I have to start this tear down with a bit of a story.

Six or so months ago, my friend David Sherry introduced me to someone he knew I’d love. David only makes introductions when he’s sure they’re going to be a huge hit so I knew to trust him on this one.

That person was Claire Suellentrop, former Director of Marketing at Calendly and current badass (also currently now Director of Marketing at Userlist.io but mostly Claire’s a badass).

David, of course, was right.

Claire and I instantly bonded. We were both the #1 marketer at high growth SaaS companies. We both got into marketing from twisty winding paths no one would have predicted. And we both had recently started freelancing and doing our own (badass) thing.

Claire has better hair than I do, but otherwise we’re cut from the same high thread count cloth.

In our talks about marketing, customer experience, and onboarding, I said to Claire something like “ya know people keep telling me that the company that really needs my help with onboarding emails is Calendly lol isn’t that great?!”

And in the spirit of new friendship and endless support, Claire intro’d me to Rachel, now heading up marketing at Calendly.

Rachel is incredibly talented and wise and one of the first things she said to me was something like:

“I totally get that onboarding is something we need to work on and it’s planned to happen. Soon.”

It’s a response I hear pretty often, tbh.

“It’s on our ‘some day, maybe’ list.”

It’s only been a few months since that conversation with Rachel so I figured I’d throw a few of my thoughts into the ring since it seems the onboarding update project is still in the works/on the Some Day Maybe™ list.

How do I know?

I signed up twice:

The Stats:

14 day free trial
Test #1 and #2:
3 emails sent over 14 days

As you can imagine, this tear down is going to take a little bit of a different approach.

So many people who know that I help companies with their onboarding emails have specifically requested I cover the emails of Calendly in a tear down.

One important thing to note is that Calendly offers both individual accounts and enterprise accounts.

Since I’m but one person, we’re covering the individual accounts here.

And, well, there isn’t much to tear down.

So instead, I’m going to share what I would write if I were to re-create Calendly’s free trial! 🎉

Riiiiight after we talk about what’s there to begin with.

(Please note before we begin: I’ll be referencing the most recent set of onboarding emails I received from Calendly in this post. The set from the first test don’t vary enough to compare the two sets in any capacity.)

Good Bones

I can’t stand HGTV’s House Hunters. Like, seriously, if I hear one more person complain about a paint color when they walk into an otherwise awesome house…

Some houses have bright yellow dining rooms and chandeliers from the 70’s and puke green bathroom tile but is that what we’re buying houses based off of? Actual changeable features?

That’s not how I house hunt.

I look for good bones.

A solid foundation. A layout that flows the way I want it to. Hardwoods under that pale pink wall-to-wall carpet. (Hint: look inside the closet to find out if hardwoods are potentially there.) 

Good bones are what I look for in a house and they’re what I look for in an email onboarding sequence too.

And Calendly has good bones here.

Let’s take a peek:

The first email, the welcome email, arrives the same day I create my new account.

The subject line is clear, but basic enough that I might skip over it.

The from name tells me it’s from Calendly, but I don’t feel a personal connection brewing here.

I see benefits highlighted – yay!

And the email is brief, but almost too brief.

Here’s what I would write:

Hi Val!

I’m so glad you decided to give Calendly a test drive today. You can finally say goodbye to email and phone tag for scheduling meetings. Just share your Calendly link – {{insert link}} with anyone who needs it!

We made Calendly so that you can simplify the scheduling process.

If you have a moment, I have one quick question:

Why did you choose Calendly for your scheduling needs?

Knowing what made you interested enough to give us a try is incredibly helpful as we build and improve upon Calendly.

Just hit reply and let me know!

As a heads up, we’ll be sending you a few more emails in the coming days letting you know how you can make the most of Calendly.

Talk soon,

Tope Awotona
Founder, Calendly

Getting personal on that “first date” isn’t going to do any harm. You aren’t asking them to marry you here, you simply want to get to know them better.

Now you might be going “Cool, cool, Val. This is great when you have like 10 new customers a day. But we have like 80 new customers a day. What happens when they all reply to this email?? That will implode our customer support reply times.”

And I hear you. So you might consider moving your onboarding emails to your email service provider and using a link trigger they can click on to tag themselves. Something like:

If you have a moment, I have one quick question:

Why did you choose Calendly for your scheduling needs?

Knowing what made you interested enough to give us a try is incredibly helpful as we build and improve upon Calendly.

Just click one of these three links to tell me which one most describes you:

I’ve never used a scheduler before and wanted to give it a try
I’ve used another scheduler but wanted something simpler
I have big scheduling needs and I’m looking for the most robust tool available

^^^ turn those last three statements into links they click to tag themselves in your email system.

But, Devil’s Advocate here: what if your team prioritized hearing from your brand new customers and responding to them like the humans that they are? What if you experimented with having someone on your support team lead this charge and reply to each one of these onboarding emails?

It could have a powerful impact to get personal.

Day 2

On the second day of my Calendly trial, I got this email:

Of course, had I actually connected my calendar, maybe I would have had a different email (I likely would have since this clearly seems triggered by my in-action here, but I’ve heard from plenty of others that Calendly sends a max of 3 emails right now so my experience is pretty accurate with the masses.)

But what about after this email?

Do I get more emails from Calendly throughout my trial?

Any more encouragement to get going and use my free trial time wisely?

You probably know the answer already.

No. 😔

In fact, if you check out that screenshot of my inbox, you’ll see that I don’t hear from Calendly again until my trial is ending.

And as a busy business owner with LOTS to do (remember, I signed up for a piece of software to help me take some things off of my plate), I all but forgot about my Calendly trial.

So is it important to send emails throughout the trial period?

Absolutely.

Do you have to bombard your new customer and annoy them to email death?

Not at all.

Here are a few emails I’d add in after this last one.

Benefits!

Look, you can talk about features all day long but your customers don’t care unless they see how that feature matters to them.

So talk about features in relation to benefits. Paint a picture of what they’ll get from using your product, even upgrading to a paid version for more of those snazzy features you worked so hard to build.

Just be sure to make it about them.

After all, the customer experience pros at HelpScout remind us:

There’s a natural inclination for craftsman to want to talk about the craft.

But remember, customers generally won’t care about the cogs that make your product turn.

Try something like this:

Hey there, Val!

How are you feeling about your schedule right now? Let’s play a little game.

Take a second to imagine that an easily managed schedule is your reality. What would you do with all of that time?

(Seriously take a second to write it down. I’ll wait.)

Me? I found that getting my scheduling organized meant more time to focus on the work I set out to do, finally.

So I have good news and bad news for ya today:

The bad news? You can’t get to an organized schedule without rolling up your sleeves and diving into the work it takes to get there.

The good news? You already have the framework to get you there! It’s all inside Calendly.

So yay you for taking that first step!

Now they say that progress is about taking one step after another so I’m here encouraging you to take that next step. Find your own version of scheduling ease with Calendly right now.

To your wild success,

Cloë
Customer Onboarding, Calendly

PS: Your free trial is on the Pro plan so you can check out all of the extra zen available to you with custom email notifications, reminders, and personal confirmation pages. Activate your account at the Pro level to keep those features and breathe a big sigh of relief.

Team Player

In that last sample email I introduced a member of the Calendly team, Cloë.

Introducing team members (real people with real roles in the company) is crucial to establishing a connection with your customers.

When your customer gets that email above from Cloë and then they send in a support ticket and Cloë happens to reply, they feel a measurable amount of trust because it’s been building over time.

See how that happens?

An email in the mix that works to build even more connection, keep the customer happy, and get them using the software takes onboarding to the next level.

I also introduced a little something called the upsell.

Remember, these emails are going out to a customer on a free trial. 👋🏽

But Ian Blair says there’s more to a free trial customer than meets the eye.

“Free trial prospects have gone beyond ‘onlookers.’ They’re actually customers – even if you haven’t charged them yet. By definition, a customer is someone who had made a transaction that would benefit the business.To use your product, customers have to spend focus, time, and money.”

image courtesy of Ian Blair

On his blog Ian points out a crucial missing piece of most free trial onboarding:

“How often do you sign up to try a new software or solution but never actually upgrade or renew account?

It’s very easy for free trial users/prospects to get overwhelmed when they first signed up to a new service. The ultimate question in their minds would be similar to this: ‘Should I upgrade my account?'”

So give them reason to ask themselves just that:

Hi Val,

Your schedule is full of different kinds of appointments. And not everyone you meet gets the same amount of time – or the ability to choose how much time they get!

With Calendly, you can send your main scheduling link and let your invitee choose which type of appointment they want…

OR

With unlimited event types (on our Premium and Pro accounts) you can send a specific link to the kind of appointment YOU want them to schedule!

How’s that for organized?

Here’s how you can find that link right on your My Calendly page:

Now here’s the important part: Calendly was designed to help you get to save time and get the right appointments on your calendar, fast. Without custom meeting type URLs, you’re missing a huge part of that.

So activate your account at the Pro level and grab those individual URLs to keep them handy. You’re gonna need ’em.

Always here for you,

Cloë

Map It Out

Let’s pause here for a quick reminder of something crucial that our original Calendly email said:

That’s right!

There’s an incredible opportunity for new customers to learn from a Calendly pro LIVE and it’s buried in a mention in the second email.

Not anymore.

Try this:

Hey Val,

It might not be a surprise to you to learn that your schedule can be simplified with Calendly. What might surprise you is all of the features that are offered inside this one powerful tool.

Since you’re currently on a trial account, figuring out how Calendly can help you, I wanted to invite you to our open Office Hours. We’ll turn you into a Calendly pro in no time.

These 45 minute sessions are designed to be heavy on the Q+A – I want to get you answers to your questions.

So join us for our free and live Office Hours – I’ll see you there.

-Jacob
Customer Happiness, Calendly

PS – Have questions right now and can’t wait for office hours? Reply to this email and we’ll help you out!

Naturally, all good things must come to an end.

That includes the free trial and this onboarding series.

But if you’ve been following along in this series, you know that the end of an onboarding sequence is only the beginning.

Here’s what Calendly sent me to warn me of my trial ending:

(Did ya notice how different this email looks from the others? Someone took the time time design this email. All of a sudden we’re pitching that upgrade so now it matters.)

And since Calendly is smart, they run their trials on Pro (a paid plan). You get all of those beautiful paid features for free and you have to downgrade if you decide you don’t want to pay for them.

Maybe if they used the other emails I added above their customers would be addicted to those Pro features.

Just sayin’.

Anywho, this email is great.

But then it just… ends.

…abruptly.

It quite literally feels like someone forgot to finish writing this email.

Plus, again, it’s all about Calendly here.

Here’s an option to make it about the customer:

Hey Val,

I know it’s been a couple weeks since Calendly first landed in your lap so I wanted to take a second to reconnect.

With Calendly you have the chance to make peace with your schedule – something so many people want to do! You just happen to be one of the lucky ones who’s out there doing it.

While your Pro trial is ending soon and you’ll need to activate your account to keep all of those features, we’re happy to keep you around on our (free) Basic plan. You can upgrade to Pro again at any time.

So do me a favor: hit reply and share your story of going from scattered scheduling to simple scheduling with Calendly. I’d love to share your successes on our website and with our community.

Tope Awotona
Founder, Calendly

I know!

I’m encouraging those customers to hit reply and interact with your team again.

How dare I.

Look, you can take an interest in your customers and their needs or they can go to your competitors. It’s that simple.

Just the beginning

And, as always, there’s more than this single onboarding track to think about.

There are the onboarding for paid accounts.

Emails based on actions (or in-action) within the app.

Then Enterprise onboarding emails.

Retention emails for each plan type.

And reactivation emails for cancelled accounts.

Dear Calendly: onboarding is just the tip off point. There’s an entire game to play once that ball drops.

To wrap this one up in true tear down fashion:

The Good

• the bones are good: new paint and a different chandelier will be game changers here
• personalization! My name and my personal Calendly link are included in that first email

The Bad

• Just 3 emails over the course of 14 days (and the first two are Day 1 and Day 2)
• The From Name is “The Calendly Team”, so impersonal
• Did I mention there are only 3 emails?

The Ugly

• the last email is beautifully formatted but ends so abruptly
• there’s no encouragement to upgrade any time before right when my trial ends
• It’s impersonal, there’s no connection, no relationship, and I feel like a commodity not a person
• almost everyone I know has said they’re completely underwhelmed by Calendly’s onboarding 😢

Calendly has some opportunities here, for sure. But they aren’t alone. In fact, I’m happy to see that hey have anything set up at all. So many people don’t.

Maybe these sample emails will end up in a future Calendly onboarding sequence (yo, Calendly, feel free to swipe these babies, k?)

No matter what happens, here’s your big lesson learned today:

If you don’t earn a relationship with your customers, you will be hard-pressed to earn their money.

Now it’s your turn.

What are your biggest takeaways from Calendly’s onboarding emails?

How will you apply those lessons to your business?

Have a set of emails you want to see dissected here? Send me a note at heygirl(at)valgeisler(dot)com with the details of where I can sign up! If I write up the review, I’ll share a draft with you before anyone else sees it.