Skip to main content

Intro to Lifecycle Emails

patrick mckenzie headshot This is a guest post from Patrick McKenzie (@patio11). Patrick is the founder of Kalzumeus software. Patrick has several successful SaaS businesses and has recently been making fistfulls of money for his consulting clients by helping them implement lifecycle emails. Take it away Patrick.

No startup has ever died because they spent too much time talking to customers.

Unfortunately, this doesn’t come naturally to the engineer in me. I would much rather retreat to the Bat Cave and bang out features in Rails. This, however, is not the path forward for the business — as the Lean Startup crowd will tell you, you run the substantial risk of building something that doesn’t actually solve problems customers care about. So I needed a way to force myself to continually talk to customers about their needs, to guide my product and marketing roadmaps.

Enter Lifecycle Emails: Sending The Right Message To The Right Customer At The Right Time

One of the best hacks that I’ve discovered for talking to customers regularly is building systems which make my customers come to me. (This ran exactly against my inclinations — what programmer wants more support email? — but it has been an epic win for my business so far.) I do this by sending people emails triggered by where they are in the free trial of the software, both in terms of how long they’ve been using it and how much value they’re getting out of it.

Here’s four examples:

The Welcome Email

You know the standard “Thanks for signing up for $FOO_APP” email you typically get right on account creation? This is a missed opportunity for most startups: why tell them things they already know (“You signed up!”) when you could focus on things they don’t which will actually create value for them?

  • Here’s what you should do right now to get value out of the free trial. (This is key, since 40~60% of your customers will end their first experience of your software without having done anything at all. Lead them to the value.)
  • Here’s the top three questions our customers have on the first day, answered right up front for you, so you’re not frustrated and don’t have to hunt around for the answers.
  • “I’m the CEO/co-founder of this company, and I love talking to customers, about either our product or your needs in this space. Reply to this email. I will get back to you, within a day.”

A lot of people worry about being the little guy. I’ve been there and done that myself, especially since I’m frequently in Enterprise Sales shootouts at hospital systems against a two-man team from the $80 million gorilla in the market… participating over the phone from Japan. But heck, if we’re going to be the little guy, we should throw our little guy weight around.

Being the little guy means your tech support questions always get answered by the product lead. Being the little guy means that if you need an integration done the timeline isn’t “Next quarter” it will be “We’ll move heaven and earth to get that done if it closes this sale.” Being the little guy means being passionate when the competition is boring, means being authentic when the alternative is lies, means being nimble when the default is statis. Doing business with the little guy resonates with some of your customers, so sell the benefit of that to the hilt, rather than sending emails signed by The FooApp Marketing Department.

The Mass-Personalized Welcome Email

Continuing the theme of being the little guy, I like to follow-up the welcome email (which is templated and automatic — and everyone knows it) with a personalized email a few days later. Let me quote my usual email in its entirety:

Hiya $NAME, I saw that you signed up for a free trial of Appointment Reminder a few days ago. I founded the company and head up development on the product. If you need anything, please feel free to drop me an email.


Patrick McKenzie
Appointment Reminder

It is sent completely unstyled, and reads like I just dashed it off in my email client. Customers have a very positive response to this — they’ll often write back “Wait, are you really the founder?” “Yep. How are you liking the software so far.” “Oh wow… I haven’t gotten around to importing my client list yet.” “Can I help you with that?”

Bam, two big wins.

#1: I just learned a thing that was blocking a paying customer from using my application — they didn’t immediately import a client list. I can now start collecting data on whether that is happening to other people, and if it is, I can make product or messaging changes to fix it. (Maybe my first email should have said “Do you have a list of clients you want imported into the system? Reply to this message with it and we’ll take care of that for you.” That’s certainly worth trying given the unit economics of my business, and if I ever get bored of it, I can either code a tool to automate it or I can write up the process and then pay a freelancer to do it.)

#2: Customers get holy-cow-OMG-WTF amazed when they deal directly with the founders. It is one of the best unfair advantages we have in sales as startups. We should work it every time we have the opportunity. I could still possibly lose that account at the end of the month, but both intuition and data strongly suggest I’m not going to.

(Having talked to engineers for years, I know some folks are a little weirded out by having the computer send this email automatically. If you are weirded out by it, I strongly suggest identifying exactly what you’re uncomfortable with because I, candidly, think your distaste is irrational. Be that as it may, I have all sorts of irrational aesthetic preferences myself, so if you absolutely cannot countenance sending this email to the customer automatically, send it to yourself instead. You can then write them a quick note when you next check your email.)

Brennan Dunn at Planscope does welcome emails so well his customers blog about them. Seriously. Go get inspired.

The 20 Day Follow-up (Two Variants)

Assuming you have a 30 day free trial, ~20 days in is a natural point to follow up with folks and see if they’re getting value from the software. You don’t even strictly speaking need to ask, though: as SaaS companies, we can often tell — with trivial inspection of the database — whether a given account is happy or not. There’s a heuristic I use for Appointment Reminder which can accurately predict, at day 20, whether someone will purchase the software or not with better than 80% accuracy. ?It is three lines of code. ?The similar heuristic for your business is probably not rocket science.

Dave McClure calls this Activation: achieving happy use of the software. (It is one of the five metrics for pirates: Acquisition, Activation, Retention, Referral, and Revenue (AARRR, get it)… and one of the easiest to adjust upwards through simple product improvements.)

Given that we can know what customers are having problems, how can we help them through those problems in a scalable manner?

  • Ask them, explicitly, why they’re having problems. I’ve run my software businesses for years, and while I started them in total ignorance, I know the types of things which likely lead to customers abandoning the product early in their trials. I learned this by a combination of asking (easy to implement!) and checking funnel analytics (slightly harder to implement, but more reliable for diagnosing UX issues than relying on subjective impressions).
  • Offer them a trial extension. Seriously, is there any reason why you shouldn’t automatically extend a free trial to anyone not likely to purchase the software yet? Heads you win. Tails, who cares, you already spent the customer acquisition costs, might as well lose the account trying versus losing it passively. I send all customers who haven’t activated yet the offer that I’ll extend their trial by a month, and all they have to do to take advantage of it is write me back. That lets me start a conversation as to a) why they didn’t get enough value out of the software yet (ideas for product/marketing development, ho) and b) what I can tell them to sell them on giving it another look.
  • Just remind them you exist. An absolutely stupid percentage of customers will, when asked “So why aren’t you doing X?”, say “Oh, I got busy.” Sometimes “I got busy” is a code for “You didn’t provide any value for me, so I bailed”, but sometimes “I got busy” is code for “I got busy.” Just getting another bite at the attention apple will rescue non-trivial numbers of accounts.

What about customers who have already activated by day 20? They’re already happy users of the software. What can we do to make them even happier?

  • Tell them they’re happy. Here’s something which is weird but true: we know our problem domains so much better than our customers that we can predict their mental state better than they can. For example, if you’re the office manager of a busy HVAC repair firm, you might not have noticed that this month was very different than last month… but my computer has comprehensive stats on a core driver of your business (appointments scheduled and fulfilled), and I have data on other HVAC firms, and therefore I can make confident statements like: “Your use of Appointment Reminder has saved you $485 of staff time and probably shaved 10% off your no-show rate.”
    This is often news to the customer, because they don’t track their no-show rate consistently and they never added up how much staff time they were burning talking to answering machines. My email does the math for them and then says that they should take credit for this win with their boss. This means my automated marketing messages literally have gotten people raises. When the credit card charge comes through later they’re thrilled to have paid it.
  • Offer ways to make them even happier. Your software has somewhat advanced features that many customers don’t take advantage of on their first try, right? Since you can know whether an account has or not, if it hasn’t, explicitly tell them to try those features out. This creates additional value for the customer (a feature they didn’t know about is a feature they didn’t have, after all) and creates additional value for you (the more use they get out of the software, the lower their churn rates.)
  • Offer to talk to them. Again, you can’t possibly talk to too many customers. Talking to unhappy customers to find out what is common about them is important. Talking to ludicrously happy customers is important, too. I never knew, until customers told me, that canceled appointments are obnoxious for businesses with offices but devastating for businesses whose employees travel to the appointment, like say HVAC contractors. This informed marketing and pricing changes to target the customers with exactly that pain point, solve it, and extract appropriate value for having done so. Makes Lifecycle Emails Like These Very Easy

Personally, I handle all my lifecycle emails with custom Ruby on Rails code, because I’m a programmer and love it. However, I work with a lot of consulting clients whose marketing teams don’t love writing code and tweaking email templates, and whose engineering teams have better things to do than write integration hooks. They used to hire me to build one-off internal applications to design emails and then write GUIs-over-rules-engines to let the marketing team figure out who gets what email when. These days I tell those clients “ already exists and it will do exactly this for you, without needing to pay me five figures to write an internal app to do it.” Seriously, try it out — the capability is transformatively amazing for the right person at the right business sending the right sort of email.

Interested In Learning More About Lifecycle Email? makes the actual sending of lifecycle emails a breeze, but there’s more to email than just the mechanics, or we’d all be using SMTP servers and getting rich. In particular, there’s a lot of art in crafting emails which convince customers to convert, doing product and page design such that users consent to contact in the first place, structuring email campaigns such that there’s an overarching narrative to the experience, and tracking the effectiveness of email in improving your business’ results. I won’t overstate it — you can totally learn to do this all by yourself, and it will only take you a few months of dedicated effort. You can also hire someone to do it for you, though they’re in incredible demand right now, due to the ability of lifecycle emails to make major improvements in the bottom line.

Want to get your emails “to market” faster and skip the few months of failing your way forward? I sell a course on every facet of lifecycle emails for software companies: timing, copywriting, implementation, optimization, etc etc. Jason Cohen, one of my consulting clients, remarked “Patrick’s advice on starting a [particular type of lifecycle email] campaign for WPEngine was an epic win for WPEngine –it permanently moved the needle on signups after just a week of work.” (That was a drip marketing campaign — another option for lifecycle email totally distinct from any of the ones discussed above. I could, literally, talk for two hours about how to implement one — that is, in fact, Chapter 2. There’s a lot more where that came from, too.)