Using Lifecycle Emails To Grow Your Business

These are the engagement notes for last week’s proposal on redoing the lifecycle emails of Planscope, part of the “Be Your Own Consultant Challenge” Today’s post is applicable to freelancers, consultants, and product founders. It’s about email, and why I wasn’t using it as effective as I should have — and why you probably don’t either. (Consultant or freelancer? Your bits at the end of this post… but you’ll want to read what comes first.) I’m no stranger to sending lots of email. My newsletter has me ending up in over 6,000 inboxes each and every week. But the majority of the email I send is broadcast email — meaning I write one email, and a lot of people get that exact email at the same time. Lifecycle emails are emails sent individually based on what someone does (or does not do) either immediately or with a set delay. The most obvious example of lifecycle emails that most of us are familiar with are “Welcome” and “Trial Expiring” emails. You sign up for a new product or service, and get an email soon after. And when your trial is about to expire, you get another email. For the majority of products, these are the only two emails (outside of announcement and new feature emails) that you’ll ever get from them.

Rethinking Planscope’s Lifecycle Emails

I’m a big fan of, and since time immemorial have been using them to send out welcome emails. But my usage has always been pretty crude, considering what they’re capable of. With, you’re able to sync user attributes (e.g., name, email, plan, etc.) and user events (invited a client, created a project.) Without making any code changes, I’m able to go into and create segments around these attributes and events. segmentation The first real segment that I made was splitting users into teams or freelancers. The needs and usage are quite different between the two. This allows me to both send emails and change the content of standard emails depending on who’s getting the email.
  • +15 mins: Welcome email, with different content depending on team or freelancer.
  • +5 days: Encourage teams to invite their company (if they haven’t yet)
  • +11 days: Send trial expiration email, with copy dependent on their product usage
  • +70 days: Send annual upsell email (details below)
These emails are all based on the delta between when someone signed up for Planscope and right now. I now have emails that are triggered based off interactions:
  • An invited client views an estimate for the first time: “Your client just looked at your estimate”, along with tips on how to close the deal.
  • An estimate converts from estimate to active (meaning: won the project): Congratulatory email on winning a $XX,XXX budget project.

Adding An Annual Upgrade Path

When you’re bootstrapping, you really, really care about cash. It costs money to fuel certain customer acquisition channels. So, let’s say a customer costs $100 in ad clicks (ad click -> reads over site -> signs up for a trial -> converts to paid) and you’re charging them $24 a month, you’ll recoup your investment in about four months (as long as your churn rate isn’t over 25%!) Now, the tricky thing about paid acquisition channels is that they won’t float you credit. You can’t say, “I have 5 new customers because of you this month, but it’s going to take me a few months to get that money for you. Cool?” (I guess you can do this if you’re into maxing out credit cards.) So this can severely hinder growth, especially if you’ve figured out a channel that will scale pretty well (what Rob Walling calls a “fly-wheel”.) I haven’t found this yet, but it’s going to take money to pursue — which is where getting paid upfront for a year comes into play. Planscope’s annual billing is 10 times the monthly rate, which reduces the cost of subscribing for a year by 2 months. And until I take the time to write the code to make upgrading an automatic thing, for now I ask people to reply if they’d like to go annual. All this requires of me is logging into Stripe, pulling up the customer record, and switching their plan from “Plan Type” to “Plan Type (Annual)”. I copied — almost to the T — the format and messaging that Patrick McKenzie used for WPEngine’s annual upsell email. The big difference, however, is that I really pointed out the benefits for the customer of paying annually. A bit of context: we had a pretty lively discussion on my Consultancy Masterclass mailing list a few months back where we were talking about SaaS, and why some businesses are averse to them. What I figured out wasn’t that people are against SaaS as in “a product that runs in my web browser that gets updated from time to time”, but rather against how SaaS companies bill their customers. So here are a few of the benefits of upgrading to annual billing that I wanted to point out:
  • Categorizing the same. exact. expense. every month sucks. By getting billed once a year, you’ll cut down on the amount of categorization your bookkeeper needs to do.
  • When a business buys software, they can generally write off that expense. Buy Planscope for a year, and get a little extra pocket money.
  • This will make you an über customer of mine and will help support my business. I’m only accountable to you, the customer — there are no investors or 3rd parties who have a stake in the direction of this product. (Note: many of my customers know me personally.)
  • And, most importantly: YOU WILL SAVE MONEY!
The benefits largely around saving money (2 months free, tax stuff) or saving time (categorizing), which are two things you should be focusing on whenever selling anything to anyone. Annual upgrade email template

What This Has To Do With Consulting

Most consultants don’t pay enough attention to the lifecycle of their clients, nor do they systematize it. One of the big things I pushed in my Masterclass is to think of your relationship with prospects and clients in much the same way that people who use lifecycle emails on their customers. So what does this mean? Let’s say you meet with someone at a networking event. At this point, they don’t trust you, they don’t know you from Adam, and they think you’re out to grab their hard earned money. This is where most of us flop — we try to sell too hard, and end up scaring away the client. What’s missing is value creation. When you’re emailing your trials, the focus shouldn’t be on how to use your software. You should be helping them realize how using your software will grow their business. So if you’re talking with prospects you just met, the focus should be on getting them to see the value you’re capable of producing and not on getting them from “prospect” to “paying customer” as quickly as possible. (Though Maslow’s hierarchy inevitably has many of us doing just that.) If you’re in the pre-sales phase, your relationship — the lifecycle of that person in relation to you — is focused on establishing that you are great at providing value. During the active sales phase, you’ll want to explain the benefits that this brand new project could have for their business. When they’re a client and actively working on the project, you’ll be helping them see how the features being developed will impact their business. And finally, once you’re done with the project (and this is where most of us drop off), you’ll want to proactively figure out 1) how successful the project has been so far 2) what data has been collected that could further influence that success and 3) how you can help by acting on that data. (For a fantastic writeup on retainer agreements, Patrick McKenzie literally just wrote about it on his newsletter. I’ve also covered this in the past.) Here’s something you could do with very little effort (again, I teach this in my workshop): When you wrap up work with a client, open up your calendar and add a few entries:
  • 1 week after delivery: How are things? Is everything running smoothly?
  • 1 month after delivery: We’ve collected a month of production data, and here a few things we’ve learned so far.
  • 2 months after delivery: Another month is done. Why don’t we work together on a retainer to improve these numbers over time?
  • 4 months after delivery: Let’s talk about how this project has meaningfully impacted your bottom line. (Take what you learn here, package it into a case study dripping with numbers and figures, and you should now have an incredible testimonial.)
  • 6 months after delivery: Data’s still coming in great! We’re helping you improve by X% month-to-month. Do you know anyone who might be interested in something like this for their business?
  • 12 months after delivery: Happy anniversary! I just sent you a little care package. (Throw in your favorite business book or two, a handwritten thank you card, and a printout about your business and show off some of the success you’ve had with your clients over the years.)
Using a minimum of 6 phone calls or emails and one trip to FedEx, you’ll have a client who gives you an incredible testimonial and case study, a possible monthly check in the form of a retainer agreement, and a strong referral source — and maybe even repeat business. Want some help getting lifecycle emails setup for your clients or your product (pro-bono)? Feel free to drop me a note below or email me.

3 Responses to “Using Lifecycle Emails To Grow Your Business”

  1. Stephen Kellett

    Nit pick, not “effective”, you mean “effectively” (2nd sentence).


    Dude. has to be one of the best SaaS apps I’ve ever seen. I’m having a very rare “I wish I had invented that” moment. My mind is reeling at the possibilities.

    But what is this Drip thing I see? I landed on their landing page a few months ago but didn’t opt in. I must know what it is!



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