3 changes Sendoso made to achieve a net dollar retention close to 120% with their mid-market and enterprise customers.

Kris Rudeegraap


Co-founder & CEO


Kris Rudeegraap
Kris Rudeegraap

Episode Summary

Today on the show we have Kris Rudeegraap, co-founder and CEO of Sendoso.

In this episode, we talked about how Sendoso helps its customers retain and delight their customers, the different ways a sales team can help avoid or decrease churn and how to make sure you’re selling to the right ICP.

We also discussed Sendoso's sales strategy when they first got started and how it evolved, their ups and downs when it comes to churn and retention, and the changes they made in order to hit a net dollar retention close to 120% today.

Mentioned Resources



Kris built Sentoso to close more deals. 00:01:59
How Sendoso helps its customers retain their customers. 00:02:40
Different ways sales can help avoid or decrease churn. 00:08:05
Ensuring you sell to the right ICP. 00:09:51
The go to market sales strategy at Sendoso. 00:11:32
3 things Sendoso did to successfully improve retention. 00:16:16


[00:00:41] Andrew Michael: Hey, Kris, welcome to the show. 

[00:01:26] Kris Rudeegraap: Thank you so much. Excited to be. 

[00:01:28] Andrew Michael: It's great to have you for the listeners.

Kris is the CEO and co-founder of Sendoso. The leading sending platform, helping companies stand out by giving them new ways to engage with customers throughout the buyer's journey, by integrating digital and physical sending strategies to improve their customer relationships practice. And also Kris started his career as a founder of all student rentals, and then set off on a career sales with roles in Yellowstone, Quora, and Talkdesk.

So my first question for you, Kris. Did you start the company to help close more? 

[00:01:59] Kris Rudeegraap: I [00:02:00] did. And it was actually started because of a pain point. I felt while I was at one of my last companies talk desk, where I found myself as an account executive and I was trying to be more creative. So I'd send out handwritten notes, I'd go grab swag from our swag closet or go online to find gifts for prospects.

And it worked really well. Terribly time-consuming to manually pack boxes, go to the post office track links. And so I dreamed up with this idea is like, why isn't there a button in Salesforce that I can just click a button and send something to somebody 

[00:02:30] Andrew Michael: that's very cool. And maybe just talk us through that a little bit as well.

Like what send us how you help customers. And obviously this was one of the use cases, but what is like the general use cases you've seen your customers use the. 

[00:02:40] Kris Rudeegraap: Yeah, so real quick, Sonos is going to three parts, one part software that really takes this offline gifts sending and direct mail sending online.

So there's teams, budgets, reporting, integrations, analytics, there's then this marketplace of all the different things you could send. And then there's all the fulfillment. So there's warehousing and fulfillment centers behind the scenes. So all of [00:03:00] that make it so easy to click a button and send something.

And for our customers that are using. And more of a customer success account management function. We see people sending things for welcoming new clients or new customers. So it's like a welcome kit. Oftentimes that'll come with some kind of collateral and then some kind of welcome swag or some kind of welcome gift.

There's also. Typically there's things that you can send for like graduation from onboarding. So it's celebrating certain milestones while using the product. There's your typical like annual, holiday gifts that you might want to send out to your customers. That's probably the most popular one historically is like Christmas and holiday gifts.

There's then just like one-off gifts that maybe a CSS. Would want to send to a customer for maybe your customer just had a baby or maybe they just had a birthday and maybe there's other life events that you want to really build a more human relationship with than just a vendor to customer relationship.

And so those are more ad hoc. They're not usually automated or triggered. They're just at the [00:04:00] discretion of the CSM to send things out when they feel like there's something to be sent to them. 

[00:04:06] Andrew Michael: Very cool. And so you gave like from the customer success perspective, quite a few different use cases, and then it actually triggered a memory as well from an earlier episode where we had a Julian cabin or GE or the mad scientist is others like to call them.

And I remember this quite specifically, cause I found it really fascinating. In the sense of I can't remember which company or is that, but obviously I know, like the company themselves, they had a really high our pets, or they could afford to send elaborate gifts to their customers. And the one thing they were doing was they were monitoring for.

When their customer champions left the company that they were currently at and move to a new company, they would send them like a set of Bose headsets and something else and said, okay, congrats on the new role. I'm like, we're here when you need us, we're waiting for you thing. And I found that really interesting.

And I think, geez, how can you send somebody a Bose headset? It's three, $400 a set. But when you think about the contract size, like [00:05:00] starting at 50, 60 K as like a way to. Keep that relationship going, even after they've left the company that you're at, I thought it was really clever and a unique way as well, to maintain that relationship.

Are you seeing any other interesting things, customers doing with your product? 

[00:05:15] Kris Rudeegraap: Yeah, we see a lot of. Interesting things on the sales side too, to attract customers through prospecting techniques, to really break through just a digital noise and get on people's desks. So we find that to be a useful technique as well.

But furthermore, on the customer side, there's interesting things you can do around timing when the renewal's coming or really trying to expand your champions at the company too. I think sometimes turn can come from just having a single. My point of contact. And so sending things to broader audiences this also worked really well when people were back in the office too, or you'd send like a group gift.

And so people would be like, oh, who sent the cupcakes? And then, oh, Sentosa did or whatever our customer. And it opened up a conversation about who sent that, [00:06:00] what it is. 

[00:06:01] Andrew Michael: Yeah. I like that actually. It's really interesting as a way it's just to get more coverage at the office.

Yeah. It's like a, 

[00:06:05] Kris Rudeegraap: it's like brand awareness almost. And then people start asking questions and then it's oh yeah, we use this vendor for X, Y, Z. And then now you've got more coverage. 

[00:06:15] Andrew Michael: Absolutely. And definitely talking through this. Enabling and expanding the number of customer champions you have with new organization is a fantastic way to protect and guard yourself against churn and retentionn.

Cause like you say, if you have a single point of entry and that person decides to leave, like you're pretty much a sort of like hoping on hanging on threads that somebody somewhere else in the organization sees value in your product or service. 

[00:06:38] Kris Rudeegraap: Exactly. There's other creative ways to like, if you hosting like lunch and learns or even wanting to do, like we select.

Demos and donuts, which was a way for, to expand more people, seeing the product. And so for both of those, if you do need to facilitate sending lunch or if it's a digital lunch and you just want to send it, Uber eats or door dash gift cards again, it's another [00:07:00] way to. I campaign that you can drive people to have a lunch and learn that's for a specific account where you're expanding the number of people you're talking to.

But then when it's in dosa, you can just with a click of a button, send out, 10, door, dash gift cards, and boom, you can fulfill that promise, but also get more, champions at that. 

[00:07:18] Andrew Michael: Nice. Yeah, I was thinking about the actually, like a few weeks ago, discussing with somebody like now in a remote world, when you want to organize maybe like a team lunch it's not really straightforward especially if you want everybody to like, eat at the same time and be able to us.

So I think I did come across like one or two. Startups like eat pizza or something like that. It was like, all the pizza was just like a click of a button. You can order pizza for your team and it came round or some similar concept. But I find it really interesting sort of this notion as well as how you can bring people together under central time and be able in a remote world to do I'm not sure to get to it if it is, I'll find it, but I just found it really interesting. Let's talk a little bit about how you got to where you are today. So you started out in sales [00:08:00] and maybe talk us through that journey a little bit. So you mentioned like a talk desk. This was the frustration where I wasn't that good point, but when it comes to churn and retention, like what are some of the effective ways you've seen sales done?

To help reduce. 

[00:08:12] Kris Rudeegraap: Yeah. Thinking about a couple of things that I, that I used to do, or that were ingrained in my head, one is making sure you're selling good deals into the right ICP. I think a lot of people will buy your software and sometimes early startups they'll sell that.

But if you're more disciplined to making sure that you're selling good deals. And I think that's a way it's semi counterintuitive to a salesperson though, because A's just want to close deals and they want, to hit their quota. But if you can sell to the right ICP and make sure that it's a good deal and for each different company, they can probably spot what's a good deal or what's a bad deal.

But if they can, if you can spot, if you can understand that, I think that's important. Another thing would be, it'd be spiffing on multi-year deals. I think if you give yourself more time to build that customer's trust over two, three years, you then reduce the chance that they'll churn [00:09:00] because they, after one year.

So I think creating spiffs around multi-year. I think finding the executive sponsors early in the process, so not waiting for the CSM or the account manager to go see a spot, more executive buyers, but as part of the sales process, you're identifying those. And, even what some of the things we do now is at my company, we get we do a lot of exec to exec engaging.

And if there is a churn opportunity, our executives are already introduced to the, our customer's executives. So there's more chances of upleveling the conversation from then maybe just a single champion or a buyer that's lower down that wants to churn. 

[00:09:39] Andrew Michael: Makes sense. You started out the first point with the ICP, the ideal customer profile and selling into it.

And I think this is it is key and early stage. You just want to sell to everybody and just trying to get in, but it's hard to be disciplined. Have you seen sales teams effectively organize around this and ensure that you are actually selling to your ideal customer profile now? Closing deals for the sake of cousin deals.[00:10:00] 

[00:10:00] Kris Rudeegraap: Yeah. So one of the things you have to do is really look back at the data. So it's hard to do day zero because it's like, you want it. Day, 100 day, 300, you can start to look at certain trends. So here's the hundred customers that we sold in the last, three months. Okay.

Let's enrich them. So we see their industry, their company size, their use case there. And so now you get all these other data points and then you can see, okay, 10 customers are having low usage or looking like they're in the red or yellow likelihood to churn, like why? And so you maybe then you spot things like, okay, they are this size of company or Hey, this industry or this use case, or maybe they this type of a title bot when we usually say.

Title or they're not you. So basically it's a little bit it's a little bit harder to just have a, again, a golden bullet to decide what it is or a silver bullet, but the approaches that you should be data-driven in to analyzing your customer. In, [00:11:00] after you've sold to them and then you can spot anomalies thereafter and try to identify why those anomalies are happening.

And then, go back to your outbound process to try to eliminate some of those things that you're selling into. 

[00:11:13] Andrew Michael: No. So it's like constant iteration , like you're saying, having a good understanding of how the sales process went, how you're acquiring them and then learning from there. The next thing I was actually intrigued as all now saying and asking the question was like at Sendoso You're introducing, I wouldn't say maybe a new concept where maybe you've done in slightly new way as well.

And there might be other competitors in the market, but starting out the business, psych, how did you go out and your first distribution strategy as a salesman? Was it a outbound sales? Like how did you launch the company to.

[00:11:45] Kris Rudeegraap: Yeah. So the two things we focused on early on was one. So me and my co-founder were both previously in sales.

So we just, hit the ground running cold, calling cold emailing, send out sewing. And so we would just outbound. And that was really effective. We [00:12:00] probably got our first 50 customers, like in the first couple months, because we just knew how to outbound. We knew how to build target lists.

We knew how to set up sequences. We knew. Set demos and closed deals. So we just did that ourselves really well. We then quickly hired a ease in SDRs. Our first SDRs were probably within our first, eight employees. So we really knew that we had product market fit. I think that was obvious for us, but we wanted to understand if we.

Really what I'd call it, go to market fit and the unit economics and the CAC and LTV, and being able to support an outbound team in and scale that engine. So then we quickly wanted to see, okay, Ken, these SDRs hit their metrics. Can these AEs hit their metrics? And so we, that was a really important goal in the early days.

And then we also invested early in kind of brand and some of marketing channels that you probably want to expected. Like we would show up at conferences very early. And we'd actually bring our whole company, which was like 10 people to the booth. And even like our CSM, even like a designer. And, we look bigger than we were because other [00:13:00] people had three salespeople at the booth.

We just had 10 people. It happened to be our whole company, but, we invested in areas where people, we wanted to get our name out there and we, sitting in a booth next to, a Salesforce or Marquetto, and we've got a lot of people and people start to say, Hey, this is a MarTech tool or a sales tech tool.

I need to. 

[00:13:17] Andrew Michael: It's very interesting, inflating yourself to look bigger than you actually have it. Nice. You mentioned something as well that caught the attention is in the sense that we actually recently has Christoph Yance on the show as well from 0.9 capital. And he has a very.

Blogposts that he wrote originally, is five ways to a hundred to build a a hundred million dollar business in Southern, like you're hunting elephants, we're hunting flies and that he revised it, I think at some point, but you mentioned as well now yourself, like you knew that there was pulling the market, but you wanted to understand did you have go to market fits and could you support a sales strategy?

Up on Salesforce, maybe talk us through this a little bit more in specific detail. So how were you going about testing this? How are you going and [00:14:00] measuring and understanding could you support this model and how did you end up saying, okay. Yes. 

[00:14:05] Kris Rudeegraap: Yeah. So I think, having founders sell is not a real S it's not real proof that you have product market fit because founders are so passionate, they can sell anything to anyone in my opinion.

And so we really needed to have outsiders who had no, no vested interest or a very smaller vested interest to see how they could sell. And so that's where, we wanted to hire a fully paid. Yeah, SDR. And to our, to fully paid STRs and to fully paid A's. And the goal with too at the same time was that we wanted to eliminate bias of one person being just a bad employee or just being a bad apple.

So we w we thought two people it also gives a little bit more competition in sales as competition. And so then we set out to say, Hey, okay, here's how many target accounts you get SDRs? And here's how many meetings we need you to set. And we did the backend man. You set this many meetings and you get this many accounts, you can hit this quota.

And we really [00:15:00] just did that backwards, napkin math on hitting quota, paying an OTE that actually was favorable to to both rep and the SDR. And then we said and it w it was really just seeing if we could back into the math that we know we needed, if we wanted to have 50 STRs and, 50 

[00:15:17] Andrew Michael: AEs, and to scale it from there.

Very cool. And then just trying to understand a little bit of what the payback period is, what the cost to acquire customers and then evaluating essentially from there, because I think with a sales model, you have a lot of upfront costs. When it comes to sales and understanding like is the business come out the back end is the LTV going to be able to support that is important than Santa.

And I think this is where obviously then churn and retention plays a big driver as well. And understanding, can you support it? So talking about that trend and attention then as well the company now, if I remember correctly is about six, seven years old. 

[00:15:53] Kris Rudeegraap: We're about a four and a half years old.

So we got started in 2016 is when I had [00:16:00] the idea 2017 is when we actually built our first product had been really 2018 was when we first went to market. We had a substantial price change to, from 2017 to 2018 where we were really testing the market and then really went to market strong in 2018.


[00:16:16] Andrew Michael: And through that time, like, how have you seen general attention for yourself as obviously you provide services that help create a lot for experiences, which ultimately helps customers stick around longer, but how's it been for you? Yeah. 

[00:16:29] Kris Rudeegraap: So I would say, we there's been some ups and downs.

I'd say we've right now, we're in a really good place with a retention. And so our net dollar retention depending on the segments, we look at enterprise mid-market and SMB, but our mid-market and enterprise segments are well over a hundred percent close to 120%. And the overall. Turn is something that works really satisfied with, I would say a couple of years ago we had some speed bumps.

And so I'm happy to get into those details and share how we grew past those speed bumps and [00:17:00] for context, we we're about 450 employees. About two years ago, we were about 150 employees. And then, year before that we were about 50 employees. So we've seen some good employee growth along with our revenue growth.

We're about, and we're about mid twenties or high twenties in a SAS era. I 20 millions. 

[00:17:20] Andrew Michael: Nice. Let's talk about the speed and, yeah, thanks. So at the speed bumps so yeah, so what's been the biggest speed bump to. 

[00:17:28] Kris Rudeegraap: Yeah. So I would everything feels big. So maybe I'll just say a few of them and we'll you'll determine which one was the biggest.

So the first one was probably about two and a half or two years ago. We really had our CSM own all post customer function. So they owned onboarding. They owned the integration, the owned renewal expansion, and they owned what we call like the project manager. Piece. And at the time we thought that was worth it because it gave a single touch point for the customer.

And what we really [00:18:00] realized is that they were not good at everything, so they were good at nothing. And so it was causing this problem where our customers were being really helped along their customer journey in an effective way. And so we analyze that and we looked at, okay what if we strip out an onboarding team that helps customers.

Time to value down and get there. And for us, that was time to first send on the planet. So if we have a team that onboards trains you really quickly, then we can get that metric down. And that contributes to churn. We then said, Hey, if we have a dedicated solution architect, w we could then integrate and have these integration conversations earlier and better, and as part of the onboarding.

So what if we had a solution architect then we said, Hey, if we have an account manager, The CSM can focus just on training and on usage and adoption and not on, Hey, pay us more money or, Hey, let's upscale, upsell you. The account manager can do that. And then we said, Hey, if we [00:19:00] can get the w if we can have these send curators, which we call them, give all these ideas and go in and actually source and find products and gift ideas for our customers.

And the CSMs don't have to focus on that either. And so it might sound like there's a lot of people, a lot of cooks in the kitchen there, but it works out perfectly now because now we have, depending on the account, 3, 4, 5 people that will work with customers to make them more successful.

And so we went from very general, CSM function to very specific functions, to help customers be successful at different points in their journey. And that was a huge one for. A couple of years ago, and we saw a ton of tailwind success in that. 

[00:19:40] Andrew Michael: Sure. It sounds like a big shift as well in the customer successful that the company, how.

So you mentioned like originally, like just having one point of contact for the customer. So how did you manage this thing going forward? Because now the customer went from having one point of contact and then 2, 5, 6, potentially. What is the makeup look [00:20:00] like there? How is the team communicating? How are they ensuring that.

The client's actually being serviced. When if you think there's five people potentially can do it. Yeah. 

[00:20:09] Kris Rudeegraap: So we call it an account team and the CSM is still the main point of contact. They'll just bring in other points of context. So the CSM still sits on the first onboarding call, but we have the onboarding specialist get them up and running quick and help them with the training with with everything there.

So it's like basically gets tagged teamed. We then also. The sake of a, a project where they want to come up with something new to send out, the CSM will likely be on the call too, but we'll also have a sudden curator, that's saying, Hey, I've helped these 50 other customers. Here's the send ideas.

Here's what I think you should be doing. And so they're tag team together there. So I think it's a, more of a less about okay, now who do I reach out to? There's five people. It's I can always reach out to my CSM, but they're going to bring in maybe another specialist that's going to help me be more successful, specific.

[00:20:58] Andrew Michael: Makes sense. So for [00:21:00] customer, the experience is pretty much the same from a single point of contact, but then they're bringing in different team members at different aspects of the journey. And there's obviously we hear a lot on the show and the makeup as well as fairly. It is a certain time and scale where this starts to make sense.

And then you start to break out the functions. 

[00:21:18] Kris Rudeegraap: Correct. And I think so that the learning there for others is just no one, the time is right to do that. I think if you do it too early, you might increase your burn too much because you're having more employees than you need. But if you do it too late, your customers are going to feel the pain of not being serviced correctly.

So I think for us, we did this at about a hundred employees or so we started to break out these functions and that was something that was really helpful for. 

[00:21:44] Andrew Michael: Tommy, you're going to say something. 

[00:21:46] Kris Rudeegraap: Oh no. I was going to I could get into some other things that 

[00:21:49] Andrew Michael: I was going to say. What's next? I think Tim struck.

[00:21:53] Kris Rudeegraap: Yeah. So number one is breaking out the CSM team structure. Yeah. Number two, what we did is we really [00:22:00] broke out our enterprise product from our SMB product. And so what we really realized was the SMB product or the SMB segment was churning more than the enterprise was. And that was something that is, I think sometimes obvious that's typical in most companies.

But what we really did when we dove into the details was that. We've looked at interviews was, w we were building for, a thousand person sales team had, these advanced roles and permission, these team functionalities, these robust reportings and a 50 person company, or a 30 person company that was more than they, that was overly unnecessary features that would actually drive them away from the platform because it was too confusing for them or.

And so I think some companies choose to just focus on one segment. We're only going to sell the enterprise so we can avoid that problem. I think some companies are open to selling to multiple segments which was something that we wanted to support because we knew there was a long tail SMB, [00:23:00] but we also knew we wanted to support.

And we have probably three or 400 public companies using us that are, multi thousands. We have some multi hundred thousand companies using us. And so what we had to do is really. Pull out what we thought was going to be needed for the SMB and what features they would care about and still build for the enterprise and still tack on all these features and in doing so, we created a much more self-service less featured focused SMB start our tool, our startup.

And that really helped with retention and tracking events through amplitude and these cohorts and seeing what features they were using. And then really understanding that, Hey, this isn't needed an SMB is not going to create like a custom role and permission set. And so when you see that feature on the teams page, and you have to do that first in order to create a team.

Then maybe you don't create a team if you're on a plan because you're it's. So anyway it, maybe it's obvious, but when you're in the weeds and you have [00:24:00] only a single product, you don't think about servicing two customers differently, but that was something that we analyze the data and said, okay, Service these two segments differently and let's break out our product team to focus on different features within the product for these different features.

And then that really entailed really rolling out LaunchDarkly and really having to get really good at feature flagging and building the same app, but for different users with different features turned on which was more difficult from an engineering and product perspective, but from a retention perspective, I think a lot of times.

People think CSMs are the key to retention, but actually product is the key to retention at times too. And so how does product thinking about it? And so we really have our product teams and our CSM teams work together when they want to improve retention. 

[00:24:47] Andrew Michael: Yeah. And then sometimes it's sales, sometimes it's marketing, but 

[00:24:50] Kris Rudeegraap: yeah, it's really everyone, 

[00:24:51] Andrew Michael: but.

Yeah, I really liked this as why now I'm trying to think as well. There's a specific bias that we have when it comes to having too [00:25:00] many features available can also be a reason for churn and not because it makes things complicated, but more because. If there's too many things and people don't take advantage of them, they feel that they're not using the full service so that they end up churning as a result.

And I like this, like it serves two needs. I got to see the one you met. You mentioned as just making it really simple for SMBs, but on the same time, it's also. And you're showing them what they're paying for and then making sure that they're using what they get at the end of this.

So it's like reduces that anxiety that you might get from using another program. You think, oh, we've paying all this money and these are the features, but we only using two or three of them where you would have paid probably that same money just for those two or three features in there, because they were solving your pain or your problem.

And you say, cool, what's number three. Let's say we have to have three. So 

[00:25:47] Kris Rudeegraap: I probably could. A couple more so I could come up with five if we wanted to, but if we don't have enough time, so the third one, this was just a small win, but we hired on a CX ops person. We call it CX cause it looks across [00:26:00] everything post customer success, but you could think about it as CSM ops.

This has an obvious one, you invest, I feel as founders or as CEOs, you invest early in like sales ops and marketing ops is right out the gate. CSM ops was something that was a semi afterthought for us. And looking back on it, it was what the heck were we thinking?

Why wouldn't we want to have someone that's data focused, that's running reports. That's analyzing, that's helping with tools and enablement for just the CSM or CX org. And so when we hired that person, we instantly had someone else that was deeply caring. Day-to-day about the data sets the tooling, the projections.

And so that was a very helpful addition to the CS org. 

[00:26:40] Andrew Michael: I think, yeah. CS ops or CX OPSEC as you call it is something as well. I've actually noticed a little bit more in discussion through the podcasts and seeing more and more of the. Of it. So I think recent episodes are with Jeff heckler, from pipe drive and just talking to his sort of like how he saw CS RCX ops, is that really the backbone that enables [00:27:00] the rest of the team to do what they're doing to scale their operations effectively.

Because a lot of times, like in their case, they're dealing with a large audience of SMBs and in order to be able to service a large audience like that, and to be able to give them like a personal touch. You need to have a solid foundation and you need to have that infrastructure, have the data available for the teams to be able to prioritize, make decisions.

And how did you see that contributing to general retention though? What was the biggest benefits that you got from having a solid ops team in place? 

[00:27:29] Kris Rudeegraap: Yes. So it really provided a more data-driven approach in terms of analyzing data, spotting data anomalies. We had someone that could help invest in tools.

So we rolled out a tool called catalyst from on the CSM side. And so that person was helpful in that rollout, which is then ended up helping reduce churn because we had a better kind of infrastructure tool that worked to help the CSMs to be more successful. And it also just created a.

Champion for a [00:28:00] churn in the sense of or champion for retention, that someone that cared about those metrics and wanted to influence them to go the right way 

[00:28:09] Andrew Michael: paradise. You've mentioned three things now. And I think none of these are really all of them, I think require considerable effort, conceptual alignment to get the team in shape to make these changes.

One of the questions I ask on the show a lot, and it's actually a terrible question in retrospect, but I'm going to ask it anyway today. Again. Let's imagine a hypothetical scenario now that you join a new company and turn our attention is not doing good at this company. And the CEO comes to, you says, Hey Kris we really need to turn things around and we need you to fast.

We have 90 days and you're in charge. What are you going to do? But you're not going to pick, you're not going to send me to speak to customers and pick the problem. You're just going to run with something you've seen. That's been really effective in your past and hope that it's going to work at this new company.

What would be one thing that you would try to pick to reduce churn and retention fast? [00:29:00] 

[00:29:01] Kris Rudeegraap: That's a great question. I guess all things considered, I might invest in like a customer success platform. If they don't have one already like a catalyst and try to roll out something that can, operationalize the success of the the CSM team at scale making it easier to communicate, making it easier to see the data insights, make it easier to build playbooks.

So I'd say if that wasn't in place, I would instantly put that. Which would, which could take maybe a month or so, and then I could instantly then build on that as the foundation. To push 

[00:29:33] Andrew Michael: for it. Nice. Yeah. It's a trick question. I think in the sense, cause general attention, like everything does take a lot longer.

It's not 

[00:29:40] Kris Rudeegraap: the question to you because you then don't want to analyze it over the couple of quarters, but it's one of those good gun to your head. What would you do? Type questions. 

[00:29:47] Andrew Michael: Yeah. And maybe that's a better way for me to phrase it as well. Nick Fisher wants to know is what's one thing that you noted about general attention that you wish you knew when you got started with your career?

[00:29:56] Kris Rudeegraap: I'd say like maybe when I got started with Sendoso, so [00:30:00] is really just investing in like amplitude or Mixpanel or one of these datas usage, segmenting tools or catalysts very early on. I think we we, from a trend perspective, cared more about revenue. Upfront and was more focused on let's close more deals than let's like analyze existing deals or analyze existing customer usage to see what what's working and what's not working.

We just poured more fuel on the top of the funnel. And so I think it's equally important to think about churn day one, as it is revenue. I think that some people are like if I don't have revenue, I can't continue. But if you have bad revenue, It's even worse than no revenue. So I think that some people are, I just want to get to my first million dollars in sales as a founder.

And it's why are you thinking that what if that million dollars is churning at a rate that's, that's UN scalable, like then at that million dollars doesn't even. So I think it's more of, you should less be celebrating [00:31:00] revenue, milestones less, be celebrating fundraising, milestones and more celebrating customer attention miles.

And in doing so you need to then track that data. And I think if you ask most founders in the early days, they don't care about that as much. 

[00:31:15] Andrew Michael: Yeah. When you said a to my bond is all almost so like tech crunch headlines or whatever, send us a hits net negative churn. 

[00:31:22] Kris Rudeegraap: Exactly. Like how many times do you hear that?


[00:31:24] Andrew Michael: enough if you don't hear it enough, but yeah, I actually a hundred percent agree with you. This is all that matters in the subscription business really? Is that your attending customers? Cause that's the whole premise of having a subscription. So yeah, celebrating that more as opposed to the actual specific numbers, once you get a really sticky product and the numbers just keep coming, like that's the video bought at the predictability about it.

Exactly. Cool. We're coming up to the end of the show. Now, is there any sort of final thoughts, anything that you really feel we should be sharing with the listeners? Like how can they keep up to speed with your work? Anything interesting. There should be. 

[00:31:55] Kris Rudeegraap: Yeah. I personally love connecting with people.

So if you want to go deeper on one of these [00:32:00] topics or giving us the weeds on one of the ways that I just solved Turner, or I think about it, feel free to email me. My email is Kris. kris@sentoso.com. You get out it in the show. Notes could find me on LinkedIn as well, but we'd love to continue the conversation and, go deeper on some of these topics.

If anyone's listening and wants to talk. 

[00:32:20] Andrew Michael: Awesome. Yeah. Kris, thank you so much. And definitely add that all in the show notes. We'll add Sendoso as well. If you want to check them out too, and really appreciate your time today, it's been great connecting and chatting and maybe we'll have to have you on again to hear then the 3, 4, 5, 6, 7, 8 different things that you've tried as all along the way.

But thanks for joining today. 

[00:32:38] Kris Rudeegraap: Thanks Andrew. Appreciate it.


Kris Rudeegraap
Kris Rudeegraap

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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