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How Philip Simon’s Leadership is Redefining Customer Success at Scale| Mastering CS – Ep 32

December 4, 2024 20 minutes read

Summary points:

In our new episode of the Mastering CS, Candid Leader Insights podcast, Irina Cismas, Head of Marketing at Custify discussed with Philip Simon, Head of Customer Success at Rule.

What You’ll Learn:

  • How to balance work life and personal life
  • The importance of a customer success team
  • How to prioritize customer success in a startup
  • How can CS help in the acquisition process

Key insights and takeaways for CSMs based on the interview:

Customer Success is Relationship-Driven: Philip emphasized the importance of maintaining a strong, ongoing connection with customers post-sale to help them succeed, which is the core of customer success.

Balancing Leadership and Operations: Effective customer success leaders stay involved in day-to-day operations to understand challenges but avoid micromanagement. Coaching and empowering team members are key to success.

Proactive Customer Engagement: Understanding customer goals and usage patterns allows CS teams to proactively offer solutions and highlight unused features, which enhances value for customers.

Scalability Through Technology: Philip advocates embedding customer success functionalities within platforms to scale engagement while maintaining a personal touch, ensuring customer needs are met efficiently.

Podcast transcript

Intro
Irina 0:02
Welcome to Mastering CS, Candy 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 Philip Simon, Head of Customer Success at Rule. Philip, welcome and thanks for joining us today!

Philip 0:18
Thank you so much! Nice to meet you.

How Philip Ended Up in Customer Success

Irina 0:21
My pleasure. Your background is in IT, security and consulting. I have to ask, what pulled you into customer success?

And what was it about CS that caught your attention over everything else you could have focused on?

Philip 0:39
That’s actually a great question. So if you look at my background, I used to work a lot with sales. What I really liked with sales was like finding the right product for the right customer and actually having a good fit for the customer.

But what I didn’t like about the sales that I used to work with is that I didn’t like getting a customer, send it over to someone else, and then they are the one that’s responsible of that customer. I felt like I still wanted connection with the customer and still helped them to build not only the relationship, but also build around the product. So when I actually saw that Rule had an application called, the role was called Customer Success Manager, over half years ago, I just felt like, okay, this sounds good.

What is Customer Success Manager? That sounds like a really interesting thing to help the customer to success. So the reason why I even applied to that and why I am in customer success today is because I really like helping existing customers and clients grow.

But not only when it comes to existing customers, I also like existing people working at the company, helping them to grow. So what I have been doing, I think last two years is that I’ve been focusing on only customers. I’ve been also focusing a lot on leadership.

So I’m not only responsible of some customers here in Rule, I’m also responsible of our customer success department and support departments. So we have divided it into two departments, but I’m the leader of both of them.

A typical day for a Head of CS

Irina 2:15
That’s interesting. And I do have some extra questions about the way you structured your team, but let’s skip them for later on, because first I want to understand what a typical day look like for you as head of customer success and what’s keeping you busy lately? Start with that and then we’ll go into your team as well.

Philip 2:37
Sounds good. So I would say there is no, it’s kind of cliche to say it, but there is no day that looks the same as every day. Every day looks different depending on what kind of challenges you have during the day.

But we do of course have some like, sorry, when it comes to like structure on things, we start actually the day with the morning syncs together with the whole team, where I’m the one that’s responsible of making sure that we have these syncs every day. And we go through actually what kind of customers are getting in touch with us, what kind of challenges, what are people getting in touch with us and where are they, where is the problem in like the product or the needs that they have. So that is always the way to start the day.

Then something we usually also do that I’m involved in of course is, we call it rule daily, where we basically connect the whole team, not only success and support, every department and everyone working at rule tells like, what is the best thing that happened yesterday? What is the most important thing for today? And if I need any help, these are like regular things that we do on a daily basis.

But when it comes to exactly where I have some things that I need to jump into is if some customer maybe doesn’t understand how to do something in the platform, or if we have someone who decided to turn, we need to speak with them onboarding processes. But mostly I coach and help people in my team grow. So that is mostly what I do on a daily basis.

And that can be, I mean, jump into meetings that they have to help them find things that they can improve in their role, understanding basically what they want to get better in.

Customer challenges and how to overcome them

Irina 4:24
I really like the fact and I think you are the first one mentioning the, I would call them because it’s similar with the daily, the daily scrub meetings that you are handling. And you basically took the concept from the agile methodology and you put it into customer into customer success. And that’s an, that’s an interesting, that’s an interesting combination.

And yeah, it seems like you are balancing the leadership or leadership part with also keeping an eye and keeping, I would say 20% of your time on the operational stuff to have one, to have a sense of actually what’s, what’s going on. And I think this is, this is very important because it keeps you connected with the day to day challenges of a CSM. So you can understand their pain and actually provide them, provide them real solutions.

Now I want to understand about your customers and what kind of problems do they usually run into when it comes to digital communication?

Philip 5:34
That is a great question. And just to get just some really short information about the company itself, basically we are a SaaS solution for digital communication, as you said. So we have a SaaS service where the customer logs into the platform, they create their newsletter, their order confirmation, shipping confirmation.

And it really depends what kind of customer you are. For example, if you’re an e-commerce customer, the only thing you’re thinking about is selling a lot and earning a lot of money. And I mean, that can be kind of boring to only speak about.

So we, we have all kinds of customers. We actually have over 2,500 customers around the world. We’re quite big in Nordics.

We compete against big American companies like MailChimp, Klaviyo, some CRM solutions. So we really compete against the hardest competitors in the industry. What kind of customers we have?

E-commerce customers, media customers, B2B companies, all kinds of customers, basically. So it’s, it’s really dependent what kind of industry you are in, but I would say the biggest challenge a lot of people have, even it doesn’t matter which company it is, it’s actually having time to sit in the platform and build things. They want to do a lot of things.

They have so many ideas, but they don’t sit down and do one thing in time. So instead of having like a list where you have like five things you want to do, they just say like, okay, we want to do 50 things. Okay.

Where do you start? They don’t even know that. So instead of setting up something, they don’t set up anything.

So I would say that the biggest challenge and the solution part where we come in is that I don’t send, we’re really upfront with our customers and say, we are not selling consultancy. We don’t want to sell hours and sit and do these kinds of things for you. However, we have agencies that work in our platform that can help you.

So instead of doing the work for them, we would highly recommend them to use agency. We want to be a provider for email, SMS, every kind of communication, but we don’t want to be their agency.

Irina 7:52
Okay. So if you aren’t actually doing the stuff for your customers, now I’m curious, how do you support and assist the customers overcome the challenges that they have from your CS role? How do you proactively engage with them to help them achieve their business goals from your CS role?

Philip 8:13
Very good question. I would say the most important thing is to understand why they even have Rood. Like what is their goal with Rood?

Is it to sell? Okay. Where should you sell more?

Is it in SMS channel? Is it an email channel? So for example, let’s say that the customer is only sending newsletter to all their customers.

Okay. That’s good. But do they do segmentation?

No, we can actually track and monetize this. We have a customer success tool for this where we track it and it’s working really, really good. So we can see how all our customers are working in our platform.

And then we can proactively call them and say, hey, I see that you’re not using our SMS feature. Would you like to see how it works? And they say, no.

Okay. Why don’t I want to see it? So these kinds of things is something that we do from the customer success part to find what are they not doing in their platform that is connected to their goals.

Low-touch or high-touch CS strategy

Irina 9:11
And in terms of CS strategy, is it a hybrid approach? Is it a low touch with a high touch? So it’s a combination between them?

And how did you decide who are low touch and who are high touch? Or how do you split? How did you do the segmentation?

I’m curious.

Philip 9:29
Yeah. So what we do have is of course, we have some kind of packages when it comes to our platform. We have actually three different kinds of packages in room.

It’s more like the pricing part. We actually do have a freemium where the customer can use our platform for free. You don’t pay anything, but then you’re not allowed to contact, get in touch with our support.

Everything is self-service. This one works really good if you’re either a really small company, or if you’re a startup. So let’s say you’re a startup.

You just want to send newsletter to up to 250 customers. Go ahead, use it. We hope you grow.

Now that’s the easy product. Then we have the professional one. The professional is basically our most used one.

That one is dependent on capacity level. And capacity for us is dependent on how many contacts you have. For example, how many email addresses you have, phone numbers you have.

The pricing is based on how much capacity you need in the platform. And those kinds of customers, the same thing, the platform is self-serve. However, they can get in touch with our support department if they need any help or guidance, or if there is something that they don’t understand.

This is the reason why we also have connected the support and customer success so they are close, is that support department can find customers that get in touch with us daily or several times a week and say to the customer success team, hey, this customer is asking a lot. Maybe they should have a workshop. Try to sell in a workshop for them so they can sit down, ask all these questions, and then it’s a better relationship, first of all, but then it’s also a better way for them to connect with us.

We find these kind of customers that get in touch with us a lot, but then we also have those customers that are really big, that have the enterprise solution, and they are required to have a contact person, a customer success manager. Those get this daily, and those that don’t have it, instead of getting them to know that you can buy customer success, I’d get in touch with them and say, hey, we see that you should actually use this. I would say that’s the best way to find this low and high.

Crucial KPIs for CS

Irina 11:54
I somehow anticipate your answer, but I want to confirm it. What KPIs are you focused on right now in terms of CS, and how do you keep them aligned with both the company goals and what are your customers’ needs? Because there’s always a balance between company goals and what the customer wants.

Philip 12:18
Of course. No, that is, of course, true. That’s really hard.

I think for a lot of companies, it’s hard to make sure that the customer goals are the same as your goals. I would say that our biggest KPI is our annual recurring revenue and our net revenue retention, our NRR. When it comes to the ARR that we measure every day, we basically have how much, for those that have not heard the term before, how much will we earn if we just stop everything and we don’t get any more customers?

This is the ARR we will have annually. The thing that is really cool with Roo is that you pay for capacity. If you grow out your capacity, the ARR is going to go up on you and the ARR is going to go up for us.

Irina 13:08
Yes, you have a value-based pricing model, which works very well. You basically grow with your customers. If they’re successful, you are also successful as a business.

Philip 13:20
And it aligns perfect because if they grow, I would say nine out of 10 customers is happy and say, hey, I have no problems with paying more because, of course, you need more capacity and we’re going to pay for it. The last customer that don’t feel, no, this is nothing for me, you know what? You can decide how much capacity you want.

If you want the lowest one, you can delete your subscribers, but we don’t recommend that because you have been growing. That’s a good thing. You should be happy.

So that aligns really good with the company goals and the customer goals. And we do have a North Star metric, which is basically engaged subscribers. And this is how we help our customers to get engaged subscribers.

Irina 14:00
And how do you measure engagement into the product?

Philip 14:06
It’s quite a simple metric, but we look a lot in the opening rate and the click rate, like how many customers of our customers, subscribers open their emails and how much they engage in that. It’s a simple metric that we actually, our companies also use as an engagement. So we basically just copy that and say, hey, okay, this is a good metric that we also look at.

And I can’t say exact numbers, but we talk about millions. I mean, we’re sending millions of emails every day. And of course, we’re going to be opening.

So that’s how we measure. And it’s growing a lot. Since we’re growing in customers, they are growing in subscribers.

We’re growing in the opening and the click.

How to structure your customer success team?

Irina 14:53
Awesome. Because you mentioned that mostly in the last few years, you invested into leadership, coaching the team, growing the team. Now, I want to understand how did you structure it to make it run efficiently, but also staying customer focused?

You mentioned something at the beginning that you are leading both CS and support. Provide me more details about the structure and the way you split this.

Philip 15:24
So I think, like, if you would ask my team why they like this kind of structure, I would think they would basically answer that the reason why they like the structure is because support and customer success, both of the teams are working with customers and they have daily contact. And why they like that I’m helping them with the leader part is that I’ve been doing this before. So when I started working at Rule, we actually, quite a funny story, but we actually talk about this and laugh at it, that the first day I started to work at Rule, I just jumped immediately into the support.

I was alone because this was during vacation. I had no idea how the platform worked. I had no idea how the customers were feeling about this.

So I just tried to find the answers that they needed. So I’ve been working as a support agent. I’ve been working customer success as a customer success manager.

And the reason why this is good is because I have this background. This is the same as someone who’s a sales manager that also works with sales, because sometimes you need to show them how things can get done instead of telling them to just do it. Sometimes you have to also show it so they can see this is actually a good way to do with the customer.

So the way I manage today is that I still keep some customers that I work with. To have this, you know, as you said, 30%. But then I also sometimes jump into some phone calls with the customers, win back cases, I show them sometimes like, okay, this is a customer that said that this is the reason why I decided to churn.

I’ll show you how I will speak with this customer jump with me into a meeting and you will see. And then I show them just how to do it. And then they take notes and then we have feedback part.

So I think that is a good way to structure it that also sometimes jump in to show it. But for me, it’s also really, really important to not do their work. There is a reason why we do have support agents.

There’s a reason why we have customer success managers, because that’s their basically daily basis what they should do. So I don’t want to take over their work. I just want to keep them engaged and motivated.

Necessary skills for customer success managers

Irina 17:39
I’m curious, because you mentioned tyou jumped into and you’ve done a bit of support. And I know that you were also when you mentioned you were in sales management, you did customer success. From your perspective, what skills do you think are absolutely must for a great customer success manager today?

Philip 18:05
That’s a really good question. So I think the best customer success managers is the one that actually understands what the customer wants. And to understand that we do have a way to do.

So for example, let’s say a customer wants to do something in the platform. Ask them why five times. If you ask them why five times, you will actually understand why they want to do that instead of just running and do what they want.

We had so many cases where a customer wanted us to, for example, develop a function in our platform. We developed it. They have never used it.

Irina 18:38
Exactly. Yeah, we know this. We know this scenario.

And I think that’s one of the hardest things to understand, actually, the why behind what the customer is telling you, because what it tells you, it’s not 100 percent what he wants. He just wants something and he doesn’t know how to explain it. So I think, yeah, the five why your strategy works like a charm.

And to be honest, this is what I find also the hardest thing to do when I’m running those interviews, when I’m trying to understand what’s the value that we are actually bringing for the user, because they are telling me one thing. But if you correlate it with the other data points that you have around you, the math is just not there. So something is something is missing.

Philip 19:24
I completely agree with you. And you need still the balance with what the company wants and what the customer wants. So customer success manager is it’s a really cool role.

I really like working with customer success overall. And to understand the customer’s needs, you still need also to connect it together with what the company from your end wants and what they have, what kind of achievements they have, because it’s so important. We we we have something in Sweden, I suppose this is something that’s around the world that we call a smart goal, which is basically, you know, that it’s specific that you can measure it.

Irina 20:01
Yeah.

Philip 20:02
And that is so important to have, because if you don’t have that, you’re just running around circles and doing what the customer tells you to do. So we back instead of doing it just back and ask, OK, why do you want to do this? OK, because this OK, why will this be a good thing because of this?

OK, whenever you have done this, why will why just ask them and understand it in a better way?

Building a team from scratch vs scaling a team

Irina 20:25
What’s more challenging in your opinion, building a CS team from scratch or scaling one that’s already in place?

Philip 20:31
So that is a great question. Quite biased in that one, because when I started to work at Ruda, I was alone in the customer success management. So I built it by myself.

So I decided basically this is the way we should do. I would say scaling is harder than building, at least. I think building part went quite good because.

I mean, there are cons and, of course, pros when it comes to it, because when you’re building it, you’re doing it alone. When you’re scaling, you’re scaling together with the team. So there are pros and cons.

But from our end, I felt like building it was a really good way to do it. And I learned a lot. But scaling part is easier when it comes to that you can get feedback.

You can tell it to your team. Hi, guys, is there something that we should do? Do you like it?

If not, OK, how should we instead do if you’re alone and you start to build it by yourself? You have to. You’re not going to get the same feedback.

But from our end, I felt like building was easier. Scaling is tougher because then you need to include so many more. So it’s not only that you need to do it by yourself, you need to include more.

And that doesn’t only mean that you get a lot of good feedback. It can also be that some people are maybe not on the same page. And then it can also mean that, you know, if it’s a fast growing company, that’s not for everyone.

And then it’s a hard way to tell an employee. Maybe this is not a good fit because you need to do it in a nice way. But usually the employee also feels the same way.

It’s tough. It’s really tough to scale.

Prioritizing What Matters in CS

Irina 22:15
Talking about the tough things, I’m curious how to navigate the following scenario. Usually, CS teams have a ton of different things thrown at them. And how do you make sure your team is focusing on the right things and make a real impact with your customers?

Because it’s easy to get busy and drown in all the nitty gritty mandate tasks and to not see the big picture. How do you make sure they are working on what actually matters?

Philip 22:49
I think by just listening in. To be there as a coach and just to listen in. Don’t do the work for them.

Just be there and listen in. A lot of like jump into the meetings they are in, not micromanagement. That is not what I try to say because I hate micromanagement and we don’t want to have this in our company.

I know it’s a lot of American companies it works. But from our we really like to just listen in and understand why do you feel that you really need to do these nitty gritty things with the customer? No, it’s because they are really angry right now.

Okay. Is the best way to solve this or is the best way to do something else with the customer that is actually bigger than what they are asking for? For example, let’s say that you have an issue and you solve that issue.

That was expected that you help them with their issue. But let’s say that they have an issue and not only that you say that, okay, I will look into this, but I do have something that is even better for you. And that is actually this.

That is unexpected. And that will also, then you will connect the curiosity that you’re curious in helping the customer. So I think by just listening in coach them as much as possible and help them to succeed.

And of course, there are some like managers who think just if you tell someone to do it, they will do it. That’s not how people work. If you tell someone to do it and they don’t do it, then you have to understand why they haven’t done what you asked them for.

And then you have to work with that. So in my opinion, there is a like good, like say this, like there is no bad soldiers. There is only bad leaders, in my opinion.

If you don’t lead good, then it’s going to be the same.

Irina 24:33
Let’s go back to the business side of things and to you. And I want to ask you what’s been your biggest challenge lately as head of CS, especially with all the changes in digital communication?

Philip 24:45
That’s a good question. I actually did have a really big challenge. We got a new customer success manager here in August that joined the team.

And whenever he joined, I said to myself, OK, he’s going to get all my customers now because I have to, I have to give them to someone else. I had customers that I have been having relationship for over four years. These are just that, you know, are so loyal.

They really like working with me. We have a really good friendship also outside the company. And to give that kind of, you know, just, hey, I really love working with you, but you’re going to have a new contact person, nothing personal.

That was quite tough. We did have some customers who said like, please tell me, are you leaving the company? I have to know.

Oh, no, I’m not leaving. I’m going to stay here, but I’m going to focus more on the leadership part. So that was a quite tough challenge, just to know from my personal perspective to give them over.

But things have been going so good. And I can also see that they are getting so good attention. And that is, for me, the most important that they still feel the same attention that they had.

And then it feels good. But it was a tough challenge to, you know, just give them over to someone else.

Plans for the future

Irina 26:00
I can relate to how your customers felt, because I know myself that whenever the account manager changed or the CSM with whom I was interacting, for me, it was totally a drama. So starting the relationship from scratch with another person, for me, it was very, very hard. It was like I was, it’s something like the relationship broke at that moment.

And we had to start it from zero. So I can relate to how the customers felt. Now, I’m curious, if we look ahead, what are your big goals for the rest of the year?

How does Q4 look like for you? What are you planning to achieve from a CS perspective?

Philip 26:47
Very good. So something that we are really looking into, because you were speaking about scaling. Yeah.

Look at, I mean, right now we have over 2,500 customers. Of course, we can’t have a customer success manager for every customer.

Irina 27:02
For sure.

Philip 27:03
So what we are looking into and trying to find is a way to build customer success into the platform. And this is actually really cool, because this will, instead of having one customer manager who tells every day the customers, hey, you should use this function, you should use this and that, the platform will tell it for them. So rule will be their customer success manager.

And this can be scalable. So we can have every customer on a daily basis. Let’s say that you log into the platform and say, hey, hope you had a great start of the week.

I see that you haven’t sent a newsletter in one week. Would you like to create one? Maybe you should write about this and that.

This happened on the weekend and this is the weather right now. Maybe you should have that in your newsletter. Imagine that as a co-pilot and same time customer success management.

That is really cool. So that is a really big, big goal that we try to achieve. And we have some really good ideas, but we just, of course, need to find time to build this.

The right tech stack for customer success

Irina 28:05
I like the fact that you mentioned technology because definitely somehow it plays a big role in the CS these days. And I’m curious, how is your current tech stack and how are you using it to keep that balance between automation and real personal customer interaction? You mentioned earlier the fact that you have a CSP.

How does that CSP integrate with the other data sources?

Philip 28:32
Yep. So a very good question. This is also connected to, as you said, when it comes to like, we don’t want to remove the personal touch because we don’t want to be in the platform where everything is automized.

So let’s say that whenever we actually also have built in the customer success part in the platform, we’re not going to remove customer success managers. We still need them to still keep growing with the customer success part. But when it comes to the tech stack, we have, as you said, we have a customer success platform where we use daily basis.

We also have a ticket system where we have all our support cases, but not only support use it, customer success team also use it. So we have our own inbox for the ticket kind of thing that we have. And that is, of course, important.

We also have that you can call us and whenever you call us, you can basically say what kind of problem you have and then you will have someone answering at the phone. Then we also use Slack. We use them on a daily basis.

It’s a really important tool for us to communicate. Since we also have developers that are based in Sweden, they are based in Europe. We need to get in touch with them on a daily basis.

I would say these are the ones. And then, of course, a CRM tool that we often use because some people actually think that rule is a CRM tool and we’re not. We’re a platform for communication.

So we also use a CRM tool where we write a lot. Things about the customer whenever we have a deal, or if a man that is important that needs to be in there. So I would say these are like the main ones. Then, of course, this makes sense. We use rule as our own communication. So when one creates a account in rule, you get Hey, thank you for creating account. You get an email from us included in our text.

Advice for CS

Irina 30:32
Philip and what’s the best piece of advice they give you that still resonates with you today?

Philip 30:44
Very good question. So without being biased, I would say that it’s actually the one I have today. It’s actually my boss. He’s the vice president at rule, and he’s been helping a lot when it comes to my career, not only from, like, a personal perspective, but also, I mean outside route, how to think, how to solve like, whenever you know, tough challenges happen, he always gives me really good recommendation on how to think and how to how to act. And he he also speaks a lot about, like, when it comes to communication, it’s not about saying what you want to say. It’s about saying what the customer wants to hear. So it’s a lot about communication on the recipient’s terms. That is the most important thing, and this kind of mindset he had been helping me to understand so I can apply it down to my team, so they can apply to the customer so it goes like a lead.

Irina 31:46
Phillip, thank you so much for sharing your insights with us today, and a big thank you to all our listeners until next time, stay safe and keep mastering customer success!

Nicoleta Niculescu

Written by Nicoleta Niculescu

Nicoleta Niculescu is the Content Marketing Specialist at Custify. With over 6 years of experience, she likes to write about innovative tech products and B2B marketing. Besides writing, Nicoleta enjoys painting and reading thrillers.

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