Activation lessons learned from Airtable, Facebook, and Dropbox

Darius Contractor


Investor and Advisor


Darius Contractor
Darius Contractor

Episode Summary

Today on the show we have Darius Contractor, Angel Investor & Advisor.

In this episode, Darius shares how he evaluates and selects companies to work at and invest in with his incredible track record at companies like Airtable, Dropbox, and Facebook.

We then discussed the psych framework he developed to help evaluate websites and onboarding experience. Why adding friction to onboarding can be a good thing in B2B SaaS and we wrapped up by discussing activation lessons that Darius has learned throughout his career.

Mentioned Resources



How Darius evaluates and selects companies to work at and invest in. 00:00:00
The psych framework for evaluating websites and onboarding experiences. 00:00:00
Why adding friction to onboarding is a good thing in B2B SaaS. 00:00:00
Why understanding the paradigm from which a user is experiencing your product is important. 00:00:00


Hey, , do welcome to the show. Thanks a lot for having me, Andrew. It's great to have you for the listener. Uh, Doris, who was previously the chief product and engineering at vendor. Uh, he was also the VP of growth at Eve table. Head of product growth for Facebook messenger and head of growth engineering and Dropbox.

He's an angel investor and he also teaches, growth psychology at Reforge. So. My first question of you device is you definitely have a knack for picking winners, not only in your angel investments, but in your career decisions too. So what has been your secrets and how do you evaluate companies who join or invest.

It's a great 

[00:01:58] Darius Contractor: question. And first I'll [00:02:00] say that I think a lot of people who are employees who take jobs at great companies really need to think about where they're working. I think a lot of people think about the work they do, but not where they do it as much. And, uh, that can make a huge difference. And so early on in my career, I kind of just took whatever was in front of me.

In fact, like when I, when I graduated years ago, it was kind of at the dotcom lull and there wasn't, weren't too many options, but as I got a few more options over time, I started to realize. You know, the market would be going a certain way. And so there was a period where a lot of social apps were being built and some were reaching great success.

And then, uh, more recently there have been times when, um, like more B2B SaaS apps were being built or web three apps were being built. So one thing is getting a sense of the market and where it's going and seeing like what is kind of hot and interesting right now. The other thing that can be really valuable with picking companies is to pick the right stage.

Um, recently I really like state companies that are kind. At like a very late a or like at a B or maybe early C round, because at that point as a growth professional, you [00:03:00] can kind of look at the business, look at the numbers and get some idea about the trajectory of the business. Sometimes at seed it's a lot harder, but if you're going to seed, you can get a bigger percentage and sometimes, um, uh, if you have a good, good feel of the business, because you understand that industry or, you know, the founders very.

Then that can be a good bet too. But, uh, one of, uh, one of Warren Buffet's ideas is to only invest in what you understand. And so as an employee, who's investing with your time, it can be a really good investment of your time first to understand these different markets and these different businesses. And then to use that understanding to pick a business, to go work out as an.

[00:03:39] Andrew Michael: That's a very cool framework and way to see it as well. Definitely. I think like the investing side as an employee investing your time and, uh, that's your, probably your most valuable asset that you do have at that point, previous guest we had on the show was Rob Dowell. And, uh, I remember looking at his career as well and his history trajectory.

He also then turned investor. But you could see, he was really, really strategic in the way he [00:04:00] selected and picked the companies that he worked at, uh, at that point as well. And I think it served him very, very well. So those listening, if you're just getting started, I'll definitely take some of the advice and follow, uh, people like Darius and, uh, Rav, uh, on the selection.

So. You've had an interesting career. And, uh, we chatted about this a little bit before the show I've previously gone through Reforge and for listeners, like Reforge has some really great, uh, courses out there. You should check them out. One of which is a course on retention engagement. And at that time, when I took the course, I came across that your psychology framework that you had called the psych framework, I think it was mm-hmm I didn't realize it was you.

And it was actually a friend who reached out and she's like, oh, have you. Heard of, and he's got this great framework. You should check it out and like, know the framework over it's familiar. So, um, maybe you could just talk us through it a little bit. Uh, like where did their inspiration come from and what is like the overall context and understanding of the, uh, psych framework that you have?[00:05:00] 

[00:05:00] Darius Contractor: Yeah, so you can find it yourself just by Googling my first name Dorys and the word psych, and it should come right up. Really the idea behind the psych framework is to give people a way of discussing some of the emotional impact of a given site design in a nuanced way that they can then use to optimize that site.

So right now, oftentimes when people come up with a new site design, they'll say, okay, I like this. Or I don't like it, or it's confusing at a high level. But what the psych framework encourages you to do is look at each element of the page, the heading the button, the color, the background image, each one, and attach kind of a plus psych or a negative psych to it.

So you could say, okay, the heading says you're gonna solve all my problems. That's like a plus 10 psych, but then the button. You know, you know, get started by paying us a hundred dollars. And that's a lot of negative psych for me, cause I don't really wanna pay upfront. Um, or, you know, some like image on the, on the site could affect different people, different ways.

So one of the nice things about the psych framework is allows your team to have a discussion about all these elements [00:06:00] and then really force yourself to think through is each piece of this page, really helping customers understand the value prop and move forward on the site. And so it's, it's a way of thinking about site to.

[00:06:11] Andrew Michael: Yeah, I found it very, very interesting. And then also applying it, not only just to the specific site, but then going through the user journey and, and how the user site goes throughout the onboarding process. So which steps are they gaining joy and getting excited about and which feel like more like a chore and, uh, uh, removing sort of that, trying to remove the friction points, I think, and adding friction only where necessary, um, was quite.

[00:06:36] Darius Contractor: One of my realizations is that there's a lot of growth work where the ideas make it easier, make it easier, easier, easier. And a lot of that comes from this kind of consumer growth perspective, but I switched into doing B2B growth at Dropbox and an air table. And one thing I realized there is that you have these higher and 10 customers.

Who are looking often at multiple solutions for their problem. And it's not that they need an easier button to click and less effort in the flow. [00:07:00] Oftentimes they need more information and more connection with either their existing data sets their existing paradigms of thinking about the problem and actually giving them.

More information more plus psych before they have to make a big investment, can be the best use of a growth team's time. So there's kind of, you know, there's taking out the bad work, but there can also be giving them good information and even good work. Um, one really interesting one that seems to go counter to the framework, but actually makes sense in it.

Is, it can be really valuable to take your most difficult onboarding actions and move them to the top of the funnel. And that's cuz people come in sometimes with a lot of plus psych. And the best thing you can do is actually use that psych to go do something important. So Dropbox. Right after you sign up, we immediately take you to like a dead end page where we download Dropbox and ask you to install it on your computer.

And in many ways it's like a lot of negative. Like you're like, oh, I was hoping to use the service. And now I'm just like stuck on this download page. But the trick is that people come in already knowing that Dropbox is valuable and hearing about it from their [00:08:00] friends and the most valuable thing we can give them to activate them is the install Dropbox client, so that they can start uploading from their computer.

So it actually, even though it's a tough moment, it's a really valuable, difficult moment. And it results in a lot of plus like later, because now they have it on their computer, they can get the full power of Dropbox. So there's these interesting kind of nuances to the framework. It's not just about, you know, happiness and ease.

[00:08:22] Andrew Michael: Yeah. I definitely see that. And I think it's a very big misconception as well. Uh, when we hear like in the industry, like get your users to value as fast as possible. Uh, and I, I think that. It's very misunderstood. We actually had a really good discussion with ENA Dorfman from segment at some point on the show.

And what they found actually was by adding friction to the product. Uh, they ended up increasing retention and engagement overall because ultimately like people wanted to come to segment and the end value they wanted to get was a good clean data set with metrics that they understood. And, uh, they could see across the board.

And what they found was if people didn't start with a good tracking plan in place, it. [00:09:00] Put the thoughts ahead of time. If they just got started setting up stuff with segment, they ended up churn because they got back to the same point where they started. So actually adding some friction to the onboarding, but necessary.

Friction's going to add value down the line, uh, is, is a crucial step. And it's something that we've heard quite a few times now on the show as well, uh, which goes counter intuitive of what, all the advice you hear out there. But I, I see maybe like what you're saying in a B2B context, potentially it is different.

And, uh, there are certain things that you really need to be pushing. 

[00:09:30] Darius Contractor: Yeah. Well, one thing that I think is different in the BBB context is you're not trying to capture the whole world. You know, if you're Facebook or some social app, you really wanna be trying to capture like 60 to 80% of the users who come through, like, it should be a universal product.

It's kind of like, do you want a cookie? Like yes you do. Um, but with B2B, it's a much narrower audience and they seek it a little bit more. So, you know, even if you might have a thousand people come to your. That might only result in, you know, on the order of like 10 or a hundred, you know, [00:10:00] best case like 50 people actually really interested in your product.

It's really unlikely that you're gonna capture the whole world, um, you know, with any given B2B SaaS product. And so when you start thinking about like that, you realize that you're not trying to get that, you know, 80% of people to succeed with your product in many ways, you're trying to. Perhaps the 5% of people succeeding with their product today and find that next 5% of what my friend Bengali calls the adjacent user.

The person who's like next, most, most nearest succeeding with your product, but isn't quite succeeding today. Um, and then trying to figure out how to convince them. And oftentimes it's more work, you know, it's, it's more onboarding more effort, which will actually turn off that remaining 90%, even more they'll like dislike it.

But the truth is that those people probably weren't gonna succeed. Anyways. One of my, I like to talk in analogies and one of my favorite. If you put a CrossFit gym on the fourth floor with no elevator, you're not necessarily gonna lower the number of people who will use that gym cause the kind of people are going to a CrossFit gym [00:11:00] are quite happy to walk on four, four floors, uh, to get there.

Now, if you put an ice cream shop up there, it probably wouldn't do so well. Yeah, I really 

[00:11:08] Andrew Michael: like analogy and definitely it's something that, that I see as well. Like ultimately if someone can't be bothered to fill in an extra field during the signup, like potentially their pain or their problem is not that big enough, that needs to be solved for your solution.

Anyway. So I just it's like that intent that they have in mind and why they're coming to the product to begin with. Ultimately, maybe even adding the, the friction or adding the additional point that you need to add value down the line, actually like get rid of bad fit customers to begin with. And in, in some respect saves you time on the end.

Supporting customers that really good fits to begin with. And I think there's a lot of counter points to it, but I think in the early stage, when you get started, you just think, okay, like we need to increase conversions. We need to raise the numbers. What do we do? Like let's get rid of friction. And I think more often than not, that's probably a mistake, uh, for the business when you're not really thinking about, ultimately you're trying to deliver.

What do we need to do? Or what information do we need to [00:12:00] have in order to deliver the most value? Um, so Doris, uh, you've had obviously some interesting challenges as well, uh, at the different companies that you worked at. We chat a little bit about this before the show as well, when it comes to churn and retention.

Ultimately like onboarding is a very key aspect to that and activation in itself. And I'm interested like from the different companies that you've worked at, what have been some of the interesting activation challenges that you've come across. And, uh, maybe some of these other lessons that you've found a little bit counterintuitive along the way.


[00:12:34] Darius Contractor: definitely. One of them is sometimes like the easiest activation. Isn't the best. Um, there's a way in which there's a kind of a dance between you and the customer. The customer shows up with a certain amount of excitement or understanding, and it's really on the site owner to direct that initial energy, that kind of psych energy in my framework towards the most valuable means for them.

Like, you know, it's the kind of same kind of thing that we experienced when we first [00:13:00] encounter a new experience, you know, we show up and we're like, okay, I heard this is. Let's give it like five minutes of my life. And in those five minutes you kind of click all the buttons and upload all the things and do whatever it tells you.

And then you see like, okay, is my life better? Now that I've set this thing up or do I think that I'm on the path towards somewhere good? And if yes, you keep investing and if, no, you do something else, there's a billion things to do online. And so that's, that's kind of my overall psychological framework around it.

Like how, how can we get this person from one place to another? And then some of the deep dives are, um, I really love. Digging into language. Because much of onboarding comes down to building a mental model in the user's mind that you build with language and then also experiences, you know, the layout of the page, the format of it really, really can make a big difference.

And so one place, I try to find that language is just out of the customer's mouth. Um, just ask them directly, you know, do you have this problem and how do you solve it? And what do you think that the site does and seeing, you know, do they describe it as online file [00:14:00] storage? Or do they describe it as cloud file storage or do they describe it as, you know, like a backup that I can send to anyone?

Like all of these are correct answers for what Dropbox is, but they're very different language. That's gonna resonate with different people and maybe with different audiences. And so trying to find that language and put on the website as much as possible, also trying to figure out whether the problem or the solution resonates more like there's some sites like litmus, um, that test email and their line is never send a broken email.

That's very powerful for a lot of people cuz you know, there's people out there who've sent broken emails to a million people and they're like, that was terrible. How can I buy a service that will prevent this from happening? That like keeps my email sending like safe and high quality. And so litmus really resonates with that.

Whereas as other services where you really wanna pitch the benefit and the value of what you're getting and in a positive way, rather than kind of connecting to the negative. So you have to think about whether it's positive or negative and what language you use. Um, let's see. Gosh, I had another [00:15:00] one.

What was it? Uh, think of 

[00:15:01] Andrew Michael: it a sec while you think about that. I wanna double, uh, check on this one, the, the positive negative, cause I think it's, it's a really interesting one to try and understand like when to lean in on the pain and when to lean in on like the, the value of the outcome that you get. How do you go about deciding?

So like you have the example of litmus and, uh, it's definitely is a clear pain. You've done that and you don't want it. When do you know what's right for your business and like, or is just something that goes through continuous testing and, uh, trying to understand what message is resonating the most.

[00:15:34] Darius Contractor: Yeah, I think there's a few ways of testing it. One is just testing it with customers directly, like person to person saying, Hey, what about this? Hey, what about that? And just seeing which one seems to resonate with them, which one they're like, yes, I want that. Um, and then it always makes sense to test messages, you know, online as well, like try out different messages, either in ads are a great way to do it because they're very high volume.

And really you're just getting that click or not getting. And then you can also test it on your website, although it's a little more [00:16:00] effort. Cause you have to often redesign the page, get images. It's a little full over experience than just an ad. Um, and then once you find language that resonates often, like the ads are a great place to.

Then you wanna build that through your experience. So, um, I recently saw someone from Adobe who was saying that the best win that they have all year was just having consistent language from the initial ad to the SEO content, to the landing page, to the sign, up to the onboarding, just using the same language, the same pitch, the whole way through.

And I think that's a good reminder because often we're so close to our products that we kind of describe them slightly different ways and it makes sense to us. But when you have someone else coming in new. All of these internet products kind of feel a little bit different. Like the UIs are different, even where the login button is or whether it's called login or sign in, you know, or access your account.

Like, you know, sometimes I feel. On the internet, we're like making cars and every car's got like a different configuration for like where the break and gas pedal are and where the turn signal are. And people just get into these cars and they're like, how do I [00:17:00] operate this thing? Cause there's, there's, there's some standards, but there's, it's surprisingly like a new refresh of like understanding how your world works on each of these websites.

So that actually ties back to one of my other things that I think about a lot for onboarding is paradigms. What paradigms are already in the heads of your users coming in? That you can like use to really accelerate the experience, because if you're building all new paradigms, it's gonna be a lot of effort.

You know, if I sell you a car and like, you know, the, you drive it, you know, you turn with your feet and you accelerate with your hands. It's gonna take you a long time to onboard. You're probably not gonna like the car and you're probably not gonna retain on the car. But if I show up and I give you the same kind of UI you have for your current car, except it works a little bit nicer and it's actually a little bit smoother, you're gonna love it.

You're gonna say this is exactly what I know, but it's even better. And so you don't always wanna do faster horses, but, and sometimes you do need a paradigm shift, but when you can match existing paradigms, incredibly powerful. And two examples of that, um, Dropbox [00:18:00] was just an existing folder. So you just drag things into a folder and they were online, incredibly simple paradigm.

Airtable took the idea of a no code app builder and just made it look like a spreadsheet. Everyone loves spreadsheets. Everyone knows how to dump data in. And then on the back end, you make it dynamic and powerful and internet connected. And so starting with a paradigm that people know, and then adding in kind of a future, maybe internet paradigm is just an incredibly, like one, two punch way to get people to succeed with your product.

[00:18:27] Andrew Michael: Yeah, I definitely see that. And I think it's like changing people's behavior is probably one of the hardest things you can do. And, uh, sometimes it's required, but I've realized this well, like in my own startup journey is at different stages. Really? Just like going with something that's more familiar and less innovative, it all wanna be innovative, but sometimes like just providing something that is better gives you then the freedom and flexibility to be more innovative.

Once you've got people through the door and understanding and have the value there. So. Um, I actually realized this most recently in my latest startup where we launched a browser extension, [00:19:00] which was going to change the way that you captured and shared, uh, insights within your organization. And just that wasn't really a familiar, uh, way of doing business.

I think everybody was attracted to the idea, but then activation, uh, wasn't there that we needed. And we took it down a notch. We sort of backtrack a little bit, and now we're seeing like really good engagement, cause it's a lot more familiar to users and to people with, uh, what they've been previously using.

And. Now slowly trying to say, okay, like how can we, uh, engineer this behavior and, uh, change things slowly, slowly, but, uh, definitely see sort of the paradigms being a thing. And you also mentioned the internet, like being, um, a whole bunch of different car manufacturers with all different configurations.

And I saw this at hot job was like, when I first started working at hot cha you, you would think that things like you design these things and you think they're incredibly simple and in your mind, like, it just makes sense. And then you watch a few recordings and you. Why aren't people getting this? Like, why don't they understand?

Can't they see the big red button. Uh, and I think it's just, we take for [00:20:00] granted when we build products, like how simple, they really, really need to be for they to be accessible and usable by everybody. And I think we have these own biases where, because we are using software all day, every day and because we are building them that everybody understands them as well as we do.

And I think that's something like it's important to remember when you're going through these processes as well. 

[00:20:21] Darius Contractor: Yeah. One of my analogies for that is like, try to think about a website and use it on like minimum screen resolution or like backed away from the computer with your keyboard and mouse, like five feet back.

So it's just like a little bit hard to understand what's going on. And then pretend that like someone you dislike or maybe like one of your exes, like build this website. So you, like, not only don't care about it, but you actually would prefer that it failed at some level. And then if you have that mentality and you use the.

That I feel like is almost a level of commitment that most people have with your website. They don't care. They're just trying to get through it. They'd probably rather be doing something else. And so you have to make each part of it, like really compelling, really [00:21:00] obvious, just, you know, absolutely like the simplest possible.

[00:21:04] Andrew Michael: I like that way, uh, to look at nothing, I'm not sure which company was, it might have even been Dropbox. Uh, but one of the companies, they started off by designing mobile first with the idea that like, you had the least amount of real estate to get across the message that you needed to get and in the simplest format, and then slowly like would go to death.

So I'm not sure was it Dropbox or, um, 

[00:21:27] Darius Contractor: we might have started some products. Yeah. More mobile first. Um, We definitely, we had a carousel, which was like a photo app that was very powerful on the mobile phone, but also worked on the web, uh, paper, you know, was a very designed first version of like a web document, you know, like kind of Google docs rethought for like a web era.

So, you know, there is some of that I do like force design constraints and try to make things work for the extremes, like the power user and like the least savvy user. 

[00:21:55] Andrew Michael: Yeah. Cool. So. You've moved on now as well. [00:22:00] And, uh, you're operating a little bit more like an investor at the stage, an advisor to different companies.

Uh, I'm interested as well from like putting on the investor hat, uh, side of things as well. Now, when you're going into companies, you mentioned like as a, um, as a potential employee, you're looking at like series a or B or C stage companies. Um, what are some of the metrics that you're looking at at these companies that sort of gets you excited and.

This team or this company is onto something. Uh, I think they're going places. 

[00:22:29] Darius Contractor: Yeah. Well, Pretty much, it comes down to like the product and the business, I would say. So looking at the product, are people coming to the product? How are they coming to the product? Is it paid users? Is it, you know, viral users, et cetera.

And then are they getting a lot of value out of the product and retaining again with B2B, you don't need like, you know, 80% of them to, but like are some sub segment getting a tremendous amount of value and sticking around. And then the next side of it is kind of the business. And are those people sticking around?

Are they. ACV [00:23:00] like an annual contract value. That makes sense for the volume that you have. So if it's a small number of companies, you know, has to be higher ACV, it's a large number. It can be lower, but then thinking, okay, are those people paying the right amounts for your volume and your channels? And then, you know, is that adding up to like a, a fast growing interesting business?

Um, that's in some ways the basics there's also. I bring, you know, years of just being, you know, someone working at companies and building businesses, and a lot of B2B businesses are helping people like my previous self. And, you know, so I love business like paid that help you like recruit and hire people or companies like product board that help you think about what to build next or companies like.

Uh, one of my latest investments is a company called loops that helps you with your data. And it's almost like an amplitude that figures out your causal data. So it figures out. This led to this led to this, and this is why your AB test worked or not rather than just giving you two numbers. And so all of these things are, are things that I have, like some kind of intuition for that I would've loved having in my operator days.

And so I [00:24:00] especially love investing in those areas of B2B SaaS, but, um, there's like a, a number of different kind of like metrics and perspectives on this stuff. Also depends on the stage seed stage investing. There's often fewer metrics, um, because the company's just getting. 

[00:24:13] Andrew Michael: Nice. And you applied sort of that same mental, uh, like framework when you were going to choose companies that you worked at.

I think like, um, were you looking for the same metrics when you decided to join, say Dropbox or a thing, or has that like evolution changed over time? Are there any metrics that you would say, like you used to think were important, but now you've realized, okay. They're not the most important thing to be looking at.

[00:24:34] Darius Contractor: Yeah. That's fair. Um, I still think growth solves a lot of problems. Like if the company is growing, like, you know, with revenue or users at a high rate, there's a good chance that there's something interesting going on there. Not always, you have to kind of dig in and see a little bit, like, is this sustainable growth?

Ideally, it's doing something new for the world that didn't exist before. And. It's delivering like real long-term value. And so Dropbox, the world just needed to move its files [00:25:00] online. And so that's real, long-term value. You also have to think a little bit of the competitive pressures, but, you know, that's the, at least the basics of is it growing and is it delivering real value?

And then there's companies like Groupon, which I think did deliver a lot of value on some level, but it, it was harder to see like, okay, is this gonna keep going at this rate, you know, forever, you know, based on like their business model and stuff like that. And so it's hard sometimes to know, and like, I think web three is a great example of.

Is it a real business or is it not, you know, like I think there are real businesses in there. And then there are very quickly growing, like businesses that don't feel as sustainable. And so I'm not saying it's always an easy thing to know, but those are some of the things I try to drill into. Cool. 

[00:25:38] Andrew Michael: Um, I wanna ask a question.

I ask every guest that joins the show. Uh, let's imagine a hypothetical scenario and you join a new company and churn retention is not doing great at this company. And obviously listen to the way you choose companies. Probably this wouldn't be the case for you, but let's say it is you've joined this company.

Churn retention is not doing great. Uh, the CEO comes to you and says, Hey, Doris, [00:26:00] like, you really need to turn things around. You have 90 days to do it. Um, you're in charge. What do you do? Catches. You're not gonna tell me I'm gonna go speak to customers or look at data and figure out the pain points and then start there.

You're you only can choose from something that you've seen be effective in the past. And you're gonna run with that. Blindly hoping that it works at this company. What would you do? 

[00:26:23] Darius Contractor: Interesting. So, I mean, obviously I wanna like map the tools that I've learned in the past to the specific company situation.


You know, one general case tool that I've seen improve retention. Um, generally at B2B businesses that perhaps could apply to, you know, a number of situations, um, We did this thing at Airtable, I thought was really cool where for some companies, after they paid for our self-serve plan, we would schedule a call with them and we actually kind of manually onboard them.

And it's kind of interesting. It's kind of like late onboarding because these people have already paid you in theory, they're already [00:27:00] committed. They're already onboarded. They're activated, they've already paid you. They're at the monetization stage, but one of our realizations and I've seen this in a lot of other businesses, is that there's a lot of kind of exploratory.

People will just sign up for a monthly, monthly service. And they're like, look, it's 50 bucks, a hundred bucks, whatever it is, my I myself or the company can, can pay for this for a month or two. And we'll just see if I like it and let's get all the features. Let's not kind of mess around with the, with the free trial or whatever.

Let's just get all the features and see if I like it. But then after two months, let's set a reminder and they're like, you know what? This actually isn't worth quite as much as it's charged I'm out. So there's a funny way in which your paid customers, I almost feel like. Your biggest activation opportunity, because one, they might not be long term customers yet, and you could keep them and they're already paid.

Like you already have a credit card on their money. And two, they're your biggest, you know, retention possibility and, and upsell. So if they like it, they might tell their friends, they might expand on their company. There's actually a tremendous activation moment there. So if I had to pick like one of my growth tactics [00:28:00] over the years, to just general case supply, I.

Like activation post monetization, maybe in a human way, if you have the scale that allows you to do it or in an automated way, you know, if, uh, if that makes more sense for your business, I think is a, is a really interesting one that I haven't seen that many companies do. 

[00:28:16] Andrew Michael: Yeah. It's very interesting. How do you, this actually, I've also recently introduced and implemented, uh, at AIO is trying to get on calls with recently, uh, new customers and.

Did you find any ways that were effective to book those demos and to get those activation calls? Was there any things that you found to be more effective? 

[00:28:35] Darius Contractor: Not, not particularly. I mean, really, it's just kind of like reaching out to them via email or channels you have, um, ideally with any reach out, you do something kind of a little more personal than.

Hey, I want, I want your time, you know, like if you can speak to their, you know, history with your company or like what their current challenges are, as you perceive them based on their LinkedIn or what have you, oftentimes people feel that connection and that be a little more open. Um, another one is frankly, just giving gift [00:29:00] cards.

Um, I think when you're asking for more than a few minutes of people's time, you know, if you're asking for half an hour, an hour, um, you know, sending them like a $50 Amazon gift card or some kind of incentive 

[00:29:09] Andrew Michael: makes a lot of. Thanks a lot. Yeah, for sure. Uh, I think cuz as well, like one of the interesting things, uh, on that aspect and, and the good learning as well is like a lot of times we try to.

Get user research from users and we try to understand, okay, what's going to make them convert. Uh, but the best sort of information you can get is from people that have just converted. And like one simple question is like asking them what nearly stopped you from converting, uh, today, or what nearly stopped you from buying.

And the information you get from there is really, really powerful because you're getting it from users that have recently just gone through the funnel that you know, that they a good fit customer to some degree already. And you're not sort of taking feedback from a wide range of audience. It might never have been customers to begin with.

So, um, I love that. 

[00:29:53] Darius Contractor: Yeah, that makes a lot of sense. I mean, one thing I've also seen is that if you have a business where like you have high churn, like the assumption is that you have like a high [00:30:00] number of people paying you to begin with. So at least there's some intent and desire to use your service and like enough to they're paying you and then churn.

And so oftentimes there's. They had an expectation coming in that wasn't fully serviced. And sometimes that means your product just isn't servicing it. But sometimes it means that you're not kind of like bringing the right tools to the front. And so one thing that I also look at is what are the parts of the site or the ways of using the site that the best users use and how can we bring that to the front?

So for instance, every now and then I'll see the best users will do like many searches to find what they. Other users will do one or two searches, not find what they want and kind of give up and you can do this on Google too. Of course. Right? Like you can get a lot out of it if you really like use it more and that can give you the realization.

They're like, oh, either we need to improve search or we need to showcase that like, Hey, you need to search a bunch more. You need to add these other keywords in order to get what you need out of the site. Like helping them get the most out of your site, even with maybe the same product, uh, can be a game changer for, for some people.

And [00:31:00] one other thing we did at air table is just encourage imports a bit more. Cuz we found that some of the best people would like import files. And if they pulled in their data from another source and they saw it in air table, they'd be like, oh my gosh, this is way better than that spreadsheet I was using.

Like I've got colors, I can upload files. I can sort it. I can have different views. This is just like, obviously better. And with your own data in there, like it's like seeing like your own kid using a toy. You're like now I like this toy. Um, But, um, but we, we only realized that looking through the data and seeing that, oh, some people did these imports and they have success with it.

And so we change around the site to just not, everyone's gonna import, but give them like another import button on the home screen. And when they go to like add a table, we say, Hey, do you wanna add a new table? Or do you wanna import data? And people will be like, oh yeah, actually I do have data import. So just these like little hooks for the people who are ready for it, um, to, to succeed in that way.


[00:31:52] Andrew Michael: Interest. Next question I have for you then is what's one thing that you know today about churn and retention that you wish you knew when you [00:32:00] got started with your career. Oh, 

[00:32:03] Darius Contractor: uh,

maybe I like to think that you can change experiences to like drive people a lot of different ways on your site, but I think churn and retention are one of those where. There are a few tools that can help people. And I think you have to be kind of generous and empathetic with people. You can't try to like push them when you're in the churn experience.

Um, because they're already showing up pretty low psych, pretty like pissed off. They're like, look, I gave you my money. I didn't get what I wanted. And so I guess what I would've liked to know earlier, and it taken me a while to learn is that it's a very different growth problem where you have to be potentially like more generous if you really wanna help people.

And it's often like too late, by the time you get there, you know, like if, if you're trying to sell people on the, the value of your restaurant as they leave, , you're probably not gonna have as much success as if you do it when they arrive or when they're there. And so in many cases, like [00:33:00] there's only so much you can do on the turn side.

Um, but I think there are a few tools that can, that can help here and. Yeah, 

[00:33:06] Andrew Michael: for sure. Uh, I definitely think this is something as well. We talked a lot about on the show. That's like if it gets to the point where somebody's actively decided to churn your service, it's more often than not too late. And, uh, some of the stuff we discussed earlier today around activation and onboarding is really where you'll see the most impact when it comes to the final output metric.

And it also compounds. Then when you start focusing on improving activation rates and improving the experience for new users, um, it retains more and more over time as. Uh, rice has been a pleasure hosting you today. Is there any sort of final thoughts you wanna leave the listeners with? Like anything that maybe aware of the work that you do, or any final, uh, tips and advice that you have for those thinking how to reduce search and increased retention?

[00:33:50] Darius Contractor: Um, Yeah, I think there's some interesting sites that are doing this today. Like, um, there's butter payments that helps with involuntary churn. Uh, there's bright back. That helps you get people like [00:34:00] back when they're like considering churning. And so I think one thing that I'm a big believer in is that today, if you're a builder, you really have to rely on like the SaaS tools out there.

I think the SaaS tools can superpower your business and build things for you that otherwise would take you months to build on your own. So a few angles on that for me is, um, of course I I've been a vendor and vendor. Helps people buy SaaS software and also choose the right SaaS software and get the best deal on it.

So that is a, is a really great tool that I recommend to people. And if you want to see how I approach the world and like what companies I'm investing in, how I think about growth, feel fall, feel free to follow me on Twitter. I'm Thery SMC. Um, and I really appreciate this chat. This has been a lot of fun.

[00:34:39] Andrew Michael: Yeah, it's been great. Well, thank you so much for joining and, uh, wish your best of luck and, uh, going forward. We'll make sure to leave all the show notes, uh, for about anything we discussed as well, to check that out later. Awesome. Thanks so much, Andrew. Thanks. Cheers.


Darius Contractor
Darius Contractor

The show

My name is Andrew Michael and I started CHURN.FM, as I was tired of hearing stories about some magical silver bullet that solved churn for company X.

In this podcast, you will hear from founders and subscription economy pros working in product, marketing, customer success, support, and operations roles across different stages of company growth, who are taking a systematic approach to increase retention and engagement within their organizations.


Listen To Next