Transcript: Learnings From Switching To A New Role as Chief of Staff to the CCO with Brittany Rolfe Hillard

On this episode, I was joined by Brittany Rolfe, whom many of you are familiar with since she’s been a repeat guest on the show. She was previously running customer engagement and advocacy at WalkMe, and has since transitioned into a role as Chief of Staff to their Chief Customer Officer and is enjoying it immensely. I think it’s always good to get additional perspectives on what other career opportunities are available that are related to our space and so Brittany came on to share the story of how she moved into this role, what the work entails and how her time in customer marketing was integral to this position. Without further ado, here’s my conversation with Brittany. 

Margot Leong: Hey Brittany, thank you for joining us on the show again. You are so far my only basically twice repeat guest, three time guest on the show. If I had a soundboard, it would be like cheers and clapping and whatnot. It’s very exciting and so thank you so much for coming back on to chat about the topic we’ve got planned. 

Brittany Rolfe: It is such an honor to be back. You know, I love this and I love your show and I love all the other guests, and so it is really exciting to be back and to be talking about a new topic. 

Margot Leong: Basically what we wanted to focus on for this time around is that, there’s been a bit of an update to your role since we last spoke. You’re still at WalkMe, but previously, you were VP on the marketing side focused on customer engagement and advocacy. And now you’ve been for about a year, a little bit over a year now, VP and Chief of Staff to the Chief Customer Officer. 

When I heard about this new role and we were chatting a little bit about it, I was like, wow, really interesting. I’ve never really heard about this idea of a Chief of Staff to the Chief Customer Officer before.

 In the sort of mindset or frame of just thinking about for customer marketers, people who are in the advocacy space and just really love the customer, what are additional ways to utilize that love for the customer within organizations? What are additional career opportunities? And so just really wanted to focus the conversation on that. 

Let’s back up a little bit first. Basically what is a Chief of Staff for those who aren’t familiar and I am definitely one of those people.

Brittany Rolfe: Perfect. I think that’s a great place to start. So people are most familiar with the Chief of Staff role within the political space. The most well known Chief of Staff is probably the White House Chief of Staff, who’s the head of the executive office of the President. 

But this role is actually more and more popular, especially within the tech space. I feel like it really started getting a lot of traction within startups, but now it’s becoming more and more common within more complex organizations or organizations looking to scale. 

And many executives, let’s say CEOs, most commonly are looking for a Chief of Staff to go beyond the role of a more traditional EA to really be a strategic partner to help the company run more smoothly.

For me, it’s actually a little unique because I’m not necessarily Chief of Staff to the CEO, but I’m Chief of Staff to a specific department, in this case, our customer success group, which is a combination of customer success, professional services, support, technical capabilities, renewals, customer experience. So it’s a very different take on the role. 

But that’s the great thing about being a chief of staff is it’s actually like extremely varied based on what company it is, what the principal is looking for in the role, but in general, the role is kind of business operations, internal communications, special projects, and it’s really this balance of leadership, influence, people management, individual contribution and so every day is very different. I’m excited to kinda dive into what it can look like at different companies. 

Margot Leong: What’s interesting too is that your background, right? I think you were doing customer success, you’ve done partnerships, right? You were on the solutions, success side, general engagement, marketing… 

Brittany Rolfe: I had pretty windy journey to get here. And I know I shared this on a previous podcast. I started in consulting. I moved into customer success, moved from there into partner enablement, moved from there into channel sales. Moved back into strategic alliances, then back into customer success. 

And then that’s actually how I made my way into marketing for the first time, which was in kind of a customer engagement, customer marketing position where I was really the first person on our marketing team that had any frontline experience working with our customers.

And so got to help bake out what is that customer experience, that post sale experience. Trying to kind of imagine everything from lifecycle to community to customer programs and events and advocacy. And so that’s really what I did for the five years prior to moving into this Chief of Staff role. I had a very diverse career before, which I think really helped in moving into this jack of all trades role where I’m not necessarily an expert on any one thing, but my goal is to navigate the org, pull in all the different experts, help to get those cross-functional initiatives across the finish line.

And so it’s helpful to have such a varied background because I can pull in a lot of different things to be successful as a Chief of Staff. It’s been a windy journey and I’m not really sure where it’ll go from here, but I’m excited. 

Margot Leong: If you could share about the story of how this came about because when, you told it to me initially, I was really inspired and I think it’s a good example of having the confidence to ask for what you’re interested in, trying to craft a role for yourself. I think a lot of people are worried about asking for what they want. You’ve always been a person that’s inspired me in that way whether it’s voicing concerns or asking for things or just being open and interested in starting the conversation. I think you’re a really good example of that. 

Brittany Rolfe: That is so kind. I was listening to one of your other episodes recently, she was talking about this same concept. I’m like, you go girl. You gotta ask for what you want. It never hurts to ask, make your hopes or dreams or goals more known because like you guys said on that episode, people want to help you get to where you wanna go and especially, it means you’re gonna stay with them or stay with your company along the ride.

So I definitely think it never hurts to ask, but happy to tell more about how I made this happen within WalkMe and for me. So actually like four, five years ago, like as I was kinda moving into the customer engagement role, I had also started hearing more about this Chief of Staff role and wasn’t really sure a ton about it. Did a little Googling and at the time there was even less information about the role outside of the political sphere available online. It was just a handful of blogs from VCs about what the role is and some firsthand accounts. 

But I was really curious and so I’d gone to our CEO at the time and said, Hey I’m kind interested in this role. I think you would really benefit from having one. Would you ever consider me for something like this? And honestly at the time he was like, no, I’m not interested in having that role. And even if I did, I don’t know if you’re the right fit. He was traveling between Tel Aviv and San Francisco and speaks Hebrew and manages the R&D department and I wouldn’t have been able to have been his right hand person or a good proxy for him in a lot of those scenarios. 

But he just also wasn’t looking for it at the time and wasn’t as familiar with the concept. So I was like, ok, no big deal. I leaned full force into customer marketing, learned everything I could about this space and met so many people.

But I had always been like, oh, one day, I want to explore this chief of staff thing further. And I actually went on maternity leave with my second kid. And at that time I was like, okay, I’m gonna really learn more and so I joined these professional networking groups on Chief of Staff and talked to some companies that had them and really just started to explore it more and more while I was out on leave and just piqued my curiosity.

I came back from mat leave and four or five months later, we announced that we were getting a Chief Customer Officer for the first time. This person was going to bring together six different departments under one roof for the first time and really reimagine our customer experience.

 I had been in this customer engagement role in the marketing department for about four, almost five years at this point. And I’m sure all the customer marketers online can probably relate to feeling a little misunderstood sometimes, either within marketing or what are you doing? How do you do it? What’s the value? What are your programs? 

I just always felt like we were super, super focused on generating net new leads and there wasn’t as much of an emphasis on the customer lifecycle and customer retention and growth. And so when this Chief Customer Officer arrived, I saw that as my opportunity. At the time, I saw that as my opportunity to just get more support for my initiatives.

I knew that he’s customer obsessed. He’s really excited about reimagining the customer experience and I was like, this is my chance to get the stakeholder I’ve been missing for the last however many years. But on that first call with him, I scheduled an hour, we went through a lot of the work, the programs, what’s working, what’s not working, vision for the future.

And I could just tell that he was so excited and so into this and he had so many ideas on what was possible within this space. And it was kind of in that moment where I was like, oh my gosh, I could either continue to do something like this with him as a stakeholder and potentially as a leader or maybe he’s looking for a chief of staff. And so I just asked him, I was like, Hey, by the way, this is something I’m really interested in. Is there any chance you’re hiring for it? And he said, that’s the first role I’m hiring for. And if it’s something that you’re interested in, I think the job could be yours.

Margot Leong: Wait, was that on the first call that you had with him? Did he already seem like a kindred spirit where you felt comfortable to ask that question? 

Brittany Rolfe: I think it’s two things. I could just tell that he was so passionate about the things that I was really passionate about as well, and that we had a lot of common, and we had a really great open hour long discussion around all of these things. And so maybe I could have waited until the next meeting or something to ask, but I was just so curious and he seemed like he was gonna dive in and move fast. And I didn’t wanna miss my opportunity.

And it wasn’t necessarily that I was like, I 100% would take the role, but it was like, if you’re looking for this, I’d be really interested in learning more. And it just started the conversation. And of course I went back to my manager and, kind of started that conversation of, Hey, I think I’m gonna apply for this other role and would talk to me more about what a transition would look like and all that. Tried to do it the right way, but I didn’t even expect him to be looking to hire a Chief of Staff. I just had to ask though. I just kinda figured what are the chances he’s probably not, but maybe if he does in the future.

And also my worst case scenario was like, okay, at least I have this really passionate stakeholder who cares about all the things that I manage and own and that’s really been missing for a couple years here. And so I’ll just get ’em more pulled into everything that I’m working on and just a lot of great opportunity, regardless of whether Chief of Staff panned out. But I just so happened to luck out and that was exactly what he was looking for. 

And honestly, the irony is now at WalkMe, I think we have four or five Chief of Staffs. Once I kind of moved into the role, the CEO hired somebody. Our Chief Officer brought somebody on, marketing. So there’s a couple other folks in roles, but like I said, every chief of staff is so different depending on their principal, their department, what the team needs, where their focus areas are. And so we have very different roles based on the need that we’re filling for our team. 

Margot Leong: How did you guys get the ball rolling from there? 

Brittany Rolfe: He created a job description. He actually opened up a formal interview process with the team so anyone could apply and go through it. I gave my leadership team a heads up that, Hey, I’m interested in this opportunity. I’m gonna move forward with it. And then once I kind of got the role more officially, then we worked on a transition plan, making sure the team that I manage went to the right places, put a little bow on everything and overlapped between the two roles for a period of time.

 I was gonna mention this earlier, I think something that really helped with the move and with identifying if I was the right fit for the role was all the work that I had done in customer marketing in the first place. 

As a chief customer officer, like I said, he’s super customer obsessed. His desire is to create an incredible customer experience. And as a customer marketer, that’s exactly what we’re trying to do all the time, right? And so he was able to see through his conversations with other people at the company, before he even came to WalkMe, when he would talk about these things, those people would say, oh, you should really meet Britney. You should meet Britney. Oh, Britney’s really passionate about this. Oh, she’s working on this and that. 

And so he had already heard my name and seen some of my work and heard from other people what I was focused on. And so it was almost like the interview process started before it really started, based on reputation of what I was trying to do and what I was passionate about.

And that’s just something that I think is the beauty of a customer marketer is you are so involved in a lot of these things. And when people think about, oh who cares about creating a great customer experience? It’s our customer marketer, they’re super passionate about it.

I think there’s a lot of great fit between a Chief Customer Officer or a VP of Customer Success or whatever it is, and the customer marketing role. And we just didn’t have that connection at WalkMe super strongly before. This was an amazing opportunity to bring it together.

Margot Leong: Two things that come to mind is you have been with WalkMe for almost eight years it looks like. 

Brittany Rolfe: Eight years. One marriage and two and a half babies, I’m due with my next baby in a month. That’s a lot of life milestones at one company, . 

Margot Leong: Yeah, exactly. And so to have been there since the company was pretty early and to also kind of have seen it evolve but also have to have grown with it. And to also have built the reputation there, right? Because you weren’t only doing customer advocacy there, you were also working on the success side, right? So like that’s really valuable because you’ve built a reputation, you’ve gotten to know people in different departments. 

And when you think about what customer marketers do, right, it’s not just the focus on the customers, we have a really interesting view of the company because we work with so many different departments. We probably touch most departments at this point, the support, you know, customer facing side, so support, success, of course, the go to market side, right? All of the marketing departments, sales, and then a lot of times if you’re running things like CABs, executive events, you’re interfacing directly with the executive team as well. And then on the product management side, the engineering side… 

Brittany Rolfe: The list goes on . 

Margot Leong: So much access, right? So I think when you’re then transitioning into a role where you have deep knowledge of how the company works, how to get things done within the company and you have existing relationships, I’m sure that was also a very appealing to your guys’ new Chief Customer Officer as well, is that wow, someone like Britney is not only obsessed with the customer, but has that deep institutional knowledge of the company. And for me, coming in new, that is an advantage, a massive advantage. 

Brittany Rolfe: You nailed it completely in terms of just what value I could bring to the table as Chief of Staff to this new leader and helping kind of navigate. The org is very cross-functional and can be very siloed. So just having someone who can access all the right people in all the right places is huge. And being a customer marketer gives you that type of access. 

And very similar to being Chief of Staff, like as part of my role now, a lot of times initiatives that I’ll own or cross-functional ones that don’t have a clear owner within one of those six departments that I mentioned and so there is no clear leader who should take it and run with it. And so I’ll step in and I’ll take it. 

So I think that cross-functional nature of the relationship of being a customer marketer has transferred super well into this role of Chief of Staff. I just had to work with everybody before and now I get to work with everybody still.

Margot Leong: What are your main responsibilities for this role and helping the CCO?

Brittany Rolfe: Like I mentioned, the CCO came to WalkMe for the first time ever. He created something called the customer success group. Combined about six different departments into one. So this makes up about a third of the company. It’s over 300 people globally. And so I work alongside the CCO and the leadership team to really drive our ambition to deliver first in class customer experience.

My role specifically is to manage the operational rhythm of the department. So our leadership meetings, our extended leadership meetings, the meetings that the CCO has with each of the different departments to understand their business, their metrics, how we’re moving across certain initiatives.

And then I also work to launch and scale new cross-functional programs, and I focus on leadership communications and people engagement. And of course, I didn’t do everything overnight. I’ve been adding new things onto my plate over time. And as I’ve conquered one new thing, putting something into place, then I can take on new things.

I’m also always looking for opportunities to pass the baton, if you will. So a lot of times our team won’t have the right person or the right infrastructure or whatever it is to own something. So I’ll get it started and then I’ll work within the org to figure out where should this really live. It maybe shouldn’t live with me as the chief of staff forever, but it actually should find a more permanent home and then I can kind of transfer things to the right place, pick up things when they lose an owner or it doesn’t make sense for it to be where it was. 

So there’s a lot of fluidity in the role and what I’m working on in the day-to-day. Every day is very different, but every quarter is very different. So Q4 is very focused on our annual operating plan and Q1 is very focused on launching that and launching our goals and cascading goals down throughout the org. Q2, Q3 might be more focused on people engagement, how are we doing org health wise, events and activities, customer success summit or regional events. So yeah, it really depends on the cycles of the business where my focus is going to be.

Margot Leong: Are there any specific initiatives or programs or projects that you’d like to share that you’re particularly proud of just to give people a sense of more specifically some of the things that you’ve been working on?

Brittany Rolfe: Some of the big things we did last year, obviously we were bringing together six different departments under one leader for the first time. So you can imagine there was a lot of skepticism, unknowns, silos that we were trying to break. You know, I’m not sure about everybody else’s organization, but a lot of times I personally think that the customer success org, the departments that fall under that, get pretty beat up on, right? 

Sales sells the deal. And then, customer success has to deal with the customer and implementation and all the challenges that come with it. Yeah. And product not living up to expectations or support issues or whatever it is. As an org, it’s kind of a lot of people coming together who deal with some of the hardest challenges in the customer life cycle. And so really wanting to use this reorg as an opportunity to boost morale, bring people together, really help them identify and be proud of the incredible work that they do to create these amazing organizations who are successful at digital adoption. And so some of the first initiatives we put into place were things like an awards program, which is now going strong.

And I think it’s one of the highlights of every quarter is actually recognizing people who are living up to our CSG vision and our values which is peer nominated. And so I think it’s just a really great exercise. And we didn’t have company awards really at all, except for at our sales kickoff. So this was a great opportunity to recognize a lot of the amazing work of the team.

I also focused on All Hands, like a monthly meeting for all of CSG to come together and this was a great opportunity for us to recognize all the change going on within the organization, get people excited and motivated, share out wins, but also share out great examples of amazing customer experience and paint a vision for the future and really motivate people to go along on the ride.

So obviously, transformation isn’t gonna happen overnight. We were really setting out on a three year journey, so how do we bring the whole org along with us and motivate them to be part of the transformation to becoming a best in class customer success group, which for me is a huge motivator after seven years at WalkMe, that was kinda my new motivation. It’s okay, I wanna stay here to be part of this three year journey. And on the other end, I wanna be a world class customer success organization. 

Some other things that I am particularly proud of is for the first time ever we set goals for the entire department of what we were trying to do in the year and exactly what it was and how we were gonna measure it. And then I ran the monthly meetings where everybody came together to report on the progress of these cross-functional initiatives and the metrics that we were seeing, the challenges we were having or the wins that we had, and then sharing that information back out to the organization.

There were so many lessons learned with this process, but just that habit of saying, Hey, let’s say what we’re trying to do. Let’s explain how we’re gonna measure it, and then every month let’s stay accountable to making progress on this. And it sounds so basic, but it’s hard to do, especially when you’re a large org and everything changing and you’re moving really fast so even just having one person, the chief of staff there to ensure consistency and accountability was so helpful with visibility and transparency to are we achieving our goals or not? And if we’re not, how do we course correct? How do we change things in order to make sure that we deliver on what we said we were gonna do? 

Margot Leong: Something that really struck me, right, is bringing together these different departments under one leader who are really focused on that customer experience. You know, you talked about the boosting of morale, which is just so important because turnover in these more support oriented customer facing roles is a lot higher on average than other roles, partly as you said, because of, kind of being beat up, whether it’s customers only turn to you totally for the bad things. Or also you just don’t get that much love from the organization. It’s almost just yeah, that’s a given, that’s like your job. Yeah, totally. Yeah. , of course, sales gets all the stuff, right? You don’t really have an equivalent of SKO for the customer-facing side . 

Brittany Rolfe: And I think that’s something that being a customer marketer really helped with as well is I could see when I talk to customers, if they had an amazing account team, right? Their CSM is super supportive and their services folks really helped to deliver on their goals and implement and support’s really giving them the level of service that they needed. They’re having this great experience. Those are usually the customers who came to me on the advocacy side and they had amazing stories, they wanted to talk at events, and so I could see just oh, these people are so important to the ultimate customer success, but they’re not getting the recognition they needed. 

And so when I moved into the role, it was like, oh my gosh. We need everybody to get shirts and I created computer desktop backgrounds, just talking about how amazing and important members of the CSG are and really pulling out, making sure that every time we talked about customer wins, it got attributed back to the people on the account teams who were helping to make that happen.

And really just trying to pull that recognition through to the efforts of the team members who were really helping to make that possible. Again, there’s always more you could do. I’m not saying we’re perfect, but I do think we’ve made a concerted effort to really say our customer’s success is through the success of our CSG employees being able to help them on that journey.

Margot Leong: They always say support is what makes customers loyal on top of the product delivering the initial promise of what they’re supposed to, right. So I really love that. I’m curious as well, is just looking at the types of work that you’re doing, what kind of person do you think is well suited for this role? What sort of natural like skills or traits do you think that they should have? 

Brittany Rolfe: I mentioned earlier this concept of being like a jack of all trades, comfortable with a lot of different types of responsibilities that might fall on your plate, but to get a little bit more specific, I definitely think someone who enjoys or has strong project management skills, is very well organized. Strong communication skills or change management experience and really is just a people person. 

I mean, the whole goal here is that you’re keeping a pulse on the organization. You’re talking to people, you are helping them navigate complex situations. They can trust you, they can confide in you they wanna work with you. I would also say, putting together presentations. Like I do a lot of creating the narrative for the team. So vision and values, but really what is our three year journey and how are we progressing on it? How do I tell that story? How do I help the leadership team tell that story? How do I pull in information to really strengthen and highlight wins? So it is a lot of different things, but I would say if you don’t like super vague and flexible situations, you’re probably not going to love being Chief of Staff.

I feel like there’s just always a lot of unknown, things are always changing. My roles and responsibilities can switch or ebb and flow based on the needs of the organization and the team. I’m not super rigid when it comes to oh, but this is what I’m doing. I can’t pivot, I can’t change, I can’t rethink or reimagine something.

 This one is probably more org dependent, but someone who’s really comfortable being both a manager and an individual contributor and doing both at the same time. Or being really great at like influencing without authority. So for example, in the past year I’ve managed three different teams.

So I kept some of my customer engagement, customer marketing, customer experience team for a while and helped to hire new people and grow the team and then eventually transition a lot of it to a new leader . And then I also for a period of time managed internal learning and development, which I have no L&D background. So I had to get up to speed very quickly and also just manage the team in a very different way than I would a team where I’m more of a subject matter expert in. So kind of a different style of management. 

And then I also manage our comms and employee engagement side of the house. I was a manager and then all of a sudden, I’m getting ready to go out on maternity leave and I’ve transitioned everything, I don’t manage anybody anymore. And so I’ve been just very flexible in terms of okay, this is what I do today and actually now I’m gonna give it all a new home and I’m gonna pass it off to new leadership and just be very comfortable letting go of things, which is a different skill that I’m getting a lot of practice with right now. . 

Margot Leong: Something that strikes me here is that your role is not super clear cut day to day versus the advocacy and customer marketing, lifecycle side of things. You had a sort of a set lane or a few different lanes that you were playing in, right, and here it sounds like you’re always learning new things, always taking on new things. There’s this element of just having that natural curiosity it sounds like.

Brittany Rolfe: There’s a lot of times in the day where I’m like, Hey, I don’t wanna step on your toes, but I’m getting involved here because it seems like you could either use some help or I wanna bring in our CCO’s vision or, make sure that certain goals are getting accomplished.

So I’ll kind of come in and outta people’s worlds or projects and I never try to step on toes, but I try to be seen as a valuable extension of their team. And again, back to being a customer marketer, that’s a lot of times what you’re doing as well, right? You’re coming in and out of an account team and a customer relationship and trying to add value in a different way. But also, having to navigate all the different parties and relationships and do so in a trustworthy and respectful way. 

Margot Leong: Is there anything specific that comes to mind as what you’re enjoying the most about this role? 

Brittany Rolfe: Yeah, again, I hope that this resonates with a lot of customer marketers out there. When I was sitting in the marketing organization, a lot of times I felt, maybe a little misunderstood or I didn’t always have the seat at the table that I wanted to have in terms of our strategy and making sure that we were being customer centric and that the customers were at the heart of our marketing efforts and all this stuff.

And so I think that’s been the really big thing that I’ve loved about this role is getting to have a real seat at the table alongside the CSG leadership team and being a trusted advisor to not just the CCO but to all of his direct reports and to other leaders at the company in representing what we’re trying to do, why we’re trying to do it, what would we wanna see as the right outcomes.

 I just feel like it’s a little bit of different access and influence that I’ve really enjoyed, which has been fun. 

Margot Leong: What’s really interesting too is when you have moved out of a role, then when you move into a different role where you’re just getting a chance to step back and I think seeing more of the macro of everything and more bird’s eye view of how things are fitting together. This happened for me when I moved into more of a general marketing role is yeah, then I was able to look back on my time in customer marketing and think, oh, okay I could see how if I were to do it again, I might do things differently. So I’m curious, like for you, what would you do differently or what advice would you give?

Brittany Rolfe: I think people talk about this a lot and it’s hard to put into practice always. But that concept of cross-functional buy-in and getting stakeholders from across the business. I sat within marketing and my main point of contact, my main stakeholders and people supporting my initiatives, a lot of times it was coming from within marketing. Or if it was coming from outside of marketing, the relationship between the departments wasn’t as strong or the influence wasn’t as big. 

When we were hiring the what I saw as this opportunity to better strengthen the buy-in I was getting from outside of the organization. And in hindsight, you know, as I look back on my career, I’m like, ah I just needed to spend probably more time investing in cross-functional relationships and really figuring out what was the sales team asking for? What was the customer success team asking for? What was the renewals team asking for?

And trying to be able to deliver more on those things versus just what the marketing organization was asking for. And again, that could have been my company. Other companies have different leaders, different structure. But that was my big takeaway. And now that I’m in this chief of Staff role, I see that a lot more clearly now because I’m helping these leaders figure out how to get buy in and support or time, or whatever it is for their initiatives. It just seems like I’m able to help unlock those things easier now viewing it in a way that I didn’t see it before. 

I feel like when I was in the role, the needs from marketing, there were a lot of them. We were building a category. We needed customer references, we needed people to talk to analysts and present at conferences and apply for awards. And we needed logos and we never had any shortage of work. And customer marketing is usually a very small but mighty team. And so we would deliver these things because that’s what marketing was asking for. 

And built the reference program and built out the community and events, but when it came time to get more headcount, more budget or expand programs, especially along the customer lifecycle and driving towards retention and growth, that wasn’t necessarily marketing’s key focus always. 

And so getting that crossfunctional buy-in from sales and customer success to say what do you guys need to strengthen the relationships to make adoption easier, implementation easier, renewal easier and really getting them to help influence the program and wanna help support getting the headcount, even dedicating their own resources to help you get it done. There’s just a lot of different ways to grow the influence and impact of customer marketing outside of just what your initial charter was or a very specific lens of it. 

And so I think sometimes that depends on like, oh, does your CS leader see the value of customer lifecycle marketing? Maybe they don’t. Maybe you need to educate them. Maybe you need to show them wins. Co-create something together and test it and then get their buy-in over time.

 I didn’t feel like I had enough time to do that and do it well, but in hindsight, that upfront time could have made all the difference if I invested a little bit more on that and then would be able to grow my programs. I wasn’t thinking about how to use always my outside stakeholders to help me grow within my current department. 

Margot Leong: Absolutely. Is there anything that you would recommend for people that are in this role, right? Are kind of in a similar situation, is there anything that you recommend that they could do immediately, right? Part of the reason why I’m asking this is everybody talks about cross-functional, working together, cross-functional influence. The actual execution of it still seems very murky to a lot of people. And there’s a difference between a department asked me to do something and I call that cross-functional collaboration , right? Like I work with a different department. That’s our cross-functional collaboration. 

This idea of the influence and then taking that to the next level of, okay, we think we have something here. How do I get support for it? How do I get the buy-in? I mean, a lot of this seems so mysterious to a lot of people actually earlier in their career. So you may have a better sense now being in this different kind of role too. 

Brittany Rolfe: So you summed it up well, like cross-functional collaboration does not necessarily mean just you do things for other departments when they ask you to do them. But that can be how the relationship starts.

If you’re a marketer, customer marketer, and you don’t engage with the customer success leadership at all, that’s a huge missed opportunity. And I know that sounds so silly, but setting any type of regular connection or check-in, even if you just join their operations meetings to understand what’s working, what’s not working, what are some of their pain points. Those are the things you need to hear to come back and say there’s a lot of different ways we can solve this.

Through technology, through marketing efforts, getting creative, different programs and they’re just probably so focused on the specifics of their team roles and responsibilities. They’re not always thinking outside of the box and you can really bring that out of the box thinking, but you need to hear from them more information so that you can come back with more pointed recommendations. If your leader doesn’t care about a customer advisory board and you’re coming in saying, I think we should do a customer advisory board without actually listening to them, you’re probably not gonna get a ton of traction or support. 

So I would say, especially at the start of the year is always a good time because people are going through strategic planning process, but sitting down and saying, I wanna understand what are you struggling with? What are you trying to accomplish next year? Tell me a bit more about it. Or you can network throughout the org to hear that. Hey, I interviewed 15 different CSMs or services or support folks or customers. Here’s what I heard. And here’s some ideas on how I thought we could go solve this together. What do you think about these ideas? Are these part of your vision? Are these part of your goals? Is this something you just didn’t think was possible? Or have you seen this done before? And I think you can just get so much information and then you really start building that partnership. 

I think the challenge is now how do you prioritize? Because you’re probably a small but mighty team, so how do you focus on something and start showing wins so that then you can get their buy-in to keep growing. And I think sometimes everybody, but especially customer marketers, they wanna deliver on everything. So they’ll sign up for a lot of different things and then not necessarily be able to show quick wins or the impact right away to get that executives continued by in and sponsorship.

 I wanna reemphasize something that I said that I actually think is so important is bringing the leaders the insights that they might not already have. I wish that’s something I would’ve done more often. 

As a customer marketer, you are talking to customers. Start to ask them questions and bring that data back into the team, or talk to the people, the frontline folks who are working with customers and collect that data and bring that up to leadership.

Like you don’t just have to go to the leaders and say, what do you want? What do you need? What do you think? They’ve got so much on their plate. You can come back and say, this is what I’m hearing. This is what I’m seeing. Now give me your thoughts. React to this. 

And if you ever feel like maybe you’re not getting engagement from a leader, they’re not super interested in partnering more, that’s a different way of bringing them added value and then getting them to respond to it. So I wish I would’ve done that more as well. 

Margot Leong: So the last question I wanted to ask about is what’s sort of next for you, right? I mean, how are you thinking about what you wanna do in the future? Do you wanna stay on this Chief of Staff side? Is there anything, other areas you’re interested in the future? 

Brittany Rolfe: Oh, Margot, don’t you know I think about this all the time. 

Margot Leong: You have the exact plan laid out. I know you do, right? You said you’re like really into project management.

Brittany Rolfe: Exactly. I love a good five year plan. No, my career has always been super serendipitous and I usually just go with the flow and I don’t overthink things. But I do think about this a lot because a lot of Chief of Staff people are usually doing this for about one to two years. They’re kind of like middle of their career. And this is a jumping ground into leading a department or becoming a Head of Operations or owning some other part of the business. 

And so a lot of times when I’m networking with other Chief of Staff, they’re asking, okay, what do you wanna do next? Or how are you planning for the future? For me, I think I’ve actually decided I really love being a Chief of Staff. And I think I could do this for my career. I love being the proxy to the principal or the leader of the team. I love being an extension of the leadership team and getting to help all the different leaders with different initiatives or challenges. I love the cross-functional nature of it and I think it’s something that I’m good at. 

Since moving into this role, I’m like maybe I am a career Chief of Staff. I don’t necessarily need to be onto the next role in the next six months or whatever. That being said, maybe there’s an opportunity for me to be Chief of Staff for a CMO or a CEO. I love being part of the customer success group and reporting to a Chief Customer Officer because we already have alignment in terms of our vision, our values, and what we’re passionate about. I do think it’s a really great fit for me and probably a lot of other customer marketers out there. But getting to learn different parts of the business I think could be really interesting as well. 

All of that being said, big asterisk, maybe in a year from now I’m gonna be like, oh, actually I wanna go back into marketing, or I wanna try something new. Don’t write this in stone. But I think for now I’m pretty happy with where I’m at. 

Margot Leong: So much of your career or your life professionally is trying to find those pieces that click and fit together. I think one of them is, you have to enjoy the work, number one. Get energy from it. Number two is there are elements of it that you are already naturally good at, right? So it’s the talent plus the interest that is super, super important. And then also there’s like a sprinkling of being pushed out of your comfort zone or just it’s like a little bit outside of your comfort zone.

Brittany Rolfe: I feel all those things.

Margot Leong: New and interesting and challenging. But you have the confidence to keep pushing forward, right? You keep like conquering these hills and these mountains. But it sounds like, there’s such a nice combination of things here that fit that, that you’re really enjoying. It was just great. I think a lot of people hope that they can find something that they are this excited about when it comes to their work.

It’s amazing to get to chat with you about this. Hopefully this gives people that are listening, another lens and perspective on what are the other opportunities for people who are super focused on the customer. I love the idea for the role. I love that you’re so into it.

So if people are interested in chatting more with you, learning more about the role, what’s the best place for them to reach out to you? 

Brittany Rolfe: Just LinkedIn is great. I always wanna come up with a more exciting way to get in touch with me. But yeah, just LinkedIn. Thank you for having me and I’m super excited to chat with anybody who is curious to explore how customer marketing could transition into different roles, Chief of Staff included, but also otherwise, so don’t hesitate to reach out.

Thanks for tuning into this episode of Beating The Drum. For more interviews with advocacy leaders and tips on creating customers that will sing your praises, head on over to our website, If you enjoyed today’s show, please subscribe on Apple Podcasts, Spotify, or wherever you get your podcasts and don’t forget to rate and review us. If you know someone that would be a great fit for the show, I would love to hear about it. You can reach out at Take care, everybody. 



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