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As long as you have their first name, I don't see why this can't be automated. It doesn't seem time well spent and there is more chance for error doing it manually.

I agree with getting in touch, I just don't agree with spending your time each day doing it.

That doesn't work. Users can spot an auto-generated email a mile away.

I answer a lot of mail and I make sure that I always refer to something in the original email that is unique to the writer. That goes a long way to getting out of the 'form letter' rut and the response is much better than with emails that contain no 'personal note'.

Reading the email in the linked post, I don't see any "personal note" in there. Other than the first name which, as redguava points out, is easily obtainable. It looks personalized, sure. But there's nothing telling me it isn't sent by a cron job.
Indeed, it just looks like an automated welcome message.

In the early days of the internet, I may have fallen for something like that... only to realise my reply went to a ticket support system or a fake 'from' address. Nowadays, I'm cynical about welcome messages and just delete them.

Doing it 1000 times may show you a few ways that automation can screw that up.

Also you may see someone you know.

You shouldn't fully automate it. I have a semi automatic process where I click a mail_to link and get a pre-filled email ready to send with the customer's name in it.

Occasionally, there is reason to do a little research into the customer's operations (e.g. visiting their website) from which I can add a personal twist.

If you do it that way, it's not a huge time suck.

Here's what wrecks the experience:

1) The email comes from info@example.com instead of your personal company email account.

2) The email does not contain your normal signature, complete with email and phone number.

3) The email contains too much custom info (nothing more than the customer's name). No real person would take the time to cut and paste a customer's custom URL, for example.

4) HTML emails, unless they are very plainly styled. It needs to look like a regular friendly email.

5) Any sort of marketing speak. Has to be in your actual voice, as if you were talking with a friend. It's not a sales pitch, but an opportunity to connect.

6) Getting the name wrong! Just because there is a name field doesn't mean your customers put their name in it. This is the main automation killer. Better to have no name at all than the wrong name or "Dear Admin User"

7) The email is too long or contains anything that a reasonable person would assume was cut and pasted in.

8) Not asking any questions - if you don't ask questions, you're less likely to get an answer.

I'm sure there is more, but this recipe works reasonably well for me.

All of this can be handled in an automated email. I do this already in my startup and I get responses from my users just like I did it manually.

When bootstrapping a startup that you want to be able to scale, automating everything that can be automated is very important.

It's okay, you'll come around. Really, it's not something worth automating and you'll realize that when you accidentally send your mom / investor / mentor / family friend a canned response.
I personally wrote thank you cards to our first hundred or so customers. It really goes a long way to show some sort of personalization.
I think it's a nice trick, and I will definitely apply it myself once we're ready to roll out. I do have one comment though (similar to redguava's).

Emailing the first 1000 users, fine. But doing it personally and manually, why? Aren't you going to end up using exactly the same text for all your users (either that or risk typos that make you look less professional, not more human)? Don't forget the risk of developing CTS while you could be doing much more constructive stuff.

I would say, have it automated but sent a couple of hours after signup, or have them sent in batches at a time where you would normally sit down and do it. I'm thinking that people either assume it's automated or they assume it's manual, one way or the other.

Its not an engineering problem, its a customer service, business and relationship problem. I contend that the more you humanize these types of interactions, the better your results will be, the more you will learn. Look at it this way, 30 seconds to send each email works out to a bit more than 8 hours work to get some amazing customer feedback. Some organizations will spend this much time in planning meetings just to setup a discussion to strategize customer sat approaches. You can get the feedback for almost free. For me, its an easy choice! ;)
But, again, what do you say in an email that is personalized? Do you switch sentences around at random, change "hi" for "hey", forget a comma, replace a dot by an exclamation mark?

Responding to "it's a waste of my time to write the same email a thousand times" with "you should reply to each email personally" is moving the goalpost. The OP is about sending a first welcome email to every user that signs up, not about replying to an email sent for customer service or technical support.

I would never reply to a client using a canned response, I hate those with a passion. But the first email being sent, the client didn't send anything, doesn't know you or your writing style, didn't offer you any chance of customizing because it's just a "welcome to our service, thanks for signing up, I'm there if you need me" email. My point is, write it as if you would send it personally, but automate the actual sending.

In theory, I think your approach is fine, but in practice, there will always be opportunity to personalize. If you are really motivated, you can google the person and see if something interesting comes up, or you might already know the person tangentially from a conference, or there was an issue with the order that your team had to fix (a great opportunity to reconnect with a potentially unhappy customer). etc. Sure, a number of them might be exactly the same, but many of them won't be if you commit to the exercise and look for opportunities to form a relationship with these clients.
I think I'm starting to see the value, especially reading other comments here. Seeing an email that I recognize may be a great opportunity for a personal hello. I think perhaps one proposed solution would work best - having a list of new users that haven't received the welcome email, see their information, and then decide to send the regular message or edit it before sending. I think that's the way I may be heading, it sounds balanced and right.
This automated approach is fine, but only if you don't try to pretend it's personal. SlideRocket does this really well - sign up for SlideRocket and watch the helpful emails roll in. Not too many, and always with a good tone and good content. But none of them pretend to be produced by hand in Gmail.

Sending personal emails to the first 1,000 customers is great, and switching to automated lead nurturing after that is great. Partly for scale - there are a hundred high-value things a CEO can do once a business gets going. But also because customers don't think it's appropriate to get a personal email once you grow to a certain size.

Anecdote: I've been heavily involved in our sales process at Zencoder since the beginning (as CEO), including writing personal emails to 500-1000 signups early on. (We've stopped that by now, but it was the right thing to do early on.) A few months ago, our sales director and I went to meet with a high-value prospect. At that point, their financial value wasn't huge (hundreds per month), but we knew they would grow, and that they'd be a good reference customer. So we pitched them and everything went well.

I ended up meeting with them a second time, and they asked me point-blank: "How is your business viable, if we're only paying you $X00/month?"

The subtext was this: "If we're only paying you $X00/month, and we get the CEO in for two in-person meetings, then you must be small, and we must be a critical customer for you to win." Customers should feel important, but never critical.

This came to a head when we sent them a final proposal. They asked for a price break and concessions, and said explicitly that because they were an important customer for us, we'd give them these things concessions. In reality, they were no more important than 20 other prospects we were working with. But because we brought our CEO into sales meetings on a small deal, they thought we were smaller than we were.

This is a great recommendation for a startup looking to differentiate based on customer service.

I don't buy the implication that this isn't a great use of "executive time". I'm not the CEO, but I run a business unit and the buck definitely stops here. I still make time to:

- respond to random emails I pick out of our customer service email queue

- read all customer feedback submitted from the "feedback" tab on our website, and pick out any submissions that I think need special handling

- put my email address on many, if not most of the automated emails that get sent out, especially renewal notices and anything else we view as "really important". This usually generates a few hundred inquiries that I need to respond to, or route to another staffer

- troll social media looking for opportunities to perform random acts of kindness for our customers and prospects. This year I've sent t-shirts to Norway, a custom order of premium teas to Capetown, a box-set of books to Lincoln and many, more little gifts to surprise our customers.

- personally manage our primary twitter account, @hover to make sure it has a consistent voice and purpose. This account is in addition to the group-managed accounts we operate in support of the primary account.

So what's the pay-off? Why should a founder or leader be concerned with such trifling things? In the three years since making our commitment to providing real customer service (as opposed to lip service), we've built a culture where everyone understands what we each need to do to meet or beat customer expectations, and fix it when we don't. I don't think it hurts for my team to see me working alongside them helping customers and fielding inquiries day-to-day. The rest of my senior team works similarly and it really makes it easy to raise the quality bar when the leadership team is "walking the walk".

In our business, this extra efforts means that our renewal rate beats industry average by light years and our customer sat metrics are world-class.

(edit to fix formatting and some stupid grammar that crept in while I was distracted)

Agree that it feels like a waste of executive time.

Although, there's probably a bit that the exec could learn from early users, perhaps initiate conversations over features, gather pain points and so on. But there's no reason why this can't be handled by someone else on the team.

And '1000' is just a ridiculous arbitrary number. How quickly did the company get to 1000 users? Imagine replying to a 1000 early adopters who've signed-up over 5 days. It's absurd. I feel dedicating a % of the day for this, might make a little more sense.

Lastly, it's astonishing you find time for the stuff you've listed.

Whether or not it's a waste of time depends on the commitment you've made to your customers. Jobs obsessed over design for a reason. Our promise is to provide exceptional customer service, so that's how we prioritize our time.
Well said.

Though, habits like these (suggested by the article) early-on could shape the startup's perception of their commitment to their customers. It could end up being a costly 'culture' thing.

It's still debatable whether dealing with customers daily, makes for productive use of an executive's precious time, even if the startup's value proposition revolves around exceptional customer service.

I've witnessed a few small companies getting infinitely better, once they started hiring the right people to fill sales and customer relations positions, that were usually handled by the founders themselves.

Well, I can say that it has been a great use of my time :-) The increased focus has demonstrably paid off in terms of real revenue and customer activity that I don't think we could have tapped into with a lesser focus. Everyday I'm seeing new things that help us improve, that help me set a strategic direction that would be muted if the feedback were filtered through intermediaries.

There are other ways of organizing of course. Someone once told me that its way better to organize around the strengths and weaknesses of the people that you have and the people that become available than it is to organize within the constraints of an org. chart "because that's the way its done". I'm sure that if we had a different mix of skills, we might choose to delegate differently, but this is what works for us. For example, I spend very little time worrying about engineering matters compared to the amount of time I spend managing customer service workflows. What matters is whether we're putting points on the board, not so much which plays we're running.

Counterpoint:

If you have < 1000 signups CEO is just a title anyway, and probably means "the only person who works here."

You've got time.

I use this formula instead.

10,000 emails x 0.1 ctr = 1000 leads 1000 x 0.02% sign up = 20 users

I want to make sure I got enough leads or first time users and assuming only 2% of my leads actually sign up. I want to still have a decent monthly recurring income.

I've mentioned this in another thread before, but Wufoo sent me a handwritten thank you note for being a (paid) customer one year around Christmas.

Now THAT made an impression.

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protip: setup a separate email account to this from
I've done this since day one in my startup (I'm in day 112). Not being a hacker I have to be really careful where to put my dev money, so any automation I might want to do I have to figure out ways to do it without involving the devs (that money goes to the service I'm building)

I have a combination of processes:

1. User must fill out a form with their name and email in order to get the download link. For this I use Madmimi.com.

2. I have setup a drip campaign. Basically what happens is that once my users confirm their email, Madmimi automatically sends out and email with an welcome text and the download links (the benefit here is obvious: I have the users email and I now have statistics about click rates on the link)

3. This drip campaign has two additional emails. One in 15 days and another in 30 days (after the signup).

The 15 days after sign up email, basically ask how's everything is doing and contains a link to a quick survey about the whole experience so far (I use Wufoo). Is a guided survey with close question.

The 30 days after sign up email is an open question about how they feel with the app. What does it mean to them, etc.

Also, my app sends me a log every-time the user uses it for the first time (here is where I haven't been able to do a full integration)

What I do is: I receive this log that contain the users email and some data about the usage. At that moment I fire up my email client and write a welcome email. This is a personal email from me to my user. I thank them, give them all my contact info and basically say: I'm here for you 24/7 (to this day no user has ever waited more than two hours to hear from me when they write) and I keep that promise.

Most of the time, the emails I get are basically about the same and my answers are very much alike.

To manage this and to be able to give it a personal touch, I installed TextExpander on my Mac and have setup several templates that contain most of my answers but not the full answer. This forces me to read what I'm writing and actually personalize it a bit.

This method, while not perfect has brought incredible benefits for my startup:

One client was having some issues with the app and my response was fo fast and so helpful that he could not believe it. Turned out the guy was a radio dj and had a show about entrepreneurship. We did a two hour radio interview.

Another client is actively pushing my app to his clients because of the customer support I gave him the first days he used the app. He was having some issues (all created by him) and I dedicated 6 hours to help this client. He is now one of my most active evangelist.

It pays, big time, to do customer support with passion. Let your users feel it and they will reward you for it.

Do you have any trouble with people reporting your drip emails as spam? I found that some people are reporting emails instead of clicking the unsubscribe link. Unfortunately, many email clients make that button more convenient than tracking down an uninstall link within the email.
"more convenient than tracking down an uninstall link within the email"

Perhaps you should make your unsubscribe links easier to find?

The link is extremely easy to find. It's the only link that appears at the bottom of my emails.

Checking the box in my Gmail inbox and clicking the "Spam" button is much easier than opening the email and hunting down the unsubscribe link.

This may be a stupid question, but are you sure your unsubscribe functionality is working? After "Successfully unsubscribing" to Appsumo (trust me, I saw the picture of the founder when I was done) about 6 times, I was still receiving emails from them, and therefore marked them as spam. I also will mark the companies that don't have an easy unsubscribe all method as spam. (IE, you didn't give me the option to opt-in/out when I signed up, and send me a whole bunch of emails which I have to log in to your app to turn off)
Yes, the unsubcribe link does work. I think the problem is that people are not interested in purchasing the product, so they mark the "your trial is ending" email as spam because it's easy to do. I don't think most people understand the negative impact of marking emails as spam. They simply want to take the path of least resistance.
"It's the only link that appears at the bottom of my emails."

Personally, I've noticed an increasing affinity for the 'tag as spam' button.

It takes a certain amount of effort to scroll down, and find the unsubscribe (I'm not even sure if it's there), vs. having my inbox cleaned up by just clicking the darn 'tag as spam' button -- dead easy. Also, there's the uncertainty about how daunting the unsubscribe experience might be. These days, quite many startups get their users to go through tedious surveys before they can unsubscribe completely. This results in a sticky association that's hard to undo: 'unsubscribe' is a hassle.

Are there ways around this?

How about a large button above the fold that says 'Don't mail me.', 'Junk!' or similar. Something that indicates they'll have their intended results: less of this sorta mail, and a cleaner inbox. On the other hand, this might result in more unsubscribes.

Adding a large button to the top would certainly make it easier for those people who open the emails and want to unsubscribe. And I wouldn't worry about the increase in unsubscribers. I'd rather help people unsubscribe than have them mark my emails as spam.

I'm assuming that the majority of people are not even opening the emails though. Hitting the spam button is just too easy. I think the system is broken.

I'm assuming that the majority of people are not even opening the emails though.

It's probably partly our fault: we geeks have been telling our friends and family not to open suspicious or unsolicited e-mails for years.

OT: we moved our unsub link to the top of our mailers and complaints have dropped to almost zero.
You know what would be neat? When you click the "spam" button in Gmail (or other clients with similar functionality) and there's an "unsubscribe" link in the email then Gmail could suggest visiting the link with some kind of a notification and buttons labeled "unsubscribe" or "no, this is spam".

I suppose that could be abused however.

Actually, Gmail does something close to that.

When you click "Report as spam", if it detects it's a mailing list, it offers to (try to) unsubscribe properly:

http://gmailblog.blogspot.com/2009/07/unsubscribing-made-eas...

It's a bit strange that they don't give you the option then to unsubscribe without marking as spam (you can do it but with more clicks), but I would think that if you unsubscribe and mark as spam the overall system doesn't take the spam factor at all or as much. In that case, it's probably limited to your own account.

Cool, I did not know that!

I actually do unsubscribe, but I would imagine that many just hit the "spam" button to "make it go away".

The customer is always right.

Maybe your emails aren't appreciated in the spirit they are sent. Just because you cajoled someone to check a box to use your site, doesn't mean they appreciate your email campaign.

No they're not. There are a lot of jackasses in the world.

He didn't "cajole" anyone to do anything and the truth is the vast majority of people don't care one way or the other.

I do this and I'd definitely recommend it to anyone else. At least "real", "evil" spam mails. Clicking an unsubscribe link is a confirmation of your email address and will usually lead to more spam than less.
Does the link unsubscribe instantly, or must the user log in bla bla bla ..

More often than not, I find following those unsubscribe links very annoying because I have to log in and fill out 5 different forms.. and then it doesn't even work :(

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At first glance, I balked at the title, saying to myself, "Who has the time to personally email 1000 people while doing everything else a founder is responsible for. "

However, after reading the article, I completely agree with this approach. The personal touch, ID of earlyvangelists, and starting a constructive conversation. Great article.

Definitely agree with the advice.

One objection that people often have is that "why should I do something that's not ultimately scalable and that I'll have to stop doing anyway?". But what they're missing is that when you're first starting a company that's when the fragile young plant needs the greatest care and nurture. In my opinion you should actually go out of your way to do things that you KNOW won't be possible to do manually or personally later because this not only increases the chances of getting off the ground successfully, but one day you're going to miss the early days when it was just you and those precious few people that valued your product enough to use it before it became a hit. So enjoy connecting with them and don't think of it as a chore.

Beautifully articulated. Couldn't agree more.
Thanks. And also thank you for writing a spot-on post!
One other thing that is also useful: for any automated message you send, make sure that it comes from a real address that you monitor. Many, many customers reply directly to the automated emails.
+1. (Especially) for a startup, there is no reason for announcements to come from no-reply@startup.com. I have, as a consumer, replied to emails coming from info@startup.com with praise/complaints/feedback, simply because it's easier than copy/pasting customerservice@startup.com from the bottom of the email. You _want_ to get those kinds of emails, so make sure you monitor whatever address the automated emails come from.
This is a great idea, my problem is we're approaching 30,000 so its far too late. But this is something i'll try. I recommend using Toutapp as you can start with a basic template and customise for the user situation. It just speeds the process of emailing lots of people up.
I wrote a little about this here: http://peachshake.com/2011/01/02/engagement-secret-the-autom...

I do it fully automated, but take steps to make it look handmade. I've found it to be incredibly effective, with probably a 30% response rate.

Doing it by hand might be a little nicer, but everything is a balancing act. If I can get 80% of the benefit by automating it, I'm happy with that.

I'll go further and say that it's the CEO's job to personally CALL as many of the first 100 users as possible (if your startup is not aimed at developers/geeks).

I've been doing what this post recommends for Cilantro. We've hit 100 signups since launching the MVP 2 months ago.

A few random things I've noticed and done in addition to what's in this post:

- My response rate is lower than I thought (below 20%). My hunch is that this partly due to a very busy user base and partly due to language barriers.

- I tried using Tout to do this but in the end, I didn't see any benefit over GMail's canned responses.

- I actually called about 1 out of 3 new users (I ask for their phone number at signup). The response rate is WAY higher and the feedback I receive is much more valuable.

Personally, I hate to be called. It's a huge interruption. Email I can choose to deal with, but a phone call is too in-your-face.

Do you allow people to opt-out (or better yet, opt-in) for this call?

Hackers hate to be called ... the average Gen X small business owner doesn't. They are used to being on the phone. Plus, a single phone call can often get you information that would require 10 back-and-forth emails.

A Phone number is required because we're building them a website. If it wasn't required, then yes, I'd probably still ask for it but include an opt-in checkbox.

This is excellent advice.

With every startup I've been involved with, the first iteration of our product was not the last, nor was it perfect. I see this more so as a means of ensuring your product doesn't get between you and the customer. Most startups simply do not value customer service as part of the opening strategy.

Side rant: I blame Google for the perception that you can automate your entire business, without any human interaction. (Ever try to get support from a Google rep for an application?) Even Apple, who offers products that "just work", offers very good customer support.

BTW, I was thinking that famous people like CEOs should sign their emails, espicially after the iPhone 4 antenna/BGR fiasco. At that time iOS 4 did not support S/MIME, but now that iOS 5 do, I wonder if famous people will use it.
How can you go wrong trying to connect with your customers as a business owner. I think this is a great strategy to follow and even beyond the 1000 users, you can still grab x number of new customers to email personally. People want to feel important and personally communicating with the founder is one way they can do that.

I can recall a time when I received a personal phone call from the CEO of a marketing blog I followed. When he introduced himself, I recognized the name, but was sort of shocked he was calling me. The guy ran a very successful business with tens of thousands of subscribers, why was he calling me? That was my initial thought. He wanted my opinion on a few things, that was all. Wasn't trying to sell me anything. My answers were lame at best cause I was caught off guard (literally shocked), but after the call was over, I had to sit down and take in what just happened. I never forgot how that call impacted me. It did make a difference. I ended up buying several of his products after that, not because he called me, but I believed his products were good and felt comfortable buying them from him.

It's simple, really, after looking back, he was just building relationship and rapport which translates into trust which translates into relationship which turned into sales. When your product has a lot of competitors, who does your customer turn to first? If you have established some sort of rapport, it will be your business. It works...

This is awesome, thanks!

I just emailed everyone who signed up in the past week using a similar template ...

Obviously I should have been doing this all along, But I'm a first-time founder, I need to be reminded ...