EP. 014

How to work with enterprise-level companies as a freelancer

Enterprise clients are the ones with names you can mention to a friend and they’ll say, “Oh, I’ve heard of them!” In this episode, Paul and Kaleigh talk about the pros and cons of working with enterprise-level companies and how doing so has helped boosted authority and ethos within both of their freelance careers.

This podcast is sponsored by our friends at Monday.com, a place to manage all your projects & marketing tasks.

Monday.com is offering 25% off any of their paid plans, plus an unrestricted free trial to our listeners—sign up today!



Kaleigh: Paul, I want to talk a little bit about working with enterprise clients because that’s kind of the goal with freelancing. You want to get those really big name clients who are the folks that when you throw their name out, when you’re talking to somebody who is trying to explain what it is that you do that people are like, “Oh yeah, I’ve heard of that company before.”

Paul:      Yup.   

Kaleigh: My first question is, first let’s get on the same page about enterprise clients and what they are just so the listeners too know what it is that we’re talking about.

Paul:      Sure. I think that there are actually might be a few ways to think about enterprise clients. I think the easiest way is like Fortune 500 companies that seems like an enterprise client. I think there are also a different that’s not really enterprise but like a type of client where, and maybe think of it when you introduce this episode. If you say the name of a client even if they are not enterprise but people are like, “I know who that company is” or “I know who that person is”, then their name has weight. They are known in that industry or possibly in related industries. Do you want to include those or do you want to talk about that kind of clients separate from enterprise or do you want to just say, that’s kind of lump when we are talking about finding enterprise clients working with them.

Kaleigh: Yeah, let’s kind of lump them together. I think that that’s going to be the easiest way to tackle this.

Paul:      Yeah, because they both kind of relate to this building authority and credibility with the people or the businesses that you work with.

Kaleigh: Right, so tell me about your experience working with enterprise clients like throw out some names. Let’s keep the ball rolling like impress us here Paul.

Paul:      Yeah, so it’s funny because like if you look at my bio on my website or even on like the creative. I’m going to pull out the Creative Class website for a sec because I’m sure we both have enterprise clients in there.

Kaleigh: We do. And again, those are the folks that you put in your bio because people are like, “Oh yeah, I know who that is.”

Paul:      Yep. For me, it’s always Microsoft, Mercedes Benz, Warner Music and then Marie Forleo and Dannielle LaPorte. They are not Fortune 500 businesses but they have ridiculous and successful businesses. Pretty much everybody knows who Marie Forleo and Danielle LaPorte are.

To me those are like the top clients, not in terms of like obviously working with them; but they are the top clients in terms of if I say those people’s names like if I’m looking for work or if I’m making a sales page for a course that you and I teach called Creative Class (creativeclass.co) then those are always the names that I kind of comeback to. There are a few others that I don’t really mention that I probably should but it doesn’t really make sense. Because I’m like in Canada but I did the website for The High Line in New York which I think is a big deal there but it’s not a big deal on Vancouver I think in Canada, right?

Kaleigh: Know your audience.

Paul:      Yeah, so I think that that’s the first thing that I think make sense is I would probably add different names or I would put different names on a website or proposal or something. I even name drop these names when I’m writing up like a statement of work or like an on boarding document. I’m going to add testimonials from Danielle, Mercedez Benz and stuff in every aspect of what I do because I want people to see, ok well if those people trusted Paul to do work for them maybe I can trust Paul to do work for me.

Kaleigh: Exactly.

Paul:      And it would change too, like if I was pitching another car company I would use BMW as well even if I don’t really say BMW. I did a lot less work for BMW than I did for Mercedez Benz. And I like cars like I liked that I got to work with this. There’s been nerdy stuff that I got to do for them. One was like a CRM Management System and one was like an internal internet design. I wasn’t making fancy sites for their M-Series or their AMG Series cars. It was like internal corporate boring interface design.

Kaleigh: That’s so funny because that is the exact same scenario for me but with AT&T. Like you here AT&T and you’re like, “Wow, cool. She was writing copy probably to sell their stuff.” No, I was working on like an internet of things project that was very high purpose specific to this one small project. But again, nobody needs to know that. They just need to know that you are hired by these brands which are true. It doesn’t matter what the type of work was. It’s just that they thought that you are good enough to work with you.

Paul:      You know what I did for Microsoft? I did 10 drawings of icons for their Photoshop competitor which I don’t remember what it’s even called because I think it died faster than it was released. Like I did icon design for one of their interfaces for an app that went nowhere.

Kaleigh: It’s not funny though.

Paul:      Yeah.

Kaleigh: You’re still hired. That’s all that matters.

Paul:      I totally was, I mean, Danielle, I was like her creative director on contract for 12 years. Some of the people I did a lot of work for but some of them were just like a little bit of work for something that nobody outside of their business ever saw.

Kaleigh: Yup.

Paul:      But still it makes sense to use those names.

Kaleigh: It does. And I think of another copywriter who did some social media help for like a local division of GE, and again like, “I worked for GE.” Like that’s a perfect opportunity to showcase a big name brand of an enterprise level client and again the details aren’t important. It’s just that you work with them.

Paul:      I want to jump around a bit because I think this is like. I’m sure I can hear people thinking right now. How because you’re a one person business, I’m a one person business for we are freelance people. How did you get a Fortune 500 client like AT&T to work with you who, you work from home; I work from home? How did that happen Kaleigh?

Kaleigh: I know, yeah. It’s all referrals. Most of my work is referral based and so I talk about this last season. You and I both discussed it kind of that length that my best projects and the biggest name clients that I worked with are always because I’ve been introduced by somebody else. Because honestly, I don’t know how I have landed those type of projects if I was just calling or prospecting or something like that.

Paul:      Hello AT&T.

Kaleigh: Yes. Please hear me. It just wouldn’t work that way. That’s not realistic I don’t feel like, at least not for me. I’m not going to sell myself and so if somebody else can sell me that is great. So yeah, it is always referrals for me. What about you?

Paul:      Ok, well, I want to dig into that a little bit more then I can answer the question because my answer is just the same. But I want to dig into this, I know listeners are probably thinking. How did it work to get to a place where somebody told somebody AT&T to hire you? I’m going to peel the onion back another layer here.

Kaleigh: So in this instance it was a website copywriting project which I don’t even really do that type of work anymore but at the time I was, and a past client of mine was happy with the work that I did. They had heard that somebody working at AT&T was looking for a copywriter to help with the various specific type of project. It was the same type of work and they were happy with the results that I’ve produced. It was just a green light automatically you should talk to this person.

Paul:      Yeah, and I think that’s pretty much how it has work for me, for the majority if everybody that I’ve ever worked with especially in the beginning was referrals. And I think a lot of people have a misunderstanding that’s just because it’s a big business or a known business or a massive business. That word of mouth doesn’t work for some reason and it totally does. Like the only reason I got hired by Mercedes Benz is because I knew another designer who have done for them and he was just too busy.

So he was like, “Sorry guys. I can’t do the project. Talk to Paul he’ll do it for you.” And it was like I wouldn’t have even known who to contact at Mercedes Benz. I think it’s American who say Benz and I think it’s, UK people or British people that say Merc. But I watch too many British shows that talk about cars so all of my car language is British even know I’m not actually British.

Kaleigh: Yeah, I have never heard of Merc before. It’s new to me.

Paul:      Watch more Top Gear or watch more the Grand Tour which is a good show even if you’re not into cars. It is three ridiculous old British men doing ridiculous things like blowing up cars, driving tanks, racing cars against planes. It’s absolutely ridiculous, totally non secretive. Back to enterprise.

Kaleigh: Oh, that’s funny. Yeah, let’s talk about some of the pros and cons of working with these types of clients. I’ll let you start because I can have my own list of stuff that I have learned from working with them but I want to hear what you have to say first.

Paul:      I think the biggest pro is you have a recognizable name in your quiver for your portfolio, for anytime you’re pitching, anytime you’re writing a bio, or a byline for yourself, anytime you mentioned anywhere people are like, even in I mean just pulled this up. I do too much of this. I should have these things. I am looking at the bio that my publisher wrote for me for the book that comes out next year.

And like the first sentence is, as a corporate tech designer I knew that I can solve it. I’ve spent years working with professional athletes like Warren Sapp, Steve Nash, Shaquille O’Neal. For some reason they feel that like pro athletes relate to this business book that I wrote for them, and with large companies like Yahoo!, Microsoft, Mercedes Benz and Warner Music.

Kaleigh: There we go.

Paul:      And then I migrated to working with online entrepreneurs like Marie Forleo, Danielle LaPorte and Chris Carter. So like my bio like the publisher I gave them. It was like 10 pages. Like they ask me, 10-page questionnaire to get to writing this, like three sentence bio which they know how to do a lot better than I do because this is what they do for work. And every single sentence is a name drop in my bio for that book.

Kaleigh: I guess that’s how it is supposed to be though otherwise it’s just like who is this guy? Why should I read his book?

Paul:      Like it gives credibility. Like right beside the picture of me covered in tattoos otherwise they would think like some totally different book. So I think that’s the biggest pro is having that name that you can then use pretty much forever. I probably did work for Mercedes Benz like 2002 or 2003, like a long time ago. Still I used that name.

Kaleigh: Still working.

Paul:      That was a 6 month project; that was a huge project too. So that’s probably the biggest pro. The biggest con for that is the red tape of dealing with the big business. So getting paid by a Fortune 500 company is not like getting paid by an online entrepreneur who has like a staff of two or three and they know how to run a super fast efficient lean business. And if somebody invoices me I pay them within 5 minutes. It’s like a personal game I have with myself where if I hired any freelancer and they send me an invoice the first thing I do is I pay because I feel that’s the most important thing; like when I was doing freelance stuff I like to get paid quickly.

But enterprise clients they have to send it to Finance. Finance is where invoices go to die basically and it’s always like net-30, net-60. So in the beginning, that’s what I did. It was just I took on whatever payment terms they would set. I’m like they are a big company I’m a one person business. But then I was like, if I have net-0 for my smaller size clients, I have net-0 for my bigger clients. One time I got, I can’t remember who it was, but it was a massive company with offices all over the place. I got them to pay me $500 everyday for like a week or 6 days to pay my invoice out of petty cash so that I will get paid right away instead of having to send it to payroll and then net-30, net-60 or net-120.

So I got them to pay with the petty cash credit card on my PayPal page just so I get paid faster. They were like let’s figure this out, like we are smart people. One of us is smart and then the other one. We could figure out how to get me the money faster to meet my terms of payment. And they’re like, sure let’s figure this out.

Kaleigh: Yeah, and speaking of money I think the other big perk of working with these companies is that they often have money to spend. Now, the but of that is it may take a while to get to you if you agree to their existing payment terms which like you said could be 30 days from now, 60 days from now, 90 days from now. And those sometimes can be very very rigid of those enterprise level companies. Like there is not getting around it. This is the way we do things so either you’re comfortable with that or like what you did; you find a way around it.

But most of the times these companies, I mean the opportunities they present are pretty lucrative. They have the money to spend so that’s a nice perk as well. The con now of that is because they are bigger company and because they have big goals they often have a lot bigger expectations. So they really want what they’re buying from you to produce results, to what you said that it’s going to do.

And so that’s a lot more pressure on you as a freelancer to provide an end product that’s really really good and it does what they need you to do for them; which I mean with writing and with design it’s kind of a question mark sometimes. Every audience is different. You don’t know what’s going to work. You have to test it and find out. It can be a little bit more stressful than kind of a smaller end client or a small midsize business who has a little bit lower expectations. And they still really want good quality work but they are not being pressured by somebody above of them to produce x result.

Paul:      I thought of one more pro and one more con. So another pro is once you have one big fish or one big enterprise client or one big known client it’s easier to get other ones because a lot of time businesses are at risk, so they want to bet on a sure thing especially if they are hiring a much smaller business like one person.

So once you get one it’s way easier to get another. It’s that the first one is typically the biggest hurdle and then it gets a bit easier. Another con that I thought of is that it will probably, even if you are a lean mean process machine it’s going to take you more time to do the work for an enterprise client because there is more red tape. Instead of me hiring you and then you send me a draft of writing, and I’m like, thumbs up emoji, approved. For enterprise client it could be your contact say yes. Now I have to run it by this project manager, or manager, or committee. If they say that then just run screaming for the hills because can be the easiest way creativity goes to die. But it can definitely take longer. It could be layers of approval and I always try to.

That was always a caveat with me with working with enterprise clients is how to sign off for my work work because I got burned by that a couple of time where I would send the design. My contact would be, “Yeah, that’s awesome.” And they would be like, “Ok, this is great.” And then it will be like, “But I have to talk to four other shareholders of this project.” And it will be like, “Wawawa.” It is actually in my contract that my contact had to have some sign off authority because I didn’t want that to happen because a few times it took months to get sign off.

Kaleigh: Well, that’s really smart though. That’s very proactive. People should write that down. That’s a good thing to have in your process document.

Paul:      It’s a good tip I guess.

Kaleigh: It is. So let me ask, we’ve talk about how we got these kinds of clients, if somebody was getting their first one; how should they convince to be hired essentially as a freelance person? What kinds of things would they need to layout on the table within the value proposition.

Paul:      Yup that’s a great question because that’s the biggest thing that freelancers should think about is how can I position myself as better than somebody else they could hire or an internal hire like hiring full time or an employee. For me it was always I produce the same level of work as an agency but I have no overhead, so you get the same quality for less money.

And same with employees, if it’s easier to hire me to do this project because I only have to do the work that you’ve hired me for. You don’t have to put me through HR staff or you don’t have to pay me anything else. I am working for a contractor for you so I’m just doing the work that you’re hiring me for. All the other stuff, like, it’s expensive for corporations and this is why the freelance economy is booming right now. It cost companies a lot of money to have full time employees, much more than your salary. Their salary might not even be the biggest expenditure that they have for each employee so hiring a freelancer can make sense. And a lot of times, and this is another reason why I got hired a bunch of times is because their team had a project that they couldn’t do themselves and they didn’t have time to hire somebody. I didn’t need to be brought up to speed. I just needed to be told what the project was given the task and then I would do it. I ended up doing a lot of work for either Fortune 500 companies, big clients, or doing work for agencies that where hired by big clients and those agencies didn’t have enough people.

There is a lot of enterprise work that I have done where I was hired by an agency and they just gave me 100% of the work other than them managing the client which I actually thought was easier. I’m just told what to do and give me my marching orders. Their payment terms with the agency is better than the payment terms with the big clients so it was easy. That was always a value proposition was that I can get to work quicker. I have less overhead and I produce the same level of work. I’m not going to guarantee any outcomes because like you said, it’s really hard to do that. But I can say I have a good track record with outcomes, here are some of them; and I produce quality work.

Kaleigh: I think there is also the angle of if you are somebody who has a very specific set of subject matter expertise that’s a huge advantage for you. So if you are a copywriter for example who specializes in sales pages for a specific type of product and you have this great track record where you’ve produced all these results for similar types of clients. I mean that’s almost a no brainer like you are the dream person that could do this job. I think just reminding the client of that and really spotlighting your expertise in those situations is a great. Like I said, it would be silly for them not to hire you in the situation because you have exactly the specialized skill set that they are looking for.

Paul:      Yeah, and that’s also a benefit of knifing down and finding like your specific audience that you serve with the specific skill set then you become known as the person that does this. It’s really hard to hire those people full time because a company may only need that for a month of the year, a month every couple of years. Whereas it could be the expert at like a CRO copywriting for SAS is this person because they’ve seen their name because I’m in this industry. Maybe I’ll just hire them to do a project for a month instead of looking to hire somebody full time because they might not even be able to find anybody full time.

Kaleigh: Right. But this also opens the door to long term relationships with those types of clients because like you said, they might only have a onetime project but they are probably going to have future projects that are similar so that’s an opportunity for freelancers to propose retainers with these types of clients and to say, “I can kind of be your on call person for this kind of agreement for the next three months.” And that’s again an opportunity for some kind of guaranteed income for at least like a short 3 to 6 to 9 month period. I could see that happening.

Paul:      Yeah. Or even just work in the future because a lot of times the bigger clients I worked with their team gets stress too thin, they bring me to do the work. That happens a lot in corporations where the team just doesn’t hand a discretionary fund where they have money in their budget to do whatever they need to do to get the work done and so they can bring in freelancer. I feel like that is so much more common now. I feel like it wasn’t as common in many many years ago but I think that more and more companies are kind of seeing the benefits of that so it even takes less convincing. It takes more convincing to convince the clients that you specifically are the right person and less convincing that they should hire a freelancer in the first place. I don’t know, I could be wrong there but I feel the tide have changed.

Kaleigh:           No, I have seen that too. I agree with that.

Paul:      Cool. So what haven’t we covered with working with freelance clients here?

Kaleigh:          You know I think that that’s the big stuff. Like you said that there is some red tape to be aware of but I think in the long term, like you said, some of the benefits that you can get from doing this type of work will last far beyond when the project wraps. You know, the money is probably pretty good but if you’re getting pieces of authority building from these types of relationships that’s something to think about too when you’re kind of weighing the pros and cons of taking on a project like this.

Paul:      Definitely, and with any project too. It’s important to think whether it’s worth it or not. Like I have had some corporate clients completely lowball me. They are like, “You are a freelancer. You don’t need to make much money on this.” It’s like, “Actually it’s a legitimate business.” I’m just a smaller one but I’m still legitimate business. I think that sometimes it cannot be worth it if they are not going to respect the fact that you’re doing legitimate work for them. But if that’s not the case then there can definitely be quite a few pros but it’s not like the land of milk and honey every single time just because they are a client you’ve heard of. They could be a crappy client regardless of how big or small they are.

Kaleigh: That’s very true.

Paul:      Cool.

Posted in Creative Class, the freelancer podcast   ·   See more articles


Want to know when new articles are published?