Women in Customer Success Podcast

122 - How to Take Next Steps in Your Career? - Heelee Kriesler

• Marija Skobe-Pilley • Episode 122

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Are you ready to transform your career and achieve your career goals?

With my incredible guest, Heelee Kriesler, who is a customer success leader, we discuss some crucial career lessons that will not only guide you on your journey but also fill you with the confidence to stride forward. Heelee shares the essential skill sets she’s developed throughout her career, including how to master public speaking and how to position yourself for your next role.

In this episode, we talk about:

  • How to take the next steps in your career
  • Developing public speaking skills
  • Positioning yourself for your next role
  • How to take control of your career path


Tune in to learn the strategies to take control of your career and confidently position yourself for your future role. Don’t miss out on this chance to improve your career and get inspired by a leader who’s been there and done that. 


Follow Heelee! 


This episode was brought to you by Deployflow.



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Speaker 1:

How do you proactively take control of your career path? Join me in conversation with Healy Kreisler, executive leader of Customer Success and a former consultant, business owner and public speaker. From being everything in your own business a cleaner and a CEO at once to developing high-performing teams, Healy has done it all. Get inspired and be ready to take notes, as Healy has such a wealth of wisdom for us today, let's get into it. Hi everyone, this is Maria Scobepile and you're listening to Women in Customer Success podcast, the first women-only podcast, where remarkable ladies of customer success share their stories and practical tools to help you succeed and make an impact. If you want to learn more about customer success, get career advice and be inspired, you're in the right place, so let's tune in. It's a pleasure to welcome Healy Kreisler to the show today. Healy is a VP of Customer Success and I'm really excited about our conversation today because it's going to be all about career journey.

Speaker 2:

Healy welcome to the show. Thank you very much for having me. I'm very, very excited to be here to talk about everything customer success, career journey, women in customer success and anything you'd like to know.

Speaker 1:

I would like our lovely audience to get to know you a bit better. Where are you calling from? Where are you based?

Speaker 2:

I'm based out of Israel, next to Tereviyu. I'm sitting in my hall office and I'm very happy to be here as I said in my whole office and I was very happy to be here.

Speaker 1:

As I said, hilly, I met you recently in London in one of the Customer Success Leaders event and I know that you love traveling, so I'm interested to know what is next on your travel destinations.

Speaker 2:

So we are planning a summer vacation with the family and our next trip will be a weekend in London for the Bruce Springsteen show and then a concert, and then we are going off to Portugal with the kids. So really, really excited about that in just a month from now and looking forward.

Speaker 1:

Oh, that indeed sounds wonderful. One question that I really like asking, because it tells me a lot about somebody's you know background and different type of career paths that they took throughout their lives. So I wonder, would the 16-year-old Healy be surprised to find you in this current job today?

Speaker 2:

100% for sure will not be surprised. First, I think I'm now in a position exactly that fits my skill set and my strength and when I can bring the most value and also be very excited every morning when I wake up. I will tell you a secret. When I was a kid, I thought I had various plans for my career. I once wanted to be a journalist, and the reason I wanted to be a journalist is because I saw Superman and his girlfriend was a journalist. So I thought, really I'll go and meet Superman like that. That was one of my plans, and I actually spent some time in a youth magazine as a journalist. But Superman came later. My husband but yes, but no, this type of role, what I'm doing, everything about it is exactly like I imagined myself growing up.

Speaker 1:

I think that it's about time we find out what are you actually doing, but maybe it's even more interesting to take a few steps back. How did you get to where you are today? So what was your career journey? Because what I was able to see? You have such a broad and wide experience, from consulting to business transformation, and then you enter customer success. So tell us more about it, because it is such a huge wealth of experience that you are bringing in today.

Speaker 2:

Yes, that's right, I am not one of those who grew in customer success or spent lots of time growing and developing in the customer success let's say, corporate ladder. I started my career as a business consultant and I spent a lot of years as a consultant and then later as a partner in PwC, which is a big consulting firm, and I worked in a few of the big consulting firms. Then I enlashed PwC because I had a dream to have my own startup, and that was a very unique thing to do, because normally when you are a mate partner you stay there for life, and for me it was really like fulfilling my dreams and me and friend, we had our own startup. We worked for a few years. We actually had, as any startups, lots of ups and lots of downs and eventually, when we needed the extra money in the next round, we couldn't get the money and that was close, but it was one kind of an experience. So that was my startup.

Speaker 2:

Then I went back to actually to management, management and leadership roles. I was a chief of staff in a financial company for two years and then from that I came into other managerial roles, also took a very, very significant part in a big, big transformation that the company I worked for was going through from becoming a real SaaS platform Through that, and part of my role was to prepare the entire poster organization to be a real SaaS organization and what it means. Obviously, customer success has a major, major role when we do that and part of that, I worked very closely with the customer success organization and eventually became the leader of the customer success organization. We needed to make a big change from being customer success in a non-SaaS environment to become a real strategic partner for our customers and drive value and monitor adoption and everything related to customer success in a global enterprise, software and company that sells SaaS solutions.

Speaker 1:

What a wonderful journey.

Speaker 1:

Healy that sells SaaS solutions. What a wonderful journey, healy. It's so interesting to see that whole journey from consultancy which is absolutely amazing, and it's awesome to have those skills and then being an executive and business owner and then being a chief of staff. Very often people think or dream about going from customer success into more operation and chief of staff, and that seems to be like you know the next big thing, which is awesome, and then you came from that environment into the customer success. So what are some of those skill sets that you brought along with you or that you developed throughout your career, especially the ones that you say are definitely you know your strengths and therefore you know that you're in a perfect position for you at the moment.

Speaker 2:

First of all, everything I did through my career helps me to be successful in what I'm doing.

Speaker 2:

This is obvious, and I have a very, very diverse and wide experience.

Speaker 2:

I am very data-driven on the one hand, and can really take on a very vague idea and make out of it a real concrete strategy and then a work plan, and then translate it to baby steps and a work plan that ends up with achieving what we wanted to achieve.

Speaker 2:

So maybe it's also my consulting times and other experience that I had that it means that, even if you are walking into a very new environment for you, which is completely different than what you knew, you have the skill set to really quickly analyze where you are, what you want to achieve, and then build a plan and then execute on the plan. So when you are a consultant, you are looking at executions from the outside Normally, because you are not doing exactly the execution, you're just helping others to do that. When you are an executive, then you really are taking part in the execution of the strategy and I think all of everything I did, including the startup, which forces you to be both the cleaning lady and the CEO, so it forces you really to know everything and to be very, very hands-on. This is on one hand, and then being an executive where you have a team, then you need to be the team and inspire them and make sure that they understand where you want to go and go with you to where you want to get.

Speaker 1:

One thing that I noticed is that throughout your career, you also developed your public speaking skills, and I believe that is something that you're still doing, and you are speaking at conferences and lecturing in universities. What is your recipe for developing those skills? I'm asking because often people say, oh, public speaking is the worst nightmare, but then as soon as you're in corporate world, as soon as you're in some positions, it comes with a job that you have to present and you have to speak, and very often it is on the bigger and public stages. Did you ever take any training for it or is it very natural? Do you just enjoy doing it? I really wonder how did you develop that and how comfortable do you feel at stage? Because I can think when I saw you on the stage, it seems that you're at home when you're on the platform and you're at the stage like absolutely beautiful, natural. How did you develop those skills? If you can reflect on the previous years?

Speaker 2:

Yeah. So I'll tell you a secret I have a fear of stage, like many, many others. I really fear of stage, okay, and at the beginning I was really nervous when going up to stage. I even had one case where it was a quite intimate four. It wasn't a huge four, there was 30 people in the room and I choked. I couldn't say the next word. It was so embarrassing really, oh wow word. It was so embarrassing, really, oh wow.

Speaker 2:

But as I gained more experience, I understood that you don't need to be perfect. Once you understand it really to the core of yourself, really to know that you don't need to be perfect, you don't need that every it's not important that every word would come with the right place, with the right context, as long as you get to saying the main messages that you want to deliver and as long as you are yourself with the vulnerability that you might have, you know, standing on stage, everybody are looking at you. And as long as you understand that people are not there to judge you. They are not there to give you a score. They are really, really interested in what you. Some of them are not really interested. Some of them are looking with their eyes right and you know, looking at news or social media, et cetera.

Speaker 2:

So this is also something that is relaxing because, you know, not everybody are so focused in every word. The others are there not to judge you. They are there to listen to what you have to say. So if you think about it like that, then you get to relax. You say, not every word counts so much, so if you miss a word or your sentence doesn't work as you plan it to be, it's okay. And the other thing is that nobody's there to give you a score, really no, they are coming there to listen to you and that gives me. That loses the edge. I'm losing the edge and I'm a lot more relaxed. And the more you're relaxed, of course, then it becomes more natural. But before that I was really anxious and I was driving in my car to work and practicing, and practicing, and practicing and imagining what I'm going to say, et cetera, et cetera. I was telling you sometimes, the more you practice, the worse it is.

Speaker 1:

Oh, wow, that's interesting.

Speaker 2:

Yes, because then you have your script right and if you forget a word then everything messes up. Maybe sometimes it's better to be more natural, to understand the entire concept, the main messages you want to say, and to understand that no missed word will count so much, and then you become a lot more natural.

Speaker 1:

That is really good advice, hilly. I would like to hear your other advice about career development. So what have been some of the career lessons throughout your really wealthy career? Um, something that you would like to tell our listeners that will help them, you know, develop and grow their careers. What did you learn in your so?

Speaker 2:

I will tell you what helped me a lot, and I am the more I speak with you, know more people who are, let's say, less experienced and want to get the best in their career. My number one advice, number one advice would be wake up every morning and imagine yourself in your next world, not in your current world. Imagine what you need to wear for your next role, what type of ownership will you take on your tasks, what you will need to do, who do you need to talk to? And start to behave as if you are already in your next role, not in your current role. And the more you do, that people will start to think about you in your next role. They will not think about you as that junior staff that just started a month ago and doesn't know anything, because you will demonstrate, right, another person, a person that is more experienced, et cetera.

Speaker 2:

So you know, you cannot do that in day number one, right? But the moment you start to think, okay, now I'm trying to build myself towards my next road, go to sleep, wake up in the morning, go to work, dress, dress the part already, wear your clothes top to top, take ownership on the things that you need to do and eventually everybody around you will start to imagine you already were next and I think that helped throughout my career. That helped me time and time and time again. I don't know that I was very prospective about that and I don't know that I basically started to think, okay, I want to be where I want to be next and I stopped caring that I don't yet have that role. I stopped caring about that. I said, okay, let's imagine I have that role, what would I do? And I did it and eventually it became real.

Speaker 1:

That is such a wonderful, wonderful advice. I remember on my very first role in kind of business environment I was a PMO project coordinator but I remember wearing always really nice clothes to work, you know, very proper, with blazers, with shirts. And then I felt people around me were, I felt were just dressed much more casual and I couldn't understand, like why are you wearing such a casual clothes to work? Like you have to be really presentable. But I always felt that at least I was trying to. You know, dress for success, because somebody told me that long time ago and that was in my mind and a few months after, like I left the company I went to a much better position. The rest of the crew, you know they stayed there. But I definitely understand that, understand that, like, so, think about your next role every day and you know almost, dress for success in your next role.

Speaker 2:

I really love that yes, it's not only, of course, about clothes. I think it's more about state of mind and um and what you project to the environment and ownership and responsibility that you take on. But eventually people will seem to say, okay, why is she just in this general position? Maybe we should give her some more responsibilities, because she's taking them anyway.

Speaker 1:

I really love that approach because, definitely, you are becoming much more visible when your mindset shifts towards it and when you start behaving like you are already in your next role. That is really great. How did you go about your next levels and your next roles? And, when you were up for promotion, how were you taking those next steps in your career? Because, from one hand, we are now talking about how you position yourself and how others will notice you, which is really good and you need to be in that mindset. But what are some of the things that you also can start doing already to position yourself for the next role?

Speaker 2:

Manifest. I mean, tell your boss that this is what you want to do next. Don't be shy. Tell the people that it's important for them to hear that. Tell them look, I know I'm doing now this job, but I want to make sure that it's here that I'm really, really aiming for that position and I want to understand. What will it take to be there? What do you need me to do? What does it take for me to be there? What are you expecting for me to be there? Don't be shy. Sometimes people are shy to really say what they want, and I think that people that say what they want to say okay, my next position is going to be that. Now, what do I need to do? Sometimes people will give you the answer. Sometimes the answer is a lot more fluid, but at least you will say look, I'm seeing myself as this manager. Okay, and this is how I see myself, this is how I want to, this is what my next one should be, and I think that will also help people again. Imagine you in your next role.

Speaker 1:

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Speaker 1:

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Speaker 1:

I remember a situation when I have done something completely opposite. I was probably shy. Yeah, I was shy. It was early on in my career. I didn't feel that I, you know, could just say, oh, I would like to be that in my next role. I thought, oh, I should just keep on doing my best job, and I did. And then I felt, well, there is not much growth in the company for me and no one is saying anything yet about the promotion onto something else, and I wasn't sure what is next and I just left.

Speaker 1:

I found a better position, but I left an amazing team and amazing company. And later on I realized, although I am convinced I have done a good choice, and you know the next company was really good and you know it speeded up my career, but I am aware that I left an amazing company and team just because I didn't speak up, and I always like to tell to people yeah, don't be shy. And then, when I became hiring manager, I realized how much easier is it when people tell you what they want to do next. Right, I know you have so much experience in developing people, so what would be your advice in approaching those conversations? Because, from hiring managers and from our bosses perspective, you want to develop those people and you want to make sure that your team feels heard and that they can have opportunity to grow their career. How do you develop your team?

Speaker 2:

Look, it's a tambo. You know, as a manager or a leader, you don't do that by yourself. It really, really also depends on the person you are talking to. Some of them are very easy to work with on those because, a, they know what they want and B, as I said, they actually act. The part they say, look, I am interested to become a manager, and I know that, and you know, not being very aggressive about it, I know that it will take time, I know that I'm probably not ready yet for that, but please, I would like to take on that responsibility, just to start to prepare myself. So normally, your manager will be more than happy to give you that responsibility because you are excited and passionate and are willing to take on something new and something more. So, as long as and that's an advice again be open with your manager and tell them what you want, if you want to do it the ones that are not there yet then you try sometimes as a leader, also to ignite this conversation, because everybody has their you know their aspirations and their plans.

Speaker 2:

Sometimes people are very comfortable where they are and they're not looking for the next big thing, and that's completely okay, yeah. But sometimes they are shy. And those who are shy, you might lose them because they will say, okay, I can't, as you said, I cannot have what I want here. So I will go and look for that in my next page. There is a third option. Sometimes people are very aggressive about you know, want to advance very, very fast and they feel like they are ready or ready. Sometimes you will not agree with that. You will say I don't think you are ready yet. It's important, of course, to explain why they are not ready yet. Or sometimes there's no real position at that specific point for these groups. So, of course, building growth plans, painting the journey for growth and for success with your teams is very, very important as well.

Speaker 1:

And that third option is incredibly important as well, right, Because people need to understand yes, you do your part for promotion, for next role, you advocate for yourself and you share. What is that next step? How does it look like for you? And then your managers support you in the journey. You know you go to development programs, you can upskill and you can managers do the part, but then not always it happens that the company has the opportunity to promote you, right? So there is always the element of patience, really. Or the option might be, you know, to go for the troll somewhere else if you are really, you know, desperate to move that quickly.

Speaker 1:

But I think it's very important for people to know that even when you do your part, it's not always up to you. And when people get frustrated oh, I haven't been promoted, but you know, last two quarters I was doing great. Not everybody can be promoted constantly, because that's not how companies function. Thank you for clarifying that. I think that's really important for people to know. What is your advice for aspiring leaders, whether they want to be leaders in customer success or in other areas? What would you tell them? Maybe?

Speaker 2:

I want to change a little bit your question and focus on aspiring women leaders, because we are in a women in customer success podcast and I think it's important and I want to share an experience that I had. I was hiring for the director of customer success and actually there are a lot of women in customer success, right? So you would expect at least 50% of CVs to be of women who are looking to be director of Castle of Success, and I was looking for someone with experience. It doesn't have to be exactly everything I wanted, but they had to have experience, and I will tell you that I think I got less than 10% of the CVs I received was women, were women, and even those women did not have the right experience, so I had to make a real effort to add them to the shortlist.

Speaker 2:

So, be bored. This is my advice to women Be bored. Don't sit there and wait for someone to pick you up. Be bored, as I said, imagine yourself in your next role and act the role as well, and and push yourself, because nobody would push you and not because people are not. Uh, do not want to see you grow because everybody are super busy and, um, you know, it's because it's because the air becomes thinner when as thinner as you climb up and people do have to Sometimes. I really wanted to hire a woman and I tried, but eventually I hired a man because you know the best person with the right experience, etc. But that was after looking for the right CVs and they just didn't come after looking for the right CVs and they just didn't come.

Speaker 1:

What do you think was the reason? Why were there not enough or not that many women applicants?

Speaker 2:

I think, because not that many women are pushing themselves to grow enough and eventually although there are, so I think less than 50% maybe even men in customer success, those men are aspiring and they are pushing themselves and they are trying to reach to those more senior positions and eventually they get it. So, as I say, be bold, don't be afraid. It's a good thing, it's a good thing that your manager knows that you want to be in a more senior position. It's not a bad thing, it's a very good thing. Don't be shy.

Speaker 2:

Don't think that if you do everything right, everybody will know that and it will happen by itself. It will not happen by itself Unless you push yourself. This is part of the job. You need to push yourself to get to the right position, and I think this is really really important and a main advice for women. And I never in my life, when someone came to me and say, okay, I want my next one it was never. It never, uh, was a bad thing. That I heard, was always okay, let's define what it means. And okay, let's see how we get you there. Or you know, at the moment there's no open position or no planned open position, but I'm keeping it in my mind.

Speaker 1:

That is an amazing advice Be bold and go for it. Go for those new opportunities. I'm really so happy that you are mentioning that and just hearing your experience how you almost struggle with getting the pipeline of really quality female candidates. It's really unfortunate. One of the reasons why this podcast even came to life was based on a conference where there was a slide that showed the gender situation in customer success and actually that slide presented that women in customer success were 60% women entering the industry versus 40% men. But then from director level above, there were only 30% women, 70% men, exactly what you're talking about.

Speaker 1:

So really there could be so many reasons why women potentially don't go for those positions and in fairness, I think that recently I've been hearing people or women saying to each other oh so now you're in this position for a few years, that's fine, just have a child now it's good, just stay there, have a child so you can have family, and obviously there are good reasons to do it. But go for it. Go for the opportunities because definitely men are out there, they are grabbing opportunities and when they see job descriptions they just know oh, that's it, I'm going to go for it. And we know from the research. If women don't tick all those boxes, they will not even apply because they feel, oh, I don't have it all. So I really like your example and your encouragement to women. Just go for it, apply for those roles and don't wait for anybody else. Right? As you said, no one else will just tell you we have a new opportunity, apply for it. Those are very rare cases. Yeah, it's a flagship. What makes your day really good in your current role?

Speaker 2:

Yeah, so, look, I very passionately believe that and I'm writing that also in my description that the leader role is really to wake up every every morning and make a significant change. You cannot make a significant change every day and significant changes are incremental and you don't do them in your day, but basically, a leader's role is to make a change. So when I wake up every morning, I'm telling myself okay, what change am I going to make today? And in this ever-changing environment, this is really, really important, because if you don't change, you will be left behind.

Speaker 2:

So a good day is a day when I look back and say to myself first, I push toward the change I want to make and second, that's also because everybody who knows me will tell you I'm very task-oriented, so I ticked enough boxes. Enough of the boxes I wanted to tick, I ticked them during the day. So that's also normally would make me happy in the day. Obviously, when I had good conversations, when I saw that my team is happy and they feel like they should proceed and they know where they need to go, that would be a good day as well.

Speaker 1:

That is such a wonderful aspiration. Have a think of what is the change that you want to do in a day, and definitely I can imagine how ticking the boxes, ticking some of the to-do lists it's about definitely create some change because you are moving towards the next goal Exactly. Really, this was such a wonderful conversation. Thank you so much for sharing your journey and your, your wisdom and your career advice for us. Where can listeners find you online?

Speaker 2:

I I'm not very strong, but generally in any social media, so generally in linkedin, uh, all the rest I'm just looking from the side, so mainly LinkedIn. Sometimes I post, sometimes I share information. So this is where they can learn, they can find me.

Speaker 1:

Wonderful Hilly. Thank you so much for this conversation today.

Speaker 2:

Thank you so much. It was very interesting and I'm looking forward to hearing other podcasts that you are preparing for us.

Speaker 1:

Thank you for listening. Next week new episode, Subscribe to the podcast and connect with me on LinkedIn so you're up to date with all the new episodes and the content I'm curating for you. Have a great day and talk to you soon.