Women in Customer Success Podcast

130 - Overcoming Imposter Syndrome: How to Feel Confident as a Woman in Tech - Ashley Stamps-Lafont

• Marija Skobe-Pilley • Episode 130

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Ever feel like you’re not good enough, even when you know you’ve earned your spot?

My guest, Ashley Stamps-Lafont, opens up about her experiences with imposter syndrome, especially as a woman in tech leadership. Ashley is a customer success executive and full-time mom. Over her 15-year career, she has led over 100 post-sales professionals in both VC and PE-backed SaaS companies.

Ashley and I talk about the emotions around the election results and how they resonate with many of us, especially women in the workplace. Ashley also opens up about her personal experiences with imposter syndrome and shares advice on overcoming self-doubt, and she introduces her fractional firm, SuccessRx, which is helping businesses and people with their customer success challenges.

In this episode, we talk about:

  • Post-election day reflections
  • Empathy in leadership
  • Creating open forums for discussion
  • The importance of empathy in the workplace
  • Mentorship and support for women
  • Future-proofing careers in customer success
  • Mindset and behaviours for success
  • Overcoming imposter syndrome
  • Advice on marketing yourself


Tune in and don't miss this conversation filled with useful information and inspiration for women in tech and customer success!

Follow Ashley!

This episode was brought to you by Deployflow.

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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 1:

Hi there, welcome back to the Women in Customer Success podcast. Today, I would like to acknowledge that many of you are processing the results of the US election. This is obviously not a political podcast, but I want to acknowledge that many of us have different emotions and need time to process, to reflect and strategize how, as leaders, we all can support our teams, we all can support women in our lives, and how it is okay to take time to heal. In today's episode, I'm joined by Ashley Stams-Lafon and we acknowledge the current reality and then we pivot our conversation on supporting women, providing mentoring and battling imposter syndrome. Let's get into it.

Speaker 2:

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.

Speaker 1:

This is really a wonderful opportunity for me to speak with Ashley Stamps Lafonde. Ashley, this has been a long time in making. I am really grateful and excited to have you today joining me on the show. Welcome.

Speaker 3:

Thank you so much for inviting me, Maria. I have been looking forward to this.

Speaker 1:

Ashley, it's Wednesday 6th of November, as we are recording, and it is a very special day in the history. It is the post-election day, and I think I'm right to say that maybe we both have particular feelings about the outcome of this election. And I'm not even based in the US, I'm not even the one to vote. So I would like us to start with that how are you feeling and what does this election mean to you?

Speaker 3:

The results are not a surprise. We knew that. This campaign was all over the place, with a change in, you know, the party candidate on one side and a lot of turmoil on the other. But one thing that I can say is the results, while not being a surprise, they are leaving a lot of uncertainty, and I certainly feel it, and I know that a lot of women in technology and non-technology industries are feeling it as well. I did issue my vote. I sit in Montreal, but I've been American my entire life and voted absentee, and while things did not go in the direction that I had hoped for, I have to say I don't know if we really have time to sit with our feelings too long. Maria, there's a lot of anxiety that has, I guess, lived within women for the entire course of this election and now that we have a result, hopefully things will start to dissipate. But for people who woke up this morning, like me, that didn't get the result that you hoped for, I think the best thing that I can say is breathe through it.

Speaker 1:

I think it is incredibly important that we acknowledge what just happened. There are so many women across America and across the world listening to us now and I would like everybody to firstly feel empowered to take a moment and to start processing. I think this is a situation where so many will be grieving, as you said, either from disappointment and anxiety and combination of so many feelings that everybody felt and loads of pressure. I believe that people felt on their shoulders in the last many months leading to this election. We have to acknowledge it and we have to acknowledge that maybe some people will not be able to do their work or be very focused this week. What would you say for anyone listening? What are the things we can start doing as we are going through this? I would call it healing process. There are so many women that are in grievance at the moment. How can we start healing and look what is ahead of us and what are the things that we actually can?

Speaker 3:

influence. I think that women are some of the most resilient people in the world. We haven't had it easy historically and it's not going to be easy moving forward, but you can only really act on that resilience after you take that moment to breathe. I think it's very important to surround yourself with people who care about you and that you care about them, especially because this has been such an intense period for so long. So I certainly reached out to my loved ones this morning just to check in and let them know that I care for them, and I urge and encourage any woman to do the same.

Speaker 1:

Being a woman in technology and a woman in customer success at the moment, I do acknowledge that there will be many members of our teams that may want to talk about it, may struggle these days. What else do you think leaders could actually do to start supporting their team members at the moment? I love your idea of you know, taking a moment let's breathe in, let's check in with each other. Do you think we should start creating open forums to start discussing our feelings? What would be really beneficial for you and your team when you're looking into this situation?

Speaker 3:

This is not my first rodeo when it comes to being a leader in customer success and there being a US presidential election at the same time. What I did with my team at Unity actually, it was 2020. And, of course, unity was a really great company. It gave time off for their employees to actually go vote and to also back it up.

Speaker 3:

Immediately after the vote, I made it clear to my team look, you can take your time, you do not have to tell me why, and if anyone on my team was just not there for a morning standup, or they pinged me and said I need a little bit, they didn't have to explain anything else. So I think, try to exercise some empathy as leaders for your team. Politics in American companies is usually frowned upon and a lot of people feel as if it's taboo to speak of. So I would respect that people want to express what they feel comfortable expressing, but it's even more important for leaders to have that culture and project empathy at its core. And if you have a company that has invested in employee assistance programs and other mental health resources, this is the time, if you are not already, to make sure that you are taking advantage of those benefits.

Speaker 1:

Thank you so much for doubling down on empathy. I think that's one of the tools that everybody has available to power up through these moments, no matter of anyone's political situation or anyone's thoughts about the outcome. We are here to support each other in the moments when people just might be feeling very different and very, very anxious, as you said. So, as women in customer success, as leaders, let's really take the moments to put the people first, to acknowledge that they are simply different emotions that everybody might be feeling at the moment and that we need to start acknowledging those.

Speaker 1:

Ashley, we are looking ahead as a leader in tech and in customer success, regardless of the outcomes of the selection and probably huge disappointment of progress of advancing women may seem to be really slow on a global level. What can we do about it? As leaders? What can every team lead do for women in this moment, for women in their teams, for women in their careers? What would you say, regardless of what is happening globally, what can we do in our very small micro communities, micro teams, to really help advanced women?

Speaker 3:

Provide the space for their voices to be heard.

Speaker 3:

Number one it is not enough that there could be a female leader in the organization, especially if her voice is the only voice of a woman in a room.

Speaker 3:

It's very important to create that space and to amplify the voices of women across the entire organization, at all levels, so we can bring the perspectives that are not going to put us in a situation where we're doing things because there's a single mind and a single voice. I think if you have the ability to mentor someone who wants to advance whether it being breaking into an industry like customer success or tech, or if they want to advance with getting a promotion, sometimes the more passive voices or those that have fear ingrained in them will not feel empowered to speak up and advocate for themselves. I think it's very important to offer that mentorship offer, that coaching offer, that encouragement to allow them to own more of their presence and therefore show up as women. It's not going to be given to us, clearly, so it's quite important for us to work together as a community to build us up you do have quite a lot of experience in mentoring.

Speaker 1:

What have you seen as a mentor? What are some of the common themes that you are seeing with your mentees, and you know what keeps you to still mentor other people? I'm asking because, as many others, we all are, I guess, involved in different types of mentoring and in a way it is incredibly rewarding in both ways, but also we can learn so much from people. I wonder have there been any particular patterns of showing up or patterns of behavior? For we can talk particularly for women that you have menteed over the years. Anything that you have noticed is common for all of them.

Speaker 3:

Sure, the first formal mentoring relationship I got into was as a coach with the Catalyst Coaching Corner, and I know that you and several other women in customer success were very active when that was running. I was part of it as well. Wasn't it so great to be able to connect with people and I just felt like the energy and the passion and the opportunity for customer success was high. So when we first got started in about 2019, 2020, there were lots of people who came to me and they said I want to break into customer success. I see it as a path to get into tech, I see it as a path to increase my earning potential. So that was one of the common themes. But they, almost without asking me directly, were wondering how can I create a space for me in tech? So a lot of the conversations that we were having were well, what kind of space do you want it to be? What are you bringing to the table? How do you articulate that to your current employer, or how do you articulate that to a potential employer? And trying to build up that personal branding and readiness to step into customer success.

Speaker 3:

Not to talk too much about what's been happening this year, but it would be really remiss of us to not discuss the different macroeconomic conditions that are also influencing what's happening in customer success. We started to see the surge of layoffs occur in late 2022, and it has definitely persisted for the last 18 to 24 months, and I think the pattern has now shifted to I've been impacted by a reduction in force, or I feel like I am in danger of being impacted by a reduction in force. How can I future-proof myself, not just as a woman, of course, but how can I future-proof myself as a customer success professional and make sure that my role is seen as valuable? So it definitely has shifted since I started working with my mentees.

Speaker 1:

You are probably 120-ish women that I've interviewed on this podcast and the majority of them have in some way being either a mentor, mostly, or mentors in different programs. But I always felt so privileged because every single conversation I'm having seemed like a mentoring session to me, and I'm sure that for women listening, they are surely experiencing you at the moment as their mentor and maybe this conversation will also become their mentoring conversation. So I wonder let's talk about it as well how do we future-proof ourselves at the moment? Because, as you said, there have been so many macroeconomical elements that came into the picture last two years, which is just incredibly interesting.

Speaker 1:

Four years ago, the surge of customer success managers was on highest and it was number one sought after job on LinkedIn. It was becoming the top of the pops, the most popular career ever, and people wanted to get in. They wanted to get in from all different sides and from all different backgrounds and all of that was amazing. It was so popular just to see boom two years after big layoffs and we are still not out of it. It is still constant thermals in the industry and even last week, basically, we saw so many of the companies again having the layoffs and having some cuts. So, for CSMs listening, would you like to give us an idea of what are those skills or behaviors, or even mindset that can really help us being future-proof, regardless of micro-economical impact? And sorry, I'm asking lots of questions at once, but I love your previous reference to how do you create those, your own opportunities or your own path. So how can we combine it? What does it even mean for us today to think about the future and becoming future-proof?

Speaker 3:

Yeah. So I would say that customer success professionals across the board need to think of themselves as business advisors and not customer success advisors. And there are a few reasons why. Number one, we need to understand the mechanics that are powering the decisions, and you can't do that unless you have the financial acumen for you to understand metrics beyond an NPS net promoter score and a CSAT score, even factors beyond, you know, renewal rate. Think about what other factors rate. What is the rule of 40? What does it mean to have a margin, and are our margins healthy in comparison to other like-minded businesses within our space? You might not have direct influence on those decisions, but I think that the first step for any customer success professional to future-proof themselves is to understand exactly how they fit into the business, and you cannot rely on your leadership to necessarily know the answers to that question either. So while you're on LinkedIn Learning and while you're, you know, pursuing all of these great certifications for customer success, which are absolutely great skill development steps for you to take, you also need to think about what it means to be a part of a business and what it means to be a valuable component of that business.

Speaker 3:

Customer success mentees that I've had. You know, several of them have been asked to shift to having more revenue responsibility, have been asked to shift to having more revenue responsibility, and one of the things that I have sort of asked them to think about is well, do you agree with that decision? Why or why not? Was there a justification provided to you as to why the company is going here? Maybe there was some attrition, perhaps the market has shifted, but if some things aren't stacking up, maybe just maybe that's a company that isn't built for you and instead of you thinking about how you can fit that square peg into the round hole, think about how you and your unique skill set can benefit another company. And it's not saying that you know, I would ask anyone to go into this market. This market is the worst job market that I have encountered since I got into tech, but I think it's very important for us to increase our proficiency of what it means to be a part of a successful business or a potentially successful business, especially as customer success professionals.

Speaker 1:

So for all the CSMs listening, where should they start? Where should they start to understand all of those financials, as you said, and financials about their business, as it's very likely that them, as individual contributors, they don't have access to many of those. What would you suggest? Like create some lunch and learn, or speak with finance person, go out, reach out to them, do some of the trainings, like what are those immediate steps that they could actually do to become so much more financially literate for customer success role that they are in?

Speaker 3:

Yeah, absolutely so. The first thing that you want to do is I think that you should get close to your finance team. Is I think that you should get close to your finance team, but if you have a RevOps team that can also help you with that, that can be a nice intermediary step for you to take. They will tell you what you might not have access to on your own. Beyond that, think about what's happening outside of your company, and there are a ton of resources for this.

Speaker 3:

One of my favorites that I recommend to mentees I do look at LinkedIn learning and just looking at a profit and loss statement, otherwise referred to as a P&L. When you have a good understanding of the financial operations of your business, it allows you to ask more questions about how you can positively contribute to the elements that are usually, you know, within your control and usually for customer success. That can be something as simple as gross retention, but also looking at a breakdown of what's contraction. What does churn mean for your business? What does it mean when a logo churns versus you having dollar churn? And a lot of this information is now sort of industry agnostic, so taking advantages of LinkedIn learning can certainly help. I would also say that some of the steps that you should take would be if your company allows you to expense a portion of your own personal development, you might want to look into certifications or short-form courses that can also help you get to that level of proficiency.

Speaker 1:

Outside financial skills. What about mindset and behaviors? What have you seen can really work well for future-proofing our careers.

Speaker 3:

One thing is that I believe customer success professionals are the best value architects of any business, and I'm really happy to say that for two of the companies I've worked with most recently, they've made the switch to value-based customer success models, and that has extended not just to the post-sales teams that are traditional customer success, but it's gone all the way up to the top of the funnel, meaning that value is created from the time that they gain initial awareness about your brand until the moment that it comes for them to renew or expand with you.

Speaker 3:

And I think you have to start thinking of yourself as a consultant, you have to start thinking of yourself as an architect to first determine what the important value moments are, engineer a journey that's going to help you deliver. And then there's often the most forgotten element of this, and I cannot stress this enough you have to communicate that you have delivered the value Absolutely. You cannot make the assumption that the customer is going to be putting two and two together. It is very important for you to advocate. You know, in sales you always have to ask for the sale. In customer success, you always have to show that you've actually delivered the value.

Speaker 1:

How important is that and how not enough we are talking about it. There is that psychology and everybody knows it, but it's not always almost easy to apply when you are speaking with customers. But you know, when things are not going well, customers will know about it. They will contact you immediately. That will be the number one topic they ever talk to you about. When things are not going well and when everything is fine, no one ever mentions anything normal right, anything that is going smoothly.

Speaker 1:

So unless you are really putting it in front of their faces, this is what we did. This is the value you're receiving. This is what happened in the last three, six months. Whatever, unless you're intentionally doing it psychologically, they're just going to forget. They will not have that on top of their minds when they are internally talking about you, like I wish they all have it. Some are really good at it, but most of the people simply remember things that are not great. It's just something we are wired for. I don't know if you have noticed it, but definitely it's like putting in front of people's eyes and you know in front of them to never allow them to forget what they are actually getting.

Speaker 3:

And you don't have to rely on a business review to do that.

Speaker 3:

I've worked in businesses that have had the entire span of customers customers that had an ARR of $250 and customers that had an ARR of $10 million and if you can work together to define that value, digital customer success can also be used to communicate that value without an actual human being being the person to do so.

Speaker 3:

So I think one thing that I implore customer success leaders who even have PLG motions to do think about how you can interpret the more enterprise value realization motions into touch lists, or rather human lists, touch points that can also do the same.

Speaker 3:

Otherwise, you're going to have a major problem on your hands, because one of the number one sort of questions that I get, especially as I'm talking to my mentees and others in the customer success community, they say what do I do? I've been asked to sort of ignore the smaller accounts, or we had to lay off 25% of our team and that means that we have fewer resources, so we're only focusing on our largest customers, and I understand that. Oh my gosh, I understand that. But just because you have these resource constraints doesn't mean that you don't get creative, you know, and have that creative application to at least have a pulse running for each customer segment, because if they're your customers, you still owe them, in my opinion, a degree of service of what they signed up for, unless your business decides that they no longer want to play in that market.

Speaker 1:

But I would agree with you no matter what segment of customers you have, they deserve communication and value from you in any way that you can really deliver. And at the moment I mean with technology and even with AI, we can be so creative in ways that are low effort and ways that can have big impact to even the smallest of the customers. I've been even coaching enterprise and strategic CSMs to scale or do some scale motions for their customers or do some scale motions for their customers. There is no reason why you shouldn't have, you know, maybe even weekly newsletter with some additional value. There is no reason not to do creative things with your customers just because you are assigned to a particular segment of customers.

Speaker 1:

We can now be much more creative than I believe, ever before and I would agree with you like being proper consultants or, as you said previously, business advisors. I think that is a number one skill for the future for customers, for customer managers or for anyone who are working in technology and for people who are in front of customers. There is no chance you can help them properly unless you are able to ask the right questions and come to the bottom of why did they come to you? What was their problem, they wanted to solve and how you can help them. Like that is the basics, so I'm glad that you are emphasizing this as well as being one of the most important future-proof skills Absolutely.

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Speaker 1:

Ashley, I think that there are so many things that I can talk to you about, but I would like to, or I would like you again to, mentor us a bit on the topic of imposter syndrome. I know that you have done lots of work on it in previous years and I know that's something that is that's been with us constantly. I personally can't get rid of it. Yes, it's always somewhere here in certain situations. I just wonder what has been your experience with it and any of your personal tools and strategies that you are implying when you are recognizing you are in that position?

Speaker 3:

The first time I ever heard the phrase imposter syndrome. I was sitting in Copenhagen, denmark, which is one of my adopted homes. I'd been in tech for about six years at that time, but it was the first time that I was in a management position and I sat here thinking I don't know if I can do this. It feels as if this job is so great I don't want to mess it up. Job is so great I don't want to mess it up. I feel as if I'm qualified, but maybe I'm not qualified enough. You know, every single question was going back and forth, back and forth, and there were so many what ifs, but all of those what ifs were telling me that I wasn't good enough. And I saw a mentor. So plug for mentoring.

Speaker 3:

I sought a mentor who had risen within customer success and I said, hey, I'm going through these thoughts. Is it all in my head? And the number one thing is that they validated me and said no, it's not in your head. So I'm going to repeat that it's not in your head. Going to repeat that it's not in your head If you are second guessing, if you feel as if there have been certain things that have been said to you that make you feel a certain way or that you haven't been able to show up.

Speaker 3:

It's not in your head, okay, but just because it's real doesn't mean that you can't overcome it, and that has stayed with me ever since. It's been about 10 years, and my tool for getting past imposter syndrome initially beyond that validation is I eat the frog first. I don't know how that translates across cultures, but you do the hardest thing first, because you will obviously procrastinate and potentially never do it if you do not prioritize it. So that's how I approach my imposter syndrome. When it does creep up is I'm going to do whatever it is that I am telling myself I can't do first, and it has worked wonders for me.

Speaker 1:

I love that. Put the big rocks first right. I've been a serious procrastinator so I know the importance of putting the big rocks not that I always put in the right place, but this is a wonderful advice. Do firstly what is most important. While you have time right, while you can still ask for help for somebody else or be more resourceful, firstly do the big important thing. I love that. That's really great.

Speaker 3:

And the other piece and this wasn't even looking at tech. This is when I was an undergrad at the University of Wisconsin-Madison. I had been pretty high in terms of the ranking for my high school class, like many people who went to the university. University and I'll never forget when one of my professors said you were probably the smartest in your class. And now you're in this room with 200 other people who can say the same exact thing.

Speaker 3:

But if you ever feel as if you do not belong here, no one is an expert in you more than you are in you more than you are, and no one knows more about what you know than you. So it has carried through my entire professional career, especially when I'm in a room with some of the most amazing people. You know. You sit here and someone articulates an argument and they do it so succinctly and you can just relate to them and you say, wow, I probably sound like I have no clue what I'm talking about if I have to follow that person, but the thing is they can speak that clearly because they feel confident in what they're saying, and this is something that I try to advise customer success managers who are trying to come into their own as well. People will believe you if you believe you.

Speaker 1:

That is so good one. People will believe you if you believe you Also meaning you have to believe in your product and your services and everything that you're doing in with such a conviction that there is no rooms for questions there, even for you personally. Yeah.

Speaker 3:

And it's so easy? Because I am a reformed yes, yes, of course person and I was often coming out of rooms with questions. Everybody knows the meeting before the meeting, but how about the meeting after the meeting? Because you're in a meeting, something is said, you don't exactly agree with it, and then afterwards you write to some of your colleagues on Slack and say can we talk about that? You wouldn't necessarily need to do that if we felt empowered to speak up in the meeting and ask the questions that allow us to get to a degree of clarity that allows us to say, okay, I can confidently back up that argument, I can confidently pitch that product, I can confidently, you know, go out and retain a customer based on these facts. If you are someone who is not doing that today, we have to change it. Otherwise it's going to come across inauthentic for your customers and it's crucial that you do not do that.

Speaker 1:

Ashley, thank you so much for wonderful advice on how to battle this imposter syndrome and how to start speaking up, as the confidence will come from speaking and will come from you believing in your competencies. As we are wrapping up, I would love to hear from you Was there any career advice ever that you received or that you wish to give to the audience that was really amazing for you, like what was the best advice that worked?

Speaker 3:

Oh yes. So I was a new leader at Uniteam and I had an amazing vice president of revenue, and marketing, and sales were under this leader. His name is Dorian Kendall. Dorian gave me some really great advice. He said Dorian gave me some really great advice. He said Ashley, you're doing awesome things, but no one knows it. Don't forget to market yourself. And that has stuck with me. Dorian is someone I consider to still be a mentor to me today and that's the biggest piece of career advice I can give anyone, regardless of if you're in customer success, a woman or not, don't forget to market yourself and don't be afraid to market yourself.

Speaker 1:

And on that note, Ashley, can you just tell us what has been your latest business venture and can we market your fractional consultancy that you have just started recently?

Speaker 3:

Please, yes, yes. So I'm actually really, really pumped about this. I have started my own fractional firm. It is called the Success Rx and I have developed a formula based on my 10 years of customer success leadership experience that will be tailored to many of the challenges any startup or private equity backed firm are facing. I've been able to see that no customer success solution is one size fits all, and even the solution that you may have in one stage should not be the solution for the next. So the success Rx will do a diagnostic, just like a service provider would, and, based on that diagnostic, will provide a-based approach to help execute according to a goal. So I am open for business and people can go to the site and they can ping for a free consultation with me so we can go over some of your needs, and I am really excited to go out on this new journey.

Speaker 1:

I'm really excited for you, ashley. All the best in this new journey. I've been a fractional for a year now and I haven't looked back. So all the best and, for the listeners, please have a look at the show notes and get in touch with Ashley, because I'm absolutely confident that she will be able to help you in a way that you need help at the moment. Thank you so much, ashley. This has been such a wonderful and inspiring conversation. Thank you.

Speaker 2:

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.