Flatfile's Strategic Shift from PLG to Sales-Led and Back

Becca Weiss


VP of Customer Success & Support


Becca Weiss
Becca Weiss

Episode Summary

Today on the show we have Becca Weiss, the VP of Customer Success and Support at Flatfile.

In this episode, Becca shares her experience in tackling churn and onboarding challenges at Flatfile.

She discusses the transition from a product-led growth approach to a sales-led motion and the subsequent realization that the issue lay not in change management, but in the product itself.

Becca explains how they then rebuilt the product to be developer-first and highly extensible, allowing customers to set up their workflows.

We wrapped up with Becca discussing why they are now returning to a product-led growth motion, targeting developers for smoother onboarding.

We hope you enjoy this episode.

Queen of Shadows

Mentioned Resources



Introduction to Becca and Flatfile1:21
Discovering and solving a churn issue at Flatfile5:03
The challenges of change management in onboarding8:53
Rebuilding the product to meet customer needs16:38
Improving the onboarding process with sales involvement21:34
Going back to a product-led growth approach25:42
The importance of transparency and trust with customers30:29
The power of open-ended questions in customer conversations33:34


00:00:00 Becca Weiss: Listening to your customers is insanely important. Product and customer success and support often have this tension with one another because product wants to be visionary and innovate and build these things that are exciting and are making them stand out in the market. And there's definitely a place for that, don't get me wrong. But if you're only doing that and you're not listening to your customers, then you're not going to learn these things that you might need to learn. And so I just think so often we pretend like our customers don't know best, but they actually do most of the time know best and you should listen to them.

00:00:39 VO: How do you build a habit-forming product? Do you need to invest… We saw these different… You don't just gun for revenue in the door.

00:00:45 Andrew Michael: This is Churn.FM, the podcast for subscription economy pros. Each week, we hear how the world's fastest-growing companies are tackling churn and using retention to fuel their growth.

00:00:57 VO: How do you build a habit-forming product? We crossed over that magic threshold to negative churn. You need to invest in customer success. It always comes down to retention and engagement. Completely bootstrapped, profitable and growing–

00:01:11 Andrew Michael: Strategies, tactics, and ideas brought together to help your business thrive in the subscription economy. I'm your host Andrew Michael and here's today's episode.

00:01:21 Andrew Michael: Hey Becca, welcome to the show.

00:01:23  Becca Weiss: Hey, Andrew. How's it going?

00:01:25 Andrew Michael: Very good, thank you very much. For the listeners, Becca is the VP of Customer Success and Supports at Flatfile, providing developers an easy, fast and secure way to build ideal solutions for importing CSV, Excel or other data files without compromising flexibility. Prior to Flatfile, Becker was the director of customer onboarding and managed services at Twilio. And prior to that was the customer onboarding team lead at SendGrid. So my first question for you Becca, is have you ever been to concerts at Red Rocks?

00:01:56 Becca Weiss: Of course. I've lived in Colorado for 15 years, how could I not?

00:02:01 Andrew Michael: I spent about a year in Boulder, Colorado, maybe a year and a half, and it was one of the highlights or the experiences that I've had that will always remember was just going to a concert at Red Rocks. That theater is just something else.

00:02:14 Becca Weiss: It's incredible. It's my go to when people come to visit me.

00:02:18 Andrew Michael: And is there always concerts available there? I think we went to one or two, but how regular do they have concerts?

00:02:24 Becca Weiss: Yeah, all summer long they do them and then they actually started well, it's been a while now. They started doing a few during the winter, too, now. So they've got like a big Winter on The Rock Show. I've been a couple of times. It snowed, but it's absolutely beautiful. Just cold.

00:02:37 Andrew Michael: Yeah. For listeners, if you're not familiar with the Red Rocks, it feels like it's in the middle of nowhere. It's basically, as it's described, giant red rocks. And they've carved out a stadium or an arena in it where they've got a great stage and then they often have really good artists performing there. So if you're ever in the US and in Denver, it's worth checking out. Nice.

00:02:59 Becca Weiss: Absolutely.

00:03:00 Andrew Michael: So maybe you can just give us a little bit of overview. I gave a quick intro into what Flatfile is. Maybe you can just let us know exactly what Flatfile is and how you operate and work within the team.

00:03:10 Becca Weiss: Yeah, absolutely. So, I mean, I think you did a better pitch than I could ever do, Andrew, but basically we describe ourselves as a data exchange platform. So I think most people, especially in customer success, have probably at one point in their career had to upload a CSV of data into their system on behalf of their customers or their customers doing it, and they're kind of hand-holding them through.

00:03:32 Becca Weiss: Well, Flatfile sits in between you and your customer and the end system and cleans up all of the data, helps you get every single one of those headers to match what the header in your system is, make sure it's formatted correctly, all of that. And so I think a lot of us here at Flatfile have experienced this. I know it's a big problem in customer success. A lot of our customers and end users are customer success people, as well. And so that's what we do. We help people get data into their systems in a formatted way. And then my role here, I lead both our customer success and support teams. So everything from helping customers when issues pop up and all the way to then to retention, expansion, things like that, as well as onboarding and implementation.

00:04:15 Andrew Michael: Very nice. When we were chatting earlier today about the topics that we can run over and discuss, I think I suggested a topic and the idea of graduation churn, because I think myself previously I'd taken a look at Flatfile, I made some assumptions of myself and sort of the idea of build versus buy. I think it's so valuable to be able to focus on your core competencies as a business. And for us at that time, my startup, we weren't really a data exchange platform being able to ingest, so it made sense, I wasn't able to convince our developers. But we also started discussing then a little bit, and you mentioned you'd be comfortable today to talk a little bit about how you discovered a churn issue at Flatfile and the process to discovering that, uncovering it and then solving it, and now starting to see really good results at the end.

00:05:03 Andrew Michael: So today I want to walk through a little bit about that journey and obviously I was excited to talk about onboarding as well because that's where a majority of your experience has been and it's happy and it's exciting that these two topics coincide with one another. So maybe if you could just give us a little bit of an overview of the events that took place in the early days when you started to realize, okay, there was an issue here. We need to figure this out.

00:05:27 Becca Weiss: Yeah, yeah. So when I first joined Flatfile, they were kind of starting to figure out we were doing the product-led growth thing. We were letting customers self-serve into the platform. And what we saw is that customers weren't able to onboard themselves. They were having a really hard time. They would try to implement the product and they would just leave. And so we started building out an implementation team that would handhold every single one of our customers and onboard with them. And so we moved into the sales-led motion. We completely killed the product-led growth motion and the self-serve sign up altogether. And the onboarding team or implementation team started to help every customer onboard. And it was helpful for sure.

00:06:14 Becca Weiss: We definitely saw less turn in that sense because customers had their contact that they could reach out to. We were able to help them with their specific questions when they were running into issues, things like that. But then, what we realized was that, the self-service wasn't the real problem. The real problem was that the Flatfile version at the time was just a very opinionated product. So instead of trying to meet our customers where we're at, we told them the specific workflow that they had to take in order to import their data into their platform. And I think a lot of us customer success career people have known the issue of change management and trying to get our customers to adopt a product, or us ourselves trying to adopt a product and how hard and difficult that can be, especially when you have a really large team that has to adopt that new product.

00:07:08 Becca Weiss: And so we were running into this change management problem, really, where the end users weren't adopting the product because we were so opinionated on how they should use the product, that they were like, well, we have to change too much. This is going to be too difficult. And so we kind of went back to the drawing board and we're like, okay, how can we fix this problem? Well, Flatfile started out as a developer first product. And then we moved into this, what we called low-code world. And people like me who pretend like they can code could set up the product not very well, but they can do it. And so we said, hey, why don't we go back to being developer first? Let's make the product fully extensible. We can get back into product-led growth because people can set up their own workflows. And then on the enterprise side, where our customer success team sits today, now we can help implement those customers in a really specific way.

00:07:59 Becca Weiss: And it's much more about best practices and fitting in with their workflows than meeting the Flatfile workflows. So instead of telling your entire customer team like, hey, stop doing what you're doing today, let's do this completely new process. We're going to fit Flatfile into that process and then over time, if we can help them implement what we think are the best practices in data onboarding or in data exchange, then we can start changing the way they actually do their workflow. But we don't have to do that on day one anymore. So we rebuilt the product from the ground up. We made everything API first. Developer has to implement it. No one like me can do it anymore. Unfortunately, or fortunately, probably is the right way to describe it. Now we're meeting our customers where we're at, and we're seeing that churn problem go away because it's a lot easier to adopt the product than it was previously.

00:08:53 Andrew Michael: Amazing. There is a lot to unpack there.

00:08:57 Becca Weiss: Oh, yes.

00:08:58 Andrew Michael: Excited to go through the various stages and steps and I think maybe let's go back to the very first step and decision that was made. So you sort of identified this was an issue and you were PLG first, allowing users just to sign up, get started. You noticed the problem, people weren't adopting. How was the decision made to say, okay, let's cut it, let's go to like a sales lead approach now onboard and handhold every single user. What were the discussions like and how did it eventually say, okay, this is the right decision for us to take right now?

00:09:30 Becca Weiss: Yeah. So I came in at the tail end of this conversation to Flatfile, but essentially we were just seeing customers sign up and then never converting. And when they would write into support or write into our customer engineering team who were helping onboard some customers at the time. It was so obvious what the issue was that especially when we had this low-code platform that people who weren't developers could set up. But then you still had to know some kind of JavaScript in order to set up what we call transformations and validations, which are basically getting the data into the format that your system needs it in. You still had to know JavaScript to do that. And so we would end up doing a lot of that work for the customers.

00:10:19 Becca Weiss: And so we realized that it wasn't the best approach because customers couldn't actually do it themselves. So a lot of the conversation was around, okay, we at the time wanted to keep the low-code version of the product, but we couldn't allow people like me to sign up and use the low-code version of the product without any kind of help because they just weren't successful.

00:10:42 Andrew Michael: Yeah, nice. So this conversation was going on, they were taking a look and saying, okay, this is an issue, we need to find somebody to help us with expertise in onboarding to join the team so that we can then take it to the next level and start testing and validating. So you identified this issue internally as a team, I guess? You joined some way towards the end of this conversation. And I think one of the things as well, like in my mind that sort of struck alarm bells raised, sort of thing, when you say, okay, we're just going to go sales-led approach is. With PLG you typically have a lot higher lead volume and deal flow and it's easy as well.

00:11:18 Andrew Michael: And in your mind, it makes sort of like sense that you might learn faster by having a large amount of people come through the door, when in actuality, what's happened is you've restricted the number of signups, potentially quite drastically, I assume, but then the learnings actually increased having that direct one to one communication with your users. And how did that look in terms of the lead volume and customers and without specific numbers, just was it a big change overnight? How did that impact the business?

00:11:49 Becca Weiss: Yeah, you know what, it's interesting. I wouldn't say it made a huge impact to the business because the lead volume stayed somewhat the same. We were kind of beefing up our sales team at the time, so we had know, growing sales team, I should call it, but also our ACV was growing. So when we were in that PLG world, we had lower ACV, we had customers coming in at the lower end. But in the sales-led approach, you're selling these deals. I think at the time our ACV was like 15k and we were selling these deals that were higher revenue. So the growth didn't really stall moving from PLG into the sales-led growth world. But yeah, it's funny because coming from Twilio and SendGrid, those are very much PLG products and very tens of thousands of customers.

00:12:39 Becca Weiss: I think once we got acquired at SendGrid, we were over 100,000 customers and yeah, you think having so many more customers, you're going to learn these things faster, but the reality is you just hear a lot more noise and then you have to figure out what that noise means. But here, especially with us handholding every single customer to onboard, we were able to figure that out a lot quickly, or a lot quicker because we had these really meaningful conversations with all of our customers.

00:13:07 Andrew Michael: It's interesting as well, like, the timing of it, because we've previously had Rahul Vohra on the show and we recently, as well, had Caroline Clark from Arcade, and Rahul's from Superhuman, and they started with the approach of, like okay, before we do the PLG motion, let's do onboard every single user to the platform, handhold them, understand their pain points, their problems, and accelerated learning. That way, you started with PLG and then you reversed back into sort of this learning mode and understanding.

00:13:38 Andrew Michael: So what did the onboarding process look like then? So this was designing like a new onboarding process. I guess you need to sort of figure out, okay, how you're going to deal with this amount of leads as well, being able to service them and give a good onboarding experience. So what did that originally start looking like? How did you plan out the original onboarding experience now going from that PLG to sales-led motion?

00:14:00 Becca Weiss: Yeah, we knew we were going to be dealing with a higher volume than we were kind of used to, and we needed to come up with something that would hit every single customer and then we kind of customize it as we went. I also have customer engineers on my team who are basically software engineers who can help customers code and things like that. And our customers needed that expertise, they needed that developer help. So we kind of came up with this broad approach to onboarding where we did our kickoff call, I think, like everybody does, did some discovery and then kind of just let customers do what they needed to do. We gave them some steps to onboard and then we'd come back together and do what we called at the time, a tech-deep dive.

00:14:53 Becca Weiss: So the developers that were implementing it, if they had developers, were diving into the SDK and trying to get things set up and then coming back to us with questions. And it was because you could only really set up the product in one way. There was no opportunity really for… part of the thing I love about onboarding and implementation is this kind of consult, like you're consulting, but you're not consulting because you're not working for a big s hire partner that you have to do things in a specific way. But I loved onboarding because you're bringing your expertise to the table. You're like starting the customer off on the best foot possible. And because the way the product was working, you had to set it up in this specific way, there wasn't really that opportunity for expertise of like, oh, here's how we suggest you do that thing.

00:15:45 Becca Weiss: It was just kind of like letting the customer know where they could find everything, what they needed to do, and then letting them go. And then they could come back and ask these technical questions, if they had any. And we would help them set up these transformations and validations, which is where the JavaScript would come into play. And then after we did that, if they needed more of them, we would keep doing those technical deep dives and then eventually the products would get set up and then we would do a reverse demo and send them over to the customer success side of things for more retention and growth.

00:16:17 Becca Weiss: But it was really generic, to be completely honest with you. I think this whole time we're trying to figure out, oh, is this an implementation problem? Is this a product problem? What is it? I think it was a little bit of a combo of both, but we weren't doing anything very specific to the customer because the product didn't really allow us to do very much that was specific to the customer.

00:16:38 Andrew Michael: Yeah. And then you mentioned change management being like one of the big issues at the stage that you figured out. And assuming again, part of that was like, you're trying to do these implementations and realizing it as a team that this was restrictive, but then also hearing it from customers. And I think change management is probably one of the most underlooked areas, I think, especially in the early stage startups and their products going to markets, not taking this into consideration and think, oh, it's so easy to use a product. Why doesn't everybody just get it or use it? And I've been guilty of this in the past of trying to maybe be too innovative sometimes or like you say, try to be too opinionated. And changing user behavior is probably one of the hardest, if not the hardest things to do when it comes to building products. So what were some of the signals you were seeing that this was the issue?

00:17:29 Becca Weiss: Yeah, so I guess to give a little bit of context, we had two products. We had our portal product, which was implemented into your product, and your customers typically would use that and import the data. And then we have our product called Workspaces, which was very much for customer success professional services teams who are collaborating with their customers, trying to get much higher volumes of data imported into the system. And it's not just that they need to get the data imported in the system, it's that they actually care what this data looks like once it gets into the system.

00:18:07 Becca Weiss: And what we were seeing was the product was set up in a way where you had to follow certain steps in order to get the data imported. And in Workspaces, a lot of our end users were professional services teams. And the Workspaces product is our highest ACV product. That's where our biggest customers are coming from. And we needed to make sure that the professional services teams, the customer success teams using this, were actually going to use it. So what we would see is we'd see, okay, you need to get the file from your customer. You need to import the data this certain way, and then you need to match all the headers to the headers that are going to be in your end system. And there are these certain steps, but then we talk to the customer and they'd say, well, in this case we do this. And in this case we do this.

00:18:59 Becca Weiss: And you're actually making it harder because you're making me follow the same exact steps for every single one of my customers. And I don't always need to follow every single one of those steps. And so the end users would be like, I don't really want to use this. It's not actually making me faster. It's actually faster for me to just use Excel and write some macros the way we always have. And we were like, no, that's not what you want. We don't want you to do that. We are here to make you faster.

00:19:23 Becca Weiss: Because we were making them go through these extra steps. We were slowing them down because they were just used to it. And so I always went back to, well, the J-curve, right? Like the change management curve, it's harder before it gets easier. But the reality was it wasn't, it was harder. And then it got harder because we were just putting more steps into their process. And so now with our new platform, we're able to take the steps that they already do. Like, we've completely changed implementation. Actually presales is even building out POCs now, which they never did before. We're understanding what the customer is doing in their workflow, and then we're fitting Flatfile into those places of their workflow versus the other way around, which is making that change management so difficult for our end users.

00:20:06 Andrew Michael: Nice. And you sort of only figured this out, obviously, going from that PLG motion to sales led being able to onboard every customer, see the frustrations from your side, but also from the customer's perspective. And then sort of realizing okay, this wasn't just a change management issue, but it was actually really our product is all on the other side, not meeting the users where they were and trying to force them into new behaviors that they weren't willing to adopt or actually end up spending more time doing.

00:20:36 Becca Weiss: Yeah, and what I think is really interesting about it, like we were talking earlier about for me at Twilio, at the bigger companies, you have all of these data points and then you're trying to figure out what those data points mean. But for us, when somebody writes into support and they have an issue, they're just writing in about that one specific issue. You're not seeing the entire picture there, right? And so that handheld onboarding was really where we figured out what that big picture was because we actually saw the entire issue from start to finish. We weren't just seeing one little piece of it because they wrote it in asking one specific question to support.

00:21:12 Andrew Michael: Yeah, exactly. You're getting the full picture. The onboarding, I guess, as well has also taken a few different stages and a few different steps in the process. So it started out as very generic, just let's start to learn. And now you've got a new product or you introduced a new product. You obviously needed to make changes, I think, again, to your onboarding experience.

00:21:34 - Becca Weiss: Oh, yes.

00:21:35 Andrew Michael: What did that look like then? So going from generic onboarding, now you have a product that's less involved from the end user's perspective of change. And I'm assuming again, like, similar how you said, being able to be a little bit, maybe more prescriptive, bring expertise around this time because you're working there at workflow. How did onboarding change for you then?

00:21:54 Becca Weiss: Yeah, so I would say we're still very much in the process of changing this. The new platform just launched in GA in July, so we're hot off the presses. Yes, but we've been in beta for a while now and have been figuring this process out. And I think there's two major pieces that have changed. One is partnering with sales a lot better. So with the old product, our customers weren't always getting into the product in the presales process, which was a brand new thing for me. I had never seen that in my career before. And so they'd get to post sales and we'd start the onboarding process and not only would we discover that we're changing their entire workflow, but we're also missing key pieces of their workflow that Sales just never uncover during the presales process.

00:22:42 Becca Weiss: So now the technical evaluation during the presales process is a lot more intensive and they're doing a lot of the discovery work building out POCs in sales, which has been an amazing thing for the customer success team because then instead of getting someone who may have never seen the product before, where we're honestly, like most of the time, in a kickoff call, demoing the product for these new stakeholders that have never seen it, which was really fun, we're getting customers who have an understanding of what they want to do already, and then we're just getting deeper with them.

00:23:15 Becca Weiss: So sales builds out this POC with the customer, the customer comes to us, we're doing a reverse demo, so we're actually having the customer show us what they've built out during the presales process. And then from there, not only are we seeing what they've built with sales, but we're also able to understand where they might not have a good understanding of Flatfile or certain pieces of Flatfile yet, or they haven't implemented certain pieces of Flatfile yet.

00:23:45 Becca Weiss: So if Flatfile implementation has steps one through ten in sales, they may have gotten through one, three, seven and nine. And then we do this reverse demo with a customer and we're like, oh, here's all these missing pieces, now we're going to go implement those things. And so we get to partner with sales a lot better and get these customers in the door with an understanding they are somewhat using the product already. And then we get to bring in that expertise, which is my favorite part of onboarding and implementation, like I said. And it's way more fun for the team than these generic question and answer sessions of the customer.

00:24:24 Andrew Michael: Absolutely. I find it crazy though as well that you would have people purchasing a product without actually seeing the product in today's age. Like you say you'd never seen it. I can't think of another product where I've been involved in the buying process where we weren't able to see it or have a demo or being able to validate. And I can imagine that being a very difficult situation for customer success to be in then, as well, when you get on a call and, but don't you do this. I thought it did that. And I'm sure those conversations must have come up. Nice.

00:24:57 Becca Weiss: Oh, yes.

00:24:58 Andrew Michael: And then so you sort of now at this stage where you figured out as well, the change management being an issue, redone the products, reworking onboarding now to add value, focus, as well, on bringing CS a lot earlier into the sales process, working on a POC. So by the time they've sold in, you're doing your reverse demos and being able to identify and understand which components you could potentially, as well, be pushing through them in that post-sales call, you mentioned as well that you're also now going back to a PLG motion. post moving to sales-led. What's driving that decision now? Why is it the right time? And what do you expect to see from this?

00:25:42 Becca Weiss: So giving a little bit more history on Flatfile, before the previous version, we had another version, and that original version was very much developer-first. That's where we saw our explosive growth. And I mean, developers were implementing the product no problem, because like you said, Andrew, it's a build versus buy situation, right? And most customers don't want to build their own CSV importer. And so when we rebuilt the product, after we figured out what the problem was, we said, hey, we're going to go back to our roots and we're going to go back to this developer-first mindset, because we can get developers in the door. A lot of times developers are tasked with, okay, we need this CSV importer in our product. And they're like, okay, I'll go research if I want to build it or if I can find a tool that can do this for me.

00:26:34 Becca Weiss: So we're going back to our roots. We built everything API first. We're dogfooding our own product. We're using our own APIs inside the product. And the whole idea is we're going to get developers in the door and then we can always expand to these professional services use cases that used to be the workspaces product or the other way around. Sometimes it happens like that, but a lot of times it's just developers looking for some way to import CSV data into their platform and they find flat files. Yeah, it's going back to our roots. And like I said, it's highly extensible. You can pretty much build whatever workflow you want to, which is really what customers wanted to see to begin with and kind of what they were able to do with our original product.

00:27:17 Andrew Michael: Nice. And then how much of this was also led then by the conversations you were having with the customers that you're bringing on? And obviously so now you're going back towards the roots, serving developers. These onboarding calls that you're having previously, what would be the ratio of developer versus services that you're having the conversations with, was it obvious that yes, this is where we need to go back to?

00:27:41 Becca Weiss: Yeah, it was pretty obvious. The vast majority of the conversations we were having, there was at least one developer present on the call. There were few cases where I joke, people like me who can't really code, pretend like they can code. But what we were hearing a lot from customers, especially developers, were that you needed a developer really to implement the product, but half of it was in code, especially if you're using that portable product which is embedded into your own product, and half of it was in the UI.

00:28:15 Becca Weiss: So you're constantly going back and forth between UI and code and UI and code to set this thing up. And really all they wanted to do was set the entire thing up in code and then hand it off to their professional service team or just put it in the product so their customers can use it, what have you. But they're annoyed at the fact that they had to go between code and the UI. And so we're like, this is silly. We actually started the process in our old product of making it developer-first and having it entirely in code. They didn't have to go into the UI. And then after we figured out this workflow problem too, we're like, it just lets entirely code. We got to do this again.

00:28:55 Andrew Michael: I love this story as well, because obviously it's a very typical startup story. A lot of pivots, changes in the product doesn't only involve product, so it's a customer success, sales is involved, obviously marketing, and everybody really trying to figure this out along the way. And it sounds like now you've got this into a groove and things are looking good from that perspective. Yeah, obviously in hindsight it's a lot easier to say like, oh, we should have done this or we should have done that. But is anything that stands out to you that you perhaps would have done differently doing this over again?

00:29:28 Becca Weiss: Oh man, that's a good question. We always heard this UI code thing at the very beginning, even before we were really even getting into the workflow stuff. And I think if I were to do this over again, well, not my entire career, but a lot of my career has been spent in years working in developer-first products. And I think if we had identified really early on that we should listen to the developer and that we should meet them where they're at instead of trying to kind of make everybody happy, that would have helped us identify it earlier. I think this whole, like we call it yes code, no code, where we were always in between two worlds. We were trying to make the developers happy and then we were trying to make the people like me happy, when really we should have just focused and niched down and made the developers happy from day one. We may have figured this out a lot sooner if we had just tried not to split our focus there.

00:30:29 Andrew Michael: Define your good ideal customer profile and… the good old ICP. Nice. What's one thing that you know today about churn rate and retention that you wish you knew when you got started with your career?

00:30:43 Becca Weiss: Oh man. I don't know. I guess this might seem silly and a little qualitative, but just like being transparent and building trust with customers is the most important thing. My team will tell you that I will never tell a customer something that I wouldn't want to hear myself. So if a customer is frustrated with something, I'm like me, too. I hope you know that I don't like the situation either. And I just feel like it's like a way of empathizing that I don't think we always do, where we're afraid to tell our customers that we're also upset with the situation or we're also frustrated by the situation. And so often we are, right?

00:31:31 Becca Weiss: And so why not just meet them where they're at and do that? And I feel like I built so much of my career off of that notion that I didn't necessarily know early on and now realize that's what it was, of just being honest with people just makes them trust you. And then you build that relationship off trust instead of being in a crappy situation with a customer and saying, like, oh, we're going to make it better, when maybe you don't know if you can make it better.

00:31:58 Andrew Michael: Customers don't want to be bullshitted that’s–

00:32:01 Becca Weiss:I don't want to be bullshitted. Right. So why would I bullshit my customers?

00:32:06 Andrew Michael: Exactly. I think having that mindset like you says how you would want to be spoken to and what you would want to be told, as well, I think really allows you to put yourself in the customer's shoes and communicate effectively. Love it.

00:32:19 Becca Weiss: Yeah.

00:32:20 Andrew Michael: So Becca, I mean it's been a pleasure hearing this story today. Listening to the experience as well. You're coming from Twilio and from SendGrid into Flatfile, sort of identifying this problem of churn, moving from a motion of PLG to sales-led in the process, like introducing new onboarding flows, moving back again now to PLG. Figured some of that out. Is there any sort of other final thoughts that you want to leave the listeners with? Any other companies maybe facing similar struggles with change management and iterating on product. Would have any other advice before we wrap up today that you'd like to share?

00:32:54 Becca Weiss: Yeah, I just think listening to your customers is insanely important. I think product and customer success and support often have this tension with one another because product wants to be visionary and innovate and build these things that are exciting and then stand out in the market. And there's definitely a place for that, don't get me wrong. But if you're only doing that and you're not listening to your customers, then you're not going to learn these things that you might need to learn. And so I just think so often we pretend like our customers don't know best, but they actually do, most of the time, know best and you should listen to them.

00:33:34 Andrew Michael: Yeah. Do you have any favorite go-to questions for customers? Is there any one that typically stands out?

00:33:42 Becca Weiss: I'm going to call my CEO out right now. But one thing that I've been doing a lot more because he does this a lot, is a customer will make a comment about something in the product, and he just says, tell me more. And it's like this way of being really open-ended. I know that's not a question for customers, but this way of being open-ended, that just like, it takes the pressure off them and it allows them to just say whatever it is that they really want to say to you. And so I've been doing that a lot recently, it's just they say something to me like, hey, we don't like this thing about the product. I'm like, okay, tell me more, and they'll just open up. And then we're like, okay, now we're uncovering the real problem here.

00:34:26 Andrew Michael: Yeah, I love that. I think it's something like a mistake we often make, as well, where we'll bring our own cognitive biases or our understanding of what we believe to be a problem, and we'll be like, okay, yeah, I understand that, and move on. But just like a simple, small thing like you said, just tell me more, and allowing them to elaborate and go deeper into the problem that they've mentioned, I think can uncover a new world of opportunity, I think, for you. I love that.

00:34:50 Becca Weiss: Oh, yeah.

00:34:51 Andrew Michael: Nice. Becca, it's been absolute pleasure hosting you on the show today. Thank you so much for joining and wish you best of luck going forward for the listeners. We'll make sure to leave everything we've discussed today in the show notes, and last question, maybe, Becca, is any way people can keep up to speed with your work? Like, anything else you'd like to share before we wrap up?

00:35:08 Becca Weiss: Yeah, no, I mean, feel free, find me on LinkedIn, happy to chat, customer success, onboarding support, whatever it is, anytime.

00:35:15 Andrew Michael: Awesome. Well, thanks so much and best of luck going forward.

00:35:18 Becca Weiss: Thanks, Andrew.

00:35:19 Andrew Michael: Cheers.

00:35:20 Andrew Michael: And that's a wrap for the show today with me, Andrew Michael. I really hope you enjoyed it and you're able to pull out something valuable for your business. To keep up to date with Churn.FM and be notified about new episodes, blog posts and more, subscribe to our mailing list by visiting Churn.FM. Also, don't forget to subscribe to our show on iTunes, Google Play, or wherever you listen to your podcasts. If you have any feedback, good or bad, I would love to hear from you and you can provide your blunt, direct feedback by sending it to Andrew@Churn.FM. Lastly, but most importantly, if you enjoyed this episode, please share it and leave a review as it really helps get the word out and grow the community. Thanks again for listening. See you again next week.


Becca Weiss
Becca Weiss

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.


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