Women in Customer Success Podcast

142 - You're Never Too Senior to Be a Rep: Leadership Lessons with Cynthia Taylor

• Marija Skobe-Pilley • Episode 142

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What makes a truly exceptional customer success leader?

In this conversation with Cynthia Taylor, Senior Vice President, Customer Experience at Culture Amp, we explore how strategic branding, international perspective, and a shoulder-to-shoulder leadership style can transform customer success teams.

Cynthia’s journey spans continents and industries, from high school business competitions to leading global teams. Growing up professionally in Australia, she was shaped by tall poppy syndrome - a cultural belief that collective achievement matters more than individual spotlight. It’s a philosophy that mirrors customer success itself, where cross-functional collaboration drives outcomes.

In this episode, we discuss:

  • How cultural values shape collaborative leadership.
  • Creative ways to use branding, themes, and even Slack emojis to align and inspire teams.
  • The evolution of customer success leadership, from being liked to driving outcomes, to building lasting connections.
  • Using yearly themes and taglines to rally teams around clear objectives.
  • The impact of creating memorable moments like “The Three Amigos” to strengthen cross-departmental relationships.

These small but mighty “breadcrumbs,” as Cynthia calls them, leave lasting markers of organizational effectiveness. For her, true success means creating teams where people feel they’ve done the best work of their careers - together.


Whether you’re new to customer success or leading at scale, this episode offers fresh CS strategies and leadership lessons that will inspire you. Tune in!


💚 This episode is brought to you by Hook: https://hook.co/


___________


👉 Follow  Cynthia Taylor: https://www.linkedin.com/in/cynthiataylor20/

👉 Learn more about Hook & grow your revenue on autopilot: https://hook.co/

👉 Learn more about Culture Amp, the world’s leading employee experience platform, revolutionizing how 25 million employees across more than 7,500 companies create a better world of work: https://www.cultureamp.com/



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Speaker 1:

I think everyone understands it's a hard time right now, but it's. What are you doing about it and how are we going to weather that storm? And that transparency and conversation as an organization is super important. Several years ago we had a new chief product officer start with the company and it was a great time to reset the relationship between the customer group and the product group. And so at that time, with my colleague in account management and the chief product officer, I named us the three amigos and I was like the three amigos are going to go and we're going to conquer the world.

Speaker 1:

And then I was at a customer meeting and after the meeting and a debrief, one of the customer success managers said to me like CT, that three amigos thing, it's really working. Like I can see it Right. And so you hear this like feedback of the branding. Come back to you. You're never too old and never too senior to be a rep. Right To have a customer think of you as someone who can solve a problem and that that relationship is okay. Like you can figure out what seat you need to play at the table. Sometimes as a senior leader, you can come in and say things that no one else on your team can say because of the leadership authority decision-making you have, there's these little breadcrumbs that you can see through an organization that demonstrate change, that demonstrate effectiveness, that demonstrate understanding, and I celebrate all those little moments.

Speaker 2:

Welcome to the new episode of the Women in Customer Success podcast. I'm joined by an incredible guest today and I can't wait for you all to meet her and to hear her wonderful career story and experience. She's currently a Senior Vice President of Customer Experience at Culture Un. Her name is Cynthia Taylor. Cynthia, welcome to the show.

Speaker 1:

Oh my gosh, thank you so much for having me. I'm so excited to be here and jump in this conversation.

Speaker 2:

Cynthia, let's start with locating you globally. Where are you calling from? Where are you based?

Speaker 1:

I am calling from the very American-sounding town of Walnut Creek, california. It is in the East Bay of San Francisco and I go into our San Francisco office in the city.

Speaker 2:

Beautiful. I wonder, would a 16-year-old, cynthia be surprised to find you in this current role?

Speaker 1:

Yes and no. I actually had an interest in a career in business very early. My parents were very career focused and definitely drove an idea of having a profession. My mom talked about, you know, having an office with like a nameplate on it, growing up Right, and so there was that aspiration that was put out there for me early, and in high school we actually had a business club called DECA and my high school was actually one of the strongest national competitors and so I was competing at 16 and 17 years old in role plays. The competition was basically role plays of sales situations and customer service experiences, plus some written tests to prove that you were kind of the best in this area of business. And so I went to the national championships at 17 in Florida.

Speaker 1:

I grew up in Colorado, so shout out to Cherry Creek High School and the DECA program there, and so I was very early on the path of being in business and being comfortable with customer situations, and so that part feels very natural. Of course, customer success didn't exist when I started in my career, living in California working for a global organization. Those are things that a 16-year-old Cynthia wouldn't have been able to imagine. For sure she would be excited.

Speaker 2:

She would be excited. But wow, amazing, what a story that you were already then competing in that aspect of like business and customer service. That's really wonderful. So, in a way, 16-year-old Cynthia is in the right place. If you had to completely change your career tomorrow, what would you do?

Speaker 1:

Oh my gosh. Well, friends and family would say I would open a restaurant of some kind. I love to cook and I love to host. It would probably be something like a breakfast restaurant. I quite enjoy making a fabulous breakfast. I also love product design and user experience, and so I have not studied in that area, but they're some of my favorite people to work with, and so if I had to do it over again, I may have gone more on that path or developed more skills in that area, because the impact of being able to improve the experience for everyone who touches your website, or everyone who touches your platform, or every time they come in, it's a delight, right? I enjoy that experience when I'm on a fantastically designed site, and so would love to be able to influence a customer's experience in that way.

Speaker 2:

What a beautiful choice of careers making a delightful digital experiences for customers, but also making delightful experiences for the taste buds. Just before we go into all things, customer success, I need to ask what is one of your favorite breakfast recipes or breakfasts that you would serve on a brunch?

Speaker 1:

Maybe I'll just talk about so. Yesterday morning I have a. My youngest daughter is a senior in high school. She was running short on time, as senior in high schools do, and so breakfast was a quick omelet with roasted tomatoes and spinach and then leftover sourdough bread with a goat cheese spread that I had made myself with basil and parsley and green onions, and so that was like seven minute breakfast to get her out the door.

Speaker 2:

Amazing. So, cynthia, would you like to tell us what got you to where you are today?

Speaker 1:

Yeah, it's been a fantastic career and I really have enjoyed the arc of being a part of a business discipline that didn't exist when I first got out of school. Right now, you can go to school in customer success, you can get a degree, you can take a class, you can go to a conference, you can buy software. Like, customer success is both a philosophy, it is a business discipline and it is like a paradigm in how we work, and so it's been fantastic to be a part of the arc of customer success really coming into its own. When I started out from that high school experience, I was in retail and always working with customers in some way. One of the interesting through lines in my career is that I have always worked in a startup situation in some way shape or form. It started in my first job of working at a grocery store that was owned in a small town by a husband and wife team. I worked in retail that was owned by a husband and wife team, and then I've also been in startups, and so it's been fantastic to see how entrepreneurship really can evolve over time and, with the advent of SaaS, what entrepreneurship looks like when you get to a $200 million business and 7,000 customers. Right, it really evolved over time.

Speaker 1:

So when I started my career, it was in sales and then into account management. I really enjoyed the sales aspect, but I enjoyed more seeing not only the promises we made to customers and what we could do for a customer in any one situation, but making sure that they actually got to that outcome. And so in that in back in the nineties and early two thousands, that was really about account management and ensuring that we met our contractual obligations. And my industries that I focused on have been mostly in two verticals one in the travel industry and then in the HR or employee experience space, as sort of the two main verticals, and then one of the through lines that actually took me from travel to employee experience, which you could kind of wonder like what that through line is is that every company I've worked for also has had a very unique data set, and so these unique data sets are able to bring insights to customers that they can't get anywhere else and can influence the health of the business, achieving the strategic outcomes that the customer needs for their long-term plans through the unique data sets we have. So, whether it was at Hotwire or Lyftopia or ADP and CultureAmp. Now all of these businesses have had really unique data sets and so the opportunity to move if you're always going to be on this side of the table right, if you're always going to be a rep of some kind a partner, you know is the ideal view that a customer has of you then having those unique data sets and being able to influence into the boardroom is a key element for me and that, I think, is really the difference that customer success can make.

Speaker 1:

And then just one other piece about my career is I uniquely started my career in Australia. So I adulted for the first time in Australia and lived there from the age of 23 to 31 and then moved back to the States and moved to San Francisco, and so when I talk about my adult life, I really talked about it in. People talk about the chapters of their life and I think about it in volumes, like volume one was the Australia years chapters of their life, and I think about it in volumes like volume one was the Australia years travel, industry, starting my career, pre-kids, all of that. Then we moved to the Bay Area, started in tech, started in customer success and started family, right, like those were all of those years. So it really felt like two volumes of my life.

Speaker 1:

And then Culturamp came into the fray, which was a startup in tech, in employee experience, but Australia founded and I was like, oh my God, I'm a trilogy, like there's a third volume to this. That really brought my whole story together, and so I would love to say it was very strategic to go find an Australian company, given the fact that I am a dual citizen and that there's all of those opportunities. But it was really just a full circle moment when the opportunity to join Culturine came about.

Speaker 2:

And there's just so much to unpack there. But I wonder for our listeners who are located all around the globe If you could pick a few things as like the major maybe behavioral elements of Australian tech and. Us tech seed. What would you say? What are those main interesting behaviors?

Speaker 1:

Yeah. So I think the earliest lesson I had in Australia was the cultural elements of how Australians win, and so we started out the story very American story At 16, I was competing to be a national championship in business, right, like that's just not culturally what other countries would experience, and so there was a lot of pressure to be a winner, to be in first place, to do all of that with an American mentality. In Australia they are very, you know, about everyone succeeding, that no one should achieve more than the rest, and so they actually have a phrase called the. It's a psychosocial, defined phenomenon called the tall poppy syndrome, and so tall poppies, right. If the poppy gets too tall, the other poppy strangle it to pull it down because they don't want it to create shade over the other poppies. They want all of the poppies in the field to rise at the same time, and so when I first got to Australia, I would be like let's go, we're going to, you know like I'm going to get to the top.

Speaker 1:

And then I found that it was a really challenging environment to succeed in, and so I realized that it was about getting everyone to succeed and getting everyone on the bus of like no, no, no, this isn't about me. This is about us. Like how can we get our office to succeed? How can we hit our numbers as a group? How can we?

Speaker 1:

I was, as a person, from that American kind of striving individualistic kid into someone who thinks about the group as a whole and how do you achieve together? And I think that has become a hallmark of my career, and I think customer success is particularly bent towards that, not only in thinking about how our customers can succeed, but actually the cross-functional impact that you have to have to make customer success successful, to work with product, to work with marketing, to work with our friends in finance and our friends in sales, of course, and so that cross-functional success is so important in our field. And without the time in Australia, to have had that experience of how do you win together to win it all really was, I think, just foundational in who I became as a person and how I do my work today nicely imagine in organizational settings, when everybody has to collaborate.

Speaker 2:

You just have to work together with everybody, and almost everybody are on board because you're working towards the same purpose. What about you as a manager of people Like? How do you then make sure that everybody are growing together?

Speaker 1:

Yeah, yeah, you know I think there is a couple of different elements of that. One is mentality of it. It takes a village Right. So like you don't want anyone to lose a customer alone, you don't want anyone to go into a challenging customer conversation alone, have people around you. And so it's a trite saying and it's used a lot, but I really do think it's true of like it takes a village to be successful in most anything, and so I bring that mentality into. You know how we review risk within our customer book or how we think about expansion opportunities and and ensuring that the team knows that there are resources of people and expertise that can help them be successful. So that's sort of that element I think.

Speaker 1:

Another one is I'm very much a shoulder-to-shoulder leader. Like I will get in the trenches, I will go on those customer calls. I still get called a rep. You know, like all these years later it's like oh, sophia's our rep of these years later it's like oh, sophia's our rep, and I'm like that's. You know it's awesome that if customers know that I can be available and I am getting my hands dirty and in solving problems and helping with customers. Of course you have a team to do that, but at the end of the day, everyone needs to know that you are also capable of doing that, and so that informs my behaviors and how I work with the team and how we divide and conquer to win.

Speaker 1:

I think the last one is really about internal mobility and how I think about mobility within the team, and so that I've been at Culture Ramp for four years and each year we've made progress in the internal mobility of our team, not only with upward mobility, of moving and going in from an IC to a people leader, an individual contributor to a people leader, an individual contributor to a people leader but also into lateral moves, where people are gaining more experience, so they don't have just singular, siloed experience, but they start to have a depth and breadth of experience that can then move them forward into more senior leadership positions. And that's a real focus in how do we win together, how do we develop all of these folks over time, so it's not at the expense of any one person, but it's really. How do we have programmatic development and creating, transforming our organization in order to ensure those opportunities are there too?

Speaker 3:

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Speaker 3:

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Speaker 2:

As you mentioned CultureAmp, I'm now really curious to find out a bit more about the industry. You've been in employee experience industry now for a few years in employee experience industry now for a few years and throughout the years that the world and the way we watch completely changed due to pandemic and remote work.

Speaker 2:

So I wonder from your daily work and from your insight, what is currently maybe top three or just top of elements and different things that employees are looking for in their employer in terms of really their experience. Maybe, like I'm fine if you want to go through any changes, how it changes from before, but what are main trends that you're seeing?

Speaker 1:

Yeah, the employee experience, I think is one of the most fast moving areas inside a business today, if you think about the flexibility that HR leaders and leadership, executive leadership teams have had to demonstrate in order to meet employees where they're at in their organization. From the pandemic, from the pandemic you know, we had the pandemic, we had a change of administrations in the US, we had the murder of George Floyd, we had all of the diversity issues and inclusion opportunities and what that looked like into an economic downturn and you know it's just one thing sort of after another that has been we've all been experiencing together and employees have looked more and more to their employer for support, for consistency, for like some reasoning in the world of how to interpret what is kind of global scale issues, but like what does it mean for me at work, in my role, but also like in in the world? So I think that we stretch much more further into the personal experience of employees than we would have five years ago if you look, if you look back to it. And so I think what folks are looking for if if I just kind of level up from where we were in the COVID times to today is they are looking for consistency. The economic environment is still too volatile to feel like they can move quickly and move within exiting organizations in order to take new roles.

Speaker 1:

The stability and consistency that they're finding at their employer is important to them, but they do want growth and development opportunities inside that experience, and so making sure that you have those opportunities within an organization to keep folks engaged and providing their sustained high performance is something that leadership really needs to think about. And then the ability to demonstrate flexibility in meeting the economic challenges, and so you can see you know a chart with the stock market on it or headlines around interest rates, and so the clarity of what's happening inside an organization and what the next steps are for everyone to weather this economic winter successfully. Like I think everyone understands, it's a hard time right now, but it's what are you doing about it and how are we going to weather that storm? And that transparency and conversation as an organization is super important so that folks can get signal from the right things and have hope, and hope can be a strategy sometimes, and I think that's a bit where we're at at the moment.

Speaker 2:

I love that Sometimes hope can be a strategy. It can be, cynthia. Since you started building and developing customer success functions in different companies, I wonder what is one framework or little print that you would always apply in your role, something that you would say oh, that's what I swear by, it always works.

Speaker 1:

One of the interesting things that I have found works for good times and bad is a focus that happens in the background around branding, and I think it's not something we talk enough about in customer success is how are we communicating to our teams and to the wider company around the strategies that we're using within our customer success teams? And so you know I have this like always be branding mentality about whether it is your strategy for the years. So you know I do a little or I do a little timeline of the four years I've been with Coltramp and what was the strategy and the focus of each year, and each has a tagline, right Like this year is stars, and it's an acronym for a variety of things. Last year was was the year of CX, because we did a large transformation and brought our different functions all together. The year before that was our friend Deb around deliver, evolve and build. So each year has a theme. I use ideas like we had several years ago. We had a new chief product officer start with the company and it was a great time to reset the relationship between the customer group and the product group. And so at that time, with my colleague in account management and the chief product officer, I named us the three amigos and I was like the three amigos are going to go and we're going to conquer the world. And then I was at a customer meeting and after the meeting, in a debrief, one of the customer success managers said to me like CT, that three amigos thing it's really working, like I can see it right. And so you hear this like feedback of the branding. Come back to you. We opened an office in Berlin and this is our general manager used this, but it was a great rallying cry of when we were thinking about growth in the EMEA market, of being bigger than Berlin. Even though we opened the office in Berlin, it wasn't about Berlin, it was about being bigger than Berlin and having that be the rally cry.

Speaker 1:

And then the last one, which is silly but is really helpful in these Slack days, is I have my team all using individual emojis. Know, when you're in Slack channels and people are like thumbs upping stuff, and you're like, oh, there's a lot of thumbs up there, but like who read it? You can see all the different colors of skin tone, but you don't know who actually was there, and so my team is all adopted like one individual emoji, one individual emoji. So if I see the dancing dinosaur, I know that Brit saw it. If I see the flouncy fox, I know Ashley saw it. I'm the green heart right.

Speaker 1:

Like so, and I've again had feedback come from other folks of, like CT, like you're everywhere, like I see that, like green heart, like how are you there? And it's so great because we run our eyes over so many different messages you don't have time to like reply to all of them, but like why not put a unique stamp on it so that folks feel seen, they know the information has been communicated and they know that you know something could happen as a follow up from that. And so the idea of branding and how we simplify communication and have shortcuts to anchor the team and have excitement about things that are novel for a year, I think really makes a difference in the routine of our work to know that we have those thematic differences and to know what we're really rallying behind.

Speaker 2:

What a wonderful example. Firstly, the years, the taglines I mean it's all about PR interception. Taglines really do the work. I really love how you are encouraging people to create their own little Slack emojis, avatars, what have been maybe some of the most surprising ones you have seen.

Speaker 1:

Oh, the emojis, I don't know. It's like sometimes it's about people's interest. We had a leader who was a boxer and so his was like the boxing glove. Sometimes it's about location. We had someone in Texas who first used the cactus and then they were like that's too prickly so, of course, like as emojis, and so that's fun.

Speaker 1:

And then also, when a moment I really loved is again with the VP of management that I did a ton of work with, someone created a shared I don't even know what they're called a shared handle. So my name is Cynthia Sin and his name was Will, and so they created an at Wilson. That was Wilson, that's the thing and it was like because they're always talking to both of us it was account management and customer success, and so when we got that shared handle, I was like again, it was like a little external sign of partnership, like people see us doing the work together and they know that, like we're in partnership. And so there's these little breadcrumbs that you can see through an organization that demonstrate change, that demonstrate effectiveness, that demonstrate understanding, and I celebrate all those, all those little moments.

Speaker 2:

How amazing is it when you say it's almost little breadcrumbs, because it almost takes that little effort to create it the hashtag or the emoji it's really very simple, but it can have such a huge aspect for months to come. That's a wonderful, wonderful strategy. Silvia, switching gears a little bit, I wonder if you were a CEO for a day. Is there any untouchable customer success practice that you would completely leave behind and replace with something new?

Speaker 1:

What would I do? Yeah, I think that's something that we're working on right now within my team, which is and it depends on your org chart, right Of like where organizations and where customer success sits. It can sit under a CRO, it can sit under a CCO, it can sit under the CEO, it can sit under marketing right Like. I've seen it sit everywhere. But what I really am focused on, and we're focused on right now, is the go-to-market strategy across everyone in what we consider our customer group. And so being CEO for the day would be like I'd break down silos and I would ensure that there was more collaboration, but we're in the process of working that out.

Speaker 1:

And so at CultureAmp, within the customer group, we have marketing, cs, cx, of course, and sales, and we have three executives, two peers that are excellent leaders, and they, with me, form CELT, so the Customer Executive Leadership Team. And so, if you think about that three-legged stool, what have you? That idea of having the go-to-market engine be very tight, tight and the three of us working for the outcomes of the customer all the way from top of funnel you know, through the bow tie if you're a bow tie person to renewal, and expansion is just very key in the ability to have impact and to not have customer success just standing at the goal trying to block, you know, churn or risk or what have you. It really means you have everyone on that field playing together and ensuring that you're winning and you're on the offense more than the defense, and so that go-to-market opportunity and the tightness of the group working in synchronization with each other, I think is the biggest opportunity for companies today, so that you're not winning by those individual stars but you're really winning together.

Speaker 2:

It's really a wonderful potential strategy. I mean, it's not potential, it's something you're working on, but it's great to see how much brands like what is the huge potential of it. Cynthia, as we're wrapping up, I need to ask for your career advice. You have been through amazing roles to make your career and I wonder do you think there is one lesson that you have learned that you think definitely everybody should learn at some point in their career?

Speaker 1:

Yeah, it's, that's a tough one of the of the one piece.

Speaker 1:

My view of how we partner with customers has really evolved over time. So early in my career I was focused on like would customers you know, like how to get customers to like me right, like like me, like my company, and like if you were tight with the customer and they would take your coffee invite, you know? Then you were like, okay, like I've got a good partnership and and we're going to grow this customer, and then you have the first one churn you right, you have the first customer who you weren't talking to, the right decision maker, the company went in a different direction. What have you? So, no matter how much you have that personal relationship, I still have relationships with folks who are my customers from 30 years ago. No matter how much they like you right that there may be a business reason not to work together and so you have to be focused on the outcome, not just on the relationship. So that was like very early career of learning that lesson of focusing on the outcome and the relationship helps too, but it's secondary, not primary. I think in the middle of my career was then really seeing where folks were starting to move around organizations and move forward, and it's focusing on having relationships that transcend the job. And so when you do a great job with a customer, for a customer not just the individual, but for the organization that transcends that one experience. It means you get referrals from other folks. It means when that person leaves, they take your product or services or platform with them. It means that you have the ability to support them in reference checks and other things over time. And so you move from focusing on the relationship and then the outcome to like, okay, this is not going to be about this one experience, it's going to be about all experiences.

Speaker 1:

And then now in this later part of my career I kind of mentioned it before is that you're never too old and never too senior to be a rep, right To have a customer think of you as someone who can solve a problem and that that relationship is okay.

Speaker 1:

Like you can figure out what seat you need to play at the table. Sometimes, as a senior leader, you can come in and say things that no one else on your team can say because of the leadership authority, decision making you have. Other times it's about being one of the team who can go and solve a problem for a customer, and so that evolution of like everyone is there for the customer and we all have the ability to help them out in whatever way we can is like the final capper of ensuring that not only do you have great outcomes for customers, you have relationships that can stand the test of time, but you can also ensure that you're always someone who is a fixer, who is a problem solver and who's available for customers and your team kind of regardless. And so knowing that that will evolve, I guess the career advice is knowing that you will learn those different lessons over time and that you take those lessons and you just use that momentum to move forward.

Speaker 2:

I really, really like and appreciate this advice because also very often when I ask this question, people focus on their own skills or things that they maybe could have done differently, or the way they would show up in their career and being the main element of career progression. And I really like how you focus so much on the evolution of your approach to customers and just working with customers and building that relationship over time. Well, that's what customer success and experience is all about.

Speaker 1:

I believe this is what we're all about.

Speaker 2:

That's right, it's in the blood. Thank you so much for sharing all of that with us today. That's our parting question. If you could be remembered for one thing, what would it be?

Speaker 1:

One thing besides my breakfast I guess we're talking about. I think it's about the teams I've created, the teams that I, that I have built or we have built together over time and that folks reflect on winning a customer together. You know it takes a village type of mentality. All of that should feel like doing your best work.

Speaker 1:

And when folks and I keep in touch with folks, you know, throughout all of my jobs, as they always look back fondly on, I mean they're talking to me, so what else are they going to say? But we're still in touch, so I will take that as evidence. But they really look back fondly and they talk about the team, like that team that I was in, right, my team at ADP, that team that I was in was amazing the time at Hotwire, that team that we created, and I can see the relationships that people have maintained over time because we did such great work together. We understood and trusted each other and delivered great outcomes and made you feel great to solve hard problems together and that is what makes you feel fantastic and why you have the relationships you do over time. And so, yeah, I would love to be remembered for folks thinking they did some of their best work while we worked together.

Speaker 2:

One of my insights into being a people leader. Thank you so much, Cynthia, for sharing all of this with us today.

Speaker 1:

Thank you so much for having me. It was so much fun. I really appreciated the conversation and the reflection. It's something we don't take a lot of time out to do, so I appreciate your thought-provoking questions.

Speaker 3:

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 this. Thank you.