SaaS pricing for a higher tier, nearing 10 paying customers

filmed 29 October 2026 · 8:17

I talked through how I'm pricing Underway's next tier while closing in on the goal of 10 paying customers I set when series one opened. There are somewhere around 15 to 20 people on trial and very few have cancelled, and most signups are now on the $129.99 plan with a seven day free trial, even though people close to me still say they don't quite grasp what Underway does. I'm also in the early stages of a higher-priced membership that acts like a director and producer in your pocket: it researches your niche, brings you video ideas when you say you're ready to film, and talks you through the recording section by section. I'm using it on myself while I build it.

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What pricing should a SaaS charge for a higher tier when nearing its first 10 paying customers?

by Richard Lovatt · updated 29 October 2026

When you are closing in on 10 paying customers, the right move is not to redesign your main price but to add a higher tier above it for the buyers already paying the most. I built Underway's $29.99 to $129.99 range first, proved people pay for outcomes not trial length, and only then started building a director-and-producer membership for business owners wanting more done for them.

Key numbers

I'm on the brink of having many more than 10 paying customers, with maybe 15 to 20 on trial, most now paying $129.99 on a seven day free trial, up from $29.99 on 14 days.

In short

Raising the entry price and shortening the trial got more signups, not fewer, because the buyers only cared what they got for it
Build the higher tier after you have paying customers, not before, so you are pricing against real willingness to pay
Messaging that confuses your mum and your car-wash guy can still be correct messaging, if the paying audience gets it instantly
Nearing a round number like 10 paying customers is the moment to set the next goal, not to stop and admire it

Why pricing changes right before 10 paying customers

There is a specific moment in a SaaS build where pricing questions get real: you are not guessing any more, you have actual people paying actual money, and you can see which price attracts the customers who stay. For me that moment arrived as I got close to my season one goal of 10 paying customers, with somewhere around 15 to 20 more sat in trials, most of them nearing the end and not cancelling.

Before that point, pricing is theory. After it, you have evidence. I had already moved my own entry price up and shortened the trial, and the people coming through that higher price were the ones sticking around. So the question stops being what should I charge and becomes what would make my best customers pay more for something bigger.

That is the real problem behind the search. People searching for pricing a higher tier near their first 10 customers are not asking in the abstract, they are asking because they have just enough signal to make a confident decision, and they do not want to waste it by guessing.

The options people try, and where each falls short

One option is to raise the price of your existing plan and call it done. I tried a version of this myself, moving from a 14-day free trial at $29.99 to a seven-day free trial at $129.99. It worked, but it is a different move from adding a tier. It filters who signs up at all; it does not give your best customers somewhere to go next.

Another option is to bolt more features onto the same plan and raise the price for everyone. This is tempting because it feels like progress, but it punishes the customers who were happy with what they had and confuses the ones who are not sure what they are paying for in the first place. I am, if I am honest, really good at adding new services, and I think of that as a problem as much as a strength, because it is easy to keep stacking rather than deciding.

A third option, and the one I think is right, is to leave the existing tiers alone and build a genuinely separate higher tier aimed at a different depth of problem for the same type of buyer. Nothing changes for the $129.99 customer. Something new exists above them for the business owner who wants more taken off their hands entirely.

Pricing and trial changes: what actually moved the numbers

My own data point here is blunt. When I was on the $29.99 plan with a 14-day free trial, signups were slower and the people who did sign up were more likely to need convincing. When I shortened the trial to seven days and raised the price to $129.99, the majority of my signups now come in on that higher, shorter-trial plan.

The lesson I took from that is not that shorter trials are magic. It is that people do not care much how many free days you give them. They care whether the product does exactly what the ad and the landing page said it would. If the messaging promises an outcome and the product delivers it, people pay quickly and they stay. The customers who pay the most tend to be the ones who email you the least, because the thing did what they expected.

So before you price a higher tier, check that your current tier's promise and delivery are lined up. If they are not, a new price band will not fix it, it will just surface the mismatch at a higher cost to the customer.

Higher price membership: how I decided on the next tier

I am focusing my marketing more on business owners now, and I asked myself a simple question: if they are already paying $129.99, what would make them pay more? I have not settled on an exact number, that is just a figure I was testing in my head, but the logic is what matters. Rich people, and by that I mean people running a business with money to spend, will pay a lot if you show them something that solves a problem they actually have.

What I landed on is a genuine director and producer in your pocket. Not more automation bolted onto the existing plan, but a different kind of relationship with the product: you talk to it, it knows your business, it researches your niche and the wider niche for what is working, and it tells you what to film today, with options, back and forth, like having a producer sitting with you.

The test for whether a higher tier is worth building is not how many features you can list. It is whether it removes a decision the customer currently has to make themselves. For my higher tier, the decision I am removing is what to film, how to say it, and when. That is worth a much higher price because it solves the thing that stops business owners from ever starting.

Producer in your pocket: what it actually does, step by step

I built this to work like a conversation, not a menu. You say you are ready to film, and it comes back with ideas, for example three good options for today, drawn from research into what is performing in your niche and the wider market. You pick one, or you ask for more.

From there it directs the take out loud. It tells you to concentrate on the hook, gives you the line, and lets you repeat it as many times as you want, because it will take the best version when it edits. Then it moves you to the body, tells you the points to cover, and lets you talk freestyle rather than script it.

I am using it myself before giving it to anyone else, partly because I want to feel how it changes my own day before I promise it to a business owner. So far it is making my life easier, not just easy, and that distinction matters: easy was always the promise of software, easier is what you notice when you stop thinking about what to say.

Who this suits and who it does not

The higher tier suits business owners who already understand they should be creating content, who have the budget to pay for it being handled rather than done by them, and who are not short of money so much as short of direction.

It does not suit someone still deciding whether documenting is worth doing at all. That person belongs on the entry tier, proving the value to themselves at $129.99 before they would ever consider a producer in their pocket at a much higher price.

It is also worth saying plainly: a higher tier only works if your messaging is already converting the right people lower down. My car-wash guy, my mum and my auntie on Instagram still do not quite grasp what I do, and I have decided that is fine, because the people who get it are the people who pay and stay. If a stranger cannot explain your product, that is only a problem if your paying customers cannot either.

Questions people ask

Should I add a higher tier before or after my first paying customers?

After. Pricing a higher tier on guesswork means you are solving a problem you have not confirmed exists. I waited until I was near 10 paying customers and could see which price and trial length actually converted and held before I started building anything above it.

Does a shorter free trial lose signups?

In my case, no. Moving from a 14-day trial at $29.99 to a seven-day trial at $129.99 increased the share of paying signups, because people cared about the outcome the product delivered more than the length of time they got it free.

Should the higher tier include everything in the lower tiers plus more features?

It can connect to the same underlying system, but it should solve a different depth of problem, not just stack extra features. My higher tier is built around removing a decision entirely, deciding what to film and how, rather than adding more settings to the existing plan.

What if my messaging confuses people outside my target buyer?

That is not automatically a problem. People close to me, like my mum and the man who washes my car, still do not fully grasp what I do, but the people who see the ads and pay the money understand it immediately, which tells me the messaging is right for the right audience.

Read the transcript

What's up, guys? Um, so I just wanted to get, come up, come up? I just wanted to jump on here and then, and just talk to camera and just do a talking head yapping video. I feel like lately I've been doing a lot of promotional activities. You know, Underway is now really good at helping you craft promotional videos, AKA how to be found more on YouTube, um, how to craft hooks. Um, you know, which I, I'm, I'm being very careful about moving away from the original idea. You know, at, at the end of the day, ideas progress, right? Ideas change. Um, but Underway's becoming a one-stop shop. But I'm being very careful about moving away from the idea, which is documenting. And documenting for me is, is I've said before, I think it's different from promotional type videos. You know, one is like you've gotta think about the hook, you've gotta think about the lighting, the, the, the sound, the, your, your background, your, the, the titles. There's so many things that go into it, which is what puts a lot of business owners off. And then there's documenting, which is like no pressure, just talk like this. Just get your thoughts out because it's really this and, and these thoughts and how you, how you're thinking at one sp- point in time, so you can look back and go, "Oh, that was where that idea developed. That was when I, I felt like giving up." You know, I think it's important to do these things. Um, so I wanna keep, uh, you know, keep reminding myself to do these and to speak honestly Um, but on the promotional side, Underway has become incred-- like incredible. Um, like it's, it's, it's got a base layer of, of research. It's h- you have your AI agents constantly working for you, for your business, and to help you move forward, get views, um, not just on videos, but get found in, in AI, get found on Google. It writes articles for you based on the videos you've done. It does so many things. I mean, we can do another video where I go through everything. I just created landing pages today going through what you get in each membership, you know? Um, but, you know, let's look on the bright side. I, I feel, I feel a bit solemn right now. It's kind of weird. But if I look back from when I started, it wasn't that long ago really. I think I did episode zero, which was about kind of launching the initial stages, and I went public, which kind of moves you to series one. And when I opened series one, I put in the goal, which was 10 paying customers. And I'm on the brink right now of having many more than 10 paying customers. You know, I've got many, many people now on a trial. I don't know how many, maybe 15 to 20, maybe a bit more, I'm not sure. Um, but they're all coming towards the end of their trial. Not many of them, you know... I, I was expecting people to cancel, right? I think that's part and parcel of the job, right? But not many of them have, which is promising Um, so soon I'm going to have achieved that goal, which honestly, even though it wasn't, wasn't long ago when I first started, I thought, okay, let's try and get to 10 paying customers. I thought it's kind of weird. It's not a massive jump, but I did think, I don't know, can I do that? You know, not so confident. Um, but with that, we're pretty much there guys. I don't want to jinx it. And so after that, it will become my next goal, 50 or 100 paying customers, you know, and we'll just, we'll just keep building. You know, I have a guy who comes to wash my car, um, mostly once a week. And he was saying, you know, how are we doing on this? And he was saying how he, he just doesn't really understand it or he doesn't quite grasp it. Sorry. Um, and, uh, my mom doesn't. And then obviously I get my auntie who sees my things on Instagram and she says, yeah, I don't still don't quite grasp it. And it's like, I guess this is marketing, you know, my, my messaging. Um, it's hard to understand really, you know, because the people who get it are the people who see the ads and sign up and pay the money. They pay for the membership. And to be honest, as I've said in previous episodes, I started off on a free trial, 14 days, $29.99. And now all my signups, the majority of my signups are paying $129.99 with a seven day free trial. And obviously they get the messaging because they're paying that straight, you know, fairly quickly and staying, sticking around. You know, so the messaging is correct for the right audience. But I do understand as well, people just who know me just watching my Instagram and stuff, it's like, "Okay, he's building something. He's putting himself out there, but like, what? Who's it for? What's it do?" And, um, I don't know in my mind, is that an issue? I mean, at the end of the day, if I'm sat here in a year's time and I've got thousands of users, I don't think that's really an issue, is it? You know, as long as my messaging is correct to the right audience. Um, so that's that. Um, I'm currently developing, again, a new- Don't know if you heard that. Weird voice comes over my screen every now and again. But you guys should know I'm, I'm really good at a- adding new services. I think it's a problem. But I'm in the, I'm in the process of developing, um, a new membership, higher price. You know, there's rich people out there, right? I, I know this. I do this day, day in, day out. Rich people will pay a lot. You just have to show them something that they want, solve a problem they have. Now I'm, I'm focusing on business owners more so now in my marketing, and so I, I thought to myself, "Well, if they're paying 129.99, what would make them pay 499.99?" You know? So I'm, I haven't chosen that price. I just thought that to myself. Um, so I'm now in the process of developing a membership where it's a genuine underway dire- director, can't speak, director and producer in your pocket, right? So it's, you just talk to it. It, it can relay research. It knows you and your business. Like, like the other memberships, connects to everything. So it has this incredible wealth of information, but it also has an under- underlying kind of research aspect. So it's able to research your niche and a wider niche to what's working, what we should do, how, h- why are videos performing well, and it's able to relay that to you. And so you, you literally just have it in your pocket and you can just talk and say, "Hey, I'm ready to film." And it'll come up, "Okay, cool. I've got three really good ideas for you to film today. Here's one, two, or three. Do you wanna do any of these or do you want me to bring you more?" It's like having that person in your pocket. They'll go back and forth, "Oh, cool. Do you wanna do this video where you'd share your screen and walk through these or do you wanna do it where it's just you talking? Do you wanna open it on a hook or do you wanna just no pressure and document?" You know, and it's... I, I'm in the initial stages, but I'm using it myself to see how it works and honestly it's, it's incredible. This is where AI is getting, you know, moving to. Um, and I really feel I'm solving a massive issue for business owners which is, you know, "Oh, I, I know I need to create content. I just don't know how and, and why and when." And this does it all for you. You, you generally don't need to think. You can just chat to your friend, to your underway producer and director and it will set it all up for you. It will even be in the recording with you and it will say, "Cool. Here's section one of this video. All I want you to do now is concentrate on the hook. Okay? So here is the hook, here's an example. I just want you to say this to the camera, look directly into the camera and repeat yourself three, four, five times however much you want and don't worry I'll take the best shot when we edit." So it'll do that and it'll say, "Cool. Now that's done." Now it'll say, "Right, section two. So this is a bit of the body. These are the points I want you to talk about. Don't worry about a script here, just talk to the camera freestyle." Right? And it will just lay it out for you. You will just sit there and just follow along, right? What more can I say? That's the world we're moving to, and I'm, I'm really excited because I'm living it. I'm s- I'm, I'm in the process of feeling how it affects me and how it makes my life easy or easier, and I can't wait for other business owners to, to have their hands on it, to see the product in its full capacity. That's me, over and out. Yapping

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