In our new episode of the Mastering CS, Candid Leader Insights podcast, Irina Cismas, Head of Marketing at Custify, discussed with Jordan Wyner, the Vice President of Customer Success at Softrip.
Jordan shares her journey in CS, the challenges she overcame, and the strategies she implemented.
What You’ll Learn:
- How to help customers with their challenges
- The disadvantages of having a sticky product
- Key metrics for customer success
- How to motivate your CS team
- The importance of prioritizing customer needs
Key insights and takeaways for CSMs based on the interview:
Proactive vs. Reactive Customer Success: Jordan Wyner transitioned Softrip’s customer support organization from a reactive, support-driven model to a proactive, success-focused approach by mapping out the customer journey and hiring a dedicated Customer Success Manager (CSM). This shift helped create more meaningful customer partnerships and fostered a proactive engagement model.
Sticky Products Can Mask Customer Satisfaction Issues: Softrip’s ERP system has a very low churn rate due to its complexity and the high cost of switching systems. However, Jordan noted that this can reduce urgency around customer satisfaction, as customers may stay but not necessarily be advocates for the product. Maintaining customer happiness and advocacy, rather than just retaining them, is critical.
Internal Collaboration and Change Management: Building a strong internal partnership with product and engineering teams was essential to driving customer success at Softrip. Jordan also emphasized that changing long-standing behaviors and mindsets required consistent communication, as shifting from a reactive to a proactive approach takes time and effort.
Importance of Customer Onboarding: Onboarding was highlighted as a crucial phase in the customer journey. Softrip revamped its onboarding process to focus on the customer’s experience rather than the company’s needs, ensuring smoother transitions and longer-lasting customer relationships.
Podcast transcript
Intro
Irina 0:00
Welcome to Mastering CS, Candid Leader Insights, the podcast where we deep dive into the world of customer success with industry leaders. I’m your host, Irina Cismas, and today’s guest is Jordan Wyner, VP of Customer Success at Softrip. Jordan, welcome and thanks for joining us today!
First off, how is everything going at Softrip?
It’s been more than a year since you took on the VP of Customer Success role. What’s the journey been like so far?
Jordan 0:33
Sure. Things at Softrip are going really well. I joined at a really interesting time in the company’s history.
We have this amazing depth of knowledge. The company has been around in some form for almost 20 years. You have folks who helped build this from the ground up, who are still around and have this incredible institutional knowledge.
We’ve also brought in some new folks who are modernizing some of our practices. They’re not afraid to say, hey, why are we doing it this way? When the answer is, I don’t know, we’ve always done it that way, we’re turning some things on their heads.
The cool thing is the people who’ve been here for a long time and the new people, the alignment there is incredible. Everybody is rowing in the same direction. Everybody’s there for the spirit of moving the company forward.
Even if somebody’s been around for 15 years, they’re saying, sounds great, let’s try it. It’s a really fun time to be joining a company like this.
Having a sticky product
Irina 1:28
Indeed it is. To be honest, I think you are lucky. It’s an interesting organization because usually when things are done like this for a very long time, they remain as is.
It’s that saying, if something works, do not break it. In some cases, you don’t evolve if you don’t change things. I was under the impression when I did the research for our discussion that you have a dream job.
Based on what you told me, you might have a dream job or at least you are working in a very nice company. You mentioned at some point on LinkedIn that you are working in a company where churn is not an issue. I have to ask you, how does it work for a sticky product?
Is it a blessing? Is it a curse? How is it?
Jordan 2:34
Yes, to both. Transitioning into Softrip, I had heard over the interview process that churn really wasn’t an issue. I was like, sure.
Now that I’m here, it’s true. Because it’s an ERP system, because it’s such a broad system that our customers use to run their business almost end-to-end, the pain of removing a system like this is a one to three-year commitment. Churn is almost non-existent because we have, and I’m proud to say this, you don’t always get to say this with confidence, we have the best system, the most robust system, it has the most breadth, it covers the most use cases.
We’ve got the best system out there. That said, because there’s almost no churn, I think it obscures and reduces the urgency around customer satisfaction. So just because they can’t leave doesn’t mean they’re thrilled with your product.
Doesn’t mean that if you ask them for a referral, they’re going to say, yes, I would love to help you grow. Who would you like me to talk to? So when I got in the door and went, okay, great, we have an intention to grow, we’re hiring some sales and marketing folks, let’s do it.
Of course, new customers who are investing in a giant system, they want to hear from your current customer base and they want to know this is the right choice for us. And the depth of that list of people that I could say, hey, would you talk to somebody was not nearly as long as I would like it to be. So the fact that there’s no churn, there’s less urgency, there’s less focus, of the business until your CS folks really say, hey, this is really important.
Let me tell you how it impacts sales. And then you get a lot more attention on it. So it’s a double-edged sword.
They can’t leave, but you don’t want prisoners. You want happy customers.
Starting out at a new company
Irina 4:18
Indeed. And it’s a very nice way of framing it. You don’t want prisoners.
You actually want people to advocate for your product. And we’re going to talk about this a bit later. Now, I know that it has been one year, but do you remember how the first 90 days were within the company?
What were your initial priorities back then?
Jordan 4:46
Sure. So when I joined Softrip, it was essentially a reactive support customer-facing organization. So we had a really great support team.
The level that these folks know the system and the way they know the customer’s business is 10 out of 10. It’s incredible. But we were operating completely reactively.
So once there was a problem, we would try to fix it. It was really project management of issues, not proactive customer success. We were a support organization, not a success organization.
So the first thing I did was map a customer journey end to end. I think that foundation and knowing what a customer experience is when is sort of the backbone to how you do CS. It informs if and when you do things like executive business reviews.
It informs what your touch points should be. It gives you the map on how to get out of reactive and how to go into proactive. If you know what the fun moments are and you know what the really friction-laden moments are.
So brought everybody in, did a big customer journey exercise, and there was low-hanging fruit right away. Also hired our first customer success manager. These brilliant technical resources are fantastic at their jobs, but their job is to be reactive.
So to ask someone to be both reactive and proactive at the same time, they’re going to do both a little poorly. So actually bringing in a resource whose job it was to be proactive, to take some of that project management burden off of them was a game changer. So we had customers say, hey, it felt like we had been in the same rut for years.
And over the last six months, it feels really different. It feels more like a partnership and less like you guys are order-takers fixing the things that we need to fix. So first two priorities were customer journey mapping.
Let’s really think about what the customer experience is and bring our CSM in the door.
How to sell the value of CS internally
Irina 6:38
Was it hard to sell it internally? And the reason I am asking is that people who are trying to convince the board of directors, senior management team, it doesn’t matter how you name it, trying to convince them to switch from a reactive mindset to a proactive one, find it very hard to take the buy-in where usually we like to call it success because it sounds cooler, but they think we are still doing support because this is how we are used to do it.
How was it in your case?
Jordan 7:13
Oh, you hit the nail on the head. I think some pieces were easy. If you add a new person in and you tell them that’s their job, you’ve got a clean slate and they’re going to try to focus on that.
When you’re trying to do behavior change, when someone has been doing something in a certain way for a really long time, we had some behavior change that took change management. I love the old adage that you have to hear something seven times for it to really sink in. So they probably heard it 70 times now over the last year.
And then once you can prove out that it really does make a difference, adoption of that behavior change gets a lot easier. That said, we still have folks who this customer has been theirs. They’ve been operating as a one-man team for a really long time.
They know everything about it. And letting somebody else come in and be a CSM on that account, still the muscle memory is not there. And it takes a lot of reminders on, hey, you should have brought the CSM into that call, or you actually didn’t need to solve that problem.
That’s an account sort of problem. That should be kicked over to your CSM. So it’s not perfect.
It’s an ongoing journey. But the executive team has been so bought in and so supportive from the get-go. That means it’s really more of a behavior change, change management task with the boots on the ground.
Irina 8:31
Who were your internal partners speaking about this internal mindset, more changing the mindset and the behavior? Who did you partner up with internally?
Jordan 8:43
Sure. So the most important partnership at Softrip is with product and engineering. Sales, yes, of course, but we do a pretty good job of bringing the right ICP customers, the ideal client, excuse me, ideal customer profile folks to the door.
So that’s more about how can we help you sales. As far as who we want to partner with, who we spend the most time talking to, it’s product and engineering. With a system as big as ours that is so support-centric, that is so support-heavy, doing the right work is what makes an impact for our customers.
We will always have more work than the engineers could ever possibly get through. You could probably map out the next three years with the things that we would love to do today. But making sure that we have really great alignment between what the customers are saying, what we as CS know will be impactful for them, and what engineering is actually up to, that has to be such a tight loop.
So we have the closest relationship with our head of product and our head of engineering.
The main responsibilities of CSMs
Irina 9:44
That’s, I would say, you are lucky to have product and engineering on board when it comes to partnering with us. Yes, it’s usually the hardest one to build. And you are lucky that you do have a great relationship with sales.
Let’s talk about your team and how you structure it and what are the main responsibilities of a CSM that is working under you.
Jordan 10:11
Sure thing. So the support organization actually does report to me. So we have folks who are dedicated to essentially level one, level two support.
So whatever’s coming in, can we triage it? Can we solve it? Can we get it back out the door?
And we have level two resources and they have account-specific specialty. So one technical resource sort of level two, level three technical resource might have seven of our customers that they are a deep expert on. They know all the strange configurations, customizations, all the nuance of each of these customers so that when something tricky does come in, whether it needs to go to engineering or not, there’s somebody shepherding that with the technical know-how.
Then we only have a single CSM today. We’re intending to add more to cover the rest of our customer base as we grow and growth projections and patterns are going really well. So we’re probably going to be hiring early next year, but it’s really a support-heavy organization for now.
There’s also a huge quality initiative that’s been underway for the last year or two at Softrip so that we are going to be able to do less firefighting. We’re going to be able to do more with the support resources we have. So as we grow the team, it will theoretically get less support heavy.
It might not be a 10 to 1 situation anymore. It might be more of a 10 to 4 and continue to evolve over time in that way.
Customer onboarding and engagement
Irina 11:39
Let’s speak about two important things, customer engagement and onboarding. Let’s tackle first the onboarding. I know that in your case, it takes months to onboard and offboard a customer.
How do you ensure the process goes as smoothly as possible? What’s your onboarding?
Jordan 12:06
Okay, another one where I’m lucky. I have a rock star. I know that phrase is overused, but I have just a fantastic director of onboarding.
One of those folks that I was talking about who’s been here for years and years knows the system at a level that is really impressive but is also very empathetic. One of those truly empathetic folks who, when a customer experiences a problem, they take it very personally, but he’s also so diligent. So he makes sure that almost nothing falls through the cracks.
So starting with the right people is a huge help in that running smoothly. That said, when I did arrive at Softrip, everything was about what we needed from the customer in order to pull off the onboarding. That was how everything was framed.
Everything was oriented about what we need, what we need from them, what we need them to do, et cetera. So I flipped it on its head. I took that resource.
We’ve been doing it this way and we’re so organized. We’ve had everything. We got a new tool.
We’re using RocketLane, which is an onboarding or project management journey system. And it was a throw all of it out the window. I know you can’t, but do your best to throw it out the window.
I don’t want to hear what we’re doing. I want to hear what the customer’s doing. What is their experience at every single one of these touchpoints?
And using Rocket Lane, we mapped out the customer experience for the entire journey and made immediate changes. We were like, that’s a really hard, they ask of them. Are we asking it at the right time?
Are we asking it in the right way? So we redid a whole bunch of our onboarding journey. We said that we’re going to iterate on it until the cows come home.
We’re going to be tweaking onboarding forever based on things that we learned, based on tools that are available. But starting with what is the customer’s experience and giving them that really clear map in a tool was a game changer. So that instead of onboarding being, we think we can do it in this amount of time, depending on how much you stick to your guns customer.
Now we know how long it’s going to take. We’ve laid this out. We know it’s something that you can do.
We know it’s customer-centric. Now we’ve got a guide and we just have to follow it.
Irina 14:11
Would you say that onboarding is the most important stage of your customer journey? And if onboarding is done good, everything, all the other pieces fall in place?
Jordan 14:25
Short answer is yes. That said, we’ve got customers much like our employees who have been around for 15 years, which in CS and SaaS is unusual. It’s almost unheard of.
Software has had an interesting journey. So for those folks, yes, onboarding was the most critical, but what have you done for me lately, onboarding was 15 years ago. So it might be a big shift in their business.
Maybe they’re standing up a new brand. They are changing the business model that takes some really intense reconfiguration. We do get, because these are long-term relationships, we get really spikes in partnership and in intensity of the relationship over the course of a customer’s life too.
But yes, the short answer is that onboarding is so critical. That first 90 days when we are building a relationship, but we are also building their system, that’s going to set the tone for at least the next three years, if not longer.
Irina 15:22
And what are the biggest challenges in the onboarding?
Jordan 15:27
Sure. The tricky part, and this is probably relatable for a lot of CS folks with a lot of products. When you have a really robust, really customizable tool that supports all of these use cases, it means it’s a pain to onboard because it supports all these use cases and getting to what the customer actually needs.
You’re building the plane while you fly it because you’re educating them and asking them to make decisions at the same time. So you can’t ask them to make decisions in a vacuum. They don’t know enough.
So how do you drip the information out so that they are informed enough to make the right decisions for their business? That’s far and away the trickiest part.
Irina 16:05
What’s the definition of customer engagement in this context? What’s the balance between, you mentioned proactive and reactive. What follows after the onboarding?
Jordan 16:17
So we’ve got a tiered customer model, depending on ARR and customer levels. For the high ARR customers, for tier ones, that is typically a weekly meeting where we are talking about, hey, what are your priorities? Again, giant system.
They inevitably run into issues, defects, configuration changes, monstrous system that’s touching almost every department of the company. So something is always happening that we’ll be talking about week in and week out.
Jordan 17:00
I’ll just pause. So we’ve got weeklies essentially going with our big customers and we also do twice a year executive business reviews. I’m in the camp that quarterly is too often.
Getting the executives to have a conversation at the right level every 90 days starts to get really repetitive and it’s less impactful if you do it too often. So I’m a big fan of the twice a year model. The next customer tier down is still pretty reactive.
So we may have recurring meetings around a project, but generally speaking, we let them do their thing. If something comes up, we meet, but they’re in more of a, I wouldn’t quite call it tech touch, but a less white glove model where we’re here if you need us, but usually their touch points start through the support team and then get to the rest of CS.
Irina 17:47
Okay. Sounds interesting indeed. And I think you are, well, I never heard of this split and the combination because it’s basically a mix between some parts of the support and you transform a supportive organization into a CS and you combined it very, very well.
And also you met CS processes with weekly meetings, executive business reviews, which are specific to CS into a supportive.
Jordan 18:20
It’s all coming together in usually a really beautiful way. There’s still learning.
How to motivate a CS team
Irina 18:32
There’s still a spotlight. I’m curious, what do you guys focus on instead? And what motivates the CS team to keep things moving?
Jordan 18:45
Any CS person hearing this is probably going to cringe with me when I say it, bug count. Bug count and what’s being, how a customer is affected by the system, how their sentiment is by what their users are experiencing is a huge priority for us as a company. And every once in a while in these models, not every once in a while, always CS is the middleman.
We’re going to hear about your problem. We’re going to triage your problem. We’re going to help you navigate your problem, but we can’t fix it.
So what motivates CS at Softrip is are we advocating for the right things? It’s one of those elements where if you aren’t having the right business level conversation with the customer saying, Hey, if there’s 10 things that we could be working on for you, what’s the biggest impact to your users because of the impact to your business. For orienting that way and then taking those things to product.
It’s a really satisfying role to play as a CS person, because you are advocating for the customer. You are getting them what they need. When that starts to become more burnout laden is when the list is this long and you know, you’re not going to be able to solve it.
And you know, you’re going to have frustration over here and you’re going to have frustration over there. And it’s a part of the job sort of inevitably, but trying to keep it to the, you can advocate, you can make a difference for your customer. You can be their voice is probably the most motivational part of a CS role and software.
Tracking and measuring crucial KPIs in CS
Irina 20:14
How do you measure those KPIs? Because I think it’s hard to measure them. How do you measure them?
How do you keep track on them?
Jordan 20:27
Good, good question. We started a net promoters for survey and the response rate to it was laughable. So we said, okay, we tried incentivizing it.
We tried doing all the, all the tricks in the book. There’s also a lot of chatter in CSN about whether an NPS is truly valuable, whether it’s a leading indicator, whether it’s a lagging indicator, whether it’s impactful to whether or not they churn. Greg Daniels has a lot of great content out there about what really does cause churn and how maybe the NPS is not as closely tied to it as we once thought.
So anyway, NPS didn’t work for us. So we have, because our technical resources and our CSMs are so close to our customer, we’re going off of anecdotal CS input for now. So every other week we have a customer health dashboard.
I ask everybody to answer two quick questions. If this customer were renewed, were to renew today, would they? Yes, no, or maybe.
And on a scale of one to 10, how healthy are they? So sort of an internal NPS that is CS populated. So tracking that on our big dashboard over the course of every two weeks helps us keep sort of a finger on the pulse of how everyone’s doing.
If there’s a drop in a score, if there’s an increase in a score, that’s the right time for us to say, Hey, what’s going on over there? Let’s talk about it. But we’re also so close to our customer base that usually we are, we’re hearing about it.
If there’s a problem, there’s not a lot of mystery there.
Challenges in customer success
Irina 22:03
I’m curious, even if churn and NRR are not on your list, as we speak, I’m sure that you do have your own challenges that aren’t so obvious from the outside. What are those?
Jordan 22:20
Sure. So there will never be enough engineering bandwidth at any company, ever. But that is especially poignant at Softrip because what we would love to do is say customer ABC, we’re going to knock out every bug on your list in the next sprint.
That will never be the case. So managing all of those conversations and managing what those business priorities are is the only way that we can get to a level of partnership and not frustration with our customers. So that’s one element.
Prioritizing customer needs
Irina 22:51
How do you convince the product team to prioritize the customer bugs? Because you mentioned that the technical resources are not unlimited.
So how do you prioritize them and how do you decide what remains or what goes into the sprint and what doesn’t?
Jordan 23:16
Sure. So when I got here, it was a little wild west where customer things come in and they could be marked as low, medium or high. And then the product team was using that.
And it’s a big pile that they can choose from. What are we going to work on next? And then the technical resources on the support team were saying, Hey, this is really important.
It might be a Microsoft team’s message like, Hey, don’t miss this one. It was not comprehensive. It was not all of support saying these are the most important things.
It was really individual account managers, essentially saying, Hey, don’t miss this for customer ABC. That doesn’t scale. It’s inconsistent.
Customers are saying, why didn’t my thing get in? Well, I did it. So one of the first things that we started was something that I call the top 20 meeting.
The number is arbitrary. 20 happens to work for us, but that’s a meeting that once a sprint I hold with the CS team and I say, what are the top 20 things? If engineering works on nothing else, what are the top 20 things?
And then we have to, we have to almost fight it out with an internal calibration into the CS team. And then it goes below this 20 line. Don’t expect it in.
So Jordan, do you want to try to take Keith number 19? Because your number 21 is more important. Is Keith cool with that?
Like we do that internal calibration. Then it goes to product and then products because they have to actually analyze what resources do we have? Can we really do this?
There’s a feedback loop there. So it’s not just us sort of shouting over the wall. They then come back and say, great, here’s what’s in the sprint.
And here’s why they help us navigate the customer ABC. This didn’t make it in the sprint, but it’s in the next one because of this or great news. The things that we hope to commit are all as expected.
So that little loop of internal calibration for CS to product calibration is how we’re, how we’re managing that pretty well.
Irina 25:10
And how do you communicate to the customer and how do you deal with the customer frustration that their bug was not where it takes longer to solve? And maybe it was less important than the other and so on and so forth. How are those types of conversations?
Jordan 25:28
And this is why we all have jobs. There’s the crux of it. So depending on the some customers we have weekly touch points with, and we’re in active conversation about what are your priorities?
Cool. I’m going to try to get this in the next sprint. We’re going to save this for a future sprint.
That’s an active conversation and that’s a really white glove management style. For others, maybe something comes in the door at Softrip and it’s a medium priority and we don’t have a technical resource who’s really championing it. That’s where it can get a little fuzzy.
So we have some triggers. We use Jira, Jira service manager, the Atlassian project product that ties directly into Jira that the engineers use. So we have a well-connected digital world where customers are able to submit things in a portal.
They’re able to see updates, they’re able to comment and advocate for their own tickets. So they get a voice in the matter too. They can change the priority of something and say, Hey, when is it went in as a medium, but it’s been a while and this is starting to really affect our front end users.
They can do that advocating also. So it’s not only CS that can champion initiatives, customers can really champion them too.
Irina 26:37
That’s so cool. I wouldn’t have expected. I used to have a CEO who told me if it would have been easy, we wouldn’t need you.
So that’s the thing. What are your big projects or things that get you excited and you are focusing on until the end of the year where Q4 priorities or maybe things that are coming next year and they are keeping you up at night to say so?
Jordan 27:10
Sure. So for Q4, we are in active conversations about what is the best way to spend our resources over the course of the year. We’ve got some customers who had made requests for an integration, for example.
And we years ago, up till recently would have said, great, you’re going to pay us for the integration. We’ll build whatever you want. Now that’s changed over the last two years where we’re saying, hang on, are we sure we want to build it?
Is anybody else going to use it? What’s the business impact? If all of those answers come together and we feel good about building something new for a customer, we’ll go for it.
There are projects that folks are saying, Hey, we’d love this by the end of the year. And we’re taking a really critical eye on how is that going to impact your business? Is it right for a soft trip?
Is it the right thing to be doing? So we’ve actually got some tough conversations ahead of us. There are some folks who have said, we want this widget.
We want this integration, whatever it might be. And we’re going to have to say no. So we’re trying to get to what we’re actively planning.
What are our yeses? What are our nos? And how are we going to navigate the nos?
Is it a no? We’ll see you in Q1. Is it a no?
It’s not a fit. And let us tell you why. Let us bring you along on that journey.
So we’re going to have an interesting Q4, but hopefully also an impactful one. Hopefully we’re going to be working on the right things.
Pieces of advice for CSMs
Irina 28:28
What advice would you give to someone starting a CS role at a company with a product that is as sticky as Softrip?
Jordan 28:36
Sure. Don’t get comfortable just because they’re not churning. My favorite tool in the world is a success plan.
And you don’t have to do it at the beginning of a relationship. You can take a customer that’s been around for 15 years. And a success plan is made up of just a couple parts.
It’s usually one or two slides. The first one is what are your business priorities? If I were to fly on the wall in your boardroom, what are your business priorities?
It has nothing to do with our product. Okay, great. Now we can orient your product priorities to supporting your business priorities.
Because this could be something that’s a really squeaky wheel. It’s really driving you crazy. But you told us that was important.
Okay, great. Now we can have a really informed conversation on it. It also gives you that north star, that source of truth when things aren’t going well to say, hey, you told us this was really important.
That’s where we’ve been focused. I know this is driving you crazy over here, but are we on the same page? Do we need to change our alignment?
And having that business level conversation means that you stop talking about bugs and you keep talking about the business and about the way that you are partnering and adding value. So success plans and don’t get comfortable just because you don’t have churn.
Irina 29:50
Before we wrap up, I’d love to know who has been the biggest influence on your career and what’s the best piece of advice they gave you that still sticks with you today.
Jordan 30:00
Sure, there are three that come to mind. One, there’s Jane. She’s done everything from HR. She is a badass consultant and she was the person from which I learned how to control a room, how to show up in a way that’s going to inspire confidence, how to make the customers feel heard and get them to an outcome where you are working together.
Another one is a founder from one of my previous roles. He was a brilliant storyteller and thinker. When it comes to an EBR, he knew how to have the right visual that’s going to express a concept. When you work internally or externally, how do you virtually whiteboarding to solve problems? Because you are going to get a better answer and you can’t do it without that visual.
And then the last one that I think was really more advice: Mark Swayer, an ex-CEO of mine. He was the best prepared for client interaction. He will think though every single way that any conversation might go which meant he was almost never surprised. I do the same today. We take the time to say what are the ways this could go well or could go sideways. We are always going to get a surprise, but it gets us the best way to get the least number of surprises and makes for some great interaction.
Irina 31:44
Thank you, Jordan, for sharing your insights with us. A big thank you to all of our listeners. Until next time, stay safe and keep mastering customer success!
