Reply To: How Doodle played with email to push pain point buttons and increase paid upgrade conversions by 64%

0:00: I was not trying to get opens based on that black hat practice of a re in a subject line prompting people to open because they think you’re in the middle of a conversation with them. 

 0:08: I hate that practice. 

 0:10: It’s so dishonest. 

 0:12: I was just playing with the idea of these endless email chains and the preview text very clearly showed that welcome to email swipes where we peek behind the scenes at the emails that catch your attention and earn their place in your swipe file. 

 0:24: Every other week, we’ll talk to an email expert about an experiment they ran. 

 0:28: And in the following episode, we’ll dive into the strategies and methods used in the email so you can inform and inspire your own email work. 

 0:35: I’m Nicky Elvas, the copywriter behind winning emails for eight and nine figure Sass and Ecommerce brands like Shopify for Stigmatic and Sprout Social. 

 0:42: And I know that hearing the background stories to these emails will help you turn pie in the sky insights into plug and play actions, ready to make inspiration tactical. 

 0:50: Let’s go first. 

 0:52: Let’s read today’s email, Nikki. 

 0:56: I’m really excited to welcome you to doodle premium Pro I used to dread getting emails with a bunch of res in the subject line. 

 1:03: Meetings are bad enough. 

 1:05: We schedule too many invite too many cooks, squeeze in too many agendas or worse. 

 1:09: Don’t set an agenda, but scheduling a simple meeting is even worse. 

 1:14: Endless rounds of emails that stuff our inboxes distract us from our jobs. 

 1:18: Confuse meeting guests or worse meeting guests. 

 1:22: Unless you schedule your meetings with Doodle Pro with Doodle Pro in a couple of clicks, you can instantly share availability, find the best time to meet and send reminders or not. 

 1:33: Your call ready to get back hours in your day and earn your coworkers applause, sync your calendar and set up your next meeting in less than two minutes. 

 1:41: Sync my calendar fast. 

 1:43: Here’s to never sorting through a million emails. 

 1:45: Gabrielle Ceo when I was planning out season one, I didn’t even think to include this email as one of my solo episodes because I’ve talked about it so much that I figured I would bore you all. 

 1:58: But even if you have heard me talk about it and if you haven’t, it means you need to go on a little email. 

 2:04: Swipes binge Fest. 

 2:05: I haven’t talked about its creation at all. 

 2:08: So let’s go. 

 2:10: This series of emails was the first behavioral email flow I’ve ever worked on. 

 2:14: This is so hard for me to believe because now I barely ever work on sequential flows for SASS. 

 2:19: They’re nearly all behavioral and wow, you should have seen how we presented it, talk about embarrassing. 

 2:26: We sent over an ugly dock table of if this then that it was so ugly and also really confusing. 

 2:34: Now we go whimsical flow charts all the way with a walkthrough video. 

 2:39: By the way, you get our whimsical template included in the SAS success pack, which you can check out in the show notes. 

 2:45: It’s a huge time saver. 

 2:48: Not to mention that it makes it really easy to plan things strategically because all the steps are laid out for you. 

 2:53: But I digress, I do believe a big part of what made the doodle email so successful wasn’t just the copy but was the fact that they were behavioral. 

 3:02: We’ll get into that more when we talk through the results. 

 3:04: First, let’s talk about the overall sequence and goals. 

 3:08: Doodle is a calendar alternative doodle actually predating calendly. 

 3:12: I’m pretty sure they were the first multi person meeting scheduler and it was pretty popular in the B to C space. 

 3:18: People used it to find a good time for party user events. 

 03:21: The first time I saw one was for an informal high school reunion when a bunch of us were back in town for the holidays, like most apps back in the day before subscription pricing became the default doodle made money by displaying ads next to the scheduling polls. 

 3:35: And then they introduced pricing plans. 

 3:37: The first was more for personal use. 

 3:40: It mostly just covered the ads. 

 3:41: And the second was for business use, it had a much more developed and pro feature set. 

 3:46: We were mostly focused on the business plan. 

 3:48: It made more sense for businesses to invest in a paid plan. 

 3:51: But we did also develop a variation of the email flow for the more personal use, lower tier plan too. 

 03:57: The original on boarding emails were sequential but they were also fairly standard. 

 4:00: I went hard on voice and the resulting emails were anything but standard. 

 4:05: They’re probably the most voicey sass emails I’ve ever written. 

 4:08: There were a few others that came close but the doodle ones topped the charts. 

 4:12: This particular email wasn’t as intense on the voice because it came from the founder. 

 4:17: It had to be in his voice, not in the brand voice. 

 4:20: So why did we decide to go hard on voice? 

 4:23: The research showed that people were really, really frustrated with the old school way of scheduling meetings, basically convoluted email chains with a whole lot of back and forth. 

 4:32: It was a huge time suck, a huge mental drain and a huge pain point. 

 4:37: That’s why we went hard on voice because there was already so much personality there, there was so much emotion and so called personality to the pain points. 

 4:45: Not only was it already there, it also would have served as really nice comic relief to something that was really frustrating for people. 

 4:55: The email change was where this particular email was born from. 

 4:59: The subject line was re re re re re can we chat Monday morning? 

 05:05: I was not trying to get opens based on that black hat practice of a re in a subject line prompting people to open because they think you’re in the middle of a conversation with them. 

 5:13: I hate that practice. 

 5:15: It’s so dishonest. 

 5:17: I was just playing with the idea of these endless email chains and the preview text very clearly showed that the preview text was something like never get one of these kinds of emails. 

 5:27: Again. 

 5:28: What’s interesting though is that we did have a decent number of people respond to the email saying that they could meet on Monday or they couldn’t meet on Monday. 

 5:36: They took the subject line at face value. 

 5:39: I think a big part of this was that this was really at the beginning of the SAS revolution. 

 5:43: There wasn’t this huge prevalence of free trials or on boarding emails, especially in this segment of the population in non marketing professions and definitely not in the non pro segment who were using it for their personal life. 

 05:56: Another reflection of this was that we got a lot of complaints about the fact that we were sending too many emails. 

 6:01: The standard on boarding flow was just not standard practice then. 

 6:06: But of course, the most standout feedback was about the tone. 

 6:09: There were some harsh replies about the tone but there was also a lot of positive feedback about the tone and even more importantly about the software and its capabilities that the emails informed them about, which led to a whole lot of conversions, 64% increase in paid conversions to be exact, that’s quite a win. 

 6:28: So anytime there’s negative feedback, it is jarring our brains default to negative. 

 6:33: So that is what stuck. 

 6:35: Plus there was one team member who was unhappy about the tone to begin with. 

 6:38: So he took this as validation and scrapped all sorts of bits in the flow. 

 6:43: Yes, even with an increasing paid convergence by 64% he wasn’t happy with it. 

 6:48: Again. 

 06:49: I do think a big part of the success of the emails was the fact that they were triggered by behavior. 

 6:52: They were extremely relevant and timely, which means that they really help people see how the software could be helping them with their particular struggle right in the moment. 

 7:00: But again, people complained about the number of emails too, not just the tone, one of those two things was working really well, the tone and the frequency, probably both of those two things were working really well. 

 7:11: It’s not fair to the brand to listen to an outlying group of customers, but we’ll get into that in the takeaways. 

 7:17: Looking back. 

 7:18: Now, I do agree that the subject line deserved to be scrapped. 

 7:21: Yes. 

 7:21: My intention was not to mimic the fake rep practice. 

 7:24: But at the end of the day, people just don’t pay that much attention when they’re checking their emails, they’re not looking for nuance. 

 7:30: So if that’s the way people are experiencing it, that is valid and that means it’s not serving them or the brand. 

 7:36: Thanks for joining me for email, story time. 

 7:38: If you enjoyed today’s story, give this podcast a review. 

 7:41: So email marketers like you can have more fun with email. 

 7:44: See you next week when we dig into this story’s takeaways.