Women in Customer Success Podcast

146 - From Intern At 40 To CS Leader with Adi Aloni

• Marija Skobe-Pilley • Season 5 • Episode 146

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What if the smartest move in your forties is starting over as an intern? 

In this episode, we sit down with Adi Aloni, Customer Success Leader, to unpack a rare kind of career resilience: going from an established career, to taking a leap into an MBA, to a humble reentry through a marketing internship, and then a decisive pivot into customer success leadership. It’s a story about trading ego for opportunity and discovering how a nonlinear path can be a competitive edge.

For the first time ever, Adi shares her career journey and walks us through the phases of building customer success from the ground up: early days with a handful of customers, finding product‑market fit, scaling teams and specialisation, and finally shifting to sustainable growth with sharper retention and efficiency. 

We discuss:

  • Why active listening outperforms any script 
  • How to price time and expertise so “free” help doesn’t become invisible
  • What it takes to maintain momentum when you choose to stay at one company for a decade 
  • AI’s emerging role in customer success


She also shares why she believes that the grass isn’t greener; it’s better watered—especially when you have the right people, a product you believe in, and permission to shape your own role.

This conversation will leave you inspired so tune in and enjoy.


💚 This episode is brought to you by Deployflow: https://deployflow.co/


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👉 Follow Adi: https://www.linkedin.com/in/adialoni/

👉 Learn more about Deployflow & P-Suite by Deployflow and get a quick squad estimate at: https://deployflow.co/p-suite/




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About Women in Customer Success Podcast:

Women in Customer Success Podcast is the first women-only podcast for Customer Success professionals, where remarkable ladies of Customer Success connect, inspire and champion each other.


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Host Marija Skobe-Pilley

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SPEAKER_00:

I have a very interesting career path. It's very not linear and had multiple restorts. When I moved to the US, uh that was a very big transition in in my life and in my career. And I really had to restart my entire professional life, which brought me to be an intern at uh about 40 years old and uh grow my career from fresh there. I think you have to in a way put your ego aside to do something like that and understand that this is an opportunity. It's look, it's not fun, right? It's definitely something that felt like a compromise, but on the other hand, it was a foot in the door. And I knew that once I get the opportunity, I'll know what to do with it and how to make it into something real. Make sure that you're you feel okay with the choices that you make at every different stage in your career and in your life.

SPEAKER_01:

Hi everyone, it's great to spend some time with you today. I'm Maria Scove-Pille, and you're listening to the Women in Customer Success podcast. Today, it's really a pleasure to welcome a special guest. She is an executive customer success leader, and I'm super excited because today she's going to tell her career story, very impressive and interesting career story for the first time, I believe. So I feel honored. Please help me welcome Adi Alone. Welcome to the show.

SPEAKER_00:

Thank you. Thank you, Lauriane. Uh, really excited. Thanks for having me and giving me this opportunity.

SPEAKER_01:

Adi, where are you from? And where are you calling from today?

SPEAKER_00:

I'm uh based in uh the San Francisco Bay Area for about 18 years now, and that's where I'm calling from.

SPEAKER_01:

And Adi, would the 16-year Adi be surprised to find you just in career where you are today and in the position where you are?

SPEAKER_00:

Great question. I think there are some aspects that will be surprising and some aspects that will not. So I, you know, I've always been ambitious and pushing the envelope. And I don't know that I thought in high school in Israel that uh I would be in the Bay Area at this point. But in in terms of career, I think there are definitely aspects that I could that I could predict.

SPEAKER_01:

As we will spend some time talking about your career today, would you like to tell the audience what they can expect to hear from you? Or is there anything surprising why they should keep on tuning in?

SPEAKER_00:

I have a very interesting career path. It's very not linear and um had multiple restorts. When I moved to the US, uh that was a very big transition in in my life and in my career. And I really had to restart my entire professional life, which brought me to be an intern at uh about 40 years old and uh grow my career from fresh there.

SPEAKER_01:

Okay, so you've been an inter at the age of 40. I love that. And I love that we are gonna dig into it. Okay, let's start. Where actually would you like to start with your career journey? What is a good place?

SPEAKER_00:

Oh, uh the start, the beginning, maybe. At the beginning, maybe, yes. Yeah, yeah. So um, like I said, my my path is very uh not linear because I'm I'm you know, I'm curious. I want to try a lot of different things, which I think my undergrad is industrial engineering, which is also some kind of uh studies that are not decisive in a way. You know, you're not fully an engineer, you're not fully uh uh a business person, you're somewhere in between. And I think that represents very well that that phase of my career. After my undergrad, I worked in supply chain management, I also worked in IT, in systems analysis and implementing ERP platforms. I was actually the the role that I liked best was the role where I was a liaison between IT and the practitioners that used the ERP system. So that was like the early um phase of my career with, like I said, multiple switches between those horizontal switches. And then when we uh decided to move to the US following my uh my husband's job, I actually didn't have a working permit. And I thought that it would be, you know, a very temporary phase. I was ready for it. I had young kids that um I actually welcomed the opportunity to spend more time with them uh and not be a working mom for a little bit, but it ended up lasting six years between the time that we got to California and the time that I got my work permit. And I'm going to speak to the older audience here. Um, I don't know if you were familiar with the TV show that aired during those years was that was called uh Desperate Housewives. Um and when people asked, when people asked me, like, what are you gonna do in the US if you don't have a work permit permit? My answer was, Well, I'm gonna be a desperate housewife. And anyone who knows me knows that that's completely enough my jam.

SPEAKER_01:

So definitely going out for brunch, lunch, the whole day, just having fun, spending time isn't your jam because you want to do something else as well. So, how was it then for you? Like what did you decide to do?

SPEAKER_00:

So, in order to keep stimulating my other parts of me, um, I actually enrolled in uh in an NBA program here in uh in a local university, a really great university, Santa Clara University here in uh in the Bay Area. And I went through an evening program. It took me about three uh and a half years to uh to graduate, but I really enjoyed it. I started this program with a nine-month-old baby. So, in a very um, you know, cosmic uh uh way, I got the the green card pretty much at the same time that I graduated uh school, and I was able to um to start looking for my next uh chapter. But at that point, I was um never employed in the US. I was six years out of the job market. I wanted to do a career change because I went from uh the back office of the business um and I wanted to be in the front office of the business after my MBA studies, so I uh wanted to actually go into marketing. And okay, where where do I even start? Right. So I started just uh networking and meeting with anyone who would meet me, and I was very fortunate to meet someone who decided to just give me a chance, and I started um as a marketing intern.

SPEAKER_01:

Okay, you've been out of the job for a few years, but you were doing MBA. So by default, in theory, once you do MBA, you know, one could think, yes, all the doors are open for you. It's like the ultimate of the education, of course, it's MBA, but it's not exactly like that. So you be networking and basically asking for the opportunities, right? So you landed that marketing intern. Now just tell us a little bit how did that feel for you after, you know, having already been accomplished in your career, yes, had a little break, but again, doing MBA, like you were still, you know, intellectually stimulated, you were still, you know, looking forward to a big career, but then you are an intern. How is that starting from the scratch again after all of it?

SPEAKER_00:

I think you have to, you know, in in a way put your ego aside to do something like that and understand that this is an opportunity. It's look, it's not fun, right? It's definitely something that felt like a compromise, but on the other hand, it was a foot in the door, and that's what was important to me is that opportunity for a foot in the door. And I knew that once I get the opportunity, I'll know what to do with it and how to make it into something real.

SPEAKER_01:

And do you remember as an intern in marketing, because that was the new feel for you at the time? What were the type of things that you were doing and learning?

SPEAKER_00:

It was awesome. So the learning was actually awesome. I was a generous marketing manager, and the internal part ended up lasting only a few months because then the marketing manager who was then in this position left and I was able to step in. And they they actually brought a marketing leader, and I was able to learn from her. So it was a really good opportunity to understand all the ins and outs of digital marketing, like the basic building blocks of marketing, and also a very good skill to have.

SPEAKER_01:

And that was the whole basis of your kind of new career in marketing. So now tell us, how were you taking kind of next opportunities to build your career? And and where did that initial marketing internship lead you? We already see next step was you know being being a manager. Then what was next? How were you navigating that whole kind of new career after 40s?

SPEAKER_00:

What I wanted to do is be much more intentional about my career than the first phase of my career before moving. Um, I think it's something that um, you know, on one hand, I I had this drive to not be left behind because I was already feeling that I'm behind uh compared to my peers, for example. And I had this drive to catch up. On the other hand, it it's about how do you create the opportunity? How do you choose the which opportunity to take? So some of these is, you know, sometimes it's just pure luck, sometimes it's understanding, you know, among the things that are available to you, what is the best thing to do. And that's actually how I found myself in uh in customer success. Because I was thinking of myself as in a trajectory for you know more senior marketing roles and how do I get there. And then I met again through just my personal network, uh, the founders of Follows, the company that I ended up spending 10 years at. And at first, I just uh we just did a project together and we were just we just really enjoyed working together. And we were thinking, okay, how what's the best way to uh to keep this relationship going? And after a couple of months, uh he tied back, the founder of Follow, one of the founders of Follows. Um, he came back to me and said, you know what? Um we don't have a marketing, a full-time marketing uh opportunity right now at Falls, but we have a customer success. Uh we want to start a customer success uh team. And um you know marketing, we sell to marketers, and so what a great synergy there. That's how I ended up in customer success. And I think that was one of the best decisions that that I've made in my career because I really found my calling in the sense that you have to know so many things when you do customer success. It's so interdisciplinary. And I had this like really varied uh broad background in in very different fields in in you know, in IT and in supply chain management and and then in marketing, and being able to talk to marketers, but also understand, for example, the back-end things that they're dealing with. That was like for me a really good home paladin uh experience that I really, really enjoyed.

SPEAKER_01:

So at some point you were very skilled marketing generalists, just knowing the industry inside out. And that skill set brought you into customer success because you were absolutely perfect persona for the company that was selling two persona that you used to be until yesterday. Right. This was an amazing foot in the door. Now, in customer success, you you're saying it was an amazing decision. It sounds like you found your, you know, again, a new professional home in that industry. Now I wonder what have been some instances of you leading different teams and spending, you know, 10 years in one company, which is pretty long time nowadays. Yeah, what comes to mind as some kind of pivotal moments, either in your career or or even in developing customer success? Like you have seen the changes and how it all went. What are the things that you can really draw upon today and say, you know, those have been not only wonderful moments, but something that I've really seen how the industry has evolved?

SPEAKER_00:

I look at my career as falls as three or four different careers. Because, like you say, you know, 10 years is is a is a long time. And and um at different points in in this journey, you know, I asked myself, like, is this the still the right place for me? Um, do I need to make any changes? And for those 10 years, the answer was always no. I'm I'm happy here. I really enjoy working with the people that are around me. I really enjoy the opportunities that I created and that I was given. And I enjoy my my leadership role there, but it's really very different phases. So, you know, the early stage is if I look at my first, you know, let's say two years, it's understanding what customer success is for me. It's learning the the basics of the of the profession, you know, it it was also a time where game site was still evangelizing customer success. So it was it was still early days for customer success as well. You know, there were some playbooks, but definitely very different from what we're seeing today. And today the profession is going through another you know huge uh change. So understanding customer success and also understanding early stage startups, right? Like what does it mean to have a few customers? To um what does it mean to retain them? What does it take to retain them? And the you know, the fun stuff of early stage where you pivot, you make decisions, you understand what's working, what's not working. And so that was you know phase one of that journey. And then finding product market fit and growing and understanding how to scale and starting to build uh teams and understanding what is the right time to specialize within those teams. So it was always learning, always growing, always trying to be one step ahead, trying to anticipate the needs. And then the last, I think the last phase uh during my time at Follows was all about getting to um sustainable growth. So understanding how to grow but in a more responsible, much more efficient way.

SPEAKER_01:

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SPEAKER_00:

Well, um it's uh it was the right decision for me. I I would say this. Um at the end of the day, the um it's about it's a lot about your personality and what's important to you, and understanding, like identifying the thing that let's call it, make you happy or make you feel uh fulfilled. And it's trade-offs, right? It's knowing how to do the trade-offs and understanding what you're getting and what you're giving away. So my personality is such that I really liked the people that I worked with in all fronts, like the customers, the the teams, the executive team. I really enjoyed that. And I knew that it's rare, and I knew that I I that's something that is important to me and I want to hold on to. And the grass always looks greener from the outside, and when when you go inside, you find so I it's also about understanding that you choose to deal with the um with the noes, like at least you know what what's not working, and you're part of fixing it, right? Uh, or at least trying to fix it. That worked for me. Does it have um disadvantages? Of course, you know, it's um it means that, for example, I didn't have anyone to learn from how to do customer success. I had to look for that knowledge outside. If I moved, I would experience uh different customer success teams, different segments, different audiences. So I gave up that type of experience. So understanding the trade-offs and making sure that you feel okay with the trade-offs that you're making at each point in your in your career.

SPEAKER_01:

Really very well said. I have just been quickly reflecting on my career and being a consultant for the last two years, thinking how from one hand, oh yes, it's amazing, you are seeing so many different types of customer success, right? You are kind of learning from different people that you're seeing there. But then on the other hand, you don't see that progression of building something within the team, within the same company. Like there is, again, so many pros and cons. Um, it's interesting for people to think what works for them and and what are the things that they are looking for in a job and in a career? What are those things that can sustain them day in and day out? Adding up from your 10 years within a company, I wonder when you think about customer success, is there any blueprint of or framework that you have either developed or you have used that you swear by, no matter what, this is exactly what I can use, what will work every single time? Is there something that you came across like that?

SPEAKER_00:

It's a really interesting question at this point in time because I think a lot of the frameworks that we used in customer success for many years are now uh being questioned and getting changed. I don't know if I identify, you know, one or two like frameworks, but um there are some practices that I will for sure apply in any any place where I am, whether it's customer success or or not. Probably one of the most important is active listening. So something that I try to practice and I try to coach my any team that is reporting to me around, which is, you know, in customer success, uh being able to put yourself in the customer's shoes, being able to find empathy for the customer, understanding the situation that they're in when they're in front of you is really important. It helps you not only build your relationship, but get the customer to where you want them to be if you really understand where they are, right?

SPEAKER_01:

And yet we can still be so bad at it. And people are now especially they are relying on their note takers and AI, uh, which is awesome for later on to summarize the call. But I think if you don't have that active listening skills, you're not even able to deep dive and go deeper and ask important follow-up questions on the moment when you are having a customer in front of you, which is incredibly important. Speaking of the topic, as you are looking into you know the previous decade of yourself in customer success, now the whole new chapter that will be ahead of you and AI changing almost everything. Outside active listening, what are the other things that you think are never going to be impacted by AI?

SPEAKER_00:

Never is a strong word, but still it's um there are some aspects to the um human connection that is created um in customer success that are hard to replace, right? What I really like about the the current AI tools for customer success is the ability to take a lot of data, both structured and uh unstructured, um and make um inferences from that and make decisions based on those inferences. And that's something that until recently was only a human skill, right? And now it's also we have that the AI tools that allow us to do that even better. So it can free our time, you know. Again, it's a little bit of a uh, you know, it's becoming a cliche even at this point. But uh, but I think it is true that AI will make time for us to be more strategic and strategic in in different ways, right? Some customers need you to be strategic in order for you to guide them and consult them and take them from point A to point B. And other customers need you to be strategic in order to understand how to help them at scale, right? So different ways of being strategic in customer success. And I think that's that's where AI will really help us in freeing us to be creative, to be innovative, to think big and to think strategically about the next steps.

SPEAKER_01:

Adi, as you are thinking about what is next for you, what are the things that you could share with the audience in terms of thinking out loud? Either what's the type of company you would like to join, or what's the type of industry where you want to be in, what's the type of work you want to do? Is there anything that you have currently as guiding principles of how you are making those next steps and how you're making decisions?

SPEAKER_00:

Some of the things that I enjoyed in my trivia's role, I want to keep. Like I want to work for a company that uh has great people that I can learn from, that I can teach, that that I enjoy being with and and that stimulate me. I really thrive in an environment that stimulates me to think differently and pushes me to think differently. So that's definitely something that I'm looking for. Um, whether it's an early stage um startup or a you know, a team in a much larger company, in that sense, I I'm looking for the same type of things. And I'm also looking for a product that I can feel some kind of of even like emotional connection to, like that I believe in and that makes people's lives better in some way or or another.

SPEAKER_01:

Adi, I'm sure that the listeners can gain so much from your career experience and the story that you just shared with us. I wonder when you're thinking back, is there one particular thing or or top three things that you believe everybody should learn at some point in their career? Either a particular lesson or particular like guiding North Star that was driving you in your career. Like, what is it that people can really drive from your experience and apply in their lives?

SPEAKER_00:

So just uh uh uh a funny anecdote. When you started talking about this uh and asking the question, like the first thing that popped into my mind was Excel. It's like learn to use Excel. Well, yes, that's a big one actually. Yeah, um, it it's kind of funny because they don't teach that in school. I'm seeing it through my my kids now who are, you know, they're um older now, like college and high school uh age, and even older, but we had to teach them how to use Excel at home. So learn how to use Excel. It's a really important skill. But if I'm looking if I'm looking at a bigger, uh a bigger lesson, things that you know, things that you give customers, things that the product is is providing uh customers with, um, they have a value. And you have to know how to put a dollar value next to this because you you'll get more valued thanks to that. You'll get more appreciated, and you're doing justice to yourself and to the to the company that you're working with. Customer success people uh are very relationship driven. A lot of them are, you know, uh, they really want to please. Uh, and I and I get it, like I've been there, you know. I've I was sitting in front of customers and the customer is asking you for something, and all you want to do is just give it to them because you want them to be successful and you want them to do great and you want them to like you. But this thing that you give them, it has value, whether it's your time, whether it's a feature that now the product team has to prioritize over something else. Everything you look at, whether it's your your expertise, those things have value and understanding how to quantify that value will protect you, right? It's something that will protect you. It's also sending the right message to the customer. And there are really um, you know, there are ways to do it in very empathetic uh ways to explain to the customers why you cannot just say yes uh right now and why you have to uh to protect your team or protect yourself. And you know, in in the same way, quantifying the value that the customer is getting out of what um out of the front of that will be using your product or your service. You know, that's the other side of the coin that is really, really important.

SPEAKER_01:

I love that you brought it up. I think I'm just in the middle of it myself trying to teach a team member how, yes, it's awesome that we want to give all of those services for free for to the customers because they are more strategic, right? But that there's nothing ever for free. There is always somebody's resources being involved from somebody in the company, either services or some other department. And on another hand, I think that we are now we have lots of evidence psychologically that humans in general value things that cost money much more than things that are for free. So just Even quantifying, as you said, quantifying that dollar value internally and also to customers is a good thing. Doesn't mean we you're making somebody always pay for things, but just presenting what they have been getting and what is the value that they have been experiencing from the whole company, it's a big deal and it has to be it has to be quantifiable. There is there is so much positives to the relationship for it. So yeah, I I can definitely relate to it. Why is it so important, especially for customer success leaders to respect everybody's resources?

SPEAKER_00:

Absolutely.

SPEAKER_01:

Adi, this has been such a pleasure. Thank you so much for coming to the show and sharing your experience. I wonder was is there anything else that you would like to share with the audience that will that can help them in their career or even in their next steps if they are wondering and thinking what is next? Shall they shall they take MBA? Shall they try to look for some you know internship with the new industry? I mean, you've been through everything. Uh, is there anything else that you would like to leave as as parting words?

SPEAKER_00:

Do what's right for you, basically. You know, it it's some people know exactly where they're going and what they want to achieve, and they just drive there. I'm not that person. There was one phase in my life where um there were I did like I said, that I want I really wanted the VP title, and that's something that I drove towards. Uh, and I made it known that that's where I want to get so that I can actually get there. And I made it known again and again until it actually happened. But most of the time when you ask me what I want to do when I grow up, the answer is I'm not sure. I there's so many things that are out there that I want to try and do. And that's okay. Because sometimes, you know, you look at someone next to you who's driving really uh intentionally and quickly towards a goal, and you're saying, Oh, I wish I was that person. But maybe it's not right for you. But if you decide that it is right for you, then find out how to do that. So, you know, and also one more thing different things are appropriate in different stages of your life, right? In different stages of your your life, you're gonna want different things, and that's also okay. So you may be really goal-driven at a certain stage, and then you find out that you actually want to take a step back and reflect and understand what's important. So that that's okay too. So make sure that you're you feel okay with the choices that you make um at every different stage in your uh in your career and in your life.

SPEAKER_01:

I really love that advice. Give yourself permission for it. Thank you so much, Adi, for coming to the show. Thank you, Maria. Thank you for listening to today's episode. I really appreciate you taking time to learn something new and propel your career in customer success and beyond. If you like this episode, share it with your colleague, with your team member, with someone you know needs to hear it today. We appreciate your support, so please follow us and subscribe to our channels so many more women can hear about it.