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

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 and management and the chief product officer, I named us the three Amigos. And I was like, the three Amigos are gonna go and we're gonna conquer the world. And then I was at a customer meeting and after the meeting in a debrief, one of the customers, the success managers sent to me. Like CT, that's 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, never too senior to be a rep, right? To have a customer think of you as someone who can solve the 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 bread crumbs that you can see through an organization that demonstrate change, that demonstrate effectiveness, that demonstrate understanding. And I celebrate all those little moments. - Welcome to the new episode of the Women in Customer Success.com. - I'm joined by 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 by his president of customer experience at Culture Am. Her name is Cynthia Taylor. Cynthia, welcome to the show. - Oh my gosh, thank you so much for having me. I'm so excited to be here and jump in this conversation. - Cynthia, let's start with locating you globally. - Where are you calling from? - Mary Bays. - 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. - Beautiful. I wonder what a thick, steel year old Cynthia, be surprised to find you in this current role. - 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 having an office with like a name plate on it and 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 Dekka. 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 like national championships at like 17 in Florida, I grew up in Colorado. So shout out to Cherry Creek High School and the Dekka 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. 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 no way 16 year old Cynthia is in the right place. Is your head to completely change your career tomorrow? What would you do? - 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 there's 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 customers' experience in that way. - What a beautiful choice of careers making a delightful digital experience is for customers but also making delightful experiences for the taste buds. So before we go into all things customer success, I need to ask, what is one of your favorite recipes or breakfasts that you would serve on a brunch? - Maybe I'll just talk about it. 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. - Amazing. So think too. Would you like to tell us what got you to ready while today? - 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 and 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 and 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, you know, from that high school experience, you know, is 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 by a small, 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. 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, back in the '90s and early 2000s, that was really about account management and ensuring that we met our contractual obligations. And my industries that I've focused on have been mostly in two verticals, one in the travel industry and then in the HR or employee experience space, this was 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 Lithopia or ADP and Culture Amp 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 current partner, is the ideal view that a customer has of you, then having those unique data sets and being able to influence into the board room is a key element for me in that I think is really the difference that customer success can make. And then just one other piece about my career is I uniquely started my career in Australia. So I adopted for the first 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 talk 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 great, those were all of those years. So it really felt like two volumes of my life. And then culture amp 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 culture came about. - And there's just so much done fuck there. But I wonder for all listeners who are located all around the globe. If you could pick few things as like the major maybe behavioral elements of Australian tech and you at tech seed, what would you say? What are those main interesting behaviors? - 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, 16. I was competing to be a national championship and business, right? Like that's just creating, 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 of 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 gonna, you know, like I'm gonna get to the top. 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. So 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 do this as a group? And so it really changed who 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 and finance. And our friends and 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. I wonder also how did you form to you as a people leader? Because I can honestly imagine in organizational settings when everybody have to collaborate, you just had to work together with everybody and all of us, everybody out on board because you're working towards the same purpose. What about you as a manager of people, like how did they make sure that everybody are growing together? Yeah. Yeah. I think there is a couple of different elements of that. One is mentality of it takes a village, right? So you don't want anyone to lose a customer alone. You don't want anyone to go into a challenging customer conversation alone. You also don't want them to win alone. Oftentimes it's to win. You need to 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 how we review risk within our customer book or how we think about expansion opportunities 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 another one is I'm very much a shoulder to shoulder leader. I will get in the trenches. I will go on those customer calls. I still get called a rep. All these years later, it's like, how's the fees are a rep? And I'm like, that'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. I think the last one is really about internal mobility and how I think about mobility within the team. And so that have been at Culturant 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, 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 to name? So it's not at the expense of any one person, but it's really how do we have programmatic development and creating a transforming our organization in order to ensure those opportunities are there too. Let's take a quick break and hear from our sponsors as they help us bring this conversation to you free of charge. Today's episode is brought to you by Hook. Have you ever felt that you're drawing in customer data but starving for actual insights? Or have you experienced another green account just turned? We've all been there and sounds like you need Hook, the AI platform that's transforming how customer success teams actually succeed. Hook doesn't just track risk or turn like other tools. It gives teams clear and strategic direction by identifying what truly matters and where to focus next. Their data backed health scores are based on reality. That means fewer surprises and more confidence in how you prioritize accounts. Whether you're preparing for renewals, identifying upsell opportunities or managing a complex portfolio, Hook integrates AI into your everyday workflows for better decision making. And what about CS leaders? Hook connects customer health directly to revenue across all the segments from enterprise to long tail, helping you scale consistently without losing strategic debt. Stop reacting, start predicting. Hook is a smarter way to run customer success. Check out the show notes for the link. Visit Hook and book your demo now. As you mentioned, Culturump, I am now really curious to find out a bit more about the industry. You've been in employees' business industry now for a few years. And throughout the years that the world and the way you work completely changed due to pandemic and remote work, the one that's 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 finding if you want to go to any of the changes, how it changes from before, but what are main trends that you're seeing? 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. 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 it's just one thing 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 some reasoning in the world of how to interpret what is global-scale issues. But what does it mean for me at work in my role, but also 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 back to it. And so I think what folks are looking for, if I just kind of level up from where we were in the COVID times 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. 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 performances, something that leadership really needs to think about. And then the ability to demonstrate flexibility in meaning the economic challenges. And so you can see 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, it's successfully. 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. 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. He calls his works. 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 I have this always be branding mentality about whether it is your strategy for the years. So I do a little timeline of the four years of bandwidth culture and what was the strategy and the focus of each year and each has a tagline. This year is stars and it's an acronym for variety of things. Last year 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 the liver of all then build. So each year has a theme. I use ideas like we had several years ago, we had a new cheap 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 management and the cheap product officer, I named us the three Amigos. And then I was at a customer meeting and after the meeting in a debrief, one of the customer's success managers said to me, like CT, that's three Amigos thing. It's really working. 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 Amiga 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. 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. So when you're in slack channels and people are like thumbs up and 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 has all adopted like 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? And I've again had feedback come from other folks of like CT, like you're everywhere. Like I see that 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 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 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. What a wonderful example. Firstly, the years that the taglines, I mean, it's all about PR and deception. Taglines really do the work. I really love how you are encouraging people to create our new Slack emojis, avatars. What have been maybe some of the most surprising ones you have seen? 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 they went to like the cowboy hat. We do also like add people's photos, of course, like as emojis. And so that's fun. And then also when a moment I really loved is again, with the VP of a 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, and his name was Will. And so they created an @Willson, that was Will Sin. Oh, man. That is 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. How amazing is it when you say, it's almost little breadcrumbs because it's all the things 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. I think yeah, Fitching Gare was a little bit, I wonder if you were CEO for a day. Is there any untouchable customer success for actors that you would completely leave behind and replace it something new? - 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 work chart rate 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 break down silos and I would ensure that, you know, there was more collaboration, but we're in the process of working that out. And so at CultureM 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 KELT. 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 and the three of us working for the outcomes of the customer all the way from top to funnel, you know, through the bow tie. If you're a bow tie person to renewal and expansion, it's 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. - That's really a wonderful potential strategy. I mean, it's not potentially something you're working on, but it's great to see how much friends eat. Like what is the huge potential of it? Cynthia, as you're roughing up, I need for us for your career, the rise. You have been through amazing roles to make for you. 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? - Yeah, that's a tough one of the one piece. My view of how we partner with customers has really evolved over time. So early in my career, I was focused on, like how to get customers to like me, right? 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 we're gonna grow this customer. And then you have the first one, churned 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 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. 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? 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 and 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 cap 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. - I really really like and appreciate it for the wise because what a very often when I ask this question, people focus on their own fields or things that they maybe could have done differently or the way they would show up in their career and being the main elemental career progression. And I really like all your focus so much on the evolution of your approach to customers and just working with customer and building that relationship over time. Well, that's what customers, et cetera. And experience is all about, I believe. - Thank you. - Thank you. - That's great. - It's in the blood. - Thank you so much from sharing all of that to be us today. - That's our parting question. If you could be a member for one thing, what would it be? - One thing besides my breakfasts, I guess we're talking about. I think it's about the teams I've created, the teams that I have built or we have built together over time and that folks reflect on the time that we work together is when they did some of their best work, the engagement, excitement, fun, through branding and silly emojis or winning a customer together, that takes a village type of mentality. All of that should feel like doing your best work and when folks, and I keep in touch with folks throughout all of my jobs as they always look back finally on, I mean, they're talking to me. So what else are they gonna say? But we're still in touch. So I will take that as evidence. But they really look back finally 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 their, some of their best work while we work together. - What in line is to be a people leader? Thank you so much Cynthia for sharing all this yesterday. - 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 about in questions. - Thank you for listening to today's episode. I really appreciate you taking time to learn something new and prepare 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. (upbeat music)