How to write a SaaS trial-to-paid sales email

Presented live on Tuesday, Feb 6, 2018

Get a glimpse of future live Tutorials

So your user has made it through your trial period. Now it’s time to go for the upgrade. Time to write the upgrader email! This is where the money changes hands. This is where your MRR goes up a notch. And if you can get this trial-to-paid sales email right, this is where your growth initiatives start to scale. In this tutorial, SaaS copywriter Sophia Le shows you how to write an upgrader email for your SaaS trial.

Sophia is writing in Airstory writing software. You can get the template she’s demonstrating here


Joanna Wiebe:                     Good morning, everybody. Good afternoon, or evening, depending on where you are. Or, if you’re in Ho Chi Minh, like our good friend and guest, Sophia Le, it is midnight there, and she is here to talk to us about SaaS Onboarding today. That’s amazing. Sophia, thank you for joining us today.

Sophia Le:                               Thanks for having me, Jo. I am all caffeined up and ready to go.

Joanna Wiebe:                     Aren’t we all?

Sophia Le:                               Aren’t we all, yes. I happen to love this particular topic, myself. I’m working with lots of SaaS clients around the globe. So, I’m here to talk about the trial … what is it, what do I call it? The trial ending hard pitch email. It’s so long I don’t even remember, so.

Joanna Wiebe:                     Right.

Sophia Le:                               Let’s see where-

Joanna Wiebe:                     Yeah, it’s awesome. It’s kicking off our whole SaaS Onboarding month, here for Tutorial Tuesdays in February, so it’s amazing. It’s about to get “SaaS-y” someone just chatted over. Well done. Little well done. I’m hesitant on how well done it was though. No, I’m kidding it was good. So, everybody filing in still, that’s awesome, and we will be turning it over to Sophia in just a second. But [inaudible 00:01:10] housekeeping, people have been to Tutorial Tuesdays and they already know because we’re seeing a lot of chats come in with, “Hey, I’m from Luxembourg and …” Oh, then there was something that wasn’t placed. Anyway, they’re all coming in so if you have something you wanna chat over to us, or you just wanna share something quickly, I don’t know … A quick question you have, chat that over. Sarah’s here, also. Sarah, we haven’t mentioned. Hey, Sarah.

I am in Salt Lake City, right now. In the offices of P.D.Q., pretty cool people here, hosting me. Going to The Killers concert tonight, by the way. But that’s a side not. I’m just really introducing everybody. Chat is for chatting. If you have a question that you want Sophia to answer, and you do not want it to be missed, please use Q and A, and we’ll do our best to have Sophia stay up even later and take some of those questions for the end of our tutorial, which should be approximately 20 minutes long. It is being recorded, it will be available as a replay later, and there is an Airstory template for today’s tutorial as well. Sophia put together an email template for the email she’s gonna talk about. So Sarah will chat that link over, if you’re using Airstory you’ll be able to just add it to your template library and use it any time you wanna write this email that Sophia is going to teach us, right now. Without further ado, Sophia, over to you.

Sophia Le:                               Alright, thanks Jo, thanks Sarah. I noticed someone was coming in from Malaysia, which is, I think, a very similar time frame, so you must really want to know about how to write the SaaS trial ending hard pitch email. And so, I’m going to get right to it. Let me see if I can share my screen. Alright, can everybody see my screen?

Joanna Wiebe:                     It’s perfect, yes.

Sophia Le:                               Alright, perfect. So, part of why I love this particular type of email is that it is the closest you will ever get to the money, in a SaaS trial sequence. You have welcome emails, you have the add your teammate emails, this is the one that’s going to pay the big bucks for your business. It’s the difference between someone who is signing up because they wanted the freebie, and wanted to try you out for 14 days, and the person who’s really going to have a future with your product and become a loyal customer. And this is the differentiation. It’s getting the person to make the decision about whether or not they’re going to pay the monthly fee and start using it to make their business better.

So, I created a little template, and it’s fill in the blank. You can use it and customize it for your needs, whether you are working for a startup, as a marketer, or you’re working with SaaS clients. But I also created another example because sometimes templates can get confusing without context. So, we’re just going to start, and get right to it.

So, the first thing that we have is a subject line, which is talking about the number of days of hours you have left to use a particular SaaS product. And so, what we want to do there is to showcase exactly how much time the prospect has left to use their product. That’s not like, minutes or hours, be specific about what they’re going to lose out on. The goal of that is just to get their attention and get them to open the email, because it might have been 15 days before they’ve actually gone into your app and opened your email. Hopefully not, hopefully they’ve had their ah-hah moment at this point … you’ve used some behavioral email stuff in order to make sure that this is going to the right person, and they’re not disengaged with your product. But, we wanna be upfront about how much time your trial has left so that they can take action.

And then it goes into a salutation, “Hey there, in number of hours or days your trial will end. To keep your data …” and then you’d write a call to action. And so, this line in particular, you are basically saying what you said in the subject line, how many days or hours you actually have left, and then talking about what is going to happen, as a result … Keeping your data … and that’s in order to kinda filter out the people that have forgotten about you. They might’ve loved your product, had their ah-hah moment, but they have said, “Oh shoot, I didn’t realize that I had only 48 hours left to use the product.” And so, you’re writing this call to action, right here, to catch those people, because they’ve forgotten and they just need to put in their credit card and they’re actually really in love with your product. So, you’re just trying to filter out who’s going to take action right away, and then who still needs a little bit more coaxing in order to sell the SaaS product.

So, we’re gonna move on to there. So, maybe the benefit of the SaaS product isn’t your top priority, but let me tell you a story of someone who suffered consequences that are related to the problem that your SaaS product is solving. And so, what we want to talk about, right there, is poking at the prospect about what their priorities are. Because, if you’ve ever studied anything about sales literature, it has nothing to do with you, it has everything to do with where their top priorities are. Because if you read any consulting literature in sales, it’ll basically say, “You’re solving one problem, and then there’s always a second one right there.” And SaaS products are doing the exact same thing. It might not be the top problem that they have, but it is a problem that they have.

And so we wanna talk about exactly what they’re going to lose out on if they don’t move forward with it. And the best way to do that is to start with a story about someone that they relate to, that they have some sort of connection with, and in this case, in the example that I’ll toggle over to in a minute, we’re gonna talk about a co-founder, or something like that. If you’ve studied Jo’s material at all, you will know that she’s a lover of Problem-Agitation-Solution, and so this is exactly what’s happening here. We’re going to state a problem that the customer has experienced, relating it to that story that we’re going to reference, agitate the problem, and then state an outcome if the customer was using a SaaS product like yours. So let me toggle really quick over to my example, just to show you exactly what I’m talking about.

So, this is a fake proposal software that I created in my mind. I really like talking about proposal software because for me, it’s solving such a big problem. Talks about … right here, I’m gonna highlight, “Maybe closing more deals isn’t your top priority at the moment but let me tell you a story about our co-founder, Max. Years ago, he had an initial consultation with a dream client, ended the call, got slammed, waited a week to send off a proposal, and the deal took three weeks to close, way longer than it should have.” So again, we’re talking about a situation of a fake proposal software. Ideally you sign up for proposal software because you’re trying to close a deal. And in this case, this co-founder was slammed, didn’t have processes, didn’t have a template, didn’t have anything set up in order to make the deal shorter, or the sales process shorter, and then could’ve used a solution in proposal template software. And then that’s how you use Problem-Agitation-Solution.

So, we’re gonna use P.A.S. at that point, and then after you finish agitating and sharing the story, you wanna talk about how, “If you or your company relies on X to make money, you need your SaaS product’s name.” And what we want to do is to allow prospects to decide whether or not they need the solution like yours. So you’re qualifying your customers, so basically, “If you rely on proposals to make money, then you need your SaaS product name.” And then, what you wanna do at this point, and I have this little article I wrote about six months ago, on a rant, about this very particular topic, as you can see I was very angry about the state of free trial emails at the moment that I was writing it. What we want to do, is to implement something that I call contrast. And so people might realize that they need a solution like your SaaS product or proposal software, but they don’t actually understand what that means for them in the long run.

If you read the article, there’s a whole story I go in there about contrast. It’s like, the second section of the trial ending part, and basically I talk about Rosser Reeves, who’s the creator of the value prop, who walks through Central Park and bets his friend that he can make the homeless guy in the corner more money if he changes the sign. The homeless man happens to be blind, the sign says, “I am blind.” With the implicit ask for money, but Rosser Reeves goes and changes the sign to say, “I am blind and it is springtime.” So, now people are understanding what this homeless man is missing out on because, they have springtime as context. And so what you want to do here is to do the same thing. This is why this line is here: “For as little as something that costs a similar amount to your product or service, you can join the X amount of customers who use your SaaS product’s name to the benefit of the SaaS product.”

And so in the example that I have, it’s basically … I’m assuming this is a freelancer based out of San Francisco, so, “For as little as the cost of lunch in San Francisco, you can join 2,000 plus freelancers who use this proposal software to close more deals.” We have this part about joining extra freelancers or customers, or what have you, because you want a little bit of social proof in this email to show that they are actually people … the other customers and people like you, and that you are not the only one with the same problem. And so at the end, just to tie it all up, if your prospect does not react to any of this at any point, we have other methods that we can pull out.  But, either they might not be your ideal customer, this might not be the right time for them … but this should change the screws on the emotion a little but, to at least understand why this isn’t the top priority at this point. And so, at this point we send a call to action that’s related to the benefit of the SaaS product, and then end the email.

I added a P.S. on this email template, just to make sure. ‘Cause sometimes SaaS products, they will … or SaaS founders that I’ve worked with, they want to wonder why, or ask why, and basically they want to set up one on one time with them. And so basically you can do that also, in order to understand why they’re not signing up if going through this whole story isn’t going to get them to go, and then work from there. A lot of other people will say, “I want, not a 15 minute demo, but 15 minutes of a B.I. consultation,” or sometimes people like development tools that I’ve worked with, something, “I can help you set up your D.E.V environment.” That sort of thing. That’s what we want to use with that email. And so, that is pretty much all that I have. The template and the example is all in Airstory, as you can see. I think it’s time for questions, did I cover everything, Jo?

Joanna Wiebe:                     Yeah, that was awesome. Nice job walking us through it, and then showing the example too. Yeah, people are saying, “That’s awesome, thank you” as well, so very cool. Thanks, Sophia.

Sophia Le:                               Yeah.

Joanna Wiebe:                     Sarah has [inaudible 00:12:54] the link to your template a couple of times , so I think she’ll share it one more time, and it will also be available next to the replay for anybody who does watch this afterward. We have some questions for you, Sophia.

Sophia Le:                               Yes.

Joanna Wiebe:                     If you’re ready, cool.

Sophia Le:                               Yeah.

Joanna Wiebe:                     Alright. Rachel asks, “As opposed to contrasting price, could you contrast time? For example, the time it takes to make a proposal from scratch versus the time it takes to use the software.”

Sophia Le:                               Yeah, do I hit the answer live button?

Joanna Wiebe:                     Yeah, I’ll … yeah.

Sophia Le:                               Okay. I’ll do that right now. So … did that go away? Alright, so-

Joanna Wiebe:                     [inaudible 00:13:37]

Sophia Le:                               Yes, you can definitely contrast time. I think it’s really about understanding the benefit to them, and what would be more of an impact. If you really wanted to go forward with figuring out, does price make a difference to my prospect versus time, you can run a test and then change the offer, and see which one gets more clicks as a result. So, that’s something that I would definitely test, but in this case it was just easy to measure money because most SaaS products are about 30 dollars. And so, you kind of back out what 30 dollars would get you based on where you are in the world. Did that answer your question?

Joanna Wiebe:                     Rachel chatted over, “Yes!” She said, “Thanks, Sophia.” So that’s awesome. Okay, [00:14:23] Katana asked this question in chat and then moved it over here, so thanks, Katana. “Have you ever used this for a membership that’s monthly.” It’s not a monthly software offer, but it’s still monthly. Is this the same kind of thing that you could use, I guess, for anything that has a trial period?

Sophia Le:                               Yeah, I think so. If I remember correctly, when I wrote the original blog post on Copy Hackers, there were a lot of people that actually asked me the same question. I think anything that you have to justify the cost of, every single month, is something that you can use this type of hard pitch for, because … especially if there’s some sort of freebie that you have, or a trial period where someone’s testing out course material, I think this would be a good representation of it. And again, this is a fill in the blank template. Obviously, the context can change and so it’s a starting point for whatever it is that you’re trying to hard pitch at the end.

Joanna Wiebe:                     Yeah, brilliant. Awesome. I’m not gonna say this right, but Nakama asked, “What did the homeless man’s sign get changed to?”

Sophia Le:                               It got changed to “I am blind and it is springtime.” So, basically, Rosser Reeves was telling everybody, that this man is blind. He cannot see how beautiful Central Park is in the spring, and so people immediately understood that and gave him more money. And Rosser Reeves won his bet as adman to the 1960’s, Jo? I don’t know the time frame.

Joanna Wiebe:                     Yeah. Yeah, no it was … that’s a very cool story. I loved reading about that in your post, too. That was wicked. And Sarah has chatted out the link to Sophia’s post for anybody who’s like, “I wanna see!” Read it, it’s amazing and it will only help you use this template better and write more free trial emails, too. So, awesome.

Paul says, “I really struggle with coming up with benefits. What resources do you recommend? Jo’s books, other copy editors …” So, any thoughts there, Sophia?

Sophia Le:                               That’s a loaded question. Always read Jo’s books. I am constantly finding gems on Copy Hackers, just based on projects that I do. I was actually having a little bit of a freak out this afternoon because there’s … weird D.N.S. rules in Vietnam right now, so I couldn’t access Copy Hackers and I was like, “Oh my god, I need this swipe file, like immediately.” So, it got resolved, thank god, but definitely any of Jo’s materials. In terms of coming up with other benefits, I really enjoy, and a lot of my work is derived on just using the psychology of persuasion, and so just really understanding what will motivate people as well as doing your customer research. So if you wanna get deep into persuasion, Cialdini is always a good read, Dan Pink … anything super academic. I have yet to get through Daniel Kahneman’s “Thinking Fast and Slow” but that’s something there.

And then in terms of other benefits, talking to your customers is always a good thing. If you don’t have time to do surveys and interviews, there are other ways to do research of the benefits, like searching on G2 Crowd, or Capterra, especially when it comes to SaaS. But that’s another tutorials for another day, just talking about how to find those benefits. Maybe we can do that, Jo.

Joanna Wiebe:                     Let’s do that, that’s awesome. That’s a great call. Cool, I love it. Thank you. Chris says, “What do you think about contrasting to competitive solutions?”

Sophia Le:                               That’s a good question. So, some of my clients are, well actually most of them, are very anti- talking about their competitors, in some way. And I think the reason for that is because once you start, feature shopping is what I call it, like landing pages. I worked with a landing page client and it’s like, what does so-and-so have, do they have A.V. testing, do they have autoresponders … You start doing priced wars, and that’s, maybe good for the email, and your test results, and getting clicks, but that might not be good long-term for your business. So again, that’s something that your client has to be comfortable with, or you as a marketer. But if you have a huge audience and you can sustain a business by doing that, then I say go for it. But if you’re trying to get genuine people on your platform then I would probably go a different direction, but that’s just me, personally.

Joanna Wiebe:                     Yeah. I get it, awesome. Tabitha says, “Is there a way to modify this template for a free to premium plan upgrade or will that be another webinar?” So can you use this to upgrade to a premium plan?

Sophia Le:                               So, if I understand the question correctly, it’s like a … I think that’s a different template. You could probably modify it, but for me those are two different emails, because I’m driven by numbers a lot of the time. And so for me this is getting people from trials users to paid users, whereas the other one is more of a metric of money. Especially if it’s a free plan, they’re already just trying to get people in there and then you can use it free indefinitely. But there’s a way to do upgrade emails, also. I think that would be a different template, but we can add that to the list, too.

Joanna Wiebe:                     [crosstalk 00:20:05] Sophia’s just doing all our tutorials from this point on. It’s gonna be awesome.

Sophia Le:                               Apparently. You can’t get rid of me now.

Joanna Wiebe:                     I know, that’s awesome. I don’t want to. Okay, cool. Thanks, for that. Bridget says, “What do you do instead when you don’t have social proof or an impressive number?” So, for the 2,000 freelancers, what do you do if you don’t have those numbers?

Sophia Le:                               That’s a good question. I would say that there’s probably, if you dig deep enough, there’s probably an impressive number that you have somewhere. If there is no social proof in the numbers way like that, I would probably go in the direction of highlighting a testimonial from a very happy client and basically say, “This person is like you, and these are the ways that they’ve benefited from a solution like ours.” And then put in the quote directly in the email. If you don’t have customer testimonials like that, I highly recommend you get some because, people really want to understand how other people are using their solution. And I think that’s really hard for business owners to realize, because they’re kind of like this a lot of the time. Doing that will help them see the benefits in a different way, because I think a lot of SaaS companies and marketing teams, in general, suffer from expert blind spots. So, you can wrap that up in your customer research also, if that makes it helpful.

Joanna Wiebe:                     Perfect. Okay, last questions here. G-street asks, “Should you adjust your messaging sequence depending on trial user engagements,” I assume this like your email sequence based on their engagement. “Example: if people are [inaudible 00:21:46] you don’t want to spam them, but if they aren’t and they forgot that they signed up, is it okay to send more ‘Your trial is going away’ emails?” So, does your planning for this, using this email, does it depend on engagement?

Sophia Le:                               Yes, it does for the most part. Depending on what my clients usually have set up, usually there’s the traditional Onboarding sequence. I have another blog post in the inter web, somewhere, about planning those other types of emails. But, yeah, I would say so. I’m trying to make sure I catch everything. If people are active in the funnel and you don’t want to spam them, but they already forgot, it’s okay to send them more ‘Your trial is going emails’. I wouldn’t necessarily say ‘Your trial is going’ emails, but definitely try to give them some sort of benefits. Either the point of the emails before that are to educate them about a certain platform, trying to get them to do that one step in order to get 80 percent of the value of your SaaS product, and also making sure that you’re just checking in regularly, whether it be through 15 minute phone calls or just getting feedback on a regular basis. I hope that answers your question.

Joanna Wiebe:                     Yeah, hopefully, it’s good. Mark asked, “Any good books or other materials about SaaS that would be helpful for a first timer?”

Sophia Le:                               That is a …

Joanna Wiebe:                     That’s big.

Sophia Le:                               I might have to get back to you on that one. I think someone wrote a tweet pretty recently, I think it’s a [inaudible 00:23:21] co-founder. She basically said, people ask her how did she learn about SaaS and she just said, “I just started doing it.” And I think that’s really what it comes down to. If you are interested in learning about SaaS, either try to find clients that are in that space, or take the work that you already do and kind of transition it. Just start reading blogs, and understanding … I can write a list of free sources about all my favorite stuff. There’s millions of lists out there. Copy Hackers is a good place to start, Lincoln Murphy’s blog is really good. I like one of the Venture Capital blogs. There’s just too may to name. But, I can definitely put together a list some other time.

Joanna Wiebe:                     Thanks, Sophia. And yeah, it’s always amazing to me, like first round, I think, the V.C. Firm does really great blog posts on all things SaaS, and Lincoln Murphy as you mentioned too. That’s awesome.

Okay, one more question, I know other ones are coming in but let’s do this one from Chris: “Is there a different strategy for more expensive SaaS offerings, where there are likely multiple decision makers in triggering the sale?”

Sophia Le:                               Yes. That is a great question. I am currently working with a client and they don’t follow the traditional ten emails where you’re Onboarding, and a lot of times, Onboarding in particular, it gets more complicated beyond email. You have in-app messaging, you have tool tips, and all these other things interacting in order to get the person to their ah-hah moment. If they are more expensive, I would probably recommend kind of a hybrid email sequence, so not necessarily a free-trial sequence, but not necessarily a cold email sequence. We’re kind of just trying to get the prospect on a demo call. Jo, I think you were the one that wrote the big blog post about “Everything I Need to Know About Demoing SaaS”, you should go read that, right now, about selling more expensive SaaS offerings. Because, for the most part, if there’s a huge barrier, either by price or by set up, then you’re gonna have to sell the demo, and if you don’t have resources to do Onboarding and whatnot, then that’s where the strategy would change in the email.

Let me make sure I got the rest of that question. Multiple decision makers triggering the sale … Again, that’s kind of a demo situation where you need to get the right decision makers on the phone, spend a little more time analyzing what exactly the needs are for the SaaS offering, and then working from there. I used to work in government and there was like 10 people that they had to ask, in terms of making a decision maker, and I think that at that point you would probably have to go and look at more traditional sales literature, and multiple meetings, and understanding the stages, and the multiple triggers, that sort of thing. Hope that answers your question.

Joanna Wiebe:                     That was awesome. Nice. I said that was the last one, but I’m gonna ask this one other one, because two people asked the same question around how many emails is too many emails, how many emails is too many for … yeah, one of them accidentally got moved to answered already but Paul asked, “How many emails are too many emails for a time sensitive offer?”

Sophia Le:                               Okay, well I keep referencing the Copy Hackers blog. Obviously, I read it a lot. If you want to know this, I haven’t seen this happen myself, in my swipe file, if someone wants to educate me otherwise, then please let me know. Ry Schwartz wrote a great article about the launch funnel, and I’ve never seen it done for SaaS, but I think his model is a good one to follow. He didn’t say a specific number, I would say there’s the whole … you have your offer, and you present it, so it’d be this template that I have presented to you today. And then you could probably start throwing in bonuses at that point, bonus one, bonus two, and then start taking it away. Depending on how engaged your users are, you can probably go up to three or four, but again depending on who your customers are. If you’re selling to developers, don’t send them four emails, like that. They’ll get very upset. But if you’re selling to marketers, they might be a little bit more receptive to it. But that’s something that I would just have to know a little bit more about the customer, and then obviously, use some testing to see if more emails actually makes a difference in conversion.

Joanna Wiebe:                     Yeah, and speaking of you knowing a little bit more about the different scenarios, how can people get ahold of you, Sophia? How can they find you online, or work with you, if that’s a thing?

Sophia Le:                               Sure, so my website is a desolate wasteland right now, so the best way to get ahold of me is through email:, I am also on Twitter @ IamSophiaLe. And if you want, at the bottom of the Copy Hackers article, there is actually another template for you to download in there. It is a welcome template, if you want that also to add to your collection, sign up. It’s not in the Airstory market yet. I’ll have to get all my templates over to Joanna, one of these days. But yeah, hopefully this was helpful to you, and I have plenty more to say about SaaS and emails in general. So, feel free to always get ahold of me.

Joanna Wiebe:                     That’s awesome. Well, thank you Sophia for coming in, especially late at night where you are. That’s awesome, and thanks everybody for joining as well and asking really great questions. Sarah has shared out a bunch of links already today, we’ll attach those to the replay online as she shared out the link on where to find those replays, too. So hopefully everybody got what they were looking for out of this, I did. It was great. Sophia, thank you so much. Awesome job.

Sophia Le:                               Thanks, Jo. Thanks, Sarah.

Sarah:                                        Thanks guys! Thanks for having me!

Joanna Wiebe:                     Have a good day! Bye everyone.

Sarah:                                        Bye.

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