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Guide to Sending Email Like a Startup (sendwithus.com)
363 points by mrmch on Oct 20, 2015 | hide | past | favorite | 41 comments

It's mentioned in there, but I really want to emphasize how important it is to ditch the do-not-reply return address and, in fact, to have actual people read every single reply.

We get great suggestions, feedback, sales opportunities, etc. from replies to automated messages. We don't get many complaint emails, but when we do the author seems to think they're yelling into a void. People seem genuinely impressed when they get at thoughtful reply back and sometimes it changes their whole impression of us.

No email should ever be sent from a do-not-reply return address. Ever. You have no idea how much email I get because some idiot used my email address to sign up for something/order something/whatever.

To this I'd also add: Always confirm email addresses. Every time someone signs up for an account, send a confirmation email with an easy means of notifying you that I'm not the person who signed up for the account. So few do this.

I see big companies do this all the time. It's annoying. Even a support@ that gives me a ticket number out of ZenDesk is better than no-reply@

Its hard to underestimate the value of sending a thoughtful reply to an annoyed (potentially angry) reply to one of your automated messages.

^ as above, multiple opportunities have come from simply being empathetic to the fact that someone was tired of your automated emails. Being a real human helps.

I worked support for a consumer facing startup. Several of our most vocal advocates were formerly angry customers who were treated as human beings in support messages.

This really works. It's a great trick. I fallen for it many times, and in the end decided to purposefully evangelize people and companies that treat customers as human beings and do other nice things like that.

Not confined to email: people who feel they are not being heard will get angry.

Remember folks, every single piece of correspondence we send should be valuable to the receiver.

Welcome email? Great - tell them something that will help them to get setup.

Referral email? Great - tell them how they can win by referring you, and I mean really win.

Promotional email? Make sure that promo is worth their while.

And never take your audience's time for granted. You're trying to build a relationship.

I notice that your examples don't include the "'begging for re-engagement from someone who doesn't need to use your app' email"

I call these the "reminder to actually cancel/close my account" emails.

This is the PERFECT attitude to email. Companies that do this really well (AirBnb for ex), their emails look and feel just like their website, and always focus on highlighting the relevant information.

Excited to share this -- we just completed the guide (5 chapters in all).

Includes contributions from Ivan Kirigin (YesGraph), Noah Kagan (AppSumo), and more.

No matter how much you may/may not like receiving email, there are a lot of people out there who do. This guide should help you reach them, without annoying the others.

It's really excellent. Nice work!

Holy shit you created an epic content article. Nice work man.

Wow, that's comprehensive. The Net Promoter survey is very powerful, if you've never used it: once you've identified and bucketed all of your users who give you a 9 or 10, you can hit them up for referrals, reviews, and shares, and skip all the users who might not have anything nice to say about you.

Yeah we like NPS a lot. Not only can you segment and specifically reach out to 9s and 10s, but you can dynamically fill your emails. So for example your standard footer could say "share for x bonus" if they're a 8-10, but "give feedback for x bonus" for <8.

direct link to that section: https://www.sendwithus.com/resources/guide#ch3-survey

There are several parts of this I disagree with, but the one I disagree with the most is onboarding emails.

Can I use your product in the email? No? Then don't send me an onboarding email, do the onboarding in-product with overlays when I log into it for the first time. Google does this with some success for Gmail if I recall correctly, it has arrows pointing at different sections and everything, and you can click to dismiss them.

Bombarding the consumer with multiple onboarding emails may generate a high click rate, but if your target market has people that hate spam, it will instantly leave a bad taste in their mouth. It really sucks when I sign up for a new product I am peripherally interested in, and they clutter up my empty inbox with 5 enthusiastic emails, none of which has any content that I can actually use -- just links to the website.

The point of onboarding emails is to boost your activation rate. Users frequently get distracted during onboarding and drop of. A drip campaign that highlights the benefits of completing the onboarding is highly effective. The majority of people consider emails spam if they aren't relevant. Someone who intends to complete an onboarding process but was sidetracked usually finds these reminders useful.

This bag of tricks seems to focus more on doing things as other companies do than on what data there is to tell you it is the right thing for you. No guarantees those companies made the right inferences from the right data, and even if they did, no guarantees their conclusions apply without modification to your situation.

Is there some inherent value to being "like a startup" or following "trends"?

Valid feedback pekk. One of the reasons we consulted with people who have run growth at a number of companies is because they could give the inside story; company X did Y because their metrics told them to.

That said, a huge caveat is that this all depends on your audience and what they're going to respond to.

I would posit that startups are more apt (than a larger company) to experiment with marketing, which is valuable.

This is such a great resource.

I helped with the referrals bits, but the other sections taught me a lot too.

Really appreciate your contribution Ivan, definitely learned a LOT about referrals from you.

These are not transactional emails, but triggered emails that are automated by a user's actions. Transactional emails typically revolve around a transaction, example emails include an order confirmation, shipping confirmation, or order cancellation email. I'm pretty sure most of these emails would require the customer to be subscribed to your email list, while a true transactional email would not.

See: https://en.wikipedia.org/wiki/Email_marketing#Transactional_...

It's a fair point to highlight what constitutes a true transactional email, but the content of this guide does cover both transactional and triggered emails (Welcome or registration email is one example of a transactional email covered).

Why is sendwithus.com allowed to advertise by posting as a blog site, why isn't it flagged by now? These are the types of people I block in my server's email configuration.

Promoting your business on HN is not a bad thing per se. This post is actually a great example of HOW TO promote your service on HN. By providing very useful information to startups and companies who need to send email to their customers, SendWithUs has made us all smarter and in doing so have improved their credibility as an email service.

I'm somewhat puzzled by this paragraph - even moreso as they seem to base a lot of advice on top of it:

For Facebook, they’ve defined core retention behavior as the point when a user has added at least 15 friends to their account. In Alex Schultz’s Startup Class lecture he discloses that, for Facebook, someone that has 15 friends is likely to remain active on the service for a long time, so their retention strategies are all focused around promoting the behavior of adding friends.

To find your own core retention behavior, look for specific actions that are common to your ideal users, then promote that behavior in your retention strategies.

I'm not a marketing expert, but this seems like a classic example of "confusing causation and correlation" to me. So, in the example above, facebook has found that "user has > 15 friends" is a good indicator for "user is loyal". Fair enough. but instead of going "we have this awesome way of identifying loyal users, now let's find out what made them loyal in the first place", the guide assumes that the high friend count actually causes the loyality and advises to do everything to bump it up.

In Facebook's case, this probably works, because friend count might actually influence retention in some ways. (e.g., your news feed might become more active or more interesting, making you want to stay). But even then, you're kept completely in the dark what made those people sign up and add friends in the first place.

i think taking this as a general advice might actually be dangerous. In the best case, you keep a high retention rate but have no idea why; In the worst case, it might tempt you to build "features" that try to manipulate or even force the users into particular behaviors, only to inflate some metric. (see, e.g. Pinterest's "auto-following" routine: http://www.businessinsider.com/wait-a-minute-pinterests-sign... )

This is the most comprehensive and useful guide on sending emails I have come across so far. Going to implement a few ideas right away and track the results.

I feel like the point on "Set a Conversational Tone & Sign from Real People" is reaching a bit of over-saturation currently. As soon as I get such an email from a company, it leads to my thinking that "they're trying to deceive me into thinking someone is actually sending out these automated messages. Do they think I'm an idiot?" It feels very disingenuous.

Clear and simple. Good job.

I've got a question about your starter/hacker plan... Up to 1,000 recipients/month means that I can do X sends up to 1,000 different emails? For instance, mandrill has 12,000 Free emails limit. Can I connect mandrill and use those 12k/month as long as I don't have more than 1k/users in your system?

Thanks joeyspn! Means a lot to the team that their work is appreciated.

You're absolutely correct about our hacker plan; up to 1,000 unique email recipients per month (it resets each month).

Following every step of this program is a very good way in making me avoid your product.

"Surprise & delight your new readers with a funny cat picture. Seriously, never underestimate the effectiveness of a well-timed cat picture."

This might work for some types of businesses, I suppose. For others it would be a huge misstep.

Thanks for this guide; I think it is great!

This article is really great for a marketer at any level!

Thanks -- we've tried to ensure there's basic information and more involved tips for experienced email folks. The guide also highlights some of the trends we've seen in the last year.

"Transactional emails are the mechanism by which you keep in contact with your users, just because they’re automated, doesn’t mean they should be robotic."

Whether its origin is a startup or a giant corporation, any email can be made to sound like a poor marketing scam - just include run-on sentences like that one.

One tip that should probably be shared - Marketing that is so obvious that it's marketing doesn't work. Most firms seem to play by exactly the book in the article, and it's a little predictable. Does it work? I don't know. Maybe it does. Though I'm interested if some experimentation can remove some local maxima.

And once you are trained to spot a NPS question, yeah, it starts to rub you completely wrong. And you can tell when you are part of a email drip campaign more quickly, or when you go from being a automated plast to a warm lead or whatever.

re NPS, I do think it's useful to ask people who aren't 8's why they don't like you maybe more so than asking the 9-10s to engage more. I am also not sold of the NPS idea of only asking that 1 question - but surveys can often be constructed to only answer the known unknowns [sic] and can be misleading. Arbitrary comment boxes without leading questions I think are great.

Use it as a learning tool, not a selling tool. It is more interesting to try to make being awesome your selling tool.

Same goes for blog posts, if it's full of buzzwords with no details, and it's obviously marketing, if the buyer audience is actually technical users, those efforts are likely misapplied.

How to blogs are much more genuine.

Oh, a spammer's manual. Disgusting.

Actually the point was precisely the opposite. If you give marketing creative control of your transactional emails, you don't have to blast your users constantly to maintain their attention.

Drip campaigns push the envelope on "transactional mail" a lot, and a lot of what the article suggests could IMHO easily push in the area that I'd consider spammy (sending multiple mails per week) and which makes sure I don't actually read any future mails unless I explicitly look for them, because they get filtered away.

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