your ego and focus on creating and producing – when in doubt, ship it! Don’t be afraid of the worst case scenario and be prepared to lose everything in order to follow your true calling.

Where is the best or worst place you’ve worked remotely?

Ubud in Bali still holds very near and dear to my heart. I was there in 2012 – just as the local ecosystem was growing with TEDxUbud, Hubud and numerous coliving initiatives including Startup Abroad. I also loved Tulum and Playa del Carmen in Mexico. I don’t have any worst locations as such – I don’t look back fondly of Vancouver because I was working remotely in 2011 while completing my masters thesis and that was just a torturous experience. I was recently in Boulder for a week where it absolutely poured back-to-back so feel it didn’t showcase as much of the benefits to being based there. Basically, there’s a pattern emerging here – it needs to be warm and sunny for me to love it!