Transcript: Lessons From A Unique Career Trajectory and Why Your “How” Is Important with Jessica Walker McFarland

On this episode, I was joined by Jessica Walker McFarland, Head of Global Customer Advocacy and Executive Programs at Rubrik. We actually did something out of the ordinary for this episode in that we didn’t talk about advocacy or customer marketing. We focus the conversation on her unique career trajectory and what she’s learned as a result. Jessica has mostly stayed at two different companies during her career, but has been able to switch departments several times, moving from comms to field marketing to partner marketing to customer advocacy. We talk about how you don’t have to jump around to different companies to get new experiences, why your “how” becomes more important as you become more senior. And her advice for dealing with stressful situations. Without further ado, here’s my conversation with Jessica. 

Margot Leong: Hey, Jess. Thank you so much for joining the show today. Really excited to have you on. 

Jessica Walker Mcfarland: It’s great to be here. Thanks for inviting me, Margot. 

Margot Leong: Would love to understand a bit more about how you got to be where you are today. So tell us about your background and your journey to customer marketing. 

Jessica Walker Mcfarland: All right. It’s been a journey, that’s for sure. How far back do we wanna go? But no, I really have a pretty diverse background in terms of what’s led me here.

I started off in the wonderful world of PR. My very first day of my very first job, the very first phone call I got working in a war room after a pretty major acquisition was from the New York Times. Fresh out of college, I was like, all right, here we go. Let’s get your skates on. We’re in the working world now. 

Spent some time in PR on the agency side and then went in house eventually over at BMC Software. And one of the things that I had always wanted to experience was living and working abroad, and I had let my manager at the time know that. And so we worked together to identify some opportunities of what that could look like. And lo and behold something came up. 

And so the way I tell the story is if you are living and sitting in Houston, Texas on a Tuesday afternoon, and somebody picks up the phone and says, Hey, do you wanna go live and work in Sydney, Australia and lead AsiaPac comms, just general rule of thumb, say yes.

So I did, I had been married for about a year at the time. And so my husband was totally up for the adventure. So we sold our house, packed up our stuff and moved halfway around the world. These opportunities probably aren’t gonna come along very often, so let’s just go see what it’s like. What’s the worst thing that happens? You hate it and you move home. So we ended up loving it and it was one of the best decisions we’ve ever made and also led to what I would call probably my first career pivot.

 In the spirit of oversharing, while I was there, I ended up breaking my foot, developing deep vein thrombosis. I had about a three inch blood clot in my left leg that pumped through my heart and exploded and then showered both of my lungs in what they call a bilateral pulmonary embolism with clotted blood and those things kill you, they can. That happened probably oh, within my first two months that I was there and I learned a lot about myself. I learned a lot about the Australian healthcare system super, super quickly. And I learned a lot about what’s important to me.

And so the company I was working with at the time did offer. They were like, Hey, what do you wanna do? Do you wanna come home? Do you wanna stay? Like we wanna try to make this work and make sure that you’re comfortable. Because it’s a long recovery process. It’s not like something you’re just like, oh, here you go. You’re fine. 

It takes a long time. For me, it was like a nine month thing. So I said, I don’t wanna go home. I think I wanna see this thing through. I felt the care was very good. I’m in it at this point, but I’m not really able to travel like I would’ve wanted to at that time and like what the job would’ve necessitated. 

So my pivot there was into field marketing. So instead of going over there to say like, Hey, you’re gonna do AsiaPac comms. It was let’s try A and Z field marketing. And I was like, I would love this. Let’s give it a go.

And so that’s how I ended up in field marketing in Australia for Australia and it was fantastic. I learned so much about the inner workings of a business and an office because when you’re in these regional offices, like everyone is there in a way that’s just different than when you’re at a corporate office. And I ended up loving every minute of it and still to this day, Sydney is my favorite city in the world. 

Margot Leong: That’s amazing to hear. I had the opportunity also to work abroad in Asia, basically similar age to you, for a few years. I was definitely trepidacious about it, but I ended up taking it and it was an amazing experience, like both good and bad, but so much I think of that has actually shaped who I am today. And it’s all these things that you end up experiencing and doing over the course of your career like, there’s skills you end up picking up that it just somehow magically ends up getting used later. Like it comes up in the most random ways. I don’t know if you’ve found that as well. 

And a lot of our conversation is gonna be around career pivots, how you think about career trajectory and growth. But it’s the accumulation of these different influences and experiences I’ve always been bullish on because it defines your perspective in a different way. There’s just so many things that you can draw on to sort of remix what you’re doing currently. 

Jessica Walker Mcfarland: 100%. The experiences that you accumulate, whether that’s personally or professionally, and this is Jess’s opinion, but are really the hallmarks of your life. 

To come back to what my first career pivot there was, I’m in the hospital and they’re like, this isn’t good. This can kill you. You know, the first thought that runs through your mind is not like. Oh my God, if this kills me, I hope they write on my headstone. I’m really good at my job. I mean, I guess that’s like a gross generalization, but that’s not where I went. 

I was like, okay. It really forces you to sort some things out in your life and as somebody who was young and going through that, it was like, okay, what am I gonna learn from this? I at least have to understand the experience and priorities and try to take that forward in the rest of my life.

Margot Leong: Absolutely. I know that obviously you’re doing a different type of marketing now, and I think there’s been a few other pivots. You were doing field marketing and then tell me about your journey from there. 

Jessica Walker Mcfarland: Sure. At some point, it was time to go home. And so when we made that choice, I stayed with the same company and continued into field marketing and just took a different position covering the US Midwest and was able to come home, decided to go back to Denver. I went to school in Ohio, then lived in Texas, then moved to Australia and then came back. But I am from Denver. So decided we would make a go of it here, did field marketing for a while, and as opportunities came along, would raise my hand to expand the patches and territories and just try different things.

And one of the things that came up was doing channel marketing and partner marketing. And they said Hey, this has been a challenging position to fill. Would you be open to it? And I said, sure. That started with building out and taking on partner marketing in the US and that expanded to Latin America. And then it became global. And so that was really my first global role was on the partner side and I loved it. Got to experience working with other cultures and countries and people, and really understand how a global business works. 

I had been with the same company for about nine and a half years, and then I decided I really wanted to go experience a smaller organization in a very high growth stage. And that was the opportunity for me to go and build global partner marketing at a different company. I took that. I leaned into that. It was me and a contractor out of the gate and we built that thing. It was a lot of work , but it was a lot of fun.

In the partner world, you get to experience so many different aspects of communications, marketing, business. It’s such a rich background and you get exposed to so many different things. That was so valuable and I loved it. 

But we’re coming to my next pivot. I’d been doing the partner thing for a while and I was getting to a point in my career where I could start to put a little more thought into where I might want this to go. I had said, I really wanna get closer to the customer, and I really want to figure out how to do that. And what does that look like? I Asked myself, the question, do I wanna go into sales potentially? Do I want to stay in marketing? Like where could I go? 

And so I kept my internal mentors and went and asked them and started having this conversation and that opened up the next opportunity that says, Hey, we’re looking for a leader for our customer marketing team and our executive briefing center. We’re gonna have these two teams come together in this new role.

And so I was like, cool. So I tossed my hat into the ring and that worked out. And that is what ultimately led me to customer advocacy and executive programs. I have switched companies again, I’m just continuing the journey, but in am currently in a very similar role. 

Margot Leong: Why did you wanna get closer to the customer? Why did you think that that would be valuable for you at that point? 

Jessica Walker Mcfarland: I mean, customers are what it’s all about really. I just wanted to learn more about their challenges and how we can help solve their problems. And their businesses are just fascinating and what they’re doing and I’m in the data and data security space, and it’s running at breakneck pace. To be a part of that and to understand the customer and their journey was something that I was just interested in at my core. 

On the flip side of the things, you know, I started to ask myself what do I wanna do professionally? What is this thing I’m gonna call a career. What do I want out of it? Where am I going? It was about that time that I said, I’d really love to have an opportunity at some point in my career to be a CMO at a high growth organization and what’s it gonna take to get there. 

And so looking at how to build that diversity in my experience and my background in different areas of marketing in the business, that was one of the things that I drew that conclusion and talking to mentors and both internal and external people that I’m just close to and, have developed those relationships across my career. There are a variety of different areas that you can kind of go in different “paths”, jungle gym is probably a better way to describe it as you kind of navigate and negotiate how you’re either gonna go up and over. So that was really the intention behind it. I’d say it was pretty twofold. So far so good. 

Margot Leong: Definitely quite a few pivots and going into areas where it sounds like you’re pretty new to having done it. Maybe you’ve had exposure from having worked with those orgs, but you’re coming in taking on pretty much a thing that’s new to you where you don’t necessarily have a ton of experience in it. Was that scary at all? Like for you to raise your hand and be like, yeah, I will do something that I don’t really have that much experience in. 

Jessica Walker Mcfarland: I would say that it’s a little bit of all the things. I love building things and trying new things and just tackling things that are challenging, new problems, bringing different points of view into trying to get to the various end results, whatever it would be. And I think that’s something that is hard even sometimes for women to say that oh I haven’t done this exact thing. There’s just no way I could do it. If you step back, all the things that you’ve done and the experiences that you have and you put them together, like most skills are really transferable.

You know, one thing, and this is why I was always so grateful for having a background in comms and PR is that in whatever role you have, being able to communicate is so critical because a lot of what we’re doing is just communicating with each other, communicating thoughts to get to the end results. And if you can write and speak and take a bunch of information, sometimes it’s often complex and synthesize that into something that people can understand, that’s incredibly valuable. Don’t ever let fear of not having enough experience, everybody gets imposter syndrome, but half the battle is just having the guts to try. 

Margot Leong: There’s another thing that I’d love to tease out a little bit here as well, which is there’s the belief, right? That you can figure it out, that you can do it and not letting fear overtake you and throwing your hat in the ring. You also have to prove with your prior work that you at least are capable enough to do that. 

Do you think that there are specific things that you’ve done or have guided how you think about your work that maybe have made you stand out? Again, I don’t think it’s on accident right that like you are getting tapped within the same company to try different pivots. That’s just not that common. Maybe it’s like principles on which you operate or whatnot, how do you get to that point where people are like, yeah. Like I think that person could lead a totally new function where they don’t necessarily have as much experience. Because I’ve seen their track record. 

Jessica Walker Mcfarland: You’re hitting on something that people who do a lot of career coaching and I think there’s books on it, like about your personal and internal brand. And I think that’s a real thing. Going back to the communication, communicating your ideas, documenting things, presenting them, you know, being able to articulate that intent and the strategy behind it, I think is part of it.

 I think your “how” right is what it also boils down to. And I tell this to people that I have worked with in my teams and when we have career development conversations, and as you get more and more senior, your “how” becomes more and more important. It’s not necessarily just about the results. Sure. That’s great. Everybody would love to have great results, but how you go about that, how you work with other teams, how you influence other departments or people and how you can build teams and cross functional teams and lead different projects. And how you react to when things don’t go well, because no one bats a thousand. 

Because I think that does reflect for me specifically is how, the personal and internal brand that that I wanna build so that these opportunities might present themselves in the future. That’s very important. 

And also just raising your hand. I’ve had the good fortune of having so many great mentors and leaders that I’ve been able to work with and for, so I feel like I’ve been very fortunate in that department and have been able to learn a lot from those that have walked the path before me and have had those open conversations with them and been willing to have those conversations with me.

 I think one of the things that I would say is common and I tell my teams this as well is I’m not gonna guess what you wanna do. Like your career is in your hands. I’m happy to work with you and partner to figure out how to get to different places and opportunities so that you can have a rich career and we spend a lot of time in our job. We hopefully can like it. 

But there’s no way I can guess that. This is a dialogue and conversation. Help me help you. 

And that’s something that I learned, even going back to how I got to Australia. That was through a conversation with my leader, who’s a wonderful man and was really helpful in guiding my career and especially early on. And I would say still to this day, we haven’t worked together in a very long time, I can still text him or message him on LinkedIn and Hey, I was thinking about this. Can I get your thoughts? We talk occasionally. 

But it’s the value of the hand raise. Like he would never have known that I wanted to live and work abroad if I wouldn’t have brought it up. Granted, he gave me the forum to bring it up in a development conversation pretty early on.

But I learned a really valuable lesson through that, which is raise your hand and if you’re truly interested in something, vocalize it, put it in your development plan, help the people around you understand what your goals are. Because most of the time I think people do really want to help.

You know somebody’s talented and they’ve got a great “how”, strong work ethic, all the things. I think you’d be surprised more often than not how many people would like to help. 

Margot Leong: If you think about all the people that you have managed over the course of your career, I’m sure everybody is pretty amazing in their own way, but who are the ones that do things specifically where you’re like, okay, they stand out to me. They put themselves in the way of opportunities, you know, like the opportunities come more to them because they actively do things to get there versus other people are a little bit more, like they’re kind of hoping for that? 

Jessica Walker Mcfarland: Again, this is just Jess’s opinion, but I think you can get really caught up in trying to fill gaps or do things that feel unnatural to you or you think you could and should be doing. But everybody has a set of their own personal strengths you should play on.

You know, I go back to some of the things I was talking about with the importance of communication, influence, like the how element of it. There’s not a wrong way to go about doing that. There’s so many different ways to reach that outcome.

I think it comes down to understanding what those strengths are and from time to time, sure, stepping outside of your comfort zone, and putting them to use to understand this would be beneficial to not only what we’re working on, but to the company and to either the customer or the partner whatever you might be working on. 

The “how” can be different, but as long as you can articulate and work through those things and kind of work in partnership, that’s great. I think understanding and having a network internally and externally is super important. There is an element of work in making sure that people know who you are and think of you and create those internal networks. So I think you just have to figure out what is that forum that works for you.

When you get a seat at the table, whether that’s a meeting, whether that’s to work on a special project or even just in your day to day, if you have a seat at the table, take advantage of it. Don’t be afraid to raise your hand or sign up or do the work. Express your ideas and opinions and either work with your manager or others on the team, like whatever the scenario might be. If you’re given a seat at that table and no one knows you’re there, you may as well not be at the table.

There’s the concept of agreement and alignment, and those two things can get conflated pretty regularly, but there’s a pretty strong difference. You don’t have to agree in order to align. So if you’re going into a meeting or a topic or what, and there’s something that you’re gonna talk about and you might not necessarily agree with the direction or something that’s ultimately gonna be what happens, that’s okay. You have to align. When you step out of that room, you’re all on the same team and everybody’s aligned and we’re all talking about the same thing and we’re all marching in the same direction.

You don’t always have to agree with everything, but the concept of agreement and alignment is really important, especially as you get more senior and more tenured in your organization. Because if everybody’s made a decision, even if you disagree with it, if you just continue to fight it, it’s not gonna be beneficial for everyone. I think disagree and commit as well is another thing that people say. So I think that concept of agreement and alignment is a really important one. It can be a little bit nuanced, but I think it’s important to understand. 

Margot Leong: You have been at a few different companies for a good amount of time and you were able to move around between departments at those companies. And you said something like you don’t have to jump around to get the experience, like you could get the experience at your same company. And I think one of the benefits that I see of doing this, if you have the opportunity to is that because you have had roots and history in the company, you can leverage existing connections. So there’s something nice actually, I think, about staying within the same company but doing a new type of role because you’re not jumping into the cold. You know people, they’re probably rooting for you to succeed, right. 

Jessica Walker Mcfarland: Yeah. I believe you don’t have to jump from company to company in order to get new experiences. My personal experience has been one where I’ve been able to pivot in the organizations that I’ve been in and really create and curate that experience by going back to some of the personal reputation and brand and things that I have done and use those strengths internally to make those pivots and kind of apply from my previous roles into the new roles and hit the ground running. You know how to get things done in the organization that you’re in, people and players. 

And so those things can be a lot easier if you’re not constantly trying to learn a new organization, because every organization functions a little bit differently as well. I think that’s incredibly valuable to explore those opportunities. 

And again, maybe I’ve just been lucky and I know I have. There’s always an element of luck in that, especially in having some really standout leaders and managers that I’ve worked with to help be open to those ideas and to champion me as somebody on their team that could be perceived as oh my gosh, I’m losing an employee. I’m gonna have to go backfill this. But to say no, like I actually understand goals this person has, where they wanna head, this makes sense. And helping me identify and put me forward for some of these as well. 

That’s important as well is, even when you’re a manager is, it could be hard to let go of people. I’ve experienced it firsthand as well, but if they’re going on to do things that are right for them, and it’s a good move and it’s what they wanna do, of course I’m gonna stand behind them. And you should never work for somebody that doesn’t want the best for you. 

So I think that’s important, making sure you have those conversations with your manager and it comes back to the how as well as like, how do you execute those things internally as well? I didn’t just go behind anyone’s back and say like, oh, hey, I’m gonna change teams. I want to go do something else. They can be difficult conversations sometimes, but if you like, Hey, there’s, I’m interested in doing something like this. If something’s not available within your organization, if you hear something I’d love to be considered for something like that.

Or if there is something open, I’d love to put my hand up and see if this is something that I might be considered for. And oftentimes having your manager’s recommendation and support to go into a role like that and to try something new, that can go a long way.

Margot Leong: Absolutely. And whenever you pivoted into different roles, there’s some instinctual pieces there’s understanding what are the sort of goals of any organization or any team within the organization? How does what my team can do ladder up to what would be valuable for the organization and thinking about it from there, but of course there’s elements of knowledge transfer or like education that are more readily available to someone who’s had the direct experience. 

So when you changed roles, was there anything specific that you did or learned over time where you’re like, okay, like how can I hit the ground running as soon as possible? 

Jessica Walker Mcfarland: A lot of conversations and a lot of listening. And I don’t think that’s anything novel that you wouldn’t do going into any new role, but I always spend the first good 30, 60 days or so, making sure that I’m doing more listening than talking. Just because understanding certain scenarios, obviously in most of the cases too, with doing internal pivots, you know the company. So you’ve probably seen some of the things in the team and that are in action. Listening to the people, listening to your teammates, listening to stakeholders. Just being super curious, asking questions. A lot of reading. 

Again, I don’t know that’s anything novel, but I’ve never found success coming in and just being like, this is the way. These are my ideas. And here we go. Take a minute to really understand what’s going on and hear it from a variety of people and different perspectives. Then assess how you’re gonna move forward from there.

That first leap, that first thing, I think could always be a little bit scary. And I do find whether it’s been at a new company or just a new role within a company, I do always go through that moment where I was like I feel like I used to be so fast in my previous role. Like things take a little bit longer when you’re newer. And I was like, why is this taking me so long? But it’s okay. I just let myself take my time in some of those things.

Margot Leong: Exactly. There’s one last question I wanted to ask about. I’m curious, especially as you go further and further within your career, I have typically found that to be associated with more and more stress. It’s really nice in many ways to lead a team because you can get help from your team. You can lean on them, right? But also you are the one that is fully accountable for the decisions that get made. 

And then for me personally, like I don’t find working within large organizations particularly enjoyable. I don’t know if you would call it politicing. Everybody has a different conception of it, but I find all of that mentally exhausting and there’s a lot of stress that people can go through, especially in a role like customer marketing, where people have different understandings of the role and you can deal with experiences where people are pushier or basically being like, Hey you know, I assume you do this. Why didn’t you do it yesterday? Which is not an uncommon experience with customer marketing. 

 You seem to think about life in this way of, I have certain goals that I’m pushing towards, obviously in my professional career, but I also have a life. And I wanna make sure that I have an enjoyable life. How do you think about dealing with some of those elements of the role, which can be more stressful?

Jessica Walker Mcfarland: Stress happens to everybody. I’m not immune to that by any stretch of the imagination. And I have definitely had those moments where I’m like, I am in it. You feel like you’re in that stress hole, like you’re just drowning in all of it. Been there a lot.

And I think those moments are gonna happen in any job, in any role, at any company, especially in customer marketing. You’re working with customers and they don’t have to do any of this. 

But for me, how I approach it is I like to get ahead of it and be proactive. So not to belabor the point, but the communication, making sure that people around the organization understand what we’re doing and what we’re working on, and this is our strategy and here’s how we’re gonna go eat this elephant.

Trying to get ahead of that in communicating with key stakeholders and peers and other teams, so they understand where we’re at. They don’t necessarily always need to understand the intricacies of the journey, but they need to know what we’re doing. 

Because I think people are starting to understand customer advocacy and customer marketing in a different way and the challenges that it can pose because it’s working with our customers and so many different things can affect that. I’ve found that being proactive in how we communicate and even on the exec program side as well, it’s the same thing. Making sure that people understand what’s going on and the communication that we’ve done our part. 

No one likes surprises in these areas. So that’s why I was like, try to get ahead of that, and if something’s going great. Let’s let ’em know. Let’s let them know what we’re working on. Oh, you know what? This one might not work out or this isn’t going as planned. You know what? Bad news doesn’t get better with time. Let’s just talk about it now. And then, okay. This didn’t work as we wanted. This story’s not gonna materialize. How can we pivot and make something work, right? If it’s a deadline or an event or something. So like we’ve all been in those scenarios. 

And I think it just comes back to communication. How I manage the stress for me is just knowing that if I’ve done my level best to enable, empower, and then get out of the way of the team, but also to make sure that I’m pulling my weight, understand the decision making and the strategy and everything that’s gone into it and we’ve communicated that out, I can sleep alright. 

Margot Leong: I really like that. think that fear that can come with doing exactly what you’re talking about is that if they know what I’m doing, then it means they can pick on me or they can dissect what I’m doing and then, it’s just more work ultimately, because they can see more of it. Most of the times that I’ve seen is that people may have questions, but you are setting a really good precedent. And like it’s better that they have questions earlier than later, because especially if they’re not sure or they don’t know what you’re doing, then when it comes up later, it actually becomes a lot harder to go backwards if it is a big thing. 

I think more of an element of trust that can come with that versus like them always like having this question in mind of what does that team do? Or like only thinking of you during a fire drill, bad situation, you know? I mean, like what do they do? The fear that I’ve had in the past about communicating things and then people picking on me, that actually doesn’t even happen that often.

And when it has happened, it’s actually brought things up earlier which is better than having them come up later and I can address it faster and you help to build more trust and then those relationships as a result. 

Jessica Walker Mcfarland: Totally. In the vein of trust, I would rather somebody hear something from me, especially if it’s not going right or as planned than to try and hide it and cover it up. And then all of a sudden, like somebody else, and then it’s like, hey, we heard this isn’t going like, and then it’s oh, I was gonna tell you, but for whatever reason, lost that fear a long time ago. 

Margot Leong: That’s really good. Jess, I know we were coming up on time, so I wanted to finish this up, but I really appreciate you taking the time to come on and and share more about your journey. I think there’s some really good things that people can take from this conversation. If anybody’s interested in reaching out to you and picking your brain on more of these things, where’s the best way for them to reach you?

Jessica Walker Mcfarland: That would be LinkedIn. If I were just to leave one last little tidbit , is to let go of the idea that there is a career path. I don’t believe that exists. I think it’s more of a jungle gym and how you navigate your own personal journey is not gonna look the same as anyone else’s. So use your strengths, use your decisions, use your network and have a go at it. Everybody’s gonna be just fine and don’t forget to have a little bit of fun along the way. Don’t get caught up in the path and what other people are doing, because I don’t think any two paths have ever looked the same. 

Margot Leong: Absolutely. And I think there’s the idea of success that most people have. And a lot of that is really just based off of, what do I see other people doing that are maybe further ahead of my career. And I do think that the know thy self, it’s super important. And that has really informed how I’ve thought about things in my own career, as well is you will start to realize, and bump up against things that you’re like, okay, I really like this. And I really don’t like this. 

If I find that I’m not enjoying some of these things, are they small necessities on the path to a certain type of thing that I think I should be doing? Or actually is this letting me know that, Hey, if the type of role that I think I should be in actually has a lot of this things that I really actually hate. Is that valuable? Is that important for a certain type of title? A lot of it really has to end up being what do I enjoy doing and what is interesting enough that, work feels more like play versus just constant challenges and not less enjoyment because yeah, at the end of the day, life is short and, you would like for the thing that you do in order to make money, at least is more enjoyable than not. That’s a helpful way for me to think about it too. 

Jessica Walker Mcfarland: And your passions and how you view things may change with the seasons of your life too. And that’s okay. I can speak to that from personal experience. Allow yourself to change your mind too. 

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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