#04 – Email Teardown: Skillshare


#04 – Email Teardown: Skillshare

July 12, 2017

Hi and welcome back to The Cold Outreach Podcast! Today we are doing a teardown on a cold email that Jack received last month from Skillshare, which is a platform where you can share your knowledge and get paid for what you know. We’re doing this solely for learning purposes, and we picked this email because it was actually pretty good compared to the rest of the cold emails we get, so we decided to analyse it and provide feedback to help you create more exciting cold emails in the future.

Here is the email Jack received:

Subject line: Marketing Collaboration with Skillshare?

Hi Jack,

I’m Kevin, Head of Teacher Operations here at Skillshare. I came across your website this weekend and was really impressed by your experience. I was wondering if you had ever thought about teaching business or marketing online?

In case you’re not familiar, Skillshare is an online learning community of over 2 million students.

Professionals from all over teach on Skillshare to earn passive income, build a brand, find clients, and grow an online following. Top teachers earn up to $40k a year and have over 25k followers.

This Spring, we’re focused on building and highlighting our business & marketing catalog to our growing student base and enterprise clients – so it’s a great time to teach business classes in particular. Luna Vega is a great example of a someone who taught online to grow her brand and business – you can check out her story here.

Would teaching on Skillshare be something you might be interested in?

Let me know!-

All the best,


Head of Teacher Operations, Skillshare

210 Elizabeth Street, New York NY 10012

please don’t email me again


We have a system for grading cold emails from A to F that we have applied to this email based on the elements such as subject line, format, introduction, value, influence, CTA, deliverability and follow up.

Tune in to hear our remarks, why we have graded this email with an overall C, and where we see room for improvement.

Want to receive the revised version we would have sent?

Podcast #4 – Skill share re-written email


And if you are interested in getting one of your cold email teared down, forward your best email, we promise to give you some tough love, but for your own good.

Thanks for listening and happy cold emailing!

Jeremy and Jack



– [Jeremy] Hey, what’s up, this is Jeremy founder of

– [Jack] And this is Jack from Emails That Sell.

– [Jeremy] Episode four, and today we are going to do a tear down on a cold email that Jack received last month.

– [Jack] That’s right, this cold email is brought to you by Skillshare, it’s a place that you can share your knowledge and get paid for what you know. They’re the ones who reached out to me with this cold email and we’re gonna go through it shortly.

– [Jeremy] Yeah, and then, this is not to bash anyone, we’re here to do, to learn, we change the sender’s name, but we left the company open so to provide some context to understand the email.

– [Jack] And kudos to the Skillshare team, before we get any further, because they did a lot of things right with this email, that a lot of outbound campaigns miss out on.

– [Jeremy] And Jack and I have a system for grading cold emails. This is, by no means, an F, in fact we picked it because it was a pretty good email, compared to the rest of the cold email we usually get. And Jack, tell us what grading scale we’re looking at here.

– [Jack] Yeah, so the grading scale is A through F. If you send an A message, for Jeremy and I, that means whoever gets that message is gonna be excited. Recipients are gonna go out of their way to reply to it, An A message will get people who, 99% of the time ignore cold emails, to hit that reply button. B is still a really good email, but instead of excited, they’re just interested. So that email stands out in a crowded inbox, it’s worth replying to. C means that it’s a neutral message, you might get some replies, but a lot of people won’t get excited about it, you also probably won’t get flagged as a spammer. If you send a D or an F email, you’re gonna annoy whoever is receiving that message. It’s untargeted, it’s not relevant, just annoying. And for an F message, this is probably an email that won’t even inbox, because it’s caught by a spam filter. And heaven forbid it goes into someone’s inbox, they’re gonna smash that flag as spam button really quickly and wish they never received it.

– [Jeremy] Awesome, you ready to go?

– [Jack] Yeah, let’s go for it.

– [Jeremy] Okay, great, by the way, we’re not going to read you this email word for word. If you want to see the full version, as well as our final rewrite, head to and search for episode four show notes,

– [Jack] And just before we start tearing down this email and offering our feedback, keep this in mind. We don’t know how this email’s performing. In fact, though it’s not likely, it could be just crushing it, for all we know. But based on experience, it could be a lot better. At least, it could’ve done a much better job of getting me, the email recipient in this case, excited to hit reply. So here’s how we would improve this email.

– [Jeremy] Yeah, so we look at multiple sections, and the first section we will be looking at is the subject line. The subject line says, marketing collaboration with Skillshares question mark. What do you make of that, Jack?

– [Jack] Right off the bat, not bad, it’s interesting, conversational, they threw in the word collaboration, which means I might somehow benefit from this. Also, it doesn’t appear salesy, so there’s no internet marketing copy in the subject line, which is great. The one thing I dinged ’em on was they capitalized the first letter of each word, which just, it’s a small indicator that there’s a chance that this is a marketing message, just because if I’m sending an email to a colleague, I’m likely not going to capitalize each word like this email did.

– [Jeremy] Fair point, for me I would say this is a plus in the length, it’s actually not like a super long subject line, the minus would be what’s Skillshare? If I have no idea what Skillshare is, then you’re just wasting one word, it’s not adding any value, any benefit for me. And the second thing is marketing collaboration, it’s a bit too vague, and it doesn’t really mean much. Are we talking about guest blogging, are we talking about ?? Sharing? Are we talking about joint venture, I’m not quite sure what it is, so a little bit too vague on that one. But overall, not too bad, how much did we give, how much did we grade this subject section?

– [Jack] The subject earned a B plus from Jeremy and I.

– [Jeremy] Not bad. Next section, we look at is the format, which basically means how does the email look like.

– [Jack] Right, so at first glance, you can tell that it’s not formally written, which is a plus, they didn’t start off with dear sir or madam, in fact, everything is conversational, except for the unsubscribe link at the bottom of the message. They basically stuck a hyperlink that said please don’t email me again without punctuation or it’s just, it doesn’t flow from the email body, and it’s clearly just stuck in there, and there’s much more elegant ways to include an unsubscribe link in a message. They could’ve put it in a PS or got a little bit more creative for that, so I marked ’em down for that.

– [Jeremy] Yeah, on the plus side, it can be considered plain text, it’s not like your typical newsletter HTML with big tables and images, so that was good, there aren’t too many links for once. When you have links, then text people focus away, especially when they’re in the middle of the email and it’s just too long. It’s 10 sentences, and it may be more than I’m ready to commit from a stranger at that point. My tip would be to break it into multiple messages, two, three, so it’s easier to read for me and digest when I have really took time or too little trust in a stranger. So how much did we give the format?

– [Jack] Yeah, the format earned a C plus from us.

– [Jeremy] Which is not all plus. Next section is intro, how good are they at getting my attention so I can read the rest of the email. Do you want to start?

– [Jack] Yeah, so the intro needs to answer one important question, which is why me? Why did they single me out and send me this message? So at first it appeared that they did a really great job of answering this. They said, I came across your website, and that told me that they were about to launch into what about my website got them to decide to reach out today. However, they followed that up with and I was really impressed with your experience. So anyone who checks out my website, that’s not a comment that it’ll leave you with. Now, if they would’ve said I checked out your Linkedin Profile or saw you on Clarity, yeah, that would make a lot more sense, but because they just came about it really broad, it appeared that they just threw this in and were not being truthful, so this intro left me annoyed.

– [Jeremy] Yeah, and before that, the first line is actually I’m Kevin, head of teacher operation, here at Skillshare, and when you send an email people can see who it’s from and if they want to have more information usually they read your signature so there’s no need, really, at this stage to really hammer a third time who you are and actually start with that. It doesn’t really add any value and yeah, so how much did we give the intro?

– [Jack] For the intro, they missed the boat. We gave ’em a D plus, one of their lowest scoring sections here.

– [Jeremy] Next section is the value section, which is quite simply what’s in it for me. What did you pick up on there, Jack?

– [Jack] Right, so lucky for Skillshare they’ve got actually tons of value to bring to the table. So something they let off with that was a really good value-add statement, they said top teachers earn up to 40 K a year and have over 25000 followers. That’s clearly a massive benefit to anyone who can achieve that. But I think they buried their value statements on top of one another. They went on to say that it’s a way that you can earn passive income, it’s a way you can build a brand, find clients, and grow an online following. I think they should’ve taken each one of those value statements and broken ’em down into their own emails. Because they’re all good points, but just crammed in on top of each other, so I wasn’t able to, I guess, appreciate each one as much as they should’ve been.

– [Jeremy] Yeah, for the top teacher earns up to 40 K a year and have over 25 K followers, I think it misses the time to be a real killer. Otherwise, what does it take? Is it 90 hours a week, like a full time job, or just a five hour a week, like a side job? So that’s a missing element here. Two more things here, we are focused on building and highlighting your business and marketing catalog, it’s making it all about Kevin, and I’m not really seeing the benefit here. As a reader, and the second thing is, they feel like they’re throwing a case study at us to prove their point, rather than actually sending it as a gift. So it’s all in the tone here, but it’s kind of a missed opportunity here to also bring value. So how much did we grade this section, Jack?

– [Jack] Value got a C. Tons there, but just not presented the right way.

– [Jeremy] Next section we looked at is influence, which is how compelled I am to reply. What you got there, Jack?

– [Jack] So they did a great job with social proof. One of their sentences explains that they have two million students currently on Skillshare, which is huge, and just that alone gives me them my stamp of approval that they’re a legitimate business, and at the very least, they’ve earned my attention with that statement. But they did two things here that sorta damaged the rest of the influence the email had on me. First was about their authority. The second paragraph leads off with in case you’re not familiar with Skillshare, is an XYZ. Now that statement basically is telling me that it sounds like they probably don’t think I’ve heard of them and for whatever it’s worth, that just made me feel like they’re a smaller company than they actually are. And finally, they had an opportunity to use some liking to show me that they’ve helped people really similar to myself with their careers, with their businesses. They could’ve said something like other people who run marketing agencies like yourself have used Skillshare to do XYZ, instead they took a really broad approach that I couldn’t relate to. And they said professionals from all over teach on Skillshare, which just didn’t resonate with me at all.

– [Jeremy] I did like on the plus side, I did like the scarcity, how they used that, like this spring, and it’s a great time, which basically means the email was a timely for me, and that’s an opportunity, so I kind of liked that, and it also means I need to act, I can’t wait for winter before doing something. The reciprocity was missed with the case study, instead of using it as a gift and then I will feel obliged to reply or do something, they make it look like they’re doing me a favor to throw a case study at me, so it kind of like totally failed at both on that one. And the commitment and persistency was simply not used, which is okay too, but it’s a missed opportunity as well, it could’ve said things like, hey, I saw that you’re already on How would you feel about applying your expertise with Skillshare? So overall, not impressed, how much did we give that section, Jack?

– [Jack] Yeah, not so hot. They earned a D plus from us for the influence section.

– [Jeremy] Right, so let’s see, their CTA section, if they do any better. The CTA is call to action, and it just means what should I do now as a reader? And the call to action was would teaching on Skillshare be something you might be interested in question mark.

– [Jack] So right away, I read that call to action and I see that they’ve missed an opportunity here because they’ve led with their feature, instead of the benefit. So teaching on Skillshare, it’s just a feature. It doesn’t, that in itself doesn’t get me excited or provide any real value. However, the benefit behind that is really kind of interesting. They could’ve worded it so that it says are you looking to grow your influence in the cold email space this year? That’s switching out a feature for a benefit and that call to action would likely be a lot more exciting to reply to than the one that’s currently there.

– [Jeremy] Two plusses, the first one is that this is conversational, so that’s not, that’s always a good thing, and the second plus is it’s actually pretty low commitment. I like that. That probably means lot of replies, there’s no phone call, no long sale to give, just a yes or not should do it, there’s no time, no meeting, no appointments, anything like that, so that was pretty good and pretty positive on my end. Overall, how much did we grade the CTA?

– [Jack] Yeah, not bad, it got a B minus from us.

– [Jeremy] Not bad. Our last section we look at is the deliverability. Basically, did they see my email, did it end up in the inbox? Did it, Jack?

– [Jack] Yeah, so it did end up in my inbox, and that’s a clear plus right there, but two things stood out to me that they could’ve improved on. First, they’re using their own domain, the Skillshare house domain, and if they get hit by a blacklist or enough people flag ’em as spam, there’s a chance that even internally it would be hard to send a message from their Skillshare domain. So marked ’em down for that. And finally they sent this cold email to my Gmail account, my personal email, which is not good. If you do that enough times, you’re almost guaranteed to be flagged as spammer, and your inbox, your emails just won’t inbox properly, so though they inboxed this time, a couple things they could’ve done to improve it.

– [Jeremy] There’s a few things I could pin them for as well. They’re using image open tracking on the first touch, and I think they get away with that, so basically open tracking means there’s a small pixel that is added like an image, invisible image. And I think they get away with it because their email is pretty long, but if they rewrite it with some of the suggestions we have, then their email will be shorter, and then the ratio between image and text will be in balance, so as a general rule, I wouldn’t actually put the image tracking, open tracking, on the first touch. The second thing is they have three links, and usually the more links you have, the less chances you have of finishing the inbox, so keep it simple, minimum links better. On the plus side, the SPF and DKIM, which are technical stuff, were actually good, and they were not on a blacklist, so that’s good, and they did something pretty good, too, which is the unsubscribe was part of the header as well, which means usually they honor their unsubscription, otherwise Gmail will remove that from the header. So overall, how much did we give it?

– [Jack] They almost earned an A. They got a B minus, but since they didn’t create a separate domain to send these cold emails, they lost out on their A rating for this.

– [Jeremy] Yeah, fair point. Any other things, so that’s it for the section, any other thing we didn’t mention there?

– [Jack] Yeah, so I got this cold email a couple months ago. And I’ve yet to receive a follow up, even though I didn’t reply to it. So that alone probably one of the biggest areas for improvement that they could make on this campaign. It’s just simply following up on people who haven’t gotten back to them yet.

– [Jeremy] So what was the final grade we give to this email?

– [Jack] Yeah, so this is a C email. Which, you know, it’s average. Some people might reply to it, but there’s clearly some room for improvement.

– [Jeremy] Okay, that’s it, so if you want to see the edited email, that we completely rewrote, just go to and look for the show notes of episode four.

– [Jack] And if you’re interested in getting one of your cold emails torn down by Jeremy and I, forward your best email to

– [Jeremy] That’s it, thanks a lot, Jack.

– [Jack] You bet, thanks, Jeremy.

  1. Johan
    July 13, 2017

    Hey Jeremy !
    Where's the link for the re-write version ? :)
    Anyway, this one was for me the greatest for now. Keep it on !

    Reply Reply
  2. Lucian
    July 17, 2017

    I was thinking the same thing. Great show tho... I have listened to it a few times!

    Reply Reply
  3. Jeremy Chatelaine
    July 18, 2017

    It's available now, just fill the form at the bottom of this post :)

    Reply Reply
  4. Jones
    September 8, 2017

    Just filled out the form to receive the re-write version of the email. Thanks!

    Reply Reply
    • Jeremy Chatelaine
      September 8, 2017

      You bet! :)

      Reply Reply
  5. Andrey
    September 18, 2017

    Just filled out the form to receive the re-write version of the email. Thanks!

    Reply Reply

Leave a Reply

Related Stories

August 30, 2017

#011 – Email teardown: CaseWave

September 20, 2017

#014 – Email Teardown:

December 6, 2017

#025 – Email Teardown