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How Training Impacts CS and Business Growth with Kristi Faltorusso, CCO at ClientSuccess

Traditional client success strategies are quickly becoming obsolete. This means continuous internal training needs to be a top priority for organizations that want to see the growth they’re hungry for, especially with more people transitioning to the role from completely different industries.

“These folks do not have experience selling yet. We're giving them the most important role right now in this economy, where we're not driving a ton of new sales, so we have to work on growing the base. If you have a team responsible for it that's never done it before—and you're not investing in training and enablement—that’s crazy to me,” says Kristi Faltorusso, Chief Customer Officer at ClientSuccess.


In our latest episode of LEARN, Kristi discusses the value of a customer education program and her philosophy around training. Along the way, you’ll also learn about avoiding misunderstandings when it comes to user data and the future of the CS category.

In this episode, you will gain insights into:

  • Investing in your client success team’s training
  • Driving more value to your clients and customers, especially in the messy middle
  • Learning new skills and mindsets to push your personal growth journey forward

Check out the episode on your podcast app of choice to discover how to successfully lead client success teams.


[02:37] Why training teams internally matters

[04:14] Training frameworks to follow

[08:56] The state of customer education

[12:17] Managing your knowledge base

[15:58] Driving more value to clients

[18:25] Understanding user signals accurately

[20:46] The future of the CS category

[27:00] LEARN Rapid-fire round


Kristi: if you think about how we've hired for customer success over the years,

This role was supposed to be strategic and consultative, almost coming from a completely different background, like educators moving to CS. These folks do not have experience selling yet. We're giving them. The most important role right now in this economy, especially where we're not driving a ton of new sales, so we've got to work on growing the base. If you have a team responsible for it that's never done it before, and you're not investing in training and enablement, that's crazy to me. you're expecting these people to fish without a fishing pole.

Ted: Hi, I'm Ted Blosser, CEO and co-founder of WorkRamp, where we're redefining the corporate learning space with the world's first all-in-one learning cloud for employee and customer learning. Welcome to the Learn Podcast, where we learn from the biggest leaders in SaaS and hear what makes them successful.

Hope you enjoy the show.

Hey, welcome back, everyone, to the LEARN podcast. We have an awesome guest on today. Kristi Faltorusso, the CCO at client success. Kristi, thanks for coming on.

Kristi: Oh, Ted, I'm so thrilled to be here. Thank you so much. This is a pleasure.

Ted: Okay. Before we get into the main line of questioning, let's get the elevator pitch. On yourself and your career,

Kristi: All right. Awesome. for the past 12 years, I've spent my career in customer success and have really focused on building, scaling, and transforming customer success teams. B2B hyper-growth organizations. I started my career as a CSM and worked my way to a chief customer officer in 10 years. So I'm pretty proud of that trajectory and have been at five different companies where I've really got to help drive retention, growth, and advocacy.

Ted: give us a little background on ClientSuccess.

Kristi: So ClientSuccess, where I'm currently the chief customer officer, we are a customer success management solution. So we help customer success teams manage from new to renew that entire post-initial sales life cycle. So everything from onboarding your customers through that entire. Life cycle orchestration through retention and growth.

Ted: Do you feel like you have an extra spotlight on you? Cause you're the CCO at a CS company. What's that feel like?

It is the most meta thing ever. I thought it would be like this exciting, really cool thing. Quite the opposite. There's a spotlight on us because they're thinking that we would be the best, flawless execution at customer success. So when we... Slip up or we don't do something that they would expect that we would. I feel like we're letting them down in a major way. So I feel like there's a lot of pressure for us to be perfect, which changes the dynamic for me and my team and how we work with our customers.

Ted: It's actually funny. We, at WorkRamp, we sell to a lot of, sales enablement professionals, also CS professionals, but every email you write, you're like, okay, how are they going to really respond?

[00:02:37] Kristi: Yeah.

The quality of this email? So actually ups your game, but it makes you a little self-conscious at Listen, the coolest thing ever is when we have our customers take our decks and take our playbooks and take our resources when we use them on them, they're like, Hey, can you send me that? Cause that's actually really good. And we want to use it. those are our like epic moments where I'm like, yes, we're doing something right.

Kristi: Okay.

Ted: That's awesome. Well, let's start with this first question. So Kristi, you and I met a couple of years back at when you were at IntelliShift, when you were a customer of work rampwhat I always admired about you is how much you cared about training up your people internally. So. What I wanted to start off with is what is your philosophy around training your teams internally?

What have you experienced, from CSM all the way up to CCO in 10 years,

Kristi: Employee success equals customer success, and I've never felt stronger about a statement. The reality of it is, if you don't empower and enable your people to do the work you expect and need them to do, they can't be successful at their jobs. And the only way to get them there is by training and coaching them. you're going to hire folks from all different types of organizations. And the cool thing about that is they're coming in with all different experiences, which means they might not have the experiences that you need them to have to execute your strategy in your program.

Kristi: So you have to train them to do that. Just because someone held the same title that you're offering them in your organization doesn't mean the work they did is the same. So for me, we've put a lot of emphasis on making sure that everyone was very clear on expectations, but that we trained and enabled them on how to get there. And it's tools like ramp that obviously helped facilitate that in a really great way.

Ted: Let me dive a little deeper into that answer. You have all different perspectives coming into your teams. Do you have any more specific frameworks or even creative things you have done to make sure that that training has gone well?

Kristi: So I think what it is, is really focused on if we think about how we're measuring the individual programs that we're training our teams on. One is we try not to train on everything all the time. And because I just feel like that's a lot, we're asking people to do a day job, not be a student. So the reality of it is, is like the ongoing training enablement of your employees. What we've tried to do is just be very specific and have themes of things that we're focusing on. So for example, one month, we might be focusing on discovery questions. And like, that is all we will focus on in all of the sessions and all of the resources that we're producing for the team is how do we conduct discovery with our customers better? And so if we're training them on it. We're going to be doing things like role-play.

We might do some training modules. We might be reading books on things. It might be me designing videos for them and then watching these things. So whatever the resources that we're providing, we'll then go.

And in that case, if it's discovery ways that we like to train on this is to actually see, Are we doing a better job? Capturing goals and setting expectations. And all of this we're tracking in our CSP client success. So we've got visibility around it. Now, obviously all of those things should be leading to better outcomes for the business. So as a lagging indicator, we will start to draw on some correlation of like.Did we have a great understanding of their goals because we asked better questions now because we did that, did it over time result in stronger advocates, growth, or retention? So being able to understand what we're training them on and direct correlation to our business and our operating models.

Ted: Unless you're almost a hot take question, because you give a lot of advice to SaaS professionals in the, the CS, world, if you had to choose which one is the most important, where you're seeing the most deficiencies, I'll give you the categories.

One is essentially being a better CSM. The next one is. Upselling, cross-selling, growing accounts. Last one is understanding the product, details more. So you can actually service your clients better. How would you stack crank those or even your top one? I think it's a highly debated topic

Yeah, I'm going to have to stack rank commercial motions as number one.

Kristi: And the reason why is because there's been a hot debate, like should customer success own the commercial responsibility? So we're talking renewals, upsells, cross-sells, expansions, and I always say it depends.

So we shouldn't have a black-or-white answer to that. Cause there's a lot of things to debate there. But given that we are giving customer success teams, commercial responsibilities, if you think about how we've hired for customer success over the years,

This role was supposed to be strategic and consultative almost coming from completely different background, like educators moving to CS. These folks do not have experience selling yet. We're giving them. The most important role right now in this economy, especially where we're not driving a ton of new sales, so we've gotta work on growing the base. If you have a team responsible for it that's never done it before, and you're not investing in training and enablement, that's crazy to me. you're expecting these people to fish without a fishing pole. So for me, I would say like that is probably the area that everyone needs to focus on the most. the consultative part of it, I'd say probably second product I'm gonna put is third.

Ted: Agree with you. I think we expect CSMs, especially those who have no background selling to just like automatically wake up and be commercial sellers and think about actual AEs have been doing it for decades. and you're expecting CSMs to learn it in days, which is crazy.

On the topic of training and learning, let's shift gears a little bit from internal. Learning to external learning. So, training your customers, getting them the customer education they need. What are your overall opinions on the state of customer education as it stands today and your thoughts around it?

Kristi: I'm going to give it a rating on a scale of one to five and give it maybe like a 1. 5. So I don't think that many companies have a really strong customer education program in place. I don't think they were doing a great job educating our customers today. When I think about it as a priority though, It needs to be every company's top priority. All we've been focused on and all we hear out there is how do you do more with less, which I absolutely hate that statement.

But the reality is we're asking these teams to scale at a different rate and pace than we have before and their customers behave differently while we're reducing resources. We've got to figure out how do you up-level and be able to provide value to your customers. And I honestly believe that a customer education is key to that. If your customers don't understand how they can achieve their goals from your product and can do so independently of humans intervening with training and conversations. You're doing a huge disservice to them. course, there's outliers. There are some companies out there that are killing it and good for them. But the majority of SaaS companies that I speak to, that I work with, their teams have just not built out really strong customer education programs.

Ted: Let's dive into the formula of customer education. like the ones that are ranking, let's call four and fives on your one to five scale, what are they doing differently?

What is it that separates OK or bad from the great ones? And this could be even like what you've seen on the market, what you think is great, and why it's great.

Kristi: It's because it's a priority. Listen, people that prioritize this and understand the value are going to staff it. They're going to put the resources behind it. They're going to design really fantastic content. They're going to do it consistently. They're going to do it often. that is what separates it is that it is a priority because they understand the value. Once it becomes a priority, they're doing all the things, They're purchasing software behind it. They're making sure that every conversation is being documented. Understanding that there is a multitude of ways that your customers consume information today.

Being able to create it in ways that everyone can learn through their own way. People like to read, people like to watch How do you provide it all the way that they want it? But all those things happen when it's a priority. And that I would say that's the difference that I see in the companies that are nailing it and the ones that aren't.

Ted: Last minor question on this topic. Where would you actually say you would put managing knowledge base? Customer education in a team. What's the ideal spot in an organization?

Kristi: It depends on how complex practice now ideally I would love to have it sit in the customer success org because I feel like we're learning what our customers need because we were working so closely with them; we can then inherently take that information about what our customers need.

Pass it over to that group very seamlessly and actually start to produce that information, get feedback easier, So like we're able to just do that cohesively under one group and one umbrella. So that would be my ideal placement for it would live under customer success, but I could see and justify a ton of other places in the business where that would make sense.

Ted: What's up, everybody. We're on the episode now with Kristi from client success. She's talking a lot about how internal training and enablement is key for your teams. If you're looking for a solution to train your team members, you got to check out work ramp. com at work ramp. We build what we call the learning cloud, which is the all-in-one platform for training your employees, but also your customers and partners.

Visit us to learn more now back to the episode.

So we talked about internal learning. Then we talked about customer education, which is heavy on the onboarding process of clients. Let's move into, the messy middle with clients. So the time between buying and renewing when they might not love you as much.

Ted: I ran across one of these posts that you put up recently, you talked about the concept of QBRs. And your thoughts on them, give us this story, love to dive into it. 

Kristi: So this was actually like one of my most recent favorite experiences. I had the privilege of joining a VC firm's summit for their portfolio. And I had a room of all founders and executives and I basically poised a question. I said, how many of you attend the EBRs or QBRs of the vendors that you work with?

Please raise your hand. And sitting in that room, Ted, not one hand went up. And I sat there and I said, how dare we ask our customers to do things we wouldn't even do ourselves. It goes to show that this mechanism that we thought was the most powerful and the thing that we almost are conditioned to do as customer success professionals is do these EBRs and QBRs.

The motion is dead. It doesn't provide the same value that it once did. And so my whole philosophy on this is that you need to rethink it. There's not one way to do this. The objective is more important than the mechanism. And to me, the meetingis the way we achieve the objective, but the objective is different and there's plenty of ways to go get there.

Ted: Yeah, it's funny. I'm just picturing myself as a founder in that room. I would probably be embarrassed to raise my hand in front of the investors.

Kristi: So I did say, well, listen, I'm sure all of your investors that are sitting around this room also are probably happy that you're not spending countless hours attending EBRs and QBRs with your vendors because your time should be spent elsewhere. But…

Ted: But let me ask you this. So if it's not the QBR, What are you seeing as other ways to drive value within this messy middle? Do you have any best practices on that?

Kristi: Yeah, so listen, I'm not saying that the EBR or the QBR or whatever, that can't work. What that you need to meet your customers where they are? The objective of all this is how do we articulate the value that our customers have seen through the partnership? We want to be able to socialize how much value they're getting, how much value they can get, And be able to make sure that the value that we see as potential is aligned with their priorities and their goals. That to me has always been the objective. So how we do that is where I say this is where it's debatable. I don't need a 90-minute orchestrated meeting that's pulling on 10 people,

So what I've decided to do is actually figure out what are the ways that we can achieve that objective that meet the needs of our customers. So instead of just assuming that a meeting is the best way to do that, when we onboard our customers, we ask, and I say, part of what we will want to do throughout the partnership is socialize the progress we're making and achieving your goals.

Also, driving alignment on what the future could look like. Here are a few ways that we can do that.

If you're working with a POC, who's not an executive, how are ways that we can train and enable them on what they're doing, but then also what the possibilities are for the future. And this is where, again, coming into education, I think is huge because if we're thinking about. All the things our products can do and all the things that our customers aren't doing with our products, being able to educate them on those possibilities and how it correlates back to their,goals, their challenges, that's where the real value lies.

When you coach your CSMs, do you push on things like executive relevance more? Product usage more what is the thing you like to push on for your team?

Goal definement and achievement.

At the end of the day, if your customers are getting value because we are helping them achieve their goals. That is the only metric. The other things are false indicators because I've seen customers use a product every single day until they off-boarded your product because they were now onboard to another solution.

So you cannot convince me that product usage and adoption is the only signal you can use to say my customers are doing great, they're happy, they're healthy. No, if my customer wants to use our product once a month, but it is achieving the one thing that they need it to do, that they bought it to do. Then great, that's a win. I don't want to have these false indicators internally. So no, I do not look for activity. I look for impact. I don't care what you're doing. I care that what we're doing is driving the right results.

Ted: Love that. So funny. They're even actively engaged in their off-boarding process.

Kristi: It's my favorite story as being a Customer Success professional Everyone was talking about, yeah, no, this customer is healthy. They're great. They engage with us. They're using the platform every day. Look, usage has never been higher. Of course it hasn't because everyone has been in there exporting data and taking everything out and getting ready to prep for this other solution that they're putting in place. So we cannot misread the signals. And that's why I feel very strongly that. The main thing that you need to do is have clarity around what your customers purchase your product to do. Ensure they're set up to do that, that they can independently use your product to get there and that eventually they do.

Ted: This will be the last question I'll ask in the CS category. I want to shift over into some personal learning experiences too. But wanted to just get your take. about the category itself and this is a very specific category, but my broader question is. What do you have in terms of predictions for the CS category in the future? Let's call it three to five years. Do you see any big trends? And that could be anything ranging from tech trends all the way to, personnel trends or how, companies engage with their customers.

Kristi: From a technology standpoint, we're going to see AI and automation augment a lot of the work that customer success professionals have to do. Not in a way that will displace them. I do believe that humans are still necessary. People buy from people,There is a very strong need to have relationships to be driving value. I think technology will innovate in a way that will empower CSMs to do the work they were hired to do. If I look at how customer success teams today are spending their time. I won't even say a percentage, but it is an unhealthy amount of work that is not engaging the customers towards value realization.

We're doing so much busy work. There's so much administrative overhead. I think technology will be a huge step forward for customer success professionals.

Ted: You think we're probably spending, on average, 50 percent of our time probably wasted on, tasks that can be automated out.

Kristi: I would say it's under 50, but like over 30 and depending on the CS team. But just too much time. And we're not taking into account internal meetings and all these other things. So if I just think about a hundred percent of a CSM's time in a week, it's still too much, right?

Because you hired them to engage your customers and to drive value with them. If that's not where they're spending the bulk of their time, that's a misstep.

Ted: I'm so excited about that too, because I think a lot of rules of thumb out there depends on your business, but roughly 2 million of ARR per CSM. But if you think about this future that you're describing, it's like, Hey, you can imagine. Let's say if that is 50 percent time, you can get even more capacity, 3 million per head, and you can continue to see us being, even more efficient but providing a great level of service.

Ted: I love that.

One thing I've really admired is you spent a lot of time personally learning and achieving things Give us your philosophy on personal learning, personal improvement. so that other people can hear about, Hey, there's other ways to learn than just sitting front of your, computer taking an online course.

Kristi: I think personal growth is something we all have to commit to and it needs to be part of our every day. I always try to say, like, am I 1 percent better? Am I a little bit better today than I was yesterday? Did I learn something new? Am I more efficient? Am I more proficient? and so it's just something that's, Become a big personal commitment of mine because I just want to have that growth. I spent a lot of my time trying to have the right relationships with folks. I find that a lot of my growth comes from learning from people, And not just other customer success professionals, learning from other professionals, period. Although I will say. I learned from my husband every day. we don't work in the same field. We don't do the same things. but I'll learn from him every day. So it's, for me, it's a lot about where can I learn from and are the right people who are surrounding me providing me with those growth opportunities I think I spent a lot of time trying to be the smartest in the room until I realized that wasn't doing me any good.

So I tried to find myself in circles where I knew the least about whatever that topic was. And I found that in the conversations I was having, I was growing infinitely faster, and being more proficient in my job because I'm taking those learnings that I wouldn't have learned otherwise. And I'm able to bring them to work, to my network, to my friends, peers, colleagues.

Ted: When you've made the biggest leaps, do you have,any tips you've made from an improvement standpoint?

Kristi: Yeah, it's discipline. if nobody's read the book, Atomic Habits, creating those habits, I think are really big and building those into your day to day and start small.I started with little things that I did every day. I mean, for me, it was making my bed, getting up and going to the gym every morning

It's just designing these little habits and they transcend into every part of my life. It is not just something that impacts me physically and mentally. And from a health standpoint, it's having good habits and staying committed to the things you commit to.

Ted: That's dedication. well, we'll head into our close here. This is called the learn lightning round. What I'll do is just ask you a few questions. Give us one or two line answers for each. So the first question I'll ask you is. What's the podcast book or blog that's top of mind for you right now.

Kristi: I think I'm just gonna have to go back to atomic habits and only because we were just talking about it and how it's really helped me reshape my behaviors every day.

Ted: And I think I've been recommending that book like 15 times. I got to actually go read it.

All right, next one. If you could learn from one person alive or dead, who would you want to learn from?

Kristi: Probably Jeff Bezos. I probably spent some time with Jeff I'd want to like rebuild my own version of Amazon.

Ted: Wait, like current Jeff Bezos or old-school Jeff.

Kristi: No, old school.

I want the who's designing the efficiency, and like, just crazy thoughts that have to go into seeing something and having a vision so much bigger.

Ted: All right. Last question I'll ask you, one to two initiatives you want to nail this year.

Kristi: I think the big one that is probably most, focused on is probably onboarding for my team, for my customers. We have redesigned it a few times I am. Really, really focused on just getting this right. So we just keep dialing it in and dialing in and trying to make it better. So I want to see by the end of this year, like we have fully optimized onboarding to a point where it becomes a machine for my team.

Ted: Love it. Sounds like, Brian Chesky at Airbnb is always talking about the, 11-star experience, but he keeps honing his experience in to make it the best experience possible. well, Kristi, it's been great having you on here today. Thanks for joining us. This is such a cool session.

Kristi: Thank you so much. This was so much fun. It was great to connect with you again.