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Interview with Maya Grossman – The Career Advice You Need If You Want To Be A Marketing Leader – Episode #84
“You just want to make sure you’re joining a rocket ship, not a sinking ship…”

Maya Grossman is a marketing executive with over fifteen years of experience taking products to market and driving growth for Fortune 500 companies like Microsoft and Google, as well as fast-growing startups.

She is a career coach, the best-selling author of “Invaluable, an unconventional business book for employees who want to deliver exceptional results,” and the creator of the Career Success Secrets Course, a transformative program that generates quantum career leaps.

Questions and topics we covered included:

✅Maya’s story of how she created her first marketing job.

✅Maya’s advice for any marketer who wants to get promoted this year.

✅Why does imposter syndrome creep up at any stage in a marketer’s career?

✅The common lessons and experiences Maya gained from each of her previous executive positions.

✅What are some mistakes a new marketing leader might make when building a team for the first time?

✅What are hiring managers looking for in marketing candidates this year?

✅What’s the best way to come up with new ideas for LinkedIn content?

And more!

Full Episode Transcript:

Kenny Soto 0:00  

Hello, everyone, and welcome to the people of digital marketing with your host, Kenny Soto, and today’s special guest, Maya Grossman. Hi, Maya, how are you?


Maya Grossman 0:13  

Hey, Kenny, I’m doing well, thank you so much for having me.


Kenny Soto 0:16  

So I’m very excited to start this episode because as I told you before we started recording, I think it’s for the past three days, if not the past four days, I’ve been binging your LinkedIn content with good reason. 


It’s not only to do research on who you are as a professional but also to learn from you because you share a lot of great content, and a lot of good insights into what it means to be a good marketer for free, which is very, very great. So my first question for you is more so about your background from the very beginning. How did you get your first marketing job?


Maya Grossman 0:57  

Yeah, so I always loved sharing the story. Because I did not start my career in marketing. I actually spent the first seven years as a travel agent, which is completely unrelated to anything that I’m doing today. But I needed a job to put myself through college. So I took a job. And I kind of got stuck, because it was nice company. 


I was paid, okay, but I wasn’t excited. And I couldn’t see myself continuing to level up with that company. And then I started doing my Bachelor’s, majored in finance and marketing, hated finance, fell in love with marketing, and decided this is going to be my career. The only problem was, I didn’t know anyone who was a marketer. 


There was no marketing team at the travel agency. So I figured I only have two options. I either quit and try to figure it out on my own starting from scratch after spending seven years, you know, as an employee, or I’m just gonna stick to this job because it’s nice. And you know, I’ll just keep climbing that letter, even though it wasn’t the right letter. 


And after going back and forth for I don’t know, a couple of weeks, probably, I realized there was a third option, I realized that I could actually create my own opportunity. And I asked myself, How can I actually gain marketing experience while working for this travel agency? And I’ve been there for a while at this point, almost six years. 


So I reached out to my manager, and I basically said, Hey, do you mind if I do some marketing work? In my spare time, you know, I’m super excited about this thing called social media. I want to open up a Facebook page or Twitter account, let me do that and see what happens. And they really trusted me, I’ve been there for a while. 


So they just let me do extra work for free. Make sense. And that meant that I had six months of real experience because I created those pages, I created content, and I was able to drive followers and drive business. And that meant when I was ready to actually look for a marketing job, I technically had experience and I was able to land a social media marketing job. Theoretically, without experience.


Kenny Soto 3:18  

Do you think that it’s possible to replicate the same experience that you had for other people who may be interested in marketing, but currently don’t have their first marketing job, and they’re looking for that chance?


Maya Grossman 3:35  

Yeah, I think you can probably land any job you want if you’re willing to take the time to actually qualify yourself. And here’s what I mean by that. There are two parts to this. Number one is learning. So you have to really immerse yourself in whatever it is you want to learn about whether it’s marketing or something else. 


So let’s say I want to get into product marketing, then you’re going to have to spend 30 to 50 hours, learning about product marketing, really going deep reading books, listening to podcasts, reading articles, talking to experts in that field, to the point where you feel like you almost know it, even though you haven’t really done the work, then you need to actually get experienced and do the work. 


And if you’re not as fortunate as I was to be able to use your current job to get some of that experience. Then go and create your own website. Go and create a go-to-market plan for a company that you really love or a brand that you admire. There are so many ways to do the work on your own. 


You can volunteer so many people think if they volunteer, the experience doesn’t count. Let me tell you something if you get results, it doesn’t matter if you were paid or not. When I did my first consulting work, it was free. I did it for free to get the experience get the customer testimonials, but it’s still part of my track record and how I got here. 


So immerse yourself learn, and get some hands-on experience so that you can cheap you can show results. And when you have that, it’s going to be 10 times easier to actually apply for the jobs that you want.


Kenny Soto 5:17  

Yeah, and I would quickly add, and I’ve mentioned this before, in previous episodes, I was a music major when I started as a marketer, and I got my first experience at a nonprofit. So if you, the listener might be wondering where to start. As far as offering your services for free, there are more than enough nonprofits that need help with their social media, their paid ads, their website design, their positioning their branding, and what have you. 

So if you’re actually considering looking for those opportunities to provide volunteer, volunteer work, excuse me, as a marketer, all you really need to do is the due diligence and the research to find those opportunities. Now, as we go through this interview, I’m going to create a kind of arc, if you will. 


So we talked about the beginning of your career, we talked about advice that people who might be interested in marketing, but don’t necessarily have enough experience, what advice do you have for them? Now I want to talk about getting promoted, right? Because everyone has their own framework for how to get promoted. 


And you’ve shared content on LinkedIn that I think could be very useful for the listeners to basically incorporate into their own strategy this year, for that upward mobility in their teams. My next question for you is, what advice do you have for someone who does want to get promoted this year, but doesn’t know how to approach that?


Maya Grossman 6:39  

Yeah, first and foremost, you need to get very specific about what you’re looking for getting promoted is very general, right? Do you want your manager’s job? Is there a specific title, so you need to get very specific? That’s step number one, step number two, you need to understand what it takes. 


The best way I know to do that is to go talk to people who are doing the job that you want to do. You’re going to learn from them how they got this job, you’re going to learn what the day-to-day looks like, you’re going to learn about a lot of unknown unknowns, they’re going to tell you what are the most important skills, and that will allow you to try and have a better view of, you know, what’s the gap between where you are today, and where you want to go. 


When you know that, that’s when you start taking action, that’s when you build a plan that will allow you to qualify yourself for that promotion. Before you know you you’re even applying. And here’s why there are two ways that you can approach a promotion, you can wait for your turn, you can potentially apply with your company and hope that someone you know will give you an opportunity, or, and this is my preferred way you can qualify yourself for the role, you can make sure that you are the best person for that job. 


So when the opportunity arises, or when you create that opportunity, it’s a no-brainer, you’re essentially already doing the work. It’s just about giving you the title. And if I look at my career, that is exactly what I have done every single time. Technically, I never actually applied for a promotion, I always was able to qualify myself to do the work that I need to do. And then justify that you know, title or additional salary.


Kenny Soto 8:28  

This is somewhat related as we continue through this. What is impostor syndrome in your, in your own words?


Maya Grossman 8:37  

Oh my gosh, negative self-talk. And the biggest problem with impostor syndrome is that it feels real. But it’s not. So our thoughts are not facts. And even though it feels real, you can feel the pain for me. The manifestation of imposter syndrome is actually physical. It’s harder for me to breathe. But technically, nothing is really happening. 


It’s just a story that your brain is telling you. And the reason is, your brain wants to protect you every time you want to try and do something new, something you’ve never done before. It’s a little bit scary. And your brain immediately thinks Oh, no danger. And your brain wants to stop you and your brain knows the best way to stop you is to tell you that you’re not good enough to tell you that you’re not ready. Because when we’re scared We don’t take action. 


So imposter syndrome. You know, I’ve felt it throughout my career. I still feel it today, right? I just started my own business. I am not sure what I’m doing. I’m still figuring everything out. I was scared on my first day as a VP. I thought someone was gonna come in and tell me I don’t belong. They made a mistake. But here’s what we obviously forget.


You’re supposed to suck at the beginning of something because You’ve never done it before. And sacking is basically the price of admission for growth and learning, you have to go through it. And the problem is a lot of people, let fear stop them. 


But a lot of the work that I do with my clients and the content that I share, to be honest, is working on mindset, on convincing yourself that you aren’t good enough, you do have what it takes. And if you’re not ready yet, you will be able to get there.


Kenny Soto 10:31  

You mentioned your previous role as VP of marketing, and correct me if I’m wrong, but after doing research on your career, you’ve had roughly five executive positions in your past, which were very notable big tech companies. What were some of the common experiences you encountered across all of those companies?


Maya Grossman 10:53  

It’s interesting, because I’ve worked for the big, you know, corporations of the world, and I worked for small startups with less than 100 people. So I would say, you know, culturally, it could be different learning styles can be different. 


But at the end of the day, it is all about people, whether it’s your direct team, or you know, the people you need to get buy-in from. And that’s one of the things I neglected very early in my career, I figured I’m just gonna keep my head down. I’m gonna work hard. I’m gonna outwork everyone. And that would be enough. 


And it was enough at the beginning, when you’re very early in your career, getting things done, yeah, that checks the box. But when you want to progress, when you want to get to those leadership roles, you really need people. And I’m not just talking politics, just having alliances, getting buy-in from other people who already have the power and already have the ability to say yes, because that’s the fastest way for you to actually, you know, move forward, get what you want, and build a great reputation.


Kenny Soto 11:57  

Recently, this is me being vulnerable. I recently had my experience as the first marketing hire for a startup that didn’t go so well learned my lessons. But I feel like, through that experience, I learned and this might also be the case for other people who are also in that first-time marketer role for a team that there really is no one set playbook or one framework to apply because everyone’s experiences are unique. 


But I’m sure you can provide advice and insight into how to approach that unique situation. So my question for you is, what advice would you have for people who are the first marketing hire for a startup? Or a company in general, for the first time?


Maya Grossman 12:46  

Yeah, that’s a really good question. And I agree, by the way, there is no playbook. I don’t believe in applying the same methodology to every company across the board. What is really important as a marketer is to really understand the landscape and think more strategically. So you can choose from a list of different possibilities, and choose the ones that are going to be right for that company at that time with that audience. 


I would say if you’re just getting started, and especially if you’re the first marketer, you need to assess what you need the most because here’s what’s going to happen, especially if it’s a small startup, the CEO is going to come to you and they’re gonna say, I want everything. I want to be on every social media platform, I want PR, why are we not getting traffic to our website, we need more demos, they’re gonna want everything. Let me tell you a secret that is not possible. I tried, but it is not possible for one person. 


To do all of that. What you need to do is to focus on the things that will actually move the needle at that stage of the company. So your goal is to really understand whether Are we still trying to find product market fit. If that’s the case, you should double down on product marketing, you should talk to customers, and should really work on messaging and positioning because you need to help your company find that product market fit. 


If you already have that. If you’re starting to see more sales coming in more consistently amazing, then you’re going to need to find one channel, not five, one channel that works really, really well. How do you do that experiment, Do you use your common sense? You talk to other people in your situation, you learn from experts, and you choose one and you try it out. 


You give it a couple of weeks or a couple of months and you see if it works. If it works great. double down on that. Do more of that and start experimenting with something else. If it doesn’t work, completely remove it. Start with something else. The biggest problem I see is people trying to do everything and they end up doing nothing. You can’t move the needle when you spread yourself so thin. 


So you really have to be able to kind of stand up and say, Hey, I understand you want everything You have a choice, we will either do everything but do it, we’re not going to do it well, or we’re going to choose one thing. And we’re going to kill it. And that is what I have done with most of the early-stage companies I’ve worked with.


Kenny Soto 15:14  

This is exciting Maya because you’re literally teeing up each question that I have. So my next question is, let’s say you’ve identified a clear problem, you can’t do the job of eight people by yourself. How do you approach as a first-time marketing leader hiring team members?


Maya Grossman 15:33  

Yeah, um, I would say it really depends, again, on the situation. So if I am the person most qualified to actually do the work, and its strategic work, then I will do it, and then potentially hire, you know, vendors to help with some of the execution, I don’t believe in outsourcing strategy for the most part. 


Now, if, for example, I’m joining a company, and what I do best is product marketing, but they have that nailed. And now we need to double down on demand generation, then I would probably look to hire someone who is better than me, at demand generation, because that’s not my you know, best skip marketing skill. 


And I want an expert. And I think some of the, you know, challenges, especially if you’re doing this for the first time, you think you need to hire people to execute. Because if you’re in charge then other people just need to do the work. That’s actually not the case. 


If you’re the leader, if you’re the VP, you need to hire people who are 10 times better than you, because what they actually execute on what they’re able to do reflect on you. And if you’re not the expert, why would you be the one calling the shots? So in my, in my previous role at Canvas, I hired a director of demand gen who was much better than me. 


And I basically told her, you know, you decide, you know, here’s the budget, do whatever you want, if anything, like really breaks down, let me know. But it’s your call, I will always give you my opinion. But you’re gonna make decisions. And it’s exactly what we did.


Kenny Soto 17:16  

Now, tying into hiring, but from another perspective, for the listeners who are applying actively for marketing roles this year. What do you think hiring managers are looking for from a high level? holistic perspective?


Maya Grossman 17:33  

Yeah, I would say there are a couple of things. And they will probably differ depending on your level of seniority. But the most basic, you need to know the job I am hiring you to do. And there’s a difference between hiring someone who is relatively junior and the position is broader, like, I just need you to get things done. 


I need to hire an expert. So if I’m hiring a director of demand, I need someone who has been in demand for a decade, there’s no way around that I need someone who is an expert, so there’s less leeway, you need to know your shit. If I’m interviewing you, you need to know exactly what you’re doing. 


Now, beyond that, I like to work with people who have a growth mindset. So they see problems and they ask how we can solve them, but they don’t come to me and say, Oh, this is not going to happen. We can do it. I really enjoy working with people who are coachable, meaning they understand they’re good at what they do, but they’re not perfect. 


They’re not done yet. And they’re willing to listen and learn from other people. I think those are two really important qualities. And lastly, you just want to have someone that wants to be there. And I understand that sometimes you just really need a job. 


But it’s so important when you spend so much time with people that they are there for the right reasons, and they are willing to go above and beyond. And that doesn’t necessarily mean working 16-hour days, it just means finding solutions. Instead of you know, just ignoring the obstacles.


Kenny Soto 19:14  

Let’s flip these questions and they may not be questioned, it could be general considerations as to what questions marketers should be asking. Should marketers ask future employers when they’re in the interview process?


Maya Grossman 19:32  

Yeah. I think first and foremost, you want to really understand where your manager is coming from. You want to know what they care about. You know, how are they going to evaluate your work? How are you going to work together? Is this someone who’s more of a micromanager? Are you going to have more of a free hand to do whatever you want? And you can get a feel when you have a conversation with people. 


I think you want to better understand the team you’re joining and their position within that company. Sometimes marketing, you know, can be like the superstars of a company. And sometimes marketing is pushed aside, it’s a cost center, you know, doesn’t get resources. I’m not saying you shouldn’t take a job in that situation. 


But you definitely want to know what you’re walking into, you don’t want surprises, and you really need to understand and know the company, things can look really nice on the outside. But when you do a little bit of digging, you understand better Hey, is the product actually working? Right? Do we have happy customers, you just want to make sure that you’re joining a rocket ship, not a sinking ship.


Kenny Soto 20:47  

Do you share? Again, I mentioned this at the beginning, you share a lot of great advice and a lot of great content on LinkedIn. For the people interested in amplifying their personal brand on LinkedIn this year, what are some general principles you can share to help them approach the work better?


Maya Grossman 21:08  

Yeah, if they want to build their own brand, yeah, on LinkedIn, okay. This is, okay. This is basically, you know, marketing one on one, finding your niche, like, figuring out what it is that you can talk about. And you don’t have to be the expert, there are actually two ways you can approach it. 


If you have a lot of experience, if you have a lot knowledge, you can be the expert. But if you’re just getting started, you can actually share your journey. So you can be the storyteller. You can just bring people along as you’re discovering new things. And then you need to figure out, okay, what am I going to talk about, because one of the biggest challenges I see is people spreading themselves too thin all over the place, they talk about everything. 


And especially, you know, marketing, it’s so broad. So very often, you actually want to narrow down again, you want to niche down, not sure how to do that. Awesome. Reach out to a few people on LinkedIn, who are marketers and just ask them, what is your biggest challenge, right? What, do you want to learn more about, and try and understand if there’s an opportunity for you to educate others? And then you’re going to have to try and experiment. When I started posting on LinkedIn. 


I wish I could show you the graph. So the first five months, I posted five days a week, that’s like 112 posts. And it was basically a flatline, I would get like five likes and seven likes, and most of them were from friends and family. But that’s because I was honing the content, I was getting feedback I was improving. And from that point five months, that’s when it hit an inflection point, and it started growing. So the last thing I would say is consistency, because most people, unfortunately, give up too quickly. And you need to stick with it. So that you can actually see the results.


Kenny Soto 22:57  

Absolutely. Two more questions for you. Can you tell us a little bit more about your book?


Maya Grossman 23:05  

Yeah, so my book is called invaluable master the 10 skills, you need to skyrocket your career. And basically, you know, one day I decided I’m going to sit down and write everything that helped me get to where I am. And it was because a lot of people asked me like, hey, how do you get to the VP level? What did you do? How did you work for Microsoft and Google, I started writing it down. 


And I assumed it was just going to be a blog post. But I had a lot to say. And it kind of turned into a book. And initially, I thought, you know, I would be talking about marketing skills. But then I realized that what really drove my success was soft skills. 


It wasn’t so much the hard skills, those are, I don’t want to say easy because you definitely need to learn and you need experience. But the show is actually very easy when it comes to hard skills. Soft skills take a lot more time to develop, and you don’t have as many resources, I didn’t have a lot of people to tell me what a growth mindset is, how to think like an owner, or that I should solve problems for other people. 


I had to figure it out along the way. So I ended up putting together the book so I can help other people build that strong foundation. So no matter what you’re doing, whether it’s marketing or anything else, you’re gonna have the tools to build your dream career.


Kenny Soto 24:27  

My last question for you is hypothetical because time machines don’t exist. But if they did, and you can go back into the past about 10 years, knowing everything you know, right now, how would you accelerate the speed of your career?


Maya Grossman 24:42  

Spend more time on my mindset. I think that’s the one thing that took me the longest to develop and it was probably the thing that held me back the most. I mean, theoretically, yes, I leveled up and I had a great career. I think if I realized how to manage my own site earlier, I probably could have made more progress.


Kenny Soto 25:05  

Maya, thank you for your time today. And if anyone wanted to say hello, where can they find you?


Maya Grossman 25:10  

Yeah, so I’m on LinkedIn, my Grossman or you can go to my and find the book, the course everything I’m doing.


Kenny Soto 25:16  

Perfect. And we’ll put links to both in the show notes. And again, thank you, Maya, for your time today. And thank you to you the listener for listening to another episode of the people Digital Marketing podcast with your host Kenny Soto. And as I’m asking this right now, this is the third time please, please, please, if you can rate us on Apple podcasts. I will be very, very, very grateful. Thank you. 


Have a good day.

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