Freelancing in the Cloud

Kate Kendall via twitter
Kate Kendall via Twitter

Marketing Podcast with Kate Kendall

Running a thriving business, with or without employees has become so much easier today. You have at your fingertips, through the use of marketplaces and technology, access to the greatest talent available in the world. You can hire that talent virtually or rent  that talent by the hour to get that very specific request filled.

The Producer Model as I’ve taken to calling it (h/t to Brian Clark) allows anyone with a game plan and some hustle to assemble teams of talent to take on much larger projects and competitors while staying nimble enough to pivot towards the next promising opportunity.

Tapping talent marketplaces for programming, legal, design and pretty much anything you might need on your team is a great way to build a thriving business while you work from anywhere in the world.

My guest for this week’s episode of the Duct Tape Marketing Podcast is Kate Kendall, CEO of CloudPeeps and founder of The Fetch. We discuss content marketing and the need for small businesses that may not have the resources to hire full-time marketing help.

Questions I ask Kate:
• How do you get the most out of freelance or remote work?
• How does CloudPeeps work?
• Do people go to CloudPeeps to fill positions permanently?

What you’ll learn if you give a listen:
• Why investing in a marketplace startup model is difficult and why you must plan long-term
• Why the “Remote Work” movement is catching steam
• Why freelancing sites like CloudPeeps must evolve to scale

Podcast Transcript

Transcription Services Provided by GMR Transcription

John Jantsch:              Hello, and welcome to another episode of The Duct Tape Marketing podcast.  This is John Jantsch, and my guest today is Kate Kendall, the co-founder of San Francisco-based CloudPeeps, where you can hire freelance marketing content and community pros.  She’s also the creator of a neat little business event board, I guess is the best way to define it, called  So, Kate, thanks for joining me.

Kate Kendall:              Thank for having me.

John Jantsch:              So, obviously, you don’t sound like you’ve lived in southern California all your life.  I wonder if you could tell us a little bit about your journey and certainly what led you to CloudPeeps, but maybe there’s an even more interesting story before that.

Kate Kendall:              Yeah, definitely.  So, you’re right, there’s an accent.  And it’s a hard one to pick up because it’s a bit of a hybrid because I was born in England and moved to Australia when I was ten.  So, I’m a dual citizen.  Then, I lived in Australia most of my life before moving to San Francisco.

John Jantsch:              So, those people in Melbourne don’t understand you a bit, do they?


Kate Kendall:              No.  So, wherever I go, I’ll be in the UK, and they’re like, “Welcome to town.  This is how you get to the Tower Bridge.”  When I’m Australia, they’re like, “Welcome, here’s the daily paper.”  And I’m like, “Yes, I used to be a business journalist.  I know a bit about how media works.”  So, I’m a tourist wherever I go.  Even when I was living in New York for two years, people would always stop me on the street going, “Do you need directions?”  So, the accent definitely has changed.  But I’m getting better at my American accent, so I’m starting to say things like “banana” instead of “banana.”  It’s really coming along.

John Jantsch:              If you say “awesome,” then we know you’ve arrived.

Kate Kendall:              [Laughs] Yeah, no.  Awesome, I’ve always tried to keep that down because it has been overused.  So, yeah, I started out as a business journalist in reporting on the equivalent of Ad Age in Australia.  It’s called Marketing Magazine.  And from there, I got really into social media around 2007 and 2008, and kicked off an event breakfast series there and that led to founding TheFetch, which was the city guide to discover all of the events that were more geared for your professional life in your local region.  We launched that in ten cities.  Around the same time, I really noticed, if you were bootstrapping your company or you were a smaller business or you need to get help, unless you have the resources to hire someone full-time, it was kind of hard to find the right people to help you grow your business.

So, I had the idea of CloudPeeps a few years ago, but really founded it in January 2014 as a way to connect with freelance talent in this space.  There’s a lot of sites out there, you know, that are very much focused on freelancers, very global, very much across all verticals, and I wouldn’t necessarily have used those as a customer.  I don’t trust maybe the quality of their service or some of the tasks that I needed doing or the jobs that I needed doing or if it was the right kind of person for the job.  So, I think that’s where CloudPeeps has really kind of come along and focused on that.

John Jantsch:              I do want to talk about some of the specifics of CloudPeeps in a second, but you know, this is a really loaded question.  There’s no good way to answer this question.  There’s no good way to ask it.  How has it gone so far?

Kate Kendall:              Yeah, definitely.  So, I think it’s like we have a model of transparency.  One of our advisors and investors is Joel Gascoigne, the founder of Buffer, and obviously they’re very transparent.  So, I’m always have to kind of share how it’s going.  I often blog about this really authentically and honestly, but the first year was really great.  We were kind of in beta mode and we were testing and we were testing out plan formats, so instead of it being a true open marketplace, we were operating more as we would be the little micro-strategists suggest what customers were doing and the plans were $690.00 a month and it would focus on long curated content and social media.

But really what we found is the majority of customers want growth.  So, they think they want this and this and this, but they really need something more to help them grow their business.  And that’s where we started really evolving beyond just curated created content and social media plans to allow peeps, that’s what we call the talent side, to service customers in a variety of needs.  So, anything from influencer outreach to content marketing to a bidder search to that social media and deeper community management in moderation.  And that’s where we’ve really found, especially this year, we’ve been able to grow a lot faster and more meaningfully.

John Jantsch:              So, I always think this is funny because I think we go in with maybe great plans, and we get a lot of surprises along the way.  So, what are some of the things that have been harder than you thought they would be, maybe for you personally or just in growing the company?

Kate Kendall:              When we were operating more in the early days, we were doing things in a very bootstrap manner.  We’d duct taped Google apps and all these forms together, and it wasn’t really a technical product.  So, starting the technical buildout and the product build, it took us a while to find that right product market fit.  It was almost like we were operating smoother and faster when we were first thinking very manually, but, obviously, that’s not scalable long-term.  So, the surprise, I guess, there was it does take a bit of an investment and a time to really find what works.  In the previous company, TheFetch, it was very much that media model, so it was very straightforward in growing audiences and that’s where, you know, I was at home with journalism and media and things like that.

And then, moving to marketplace, this was an interesting challenge for me as an entrepreneur because they’re such wild beasts.  Everything that you do can make a big positive or negative impact.  You have to be a lot more data driven, so if you’re in journalism or media, understand the zeitgeist, produce great content, and you’ll be on your merry way.  Marketplace is a lot of things that you have to measure, tweak, monitor.  You have two sets of customers.  You have your supply side and your demand side and making sure everyone’s happy has been a huge learning curve as well and what to focus on at each stage can really make or break your business.

John Jantsch:              It is really tough because in that two-sided thing, you’re always chasing supply and demand.  If a great copywriter comes on as a peep and gets no jobs from you, then maybe they’re going to move on or not pay much attention.  Same thing, if a company comes on and has a lot of needs and a lot of budgets, but they can’t find the right people, then they’re going to move on.

Kate Kendall:              So true.  And the thing about marketplaces is they often take five to seven years to really establish and get liquidity.  You see a lot of start-ups out of San Francisco and the Valley, overnight success stories raising lots of money, get acquired within a few years.  Marketplaces, you really need to invest in in the long-term, and you have to grow mindfully.  So, just as you said, we have to make sure that we don’t have too many jobs at the same time that we can’t fulfill them.

We have to make sure that we have enough supply side that is happy and engaged, and they all come and work and it’s not too many people.  It’s almost impossible to make these things happen overnight, so that comes down to even when we see new sites popping up all the time.  The learnings that we have now after a year and a half, there’s already so much that’s gone into it, I can sleep well at night knowing you can’t just clone it.

John Jantsch:              That’s a really great point.  When you have that kind of supply and demand, you really almost have to control the growth.  It’s kind of a brick-by-brick thing, but the beauty of that, of course, is you build a pretty strong foundation.

Kate Kendall:              Exactly.

John Jantsch:              So, I’ll ask you the flip side of that other question.  Have there been some things that have been easier than you thought they would be?

Kate Kendall:              So, I think finding customers has been pretty straightforward.  I mean, that’s often a challenge, especially for more of the SaaS companies, you know.  How do we get customers?  How much are we paying to acquire customers?  What’s the lifetime value?  All of those things.  We’ve had a really healthy demand side, so it’s not that we’ve ever been short of customers.  It’s more, you know, finding the right match, teaming them up with the right people.  All of that stuff is more of a challenge.  So, every day, we’ve had customers register.  A lot of organic and referral-based marketing.  We’ve yet to begin, like, hardcore customer acquisition in the paid capacity, but I’ve been really surprised with how much people have managed to sniff out CloudPeeps and discover CloudPeeps based on reputation.

John Jantsch:              Do you think some of that is actually being driven by the kind of the change in the way that people are working?  It used to be if you had a real business, you had a real marketing department.  I’m running into a lot of companies that are saying, “Hey, we need a strategic marketing mind or somebody in here thinking about our vision, but, gosh, we can get all this great talent without the overhead.”

Kate Kendall:             It is so true.  And the thing is, a lot of channels, they need to be tested first, so, say, if you want to test out this channel or you want to do this, being able to hire a specialist or someone to come in and focus purely on execution is really helpful.  The days of the 50-page marketing plan and two-year spend-in-advance and all of that are well and truly gone.

We’re seeing a lot of opportunistic in our job marketing, and that means you need to be able to have that workforce in that on-demand or augment your talent internally in a very swift capacity to make the most of it.  So, we’ve seen all sorts of companies, even Google and Adobe have registered on CloudPeeps.  They’ve yet to get working with peeps, but it’s not just small business that don’t have resources.  It’s a lot of big companies that have the capacity, but they need speed, and they need people to focus on getting the job done.


John Jantsch:              Yeah, and I think it used to be seen as having the assets internally was, you know, a good thing because it was a show of force, but I think a lot of people have realized three years from now, everything about their industry could change, and then having that big sort of warehouse all of a sudden became a liability.  Somebody else can jump in a steal your market because business is done in a new way.

Kate Kendall:              Totally.  Yeah, it’s much more responsive.  You see that often with the future of work as well.  I think when the recession hit, that kind of started to change the psyche.  In Australia, we’ve been “outsourcing” or working with people globally for many decades, and I think in the U.S., it’s really catching up now.  Just because you can’t have someone sitting right next to you in-house doesn’t mean that you can’t trust them or work with them or that they’re not necessarily better.

So, a lot of the work we do is around educating people around the concept of remote work.  You often hear it called “remote” now.  It’s not “virtual.”  It’s not “outsourcing.”  “Remote” has become sexy, and those terms are kind of mid-90s and things like that.  So, again, there’s a huge remote work movement.  A lot of people that would be working with agencies in the past, the agencies are remote to the companies and the clients.  I think it’s just around this re-education and reframing around what it is to be a modern day worker and how that work is performed and work is no longer a place.

John Jantsch:              Back when Jason Fried’s book, Remote, came out, I had had him on the show, and we talked a little bit about how there are some differences, though, in managing remote or virtual or freelance workers, I think.  And sometimes people struggle with wrapping their arms around the best way to still be productive and efficient, even though you’re using a remote workforce.  Obviously, I’m guessing that one of the things that you try to do is educate people on how to get the most out of freelance work.

Kate Kendall:              Exactly.  So, I think there are two types of customers that we kind of see.  There’s the customer that comes in, and they are so time-poor they really don’t want the management overhead or the emotional overhead of managing freelancers.  So, someone to come in, get the job done, focus on execution and not really be as absorbed internally.  There are some people looking for that.  And then, the other side is that people do think of freelancers like part of their team and how to make the most of them and give them feedback and everything like that.  It’s similar to how they would in-person.

One of things I’ve noticed is I’ve been going to offices, even around San Francisco and New York and things like that, is you walk in and people are still communicating on Slack and hosting their meetings and communication on Slack anyway, so the offices are quite quiet anyway, apart from the sales department.  So, it kind of comes in as if all the communication’s happening online now, people are becoming a lot savvier at knowing how to give feedback and [inaudible] [00:13:47] and, you know, hold the focus and get the job done in a wide region of communications.  So, I think that, again, people are getting better at managing and understanding how to get the most out of teammates in-house because a lot of that is becoming online, and then, just because someone is not in that same room is not having as big an impact as it once did.

John Jantsch:              You mentioned Buffer.  One of my daughters actually works for Buffer, and you know, I don’t know how big their staff is now.  Let’s say it’s 50 people.  I think only six or seven of them are in the San Francisco office.  So, my daughter will come home for a week because she can work remotely.  They have almost a dashboard of communication tools queued up at all times, so they’re seeing people in the office, and they’re seeing other teammates in other parts of the world.

Like you said, I think they use HipChat, but they’re constantly in communication.  In effect, I’m sure you know this, they hold three big get-togethers a year so that they do kind of have that ability to give each other hugs and that kind of thing that you can’t replace with any technology.  Certainly, if you put in the effort in the process, you can certainly do a tremendous amount of very efficient communication in this way.

Kate Kendall:              Yeah.  That’s what we really think at CloudPeeps is that it’s not necessarily 100 percent remote or it’s not 100 in-person.  It’s just giving people the opportunity to work how they want to and how they best work.  So, we really focus more on productivity and counting hours, and I think that allows people to get more work done and be happier.  And then, the same with the freelancers who’ve asked for full-time.  We’re not necessarily, “Oh, you can’t be a full-timer.  We’re pro-freelance.”  It’s about opening the world work up to different ways and different formats.  I think that’s positive for everyone.

John Jantsch:              Well, I was going to ask you that question.  Do people go to CloudPeeps to fill positions permanently from time to time?

Kate Kendall:              They do, but they often see it as a contract-to-hire capacity.  I think one of the things I’ve found personally, as I’ve been working full-time in the past, is you often meet someone, have a conversation, do a quick interview, then you embark on this big, full-time job.  And it’s almost like getting married straight away without dating.  So, that’s the way people often love that referral.  I’ve hired peeps for HQ.  Tessa, our happiness lead, was a peep herself first.  And in the past at TheFetch, a lot of those people grew from my network.  I think getting straight into hiring someone isn’t what they come to CloudPeeps for, but you build those relationships, and then potentially hire them full-time in-house as W2s.  We’re happy to do that, and we’ve built that as a way that customers can acquire talent within the platform.  It’s different from going to LinkedIn and going, “I’m just looking for a full-time person.”

John Jantsch:              And then it becomes, as you said, the 90-day or 120-day interview.

Kate Kendall:              Yeah, exactly.

John Jantsch:              So, how do people get paid?  How do people pay for these?  Is it competitive?  I’m guessing questions that people are out there thinking, “Gosh, this sounds like a good idea.  Can I afford this?”

Kate Kendall:              Definitely.  So, the average price right now for what a customer spends on CloudPeeps is around $1,000.00.  So, we’ve really seen that increase as we’ve opened up to different things, and it’s still rising.  Some people might list a $300.00 quick, basically, “make my social media presences look alive each month.”  Some people might list an $8,000.00 much more intensive per month job.  You’re seeing that range from what customers are actually spending and what they need.  It’s our role to educate them.  If they’re coming in and they’re wanted to spend $500.00 and get the equivalent of a CMO a month, we’ll say, “That’s pretty unrealistic.”  So, we’re doing a lot on the education side to the customers.

And the peeps get paid in real-time, which I think is different from freelancing externally in that you often send an invoice in and hope you get paid within the next two months.  Especially if you’re dealing with large corporations.  Even getting paid within 90 days or so is impressive.  So, we take payment in advance, pay the peeps every two weeks or month, depending on the style of work.  We have hourly and fixed-price work, which is more like retainer.  In terms of the process, we work in a pitching contest model right now.  We actually got asked this question last night at the online community meetup, “Is it competitive?”  A peep answered.  She said that it’s kind of a blend of both.  The community’s super supportive.  We’re really focused on building that internal freelancer community, so people will actually share tips, advice, they’ll get feedback on things in their work.  So, it’s very collaborative, and there are lots of customers now that are coming through the doors.

We have 500 peeps, so the volume ratio is actually really good and in the favor of winning works.  So, it’s not as similar to services like Freelancer or Upwork, which was previously oDesk, in that you might be competing against hundreds of people.  Yeah, that’s a big thing.  And over time the pitching contest models don’t scale super well, and that’s where we’re starting to take a much more data-driven, instruction data-driven approach to matching customers and peeps, which gets to be more like a dating Website and those kinds of tools.  What are you looking for?  Here’s a list of search results.  Here’s maybe the top two or three picks.  Then, connect with your favorites.  That are a lot of people that are looking for specific things, so the main expertise, passion, all of that on the peep side.  So, we can start to match people based on their availability, time zones, needs, and do it in a much more sophisticated way than spray-and-pray pitching.

John Jantsch:              So, they’re not trying to establish an hourly rate necessarily, like you might hire a virtual assistant.  It’s more of a project that people are bidding on?

Kate Kendall:              It really depends on the style of work.  We do both ongoing and on-time work.  We’ve had customers over a year now, so I’ve been really surprised at the length of usage that have said, “I need ongoing social media or community manager to moderate my social media channels and build community and audience there.  And I want to spend $1,000.00 a month and this is what I’m looking for.”  They establish guidelines and say, ten peeps would reply to that pitch call and state their background experience and why they’d be interesting in working with that customer.  So, that’s often the No.  1 use case that we see.

John Jantsch:              Have you found some tools that are your favorites?  We mentioned a couple of them, but some of your favorites for, if you’re going to be going to more of this virtual workforce, for communicating, for tracking projects.  Do you have a few that you would like to share that are your favorites?

Kate Kendall:              Definitely.  We use a lot of Marketplaces ourselves, so I’ll talk more about the services that we use then some of the tools.  I use a tool myself for personal assistance, and I think that Maren Kate has done a brilliant job there at vetting and training talent on there.  Then, I also use UpCounsel, which is where you can get legal help on demand.  So, if we need to get our terms of service updated or anything like that, I’ve found that service brilliant.  San Francisco is almost like the home of the service economy.  You can get everything done on a push of a button, so there’s lots of great services that have the pros and cons.

With tools, we have started to form a few partnerships or look at other freelance tools.  Things like Timely and Harvest for time tracking have been fantastic, so the customers are looking for a bit more of that hourly accountability.  They’re both great tools.  We use Slack.  We use JustWorks for all of our HQ.  It’s a bit like Zenifits meets ZenPayroll.  Xero for all our accounting.  Absolutely love Buffer, of course.  We use SumAll to pull together all of our social media stats internally.

What else do we use?  GitHub Issues, so we do all of our project management in GitHub, but we also use Asana and Trello.  Kind of a common remote stack that you hear people almost use after a while, and we always look to that.  We haven’t tried anything like Squiggle yet, which is when you’re talking about that remote, you can see people.  We haven’t gone full-on, but we should check that out.  We still use a lot of Hangouts and Skype and things like that.

John Jantsch:              What was the first one you mentioned for personal assistance?

Kate Kendall:              Zirtual.

John Jantsch:              Great.  I’ve seen that.  Well, Kate, I appreciate you stopping by to join us today and share some of your journey and share certainly, I think, what is an essential and needed.  You started to talk about how there have been these places you can go say, “Hey, I need this done.”  The E-Lances of the world, but I think by kind of curating a community of people that do very specific online digital marketing kind of work, I think the need is huge, and I’m guessing the demand will show up for you as well.

Kate Kendall:              Thank so much.



Content Marketing, Freelancing, Kate Kendall

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