Directory · Building Underway · S1 · Episode 92

S1 · Episode 92

SaaS positioning change and pricing the plan at $129.99

filmed 26 October 2026 · 3:54

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I changed the positioning of Underway from day-one urgency to the pain of not having posted content for years, and raised the cheapest plan from a 14-day trial at $29.99 to a seven-day trial at $129.99. Signups came in faster and the cost to acquire each one dropped a lot. That lets me start working out CAC, margins and recurring revenue, which matters after the Anthropic bill gave me a scare. I'll go through the ads I crafted in another episode.

The episode, in writing

by Richard Lovatt · from the episode above, checked against what was said

I'm just recording this moment because I'm super happy, I'm super excited. I was saying, when was it, last week, a few days ago, who knows, but I had the feeling, the positioning change, I knew I was onto something with the don't miss day one, spoke to the client, had a revelation. It was not quite hitting.

So I changed the whole positioning, because I know I needed to hit people who have that pain point where they want to solve it, but a pain point that they feel always, not just day one. So it was a minor change. It was more so like, don't miss, you know you need to put out content, you've missed it for the past five years, so start now, and then Underway is the solution because it does all these things for you, you just have to sit there.

And guys, I just got sign up, sign up, sign up way quicker. And guess what, two things played a role. So before, I was doing a 14-day free trial on $29.99, the cheapest one. And I changed this to a seven-day free trial, so much like, you don't have as long, and $129.99. So way more, $100 more.

And at the end of the day, I should know this because this is my bread and butter, sales and marketing. You'd be surprised what people will pay to solve their issues. And I still think $129.99 a month is cheap because the things that Underway does now, and I'm not blowing my own trumpet, I'm just saying it's a very good product. It really does a good job. And the fact that I've now crafted ads, and we'll go through those on another episode, but they really do the job.

And we've had a number of signups, and not only that, but the amount that I've paid for those people to sign up is so much cheaper. And it makes you realize, okay, so now we can start to optimize on these and what works. Now we can start to form what it will cost us to acquire a customer, the CAC. We can start to look at margins.

Because I'll tell you what, I was a bit scared the other day because I got the bill from Anthropic, and I was like, okay, we need to start making money. But after these last few signups and now working out the monthly recurring revenue, the annual recurring revenue, I am very pleased, I am very happy. And mostly because I look at this now as a long-term thing.

So I know consistently do what I'm doing now, and in one year's time, not only is it gonna be a fully fledged business and I want to make hires and have people the best at what they do, working for Underway, because I'm not the best, but what's even more exciting is how good Underway itself will be in a year's time. The tech itself, because it's improving rapidly, and I've got so much to show you.

Read the transcript

I'm just recording this moment because I'm super happy. I'm super excited. You know, I, I was saying like, when was it? I don't even know. Last week, a few days ago, who knows? But I had the feeling, you know, the, the positioning change. I, I knew I was onto something with the, you know, don't miss day one, spoke to the client, had a revelation. It was not quite hitting, so I, I kind of... Hello. You wanna say hello? This is Sunny, everyone. He's only a little cat. Come on then. You sitting here? Anyway, guys, um, just concentrate. Concentrate, guys. So, getting back to business here. I re- I, I changed the whole positioning, right? Because I, I know I needed to have hit people who have that pain point that where they, they wanna solve it, but a pain point that they feel always, not just day one. So it was a minor change. It was more so like, "Don't miss. You know you need to put out content. You've missed it for the past five years, so start now," and then like, Underwear is the solution 'cause it does all these things for you. You just have to sit there, right? And guys, I, I just got sign up, sign up, sign up way quicker. And guess what? Two things played, played a role. So before, I was doing a 14-day free trial, um, on $29.99, the cheapest one, right? And I changed this to, um Seven-day free trial, so much like you, you don't have as long, and $129.99. So, uh, way more, $100 more, you know? And at the end of the day, like I, I should know this because this is my bread and butter, sales and marketing. You'd be surprised what people will pay to solve their issues, right? And I, I still think $129.99 a month is, is cheap because the amount that... The things that Underway does now, and I'm not blowing my own trumpet, I'm just saying it's a very good product. It, it really fucking does a good job, you know? And the fact that I've now crafted ads, and we'll go through those on another episode, um, but they, they really do the job, you know? And we've had a number of signups, and not only that, but the, the amount that y- I've paid for those people to sign up is so much cheaper. So much cheaper, you know? Um, and it makes you realize, okay, so now we can start to form, we can start to optimize on these and what works. Now we can start to form what it will cost us to acquire a customer, the CAC. You know, we can start to look at margins. 'Cause I'll tell you what, I was a bit scared the other day 'cause I got the bill from Anthropic, and I was like, "Okay, we need to start making money," you know? But after these l- last few signups and now working out kind of the monthly recurring revenue, the annual recurring revenue, I am very pleased. I am very happy. And mostly because I, I look at this as now as like this is a long-term thing. So I know consistently do what I'm doing now And in one year's time, no, like, not only is it gonna be full, fully fledged business and I wanna make hires and I wanna have, you know, people, uh, the best at what they do in different, in, uh, working for Underway, um, 'cause I'm not, I'm not the best, but um... What was I gonna say? But yeah, the, what's more e- what's even more exciting is like the, how good Underway itself will be in a year's time. The tech itself, 'cause it's, it's improving rapidly and I've got so much to show you. So see you later, guys.

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