The Path profiles people working in what we think of as “dream jobs,” living their best professional life, and looks at the people and practices that helped get them there. We talk to these amazing folks about how goal setting, great leadership, tough decisions, and other key moments helped them get to where they are now. And, because so many career paths are inherently winding, we examine what it can look like to handle unexpected experiences along the way.
Maya Grossman started her career late. After working for years to pay her way through college, Grossman’s professional trajectory took off thanks to a series of bets that paid off. The first? Pitching her company on letting her start and maintain a Facebook page which, at the time was a relatively unknown platform. From there, Grossman spent years growing into a marketing expert and eventually went on to work as the Head of Digital Marketing at Sodastream and the Head of Global Product Marketing at Microsoft, among other roles.
Throughout her years as a marketing executive, Grossman built up a powerful skill set that eventually led her to do what she currently does, advise big-name companies like Google, as well as startups like BetterHelp and Openbase. Currently the Vice President of Marketing at diversity recruiting platform Jumpstart, Grossman shares her views on strong leadership, tackling difficult conversations with empathy, and how she learned to build an identity for herself outside of her work.
What did you go to school for and what did you think you wanted to do at that time in your life?
I started very late; I took a job very early in my career because I had to put myself through college. I worked for about four years as a travel agent. It was a nice job and very convenient. I majored in finance and marketing; I hated finance but fell in love with marketing. I didn’t really have anyone around me doing marketing, so I did some online research. Around the time, Facebook just started and I started reading about social media and it seemed so interesting. I decided this was what I wanted to do. I taught myself, read blog posts online (there was no YouTube at the time), and taught myself everything I could. I then went to my manager at the travel agency and said I was willing to open a Facebook page for the business and manage it. They were very open and let me do it.
Can you give me the ‘Spark’s Notes’ version of your career history so far?
I spent about six months running the travel agency’s Facebook, creating content, and building their audience. I gained some practical experience, which gave me the confidence to apply for a social media job, taking a step back to an entry-level position to enter this profession. I joined a company with five people. I was so happy and got to do what I really love. The founder taught me everything I needed to know about social media and I was able to grow with them. In less than a year, I became a manager. Four and a half years later, I managed a team of 25 in an executive role. I started digging into digital marketing, and decided that would be my next move. I was doing my MBA at the time, and we had a case study about SodaStream. I started stalking them, basically, waiting for an opening. When an opportunity came up, I reached out to a couple of people on LinkedIn, sent my resume, and basically didn’t take no for an answer. They brought me in for an interview, I got the job, and got to really own that discipline and do a lot of experiments — try new things, and really go outside of my comfort zone. That drove me to my next role with Microsoft where I was focused on product marketing, which was my sweet spot. From there, I joined a fintech company. Problem-solving and joining a company early means you have to help find product-market fit and deliver the right message. It was a perfect fit, and I was able to grow with them. Everything was going according to plan, but then my husband and I had the opportunity to relocate to San Francisco. So that’s where the relationship with that company ended.
You’ve previously been the Head of Digital Marketing at Sodastream and the Head of Global Product Marketing at Microsoft. Now you work as an advisor to companies like Google and BetterHelp. What’s it like doing the work you are doing now?
It was definitely a change. I had this great background as an employee but I had never been an advisor before. So my first couple of projects, I did for free to prove I could do it and figure out what my process looked like. From there, I was able to start working on bigger projects. It was definitely a challenge. I was actually referred to Google by my manager at Microsoft, but most of the time you are kind of on your own. It’s taken some getting used to. But I really like it, because it allows me to focus on what I do best and not spend time on things I’m not great at and don’t enjoy doing.
What are some daily habits you absolutely make sure to schedule into your day?
I have a routine and plan everything. I exercise three times a week, whether yoga or running. I find both get me into this zen space. These two activities you need to fully focus, like you can’t watch TV and do yoga. It allows my brain to disconnect from everything else. I start my day at 6 am. I spend time writing and sharing content in the morning and try to only schedule calls on specific days. I did a lot of career coaching calls with young professionals, and I’d only do them on Mondays. This way I can have the right mindset for whatever I’m doing. I also always have lunch and dinner at the same time.
Tell me about someone who’s made a significant impact on your career trajectory—whether that’s a mentor, a manager, or someone else crucial to your success.
The first are the two founders who believed in me and gave me a chance when I didn’t have a lot of experience first getting into social media. They taught me so much in the four and a half years I was there. Later in my career when I was at Microsoft, my manager was one of my mentors. They basically gave me the freedom to kind of figure out how to do things myself. They were always there to help me if I needed it, whether it was taking the blame for things that went wrong or just being able to give me the tools I needed. For instance, while at Microsoft I started building a personal brand and wanted to do a podcast. I couldn’t bring myself to actually do it, but I shared it with my manager and they said, “We have the equipment, you have my approval to use it. And you can do it during work hours as long as it takes about an hour a week.” Being able to not only have my back but also giving me the tools I needed to empower me, they did that throughout my time there and still does to this day.
What’s been the biggest learning lesson in your career so far?
That careers don’t just happen; you have to build and develop them. A lot of people think “I’ll just do my 9-5 and get a promotion or get to my next role,” but if you don’t actively work on deciding what you want and doing what it takes to get there, then you’re basically relying on luck and that’s not a great strategy.
What do you think makes a good leader?
There’s a really great book, Radical Candor, and I think how she describes leadership is pretty much what I believe in — that you need to be very transparent, straightforward, and shouldn’t hide things from your team. You should be open and give them all the tools they need, and not sugarcoat things, but also lead with empathy. It’s about leading from a place of helping others grow and learn not to discipline or show your superiority.
How do you approach difficult conversations at work?
I think you need to be direct but do it with empathy. I think people are quick to realize when you’re not being authentic. I always try to understand what I want to get out of a conversation but also what the other person needs to get out of it. So even if it’s a really difficult conversation, say I need to let someone go, I start by thinking how this conversation can be easier or more beneficial for them, and what I want them to take out of it. By understanding that, I then construct a conversation that’s more focused on their needs as opposed to mine. I give them the courtesy of not trying to sugarcoat anything and be very direct, but then have the empathy to really understand where they’re coming from and provide any support that I can to make their process easier.
Today, industries and culture are evolving more rapidly than ever in the wake of the COVID-19 pandemic and the ongoing revolution in the fight for racial justice. Has your personal relationship to work changed?
I don’t think so necessarily. I always try to focus — when I hire people or build teams — on what people bring to the table, not who they are on paper. I don’t think remote work changes that. It just emphasizes how important it is to focus on what people do and now where they come from. Sometimes people focus too much on external statuses like having an MBA or what university you went to. It doesn’t matter. I have had people with Ivy League degrees that were terrible marketers and I would never hire them. This is why I always ask people to demonstrate what they can do and sometimes prefer to hire for potential rather than experience. I definitely pay more attention to that process and I would like to think that that’s the right way to go. But that’s also the only way I know.
What do you think managers and leaders need to be doing to create better workplaces as we move forward from this moment?
I think a lot of it has to do with communication and setting expectations. So, actually telling people what you expect from them and what they’re supposed to achieve in their role is so important, especially for people early in their career. Also, with communication and transparency, a lot of the time, especially as a manager you have more information and are more exposed to what’s going on at a higher level, and I see people sometimes not sharing this information and it’s a huge mistake. The only way to actually empower a team is to give them all the information they need. For me, that’s the best way to build stronger teams. I also think different people require different levels of support, so being attuned to that and understanding that people are going to be different and need to be approached in different manners. I learned it the hard way, I tried to treat everyone the same way earlier in my career and it didn’t work. Some people became superstars and some people crumbled under the pressure because they needed more time and guidance. I think once you figure out who’s who, it will definitely help you create a much stronger team.
What advice would you give to your younger self?
The most important thing is to remind myself that I am not my job. What I do is not who I am. I was stuck on that for a really long time, focusing on titles and achievements. And those are all great but they’re not what actually makes you who you are. Also, these days, when a lot of people have been laid off, they immediately think there’s something wrong with them or they’re not good enough, and that’s not true. They’re the same person they were three weeks ago when they were a director or a manager, and we sometimes forget that. I also think it’s important to find something that you build your identity on that is not as volatile as work. For me, I try to focus on the fact that I am a learner — that, on a long enough timeline, I will outlearn anyone and will figure things out. Having that identity means that, even if I don’t have a job, it doesn’t make me any less.
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