
SaaS Open Mic by ChartMogul · 2023-01-27 · 34 min
Key moments - from our scoring
Substance score
52 / 100
Five dimensions, 20 points each
Matt Lerner draws on a decade at PayPal and experience as a VC at 500 Startups to reframe SaaS pricing through the jobs-to-be-done lens. Rather than viewing pricing in isolation, Lerner advocates understanding the four forces driving customer behavior: push (pain with current solution), pull (desired future state), anxiety (specific concerns), and inertia (switching costs, data migration, approval processes). The core argument is that most early-stage SaaS companies make two critical mistakes: they lower prices when conversion is weak without understanding that customers don't grasp the value proposition, and they ignore non-financial barriers to purchase. Lerner illustrates with examples like Leadsie (enabling agencies to onboard clients professionally) and a UK estate agent experiment where raising price 25% had zero impact on conversion once value was clearly communicated. He introduces the Van Westendorp price sensitivity model for testing willingness-to-pay across four price points, positioning this as superior to premature price cuts. Bianca Wilk guides the conversation through practical pricing mistakes, mental math of prospects, and price-sensitivity testing methods.
The push (unpleasantness of current situation), pull (attractive future state), anxiety (specific concerns about the solution), and inertia (switching costs, habits, non-financial friction like data migration and approval processes).
Customers typically aren't buying because they don't understand the value, not because of price; lowering price without clear value communication wastes margin and can signal low quality, introducing more doubt rather than solving the real barrier.
A four-question technique (too cheap, good deal, expensive, ridiculous) asked after customers understand product value; average the "good deal" and "expensive" answers and price between those points, ideal for new product categories without competitive benchmarks.
Ask what the product enables them to do, test with a ridiculously high price and ask what would justify it, ask which budget it comes from in B2B contexts, and listen to how they articulate value without leading them.
B2B buyers face inertia like data migration, stakeholder approvals, retraining, and quality concerns; addressing these barriers removes actual friction to purchase, whereas lowering price doesn't solve these adoption obstacles.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a handful of genuinely useful ideas - particularly the 'high anchor price in an interview' technique and the counterintuitive point that lowering prices can amplify anxiety about quality - but the episode is padded with repeated refrains about the '10% principle' and long JTBD preamble that dilutes the density significantly for a 34-minute runtime.
lowering the price can often be counterproductive because if they're worried about the quality of your product and you lower the price, you're basically saying, hey, we're cheap
what price would be so cheap that you would have doubts about this product's quality
The JTBD-as-pricing-lens angle has some freshness, but the episode recycles well-worn frameworks - anchoring via BMW and the famous Economist experiment (popularised by Dan Ariely), freemium basics, and the generic 'communicate value before cutting price' advice - making most of the content familiar to any attentive B2B operator.
the famous experiment from the Economist magazine where they would say okay, the print edition is like $100, the online edition is $100 or you can get them both for $120
nobody ever got fired for buying IBM
Matt Lerner has genuine practitioner credibility - 11 years as a PayPal GM running B2B/SMB units, meaningful VC experience at 500 Startups - but he is now primarily an accelerator coach and educator rather than an operator actively scaling a SaaS business, which caps how deeply he can go on current, first-hand execution.
I was there for 11 years, general manager of different B2B and SMB business units
I left PayPal to become a VC investor
The episode earns its points with named companies (PayPal, Charlie HR, Leadsie, Stripe, Square), real numbers (10M merchants × $3/year = $30M free cash flow, 40% conversion lift, 399→499 pound price test) and a named, repeatable methodology (Van Westendorp), though several figures are approximate and the Charlie HR case is thin on measurable outcomes.
PayPal had 10 million merchants, so that's $30 million a year in free cash flow, which I think was like 2 cents a share
we changed the price to 499 instead of 399. And it made no difference in conversion
The host steers the conversation competently and covers logical ground, but every substantive claim goes unchallenged - there is no pushback, no 'but what about X', and responses frequently consist of praise ('that's absolutely impressive', 'that's a great summary') rather than probing follow-ups that might extract harder, more specific insights.
That's an absolutely impressive story
That's a great summary of this podcast. Thank you so much again, Matt. We were so lucky to have you here
Computed from the transcript - who did the talking, and the words that came up most.
On this episode of SaaS Open Mic: Two common pricing mistakes founders make How to apply the Jobs to Be Done framework to pricing strategy Pricing experiments to test for price sensitivity 90% of growth comes from 10% of the activities Matt has worked with dozens of startups and scaleups in his time at 500 Startups and Startup Core Strengths. A challenge that every company must face at some point is optimizing pricing or setting a price for a new product or feature. Matt shares his perspective on establishing and optimizing pricing using the Jobs to Be Done framework.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Any decent salesperson can sell a Ferrari for a dollar. That's not the magic. The magic is making a product that people are willing and happy to pay a premium for. Make sure that you understand the value and the barriers before you start mucking about with the price.
Speaker B: Welcome to the SaaS open mic by Chart Mogul. Today I'm speaking with Matt Lerner, the founder and CEO at Startup Core Strengths and Accelerator for Seed and Series A companies. Matt spent many years as a marketer and GM in Silicon Valley, including 10 years at PayPal. He also led 35 early stage investments as a VC at 500 Startups. And the topic of our conversation today is pricing. And we're going to be looking at pricing from a different perspective, from a perspective of jobs to be done. My name is Bianca Wilk. Here's my conversation with Matt. We actually met a few months ago at SaaS Talk and we connected again and decided to record this SaaS open mic episode. Welcome.
Speaker A: Yeah, my pleasure. It's great to meet someone else who actually enjoys thinking about SaaS pricing and metrics and things like that. Does this sort of thing for fun.
Speaker B: Oh, definitely, definitely. Yeah. I'm very excited to talk to you about pricing today. To get started though, could you tell us a little bit more about yourself?
Speaker A: Yeah, sure thing. So you can probably tell from my accent, I'm American. I started my career in Silicon Valley. The first startup I joined was dead in nine months. The second startup I joined was dead in six months, which in Silicon Valley terms is actually progress, fail fast. The third startup I was running marketing, and we managed to sell it for 40 million bucks, which wasn't a bad exit in, uh, 1999. Took some time off, traveled, and then I came back and by 2004 I joined PayPal. And, you know, I guess I don't need to tell you how that worked out.
Speaker B: Okay, a little bit longer than the six, uh, nine months it went.
Speaker A: Longer than nine months. Yeah. PayPal, in fact, they're still going, doing quite well. Um, really impressive group of people. And, you know, so I was there for 11 years, general manager of different B2B and SMB business units, marketing teams, did a little bit of pricing work, which we'll talk about later, I'm sure. And then I left. I moved to London and I left PayPal to become a VC investor. And you know, to go from big successful PayPal to starting to see early stage startups. The one thing that jumped out at me, in hindsight, for me, that really struck me is when I look back at PayPal's growth and success, everything, all of their growth really just came down to five things, if you're being honest. You know, like first was getting on ebay and then reaching out early to web developers who are building sites, partnering with shopping carts, hosting. Anyway, we don't need to go through the whole story. But the point is PayPal did obviously a lot more than five things. You know, they spent millions, tens of millions, hundreds of millions on different campaigns building products that didn't really have a big impact. And I think that's true. If you look at any startup is, you know, looking backwards. If you're honest, you can say that 90% of their success came from like 10% of the stuff they did. So when I became a VC and I started working with startups, I was, we were always looking for like, okay, what's the big lever we can pull? We, we only have whatever a dozen people, 8, 10, 12, 14 months of Runway. You got to find that 10% fast and really focus on it. So I think kind of that was my big takeaway. And uh, so now I run a business, I left the world of VC and I founded a business called Startup Core Strengths and it's really based on that principle. It's a lifestyle business. We only, I've got a partner and a team of a dozen coaches and we only work with 60 companies per year startups and we do that, we help them in our 10 week program to figure out what's going to be your 10%, what are the big levers they're going to move your business. Because great startups don't cannot waste time on little stuff. So we do that, we get the team running experiments and testing stuff, validating stuff and going deeper on that and ultimately uh, then they sort of shift from this mindset of like kind of an employee mindset of like do all the things and do them well to let's move quickly, let's try stuff and let's really only focus on stuff that if it works can be really big. Anyway, so that's sort of what got me here and that's what I'm up to these days.
Speaker B: I imagine pricing is also a big topic when you're running Startup Core Strengths. But so the topic of pricing is absolutely immense. Right? There are so many pricing frameworks, uh, pricing methodologies, tips and tricks. And I know that you have a very unique perspective on pricing and pricing optimization because you're advocating to think about, to think not just about pricing but about a business from a, uh, jobs to Be done perspective. So now that you're working with startup core strengths, advising many SaaS companies, how did that get you thinking about jobs to be done and pricing?
Speaker A: That's a great question. So what does jobs to be done even have to do with pricing? So working with companies, obviously, you know, we, we'd be quite remiss if we didn't look at the question of pricing. And when I needed to start introducing a pricing module to my program, the first thing I did was I went out there and just consumed all the great stuff on pricing. There's brilliant podcast, there's a Y Combinator talk. There's a lot of great stuff and you know, there's a lot of like bundle strategy and psychological factors and sensitivity analyses. But I found it at least that seed stage and series A stage. It was often, it was a lot more basic than that. It was much simpler than that. And maybe I'm like the person with a hammer, everything looks like a nail. Maybe that's me with jobs to be done. But we start companies out thinking a lot about jobs to be done and it just sort of the information we were getting from companies and the jobs to be done interview sort of matched so nicely to thinking through a pricing strategy.
Speaker B: I personally only heard about jobs to be done in the context of product management. I'd love to for you to explain the framework overall.
Speaker A: Yeah, it's funny, people always think about jobs to be done as a product methodology framework. But for me, like since I started doing it, it's the most obvious thing in the world that it's really about growth and customer acquisition. So if we're trying to find the 10% that makes a big difference for companies, there's two pieces of this. One is just literally the math, the numbers in their business, where's the leverage? You have this much traffic and signups and free trials and conversion, activ retention, all that stuff. And if you map out all those metrics, as I'm sure every one of your listeners does, you'll find constraints in that system. You'll find a rate limiting step and if you focus resources on the rate limiting step, you'll have maximum impact on the system. And if you focus on other peripheral parts of the system that aren't broken, it's not going to work as much. The other side of it though is these sort of, you know, 10% things that companies come up with are usually rooted in a deep understanding of customer psychology. If you're introducing a new product, nobody's out there looking for it, right? They might have the problem. They might need your product, but they don't know it exists. They're not going to look for it. 99% of your customers. So we use jobs to be done interviews to understand their life before the product. What do they think they were looking for to solve this problem? What alternative solutions did they consider? Who do they ask? Where do they look? What do they expect the solution to look like? And that is, you know, growth. People gives us lots of ideas for like where do you turn up? What do you call the product? How do you talk about the product? You know, how do you sort of insert yourself into people's lives in a logical place? It's not even sas, but the simplest brilliant example I like to use is soy milk, right? So imagine, you know, you figured out this process to get this nutritious white liquid, delicious white liquid, out of soybeans. You could call it, you know, a soy liquid and put it in a tin next to the soup and nobody's going to buy it because nobody wants soy liquid. So they called it milk. It's obviously not milk, but they call it milk because it's white. And they put it in the refrigerator aisle of the supermarket next to actual milk. It does, it's non perishable. These are vacuum packed so it doesn't have to be refrigerated. But they uh, pay the supermarkets extra to put in the refrigerator section because that's where people would expect to find it. And that's exactly what you know, companies need to do with their software anyways. We're far away from pricing. But the only way to get this customer context is to understand their jobs to be done. And jobs to be done has these, they call them four forces. These are the forces that are at play in customers lives during the customer journey. So the two forces pushing them, moving them towards your solution. One is called the push. And that's like the unpleasantness of the current situation they're trying to get away from. And then there's the pull, which is the wonderful future they're imagining for themselves if they're successful on this journey. And then the two things that are sort of pushing back against them are anxiety and inertia. And anxieties are the specific concerns they have, the specific things they're worried about. And then inertia are like habits and switching costs and things that make it hard for them to switch or adopt a solution. Non financial costs. I think of them. So like as an example, uh, some friends of mine started a software company called Leadsie and It's very simple. All it does is for agency owners. And if you, if you run an agency, you should check out leadsie and digital marketing agencies. So you bring in a new client, you need to onboard them, you need to get access to all their paid ad accounts, whatever, TikTok, Facebook, Instagram, AdWords, all that's LinkedIn, Twitter. And all this does is if you send uh, the client a link, they click the link and it automatically gives you the agency access to all their accounts. Agencies love this. They pay, I think it's like 40 or 80 bucks a month, depending on the plan, to have a tool that just does this one little thing. You send a client a link. So why would, why would agency pay so much money for that? Why not just say, okay, give me your Twitter login, give me access to your. And the reason is that when an agency onboards a new client, they're trying to impress that client and make a great first impression. They don't want to seem like a tiny little Mickey Mouse agency. They want to seem buttoned up. And this tool gives them the uh, chance to make a great first impression. So the reason I'm telling you this is that a lot of times people's jobs to be done are not functional. They're social and emotional, they're trying to impress other people, they're trying to make a good impression. They're worried about what people will think of them. And that's, you know, what leads these figured out. That's the value their customers are paying for anyways, we're getting ahead of ourselves. But you know, the key here is you've got to really understand the value you deliver to customers in order to optimize your pricing.
Speaker B: I think that's a really great story because, uh, it shows how people are not just buying products because they know they need a product, they buy products because they want to get a job done, they want to solve a problem.
Speaker A: So perfect. Exactly.
Speaker B: That's what you're saying, right? Like that. That's how jobs to be done and affect pricing in a way.
Speaker A: Yeah. So that's the start of it. And then the way that connects to pricing is I guess it starts with like when I saw pricing mistakes. So I remember an experiment I was working a few years back with an online, in the uk, an online real estate agent, or they call them here estate agents. So you sign up for them and they'll sell your house. And I think it was 399 pounds or something to sign up anyways. But all it said was like we'll sell your house on their website. So we made some changes to really show the benefit. You know, 98% of houses sell in, you know, for above the asking price. You know, they sell in this many days and this and that. So we just put a few benefits on there that would matter to home sellers. And that increased our conversion, I think by 40% or something. So then the next, uh, and it said, you know, sell your home for just 399 and then it had the benefits under it. And then, uh, we changed it to say, the exact same website, but we just changed the price to 499 instead of 399. And it made no difference in conversion. So they raised the price by 25% and it made no difference at all in their conversion rate. And my takeaway was like, okay, you know, you could have just lowered the price, lower the price. But people aren't signing up for your product because they don't understand the value. Once people do understand the value, they become a lot less price sensitive. So I think the big mistake, the first big mistake that companies make is if people aren't buying the product, they lower the price. And the real reason they're not buying the product probably because isn't the price. It's probably that they don't actually understand the value of the product. So the first thing you got to do is, uh, before you start mucking about with the price, is make sure that that value proposition, that you understand your customer's job to be done. Then that value proposition is super, super clear. And then the next mistake, the sort of flip side of that is, remember there's those forces pushing against you, the anxiety and the inertia. So even if they understand the value, it's quite possible they're not buying your product because of some other blocker. So especially in like B2B SaaS, right, the sources of inertia are like switching costs. We have to migrate all of our data stakeholders. You know, I have to get approval from finance and the IT team and uh, you know, we have to retrain our staff to use a new process. If this works, we're going to have to lay some people off because we're going to eliminate their jobs. Like there's all these other reasons that a company or somebody or, you know, you don't have a free trial or the free trial was too short and we weren't able to really find out if this works or it's not compatible with our stock. There's all these reasons that have nothing to do with money why people might not buy your SaaS. And so again, instead of lowering the price, what you want to do is find out the real barriers to purchase and remove those first. And in fact lowering the price can often be counterproductive because if they're worried about the quality of your product and you lower the price, you're basically saying, hey, we're cheap. You're introducing more doubt, more anxiety about the quality of your product. So all that is to say the way jobs to be done works, affects pricing is like one is make sure that you frame up the price in terms of clearly communicating the value and two is remove all the non financial barriers. First, don't try to fix non financial barriers by lowering the price because first of all you're giving away money. And second of all, it doesn't work.
Speaker B: To reiterate your points, Matt, so the common mistakes that SaaS companies make when it comes to pricing is not really putting enough attention into explaining the value of that product and also not really considering all the costs that people have in choosing your product that have nothing to do with the actual price. Do you see any other mistakes that founders and SaaS leaders make when it comes to pricing?
Speaker A: I think that tends to be the main one I think is people, because it's obvious and it's simple and we sort of have this mental model that is value and price. People just tend to pull the pricing lever first. Either underprice a product or give it away for free. And um, you know, if you can't build a product that people will happily pay for, you don't have a business. So forget about pricing until you've got really good traction and you've, yeah, you've sorted out the other pieces of the puzzle. Value and eliminating barriers to purchase.
Speaker B: I think you've, you've said it before but you called it mental math. Right. So all the things that go through the head of a prospect before making a decision. So do you have any advice on how we can better understand the mental math of our prospects?
Speaker A: Yeah, I'll give you a link to a list of jobs to be done interview questions that we tend to use. But a lot of times, you know, for me the questions that sort of get at that first thing is like what's this going to enable you to do? And then the second one you know is, and this is, this is a technique that you can use in some situations is suppose you're doing like a uh, product validation interview and you get to this point in the interview where you've now, explained the product, you've talked about, what's going to enable them to do, and they have the value clear in their head. Then sometimes we'll hit them with, you keep it friendly. You don't want to, like, upset them, but basically hit them with a ridiculously high price. So just say something, okay, now you understand what the product does. Suppose I told you this cost a thousand bucks a month. And then just be quiet. And then, uh, what they're going to do is they're going to say, I would say, no, thank you, I'm not paying a thousand bucks a month for this. Right. Or whatever. And then you're like, okay, yeah, fair enough. What would this product have to do to be worth a thousand bucks a month? And that question. And then they're going to be like, wow, for a thousand bucks a month, it would need to eliminate all of our support queues and all this money we're doing here. And it would have to connect to this. And, and suddenly when they're thinking about what would they pay 1000 bucks a month for, you get to the real value. You get to the real mental math of that or another way. Sometimes, like I've told somebody, this is a long time ago, but I was selling workshops, like in person training workshops. And, uh, so I said, okay, it's 5,000 bucks, you know, and you can bring up to eight people from your team. And he's like, okay, so that's about 650 a person. Yeah, okay, we can do that. And then I realized from just him saying that, that, okay, he thinks about it in terms of his training budget per employee. So if I want to defend a higher price, I need to allow more M employees to attend the seminar. Right? I didn't know that, but that was sort of again, me getting to this person's mental math. So it's sort of like once you hit them with a price, uh, and by the way, if you hit them with a very high price like I suggested, then tell them afterwards, like, don't worry, it's not really going to cost 1000 bucks. It was just a research question, you know, and then tell them what you're really going to charge so you don't annoy them. But, um, when, you know, once you talk about price, just leave some space and hear how they talk through it and how they sort of calculate the value. You can ask, you know, what budget is that going to come from in a B2B sale? That might give you some insight too.
Speaker B: And what other methods can companies use to Test for price sensitivity.
Speaker A: Well, I think, um, one of my favorites. And again, I tend to deal with earlier stage, you know, seeds companies or companies who are just launching a new product. And a lot of times, especially if it's going into a new category, you know, like if you're launching another email, you know, marketing system, you're going to look at Klaviyo and mailchimp and Drip and right. There's kind of a range of what those things cost, but what people, sorry, what the people expect to pay for those things. But if you're creating, you know, a new space, it's really green field out there. So there's this really cool technique called the Van Westendorp pricing price sensitivity test. And so basically you get again to that point in the customer interview where they understand the value of the product and then you ask them these four questions in order. Number one, what price would be so cheap that you would have doubts about this product's quality? And they're going to tell you, six, six quid a month, $6 a month. Okay, at what price does this start to seem like a good deal? And then they'll think about like, oh, well, 14amonth. Okay, and at what price is this starting to seem expensive? They say, well, 50 bucks a month seems like kind of. I'd have questions about it, you know, if it were any more expensive than that. Okay, and at what price would this be just like ridiculous? Like, okay, I'd never pay 150 bucks a month for this product, no matter what. So you can do this in a survey form or in. I'd start usually in interviews and in a survey form. But it's essential that they understand the product value before they answer these questions or else they're just making up numbers anyway. So you take the results of that and there's like, you can Google the Van Westendorp model. Like, there's complicated spreadsheets, but the simple way to do the math here is whatever they said was like the cheap price, where it's like starting to feel like a bargain. Average the numbers that you got there and then average where they said this is starting to feel expensive. Average those numbers and then you want to price yourself somewhere in between those two middle points. Now you don't want to be bang in the middle of those two middle points because middle is never really a good pricing strategy. Either you're trying to be kind of the low end, cheap and cheerful provider, or you're trying to be a premium product. So you're normally going to want to be closer to one of those sides or the other. But if you're trying to just like set pricing for a new feature or product from scratch, that's a really good way to start.
Speaker B: That's super useful. Absolutely. And then you can like sort of decide if you want to be on like the high end, on like the high price or a little bit lower. But like at least you have a uh, benchmark from your research. That's amazing. And what, what other methods are commonly used for maybe for a little bit later stage once the pricing is already set for pricing optimization?
Speaker A: I m think um, so typically you know, in terms of like defending your price, improving conversion for the price, you've probably seen this and you know these are like psychology tricks. So like to help a bit but they're limited because like their gimmicks, you know. But obviously anchoring is going to be one of those. And it's funny because we tend to think about anchoring. Most people have heard of this. But the idea is either there's a high anchor so you're going to have a really expensive product and that makes your middle of the range product seem like a better deal. I mean uh, like in real life, non SaaS example would be BMW. They sell this like 7 series, top of the line BMW. They don't sell too many of them, but that allows them to charge a lot more for their 3 Series and their 5 Series models because it has this premium cache of sitting next to the seven series instead of like, you know, basically being, you know, the technological equivalent of like a Toyota Camry. So you can have a high price and then the price you want them to pay looks cheaper by comparison. Or you can have what's called a low anchor. And this was like the famous experiment from the Economist magazine where they would say okay, the print edition is like $100, the online edition is $100 or you can get them both for $120. So you have the cheapest thing be kind of expensive and then a much, much, much more valuable thing be only a little more expensive than that. In software. A lot of companies will do this with their uh, sort of month to month versus annual subscription. So it'll be like you know, $70 a month or $200 for the whole year. You know, I mean that's a kind of ridiculous example. But so anchoring would be, especially if people don't know pricing in your product category to have, you know, one really high price to make the other price the price you actually want. Them to pay look like a bargain. And then the other ones I think that really play into pricing are freemium and free trial. So remember, you want people to get maximum value from the product. So one option then with freemium is just like, make sure that they can go in and use all the features and really see what the product does and, and then charge for it or, you know, sorry, that's for a free trial or for freemium. Give them like the first thing that they need. Get them using it, get them loving it. But then, you know, once they're successful with feature one, they're going to want feature two, three and four, and they're going to start to. And they're going to be willing to pay for that because they're so comfortable with like feature one.
Speaker B: I want to ask you about increasing prices and how pricing can be like this maybe obvious growth lever to pull that. Like, okay, you increase the price, you increase a company's profit margin. And I know you have a story about it from PayPal. Can you tell me a little bit about what you've experienced about price increases at, ah, PayPal?
Speaker A: So I think a lot of people like to pull the pricing lever because, well, it makes money, Duh. But again, you want to zoom out and take the bigger perspective of what's going to have the biggest impact on this business. So many, many years ago, 2009, I was working at PayPal, and the beginning of the year, we had this strategy meeting. And the strategy for the company was to try to make as much money as possible. I thought, oh, gee, that's really clever. How much should they pay you guys to come up with that? But it wasn't just make money, it was free cash. So remember, 2009 was like the crest of the global financial crisis, and cash really was at a, you know, hard to come by. And so they said, we want as much free cash flow as possible to win our, uh, win back our shareholders trust. And of course, when you've got a bunch of existing loyal customers, the quickest way to generate free cash flow is to raise prices. So, you know, we did, we made a price increase. We took our time and found some changes deep in the pricing table. Not the prices we displayed to customers, but the way we handled certain, you know, oddball edge case transactions and things. And, uh, we try to make it as painless as possible for everyone. We communicated very clearly, made sure everybody was briefed with reactive talking points. And at the end of the day, this only cost the average merchant, the average PayPal merchant about $3 a year. But PayPal had 10 million merchants, so that's $30 million a year in free cash flow, which I think was like 2 cents a share. I might be remembering the details wrong, but the difference, 2 cents a share can make a huge difference in your earnings in a given year. But I think, you know, when I look back on it, I realized 2009 was kind of a crazy year in payments. I mean the, uh, the Collison Brothers, you know, launched Stripe, which is now, you know, privately held, but I think it's valued, you know, in the uh, high eight, low nine figures. No, it's like $90 billion or something. And Jack Dorsey launched Square, his little card reader point of sale and that, you know, that company is publicly traded and I don't know how many tens or hundreds of billions of dollars that's worth. So the point is we were mucking around, we made 30 million bucks. But the big levers, the big opportunities and payments were in really, in delivering value to customers. And other companies went and, you know, with this sort of a more of a long term focus and they were able to capture that value. And so, but most people don't, most people think in terms of the work they're doing, not in terms of the opportunity costs. They don't think in terms of if we're doing this, what are we not doing? And again, that brings back to this idea of like, find the 10% of stuff that's going to have the absolute biggest impact on your business and focus on that first and foremost.
Speaker B: And I feel like we're circling back to jobs to be done and actually creating and demonstrating value. Right?
Speaker A: Yeah, that's ultimately sort of sound like a broken record. Um, for those of you who don't have 10 million active customers, I was working with this SaaS company called Charlie HR. It's HR software. It's really good HR software. And when they originally launched, their product was free and you know, so HR software, what does it do? You know, onboard employees track performance, you know, absentee requests, paperwork, all that. It manages all that stuff for you and it was free and people loved it. And very good retention, very high, likely to recommend. Most of their new business was coming from word of mouth. And the idea was that they'd find other ways to monetize the software. But a couple years in, none of the other monetization routes were really panning out. But the founders did not want to charge for the software because they didn't want to do that to their customers. Right. They really Liked this idea that we can be really helpful to the world and you don't have to pay for it. And more than that, they'd even literally promised this software will always be free. But ultimately they sort of got to the point where they realized the only way to keep making great software and delivering value to customers was if they could charge product charge for the product so they could keep paying engineers and designers and keep building and maintaining great software. So very reluctantly, they eventually decided that they were going to start charging for the software. And this was a, uh, you know, it was a hard personal decision, you know, and they sent like a mea culpa email, you know, basically saying, hey, we never wanted to do this, we never expected to do this, but we need to and we're sorry. And they still left the product free for smaller companies, but they started to charge for larger companies. And as, ah, you can imagine like switching, creating and switching on pricing is a big operational thing for a company. There are a lot of details and it was just very stressful. And they made all kinds of forecasts about the different churn, you know, sensitivity, churn levels they expected. And bottom line is they had very little churn. And, and the customers generally were very receptive and understanding. You know, from the customer standpoint it's like, this is very good software. We're happy to pay for it, we pay for all kinds of software. It makes our lives better and this is fine. And so that was, I think, an example, you know, of uh, where it really was kind of a nothing burger, something that was, that was really quite stressful. And that's, I think, you know, the more common lesson is if you have a really good product and you've got happy, loyal users, they're happy to use it, they're okay to pay money for it every month. In fact, you know, that that's really helpful to your business because it means you're going to keep making great software and you can keep delighting your customers. So I hope people again frame up pricing in terms of customer value.
Speaker B: Um, that's an absolutely impressive story. And uh, I think it's still like a rare story. You know, maybe not everyone is PayPal, but also not everyone is in such a privileged situation where they can charge from zero to.
Speaker A: I mean they, they had built a great product and the leaders themselves has so much personal integrity. And that's, you know, that's what I really like about that story. I was just so impressed with, you know, how personally they took the entire thing.
Speaker B: Impressive. So Matt from From your perspective, what do you think SaaS founders, SaaS executive leaders should understand about pricing? To summarize, summarize a little bit what we've talked about today.
Speaker A: Yeah, I think bottom line is, you know, my three points here, right. Number one, think about the big levers. If you're in a startup, if you know, you're running around saying we don't have enough budget, we don't have enough headcount, we can't do all the things we want to do, focus on the big stuff. And the big stuff may or may not be pricing depending on where you are in your business. If it is pricing, then make sure you know, number one, that at the point you're talking about pricing and you know, people have, are in a position where they'll need to make a decision, make sure they fully understand the value of your product in the context of what they're trying to do in their lives. And then number two is make sure that you've removed or addressed all the non financial barriers first. Don't just like always go to like, let's lower the price, let's lower the price, let's lower the price. Any sales, any decent salesperson can sell a Ferrari for a dollar. That's not the magic. Like the magic is making a product that people are willing and happy to pay a premium for. So make sure that you understand the value and the barriers before you start mucking about with the price.
Speaker B: And if people want to use your approach of jobs to be, of the jobs to be done framework and optimize their pricing through the jobs framework, how can they do that?
Speaker A: So if you already know how to do jobs to be done interviews, uh, it's a very special kind of interview technique. Like go for it, uh, you know, go through your jobs to be done interviews. Make sure you understand, you know, people's first conception of how, how do they value the product, particularly what are the social and emotional outcomes. Because look, you know, you can pay a hundred dollars for a wristwatch or you could pay $100,000 for a wristwatch. They tell time. They both tell time, right? The difference in value is one of those watches says hey, I'm super rich, right? So a lot of the, the pricing, a lot of the power is going to be in social and emotional outcomes. And that's also true in B2B and Enterprise, right? They say nobody ever got fired for buying IBM. So you know your reputation in the company, so understand the desired outcomes. If you're not familiar with the uh, jobs to be done interview technique. I'll give you a link. We have, um, like a jobs to be done cheat sheet canvas that, uh, your listeners can download. And what we'll do is we'll give you each of the questions you'd ask in the interview and, and then what to listen for in the answers. And then there's like, it's like, um, a canvas, a document that lets you then map out, you know, an overview of your customer journey and the different four forces and where they come into play. And so you can use, uh, that kit to figure out your own jobs to be done and think about how you communicate value in your customer journey relative to price.
Speaker B: That's perfect. We'll definitely leave our listeners with the link in the podcast description and in the blog posts, uh, so you can always find it. Matt, thank you so much for joining me on the SaaS open mic today. Is there anything you'd like to end with? Any other advice or insight?
Speaker A: Hey, this very good questions. Thank you very much for having me on the podcast. Thanks to James Mays for making the intro. I'll just come back to the point I made in the beginning, which is that for any successful business, when you look back in the beginning, 90% of their growth came from 10% of the stuff they tried. So find your 10% pricing or not, as quick as you can and focus on it relentlessly.
Speaker B: That's a great summary of this podcast. Thank you so much again, Matt. We were so lucky to have you here on the podcast.
Speaker A: My pleasure, Bianca. It was great talking to you.
Speaker B: This was the SaaS open mic podcast by Chart Mogul, where we talk to SaaS leaders about the inner workings of growing a business, the daily challenges, strategic moves, inspiration, and mistakes made along the way. The best teams in SaaS use Chartmogul to measure, understand and grow their recurring revenue. Head over to chartmogul.com for more content like this and to try the leading subscription analytics platform, that's chartmogul.com.
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