Tips for a successful B2B tech marketing career with Maya Grossman, VP Marketing at Canvas

Whether you’re at the start, middle or end of your B2B tech marketing career, up-skilling and personal development can help you along your journey. 

On this episode of the FINITE Podcast, Maya Grossman shares her tips for having a long, successful B2B tech marketing career, including building your own portfolio.

Maya has had her own amazing B2B tech marketing career spanning leading tech companies like Microsoft and Google. She’s written a best seller on career development, and is now in her second VP Marketing at Canvas, a diversity recruitment platform. 

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Listen to the full episode here:


And check out more of the FINITE B2B marketing podcast here!

Full Transcript

Alex (00:07):

Hello everyone and welcome back to the FINITE Podcast. If you have your sights set on a VP of Marketing or a CMO role, this could be the episode for you, because today I’m pleased to welcome Maya Grossman onto the show. Maya is VP of marketing at Canvas, the diversity recruiting platform, and she’s in her second VP of Marketing role. 

Having previously spent time in marketing roles at both Microsoft and Google, today we’re talking all about the journey to the VP of Marketing role and how Maya made very active decisions to enable her to arrive at her dream job. 

Maya is also the author of a book called Master the 10 Skills You Need to Skyrocket Your Career. So she really is an expert when it comes to helping marketers progress on their career journeys.


FINITE (00:45):

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Alex (01:07):

Hi Maya, and welcome to the finite podcast. Thank you for joining me.


Maya (01:10):

Hey Alex, it’s lovely to be here.


Alex (01:12):

Looking forward to talking. I was saying to you before that these more career-focused episodes, I think are one of my favourite types of discussions. So we’re going to go back over your journey to VP of Marketing, and will actually shed some light on that journey. But before we do, let’s start with the here and now, and you can tell us a little bit about your current role and everything you’re up to currently.


Maya (01:32):

Yeah, of course. I am now the VP of Marketing at Canvas and Canvas is a diversity recruiting platform. So we help companies hire more diverse teams and have great representation in their workforce. And I started in December. So I’ve been with the company for about nine months now and we’ve been through a rebrand. We changed our names, we launched a podcast and we really started building a brand from the ground up. So it’s been a wonderful journey and I’m excited to see what’s what we’re going to do next.


Alex (02:08):

Cool. And tell us a bit about your current team and structure and how marketing works at Canvas.


Maya (02:15):

Yeah, of course. So canvas is actually a marketplace. So we have two sides to the marketing team, the B2B side that’s focused on bringing in more business and we have the B2C side where we encourage more job seekers to join Canvas and be part of the platform. So we do have one amazing person on the B2C side taking care of our candidates, and we have a bit of a bigger team on the B2B side where we have demand product marketing and content right now.


A summary of Maya’s career journey 

Alex (02:46):

Awesome. Should we throw it all the way back to the beginning and start with your journey into the world of B2B marketing to begin with. I’ll let you decide what you think is most relevant start, but tell us a bit about how you ended up here in the B2B marketing world.


Maya (03:02):

Well, honestly, if you look at my career, I went back and forth between B2B and B2C and landed with two marketplaces. So apparently I love both worlds, but I think my first interaction with B2B was with the tech world in general. That was in my first marketing job. 

I worked for a PR agency and most of our clients were these giant tech companies. I worked with Microsoft and with HP and just really got a glimpse into that world and really liked it, really enjoyed it. But I wanted an adventure, so I kind of ventured out of B2B and tech and I joined a company called Soda Stream that builds soda machines for consumers. 

And while it was a phenomenal experience and I learned so much from the consumer world, I really missed the tech world. So my next jump was back into Microsoft and that’s where I got to do more B2B and basically what I’ve been doing since.


Does a B2B tech marketer need a formal education?

Alex (04:03):

Awesome. And what about the education side of things? Because it jumps out at me that you’ve done an MBA with a marketing focus. I think there’s always a lot of debate around how valid or valuable more formalised marketing education is. 

But then I know a lot of senior marketers have done an MBA and that really helps them in the C-suite environment, talking to other stakeholders from a business perspective. How important do you think that’s been? And at what point did you do that in your career?


Maya (04:34):

Yeah, so that’s actually a funny story. I wasn’t sure if I wanted to do an MBA, but I knew that I wanted to become a CMO one day very early in my career. I was still an IC and I knew what the end goal would look like for me. And I started asking myself, okay, what do I need to get there? 

And about 10 years ago, I think the market was still looking for those signals. People cared more about your education and less about your experience and skills. I was concerned if I don’t have an MBA, I’m not going to move up the ranks. But if I’m being super honest about the actual experience and I did my MBA, I had seven years of marketing experience. I was teaching my professors things they did not know. It felt like a lot of the conversations were detached on the marketing side. 

On the business side, I 100% agree. It was helpful to better understand how a business works to be a better partner. Now, when I am working as the VP, could I have learned it without that MBA? Probably. So I’m kind of torn when people ask me, should I do an MBA? 

I really ask them, what is your goal? If you’re really looking to learn marketing, there are better, much cheaper ways to learn and excel at your job. But if you’re doing this because you want to move into that executive level, because you need more business education, that’s definitely one option. Today you can learn pretty much everything online. So I would compare that to the other options.


Alex (06:14):

Okay. Interesting. Cause there’s that difference between a hard skill where you can complete a course and do something online as you say, but I think there’s something about an MBA and from a good university, it just carries so much more weight than a short course. Whether or not that’s right is a different question.


Maya (06:31):

Exactly. And they do have to tell you throughout my career, I have never, ever been asked about my MBA.


Alex (06:39):

Okay, interesting.


Maya (06:40):

No one brought it up. It was never a question whether or not I have it. And I think more companies these days are removing that barrier. Even companies like Google and Microsoft, they care less about that specific education and more about skills and what you actually can do. And I do think it’s the right way to go. 

Because as a hiring manager, I’ve interviewed people with Ivy league MBAs, people who, as we were taught to believe are probably going to be excellent at what they do. And I will be honest Alex, they were not good marketers and I did not hire them. So it’s not necessarily the best signal.


Should B2B tech marketers work in enterprises or startups? 

Alex (07:20):

Cool. Something that lots of marketers early in their careers or at any point in their careers to some extent are thinking about in terms of their own growth and getting to the next level is, am I best to spend time in a larger enterprise business or a smaller startup? Which is a fraction of the size and things are maybe more scrappy and you’re more hands on and more generalist. 

But maybe you’re missing some of the larger enterprise experience. What’s your perspective? Obviously you’ve been in some pretty sizeable organisations and some smaller ones, but what’s your take from the perspective of progressing a marketing career?


Maya (07:56):

I truly believe that you build your own opportunities. So it shouldn’t matter whether you’re at a bigger company or a smaller one, you will be able to grow with a company if you’re building your own opportunities. And as example, I worked for a really small PR company and I grew from an IC to a director within four years. 

But when I worked with Microsoft, they had a more structured career ladder and I couldn’t move as quickly as I wanted. So it really depends on your goals. Here’s what I learned working for the bigger enterprise companies and the smaller startups with a big company. You’re going to have a lot more structure. You’re going to have more resources. 

So if you want to specialise, if you want to go very deep into one specific discipline within marketing, that actually might be a really good place to start. You will also have a huge network and a lot of people around you to help you or to mentor you. 

When you work for a smaller company, especially if it’s a startup, you’re going to wear a lot of different hats, no matter what your job description says, you’re going to do pretty much everything you can think of in marketing. And you’re going to learn by doing and making mistakes and experimenting. And you may not have that much support from anyone else. You’re going to have to figure it out on your own. 

Now, my experience says you would actually learn a lot faster. So the learning curve is just going to be phenomenal. And I was also able to move faster and advanced faster and jumped from IC to director and eventually VP with the smaller companies, because you just have more room to grow. 

So it really depends on your goals and what you’re looking for. Maybe if you’re earlier on and you want to specialise and just learn one thing and get really good at it, you should aim for the bigger companies. If you already know where you want to grow, if you’re not sure at all where you want to grow, go to a startup experiment, try different things, see what you like. And maybe then take that experience and go to a bigger company.


Alex (09:59):

Do you think some of the bigger companies, similar to the MBA question, but having them on the CV lends you credibility and experience? And you then go to a startup or a scale up looking for that next job, and they go, well, she’s been at Microsoft, she must know what she’s doing. Again, it’s not necessarily an indicator that that’s the case, but for a lot of people reviewing CVs, maybe it’s not a bias, but those ways of thinking exist.


Maya (10:24):

Yeah, I do think that bias still exists. And if you look at my resume, I obviously share with people, hey I worked for Microsoft and Google because it does open up a door. It opens up a conversation. It doesn’t get you to job, but it definitely gets people’s attention. 

What I would say is actually for me as a hiring manager, I learned to almost always assume that that’s not the case. I try to give people a chance, not just based on the name of the company they worked for, but what they actually can demonstrate that they’ve done. 

Whether or not its worth investing going into those companies. I know a lot of people, especially new grads, they just want to go to the faang companies. And it is very, very, very competitive. It is very hard to get there. And I actually had a very different career journey. I did not start there. I didn’t start with Microsoft. It took me almost 10 years to get there. 

It was easier to get in because I built a career, I had a reputation. I already had something to demonstrate and to prove my abilities. Same goes for Google. Google was actually a referral because I did such a good job. When I worked for Microsoft, they actually referred me to the role I eventually took at Google. 

So there’s more than one way. You don’t have to start with those bigger companies. It just really depends on the opportunity and whether or not you see something that excited about


How can B2B tech marketers break through the noise to get hired? 

Alex (11:54):

Makes sense. And I think we should spend some time talking about that in terms of, I think it sounds like you’ve considerately made active moves and planned your progression. And you’ve created your own opportunities, as you said. Particularly in the faang companies, but others too, things can be pretty competitive. 

What are your tips for breaking through that noise? And I guess to some extent also building that profile, building that reputation, to then kind of boost your own career?


Maya (12:28):

I would probably start with the first question. What do you do to stand out? And it is quite challenging to do that these days. There are a couple of things that I’ve done throughout my career, but also that people have done for me as a hiring manager that really stood out. 

One example would be to build a portfolio. So this is something I learned from one of my managers at Microsoft. I was interviewing for a role there, I wanted to get a promotion and I didn’t actually get that opportunity. But I asked the hiring manager, why, what’s missing, what am I maybe not doing? What could I do differently? And she said, you should probably create a portfolio. 

And my initial reaction was what, but I’m a marketer, I’m not a designer. What do you mean portfolio? And I dug a little bit deeper and I started seeing other people doing that and demonstrating and showing what they can do rather than just saying, I can do it, because anyone can lie on their resume. And being able to show what you can do makes a huge difference and actually build a portfolio after that conversation. And I’ve used it throughout my career. 

Even now joining Canvas, it was a really great way to demonstrate what I can do. So a portfolio is not a replication of your resume. That’s very important. It’s proof that demonstrates everything you said in your resume. So that’s one thing that I found really helpful. And if anyone wants to learn more, I actually have a full blog post on my website explaining how to build one.


Alex (14:05):

Cool. Well, we can link to that. But just to give listeners a sense, I assume that’s case studies campaigns that you worked on a testimonial, almost like a marketing agency website in terms of what a portfolio might look like.


Maya (14:17):

Yeah, exactly. And I can give you a specific example. One of the things that I write on my resume is that I have experience doing sales enablement and you can really spend a lot of time explaining exactly what that means, because you want to keep your resume very concise. 

So in my portfolio, I shared an example of the actual pitch deck that I built and my team used to close their first six-figure deal. And that proves that I can do it, but it also shows the hiring manager exactly what to expect, what my deliverables would look like. And I think it just paints a picture that is very hard to do with a resume.


Alex (14:56):

Yep. Makes sense. I think that’s a great step. And anything else you think is worth mentioning?


Maya (15:01):

I think something a lot of people overlook and I’m probably guilty of doing that as well. And I got a reminder from Scott Barker recently about this, when you’re trying to build a relationship, most people go directly to the hiring manager or to the recruiter, but you should actually spend time with your potential team members. 

So people who might be on your team because it’s easier to reach out to them. They’re usually colleagues, they may have a little bit more time. They have an interest in knowing who’s going to join them. So they might be open to a conversation. They can give you information, but they can also become your champions because at some point they will be part of the hiring committee. So just something that I’ve seen work really well. If you reach out to a few team members, you increase your chances of becoming the person that they want to hire.


FINITE (15:54):

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How can B2B tech marketers build their personal career profile? 

Alex (16:13):

And what about the second question? I apologise for asking you two questions back to back, but in terms of building the personal profile reputation, social media. I guess having a portfolio maybe falls into that category too, but what are other things that you’ve done that you think have given you a bit more visibility in the jobs marketplace?


Maya (16:33):

In full transparency? At the beginning of my career, I did not think about this at all. I was heads down doing the work. Didn’t really think about how I show up and maybe build that persona. But after about 10 years of working, I built up a reputation. I also lived in Israel, much smaller countries. 

So it was actually very easy for me to reach out to people or get opportunities. But a few years ago I actually moved to the US and I had to build everything from the ground up. So I can actually share what that looks like. And this is something I think anyone can do, whether it’s your first day as a marketer, or if you’ve been doing it for 10 years and just a little caveat, it will take time. 

It took about a year to get the wheel moving, but here’s what I did. I started by mapping out all the marketers I wanted to talk to. And for me it was very specific VPs or CMOs and Silicon valley tech companies. And I probably mapped out a hundred of them and I reached out to them on LinkedIn and I had a very simple but personal message. 

Hey, I’m new in the bay area. I would love to chat with a fellow marketer who knows the lay of the land. And I also, this was very important, I also reached out to people who are at the same level that I was, it’s a lot harder. If you try to reach out to, if you’re IC and if you’re reaching to a VP, it will be really hard to build that relationship. 

Peers will probably be more likely to chat with you. And for out of those hundred, I probably had like 30 meetings, but it took months to schedule everything and have a conversation. But not only did I build relationships, they also told me about events and they told me about groups that I should join. And they introduced me to other people. 

So after about nine or 10 months, I really had a network and people were starting to circle back to me with job offers or opportunities. And at the same time, I also started writing on LinkedIn because I can’t just rely on those 30 people. I wanted to demonstrate to the world what I can do, and that really also helped propel kind of that reputation. 

And at the beginning, I reached out to event organisers and basically, I wouldn’t say I begged them, but I had to sell myself to get opportunities. Now I have people reaching out to me, but it is work and it takes time. And what it mostly requires is consistency. Because the first time someone says no, or when the first 10 people do not reply to you, people just want to give up, you can’t, you really need to keep working at it. And then it will build and multiply.


Alex (19:26):

I think that’s great advice. I think for all walks of life, not just careers. Just sticking at something and keeping going is often part of the solution. But I’ve been through similar situations myself, where I think people are generally quite happy to help often.

I think we often feel like we’re being a complete pain by getting in touch with someone and asking for too much. And I think even more senior people are often people are willing to give up some advice. And even if it’s a quick call or whatever it is, I generally found people are more open to doing that than I thought, at least before going into that kind of process. I don’t know whether you found this the same thing.


Maya (20:05):

I agree. 100%. And I know it from both sides of the conversation, right? I do that for other people right now, but I also had people circle back and say, of course. Because essentially you’re telling them that they’re awesome and you want their advice and people like talking about themselves and they like thinking that they can help. It’s a very selfish but not selfish act. So yes, I agree. 100%, most people would actually want to help.


Is it better to be a generalist or specialist B2B tech marketer?

Alex (20:35):

We talked a little bit about kind of bigger organisations versus smaller organisations already, and the pros and cons which I think you alluded to. I guess it’s tied into the generalist versus specialist debate in that in a smaller company you’re generally going to be doing a bit more, whereas in a larger company, you might be in a more specialist role. 

I guess if someone else is wanting to get to a similar stage as yourself and be VP marketing somewhere, do you think that that better off spending some time as a specialist? Or touching on a more specialist discipline at some point or remaining more of a generalist?


Maya (21:10):

Very, very good question. And I’m very biased because if you look at my career journey, you would definitely point out that I’m a generalist. I have done anything you can think of in marketing from PR to social media, to demand, to digital, to product marketing. And while now I think that’s an advantage as a VP. You want to have that more strategic view. You want to understand how the different parts of the business works. 

It was really hard moving from one role to another throughout my career, because I essentially pivoted every time I moved and I had to convince a hiring manager to take a chance on me. And that’s probably 10 times harder than to just kind of stick to a more structured career path. 

Now having said that, I do think it gave me a really unique perspective and the ability to connect dots that sometimes other people don’t see. But when I started building my career journey, I actually did some research. I wanted to try and understand how do most marketers become CMOs? 

What is the path that you need to focus more on demand generation on product marketing communications and from my research, which included about 30 to 40 people that I reviewed. Most people became CMOs if they came through product marketing or demand, which makes sense because those two disciplines are closer to revenue, which drives the business. And if you know that you can optimise for that. 

So if I was starting today and I only found that out like two thirds into my career, and if I was starting today, then I would probably pick one of those. I will specialise for a little bit. So maybe work for one or two companies get a little bit experience, go really deep, but then start venturing out. 

And here’s a little tip. You don’t actually need to have a job to learn something. So you can be a product marketer for five years. And on the side, learn more about communications or copywriting or demand. You can do projects, you can volunteer the amount of startups, early stage startups who would love to have a marketing intern, especially in Silicon Valley. You just need to put yourself out there and give them the opportunity. 

So I think if you have a combination of both, you’ll end up being this T-shaped marketer, but you’ll have a really strong foundation in the professions that are most likely going to help get closer to that VP or C-level roles.


Alex (23:48):

Makes sense. Was that a Google thing that T-shape? Didn’t Google kind of pioneer the T-shape person thinking?


Maya (23:55):

Yeah, I’m not sure, honestly. But it’s definitely something I think could be really valuable in your career. What I see people do sometimes if they go too deep into one area, they kind of neglect everything else. And not only is marketing moving really quickly these days and everything is changing. It all ties together. So you need to have at least a little bit of knowledge and information about everything around you.


When should a B2B tech marketer move on from their current role?

Alex (24:23):

It makes perfect sense. I guess tenures in marketing get a lot of attention. Every time I see a stat it’s like the average tenure of a CMO is two years or three years. It’s getting shorter and shorter average every time we see a new piece of research. I guess there’s lots of reasons for that, particularly in higher growth, often VC or PE backed technology companies that have some pretty tough targets to hit and some pretty short timelines. 

But you’ve moved around about over your career. I don’t know what the average is in terms of number of years, but I guess it sounds like if you haven’t been able to move up the career ladder such as in a slightly larger enterprise where it’s a bit more formal and it’s a bit more computer says no, because there’s just no way of getting around this. I guess you’ve taken the decision to move on at that point. Is that a fair summary?


Maya (25:17):

So I do things a little bit differently because I do have this idea in my head. And this is why I wrote a book about career development. That you need to have a plan and you need to have a goal. It doesn’t have to be a ten-year plan. Maybe you just know what your next role would look like. And knowing that is what drives my decisions. 

So for example, I knew I wanted to be a CMO and I asked myself if I stay at this fortune 500 company, over the next five years will I get closer to that goal? Or if I move to a smaller startup and I can probably jump at least one or two levels up, would that actually get me closer to my goals? 

So for me, that was a no brainer. I knew exactly what I needed to do, but you need to have that goal to help you make those decisions. And with some companies where I had the bandwidth to grow, I stayed for four and a half years. And when I didn’t feel like I was making the progress I wanted, I just ventured out and find new opportunities to grow.


Alex (26:23):

Cool. Makes sense. And I think is a sensible way of approaching things. When you look back and you think about your time as an IC as an individual contributor. And actually maybe also to some extent, I guess there’s some learnings from SodaStream in the B2C world. Maybe that’s a topic for another episode another day. But I’m interested in the value of being that individual contributor brought to you. And I guess how it’s helped you become a better VP marketing now?


Maya (26:49):

I think most people start by being an IC. You at least want to get some experience doing the work. And honestly, I’ve seen situations, especially people who come from consulting firms where they haven’t done the work and they know the theory. And there’s a huge difference between the theory and the day to day. 

So I definitely think that has really helped me understand how things work and how they would work together. Having said that I never really liked being an IC so very early in my career, I figured out how to get to the next level or get more responsibility or do more. 

And actually very early into my marketing career, about a year in with the PR agency, I saw a problem. We were a really small company, but we weren’t growing really, really fast and things were falling apart. And our founder was very focused on bringing in more revenue, which makes sense. That’s their job. And I was an IC, like five other ICs I worked with, but it really bugged me. 

I could see there was a problem and I wanted to solve it. I wanted to fix this problem. So I had this Jerry Maguire moment. I sat down, I wrote a couple of bullet points and I called it a plan. And I went to the CEO and I said, I know you’re really busy bringing in more money, but you’re not seeing that in the day to day things are breaking or falling apart. Here’s my solution. And I will never forget he had the biggest smile on his face. And he was like, you know what, you’re right. And my plan said, you need to hire a manager. So he said, congratulations, you’re the new manager, go fix the problem. 

And that was a year into my marketing career. And within four years I was a director at that company. And I had 20 people reporting to me. So yes, being an IC really helped. And I still did a lot of hands-on work, but I knew what my journey should look like. So I very quickly tried to optimise for that.


Alex (29:00):

I think that’s great though. It’s a very specific point, but for anyone that is an IC wanting to go to that manager level, just having the proactiveness to say I’ve identified a problem. But more importantly, this is what I think the solution is. So it can be a pretty effective way of demonstrating ambition there, which is great.


Maya (29:22):

Yeah. It’s actually a combination of two things. One is having the right mindset and what I call an owner’s mindset. You need to think outside of your job description and your really narrow point of view, think about the business as a whole. And number two, you want to take action. 

So actually care enough to see a problem and one to fix it. What most people do is just stick to their job description, do their nine to five and hope and pray and wait for someone to give them a promotion. And at least from my experience, after 15 years and 10 promotions, you need to create your own opportunities. Just like the story that I just shared and people do not understand how relatively simple it is to create those opportunities. You just need to want to invest in that.


What should B2B tech marketers know about being a VP?

Alex (30:17):

And I guess to wrap up, we should spend a bit of time talking about the role as it is now. I guess you’re in the VP of marketing role, is it everything you thought it would be? And what do you think you would tell others that are maybe kind of hoping that one day they’re in a similar role and now that you know a bit more about the role having done it for a bit?


Maya (30:37):

Yeah. So this is my second time as VP of marketing for a fast-growing startup. And it is a very rewarding role, at least from my perspective, but also a very demanding one. It’s not like you get to the VP level and you just sit back and relax and let people do the job. It’s actually the opposite. 

You have to combine so many different streams of information. You need to not only understand what you’re doing in your discipline within marketing and lead a team and coach them. You also need to understand the business as a whole and how it works. And you really need to invest in building relationships with your executives so that you can all come together and really drive the business forward as a whole. 

So a lot of responsibility and accountability, I personally love it, but I don’t know if it’s for everyone. What I would also say is, and I get this a lot from people who are a little bit earlier in their career, even when you get to the VP level and I would say the C level, you don’t know everything. 

No one knows everything. I do not have the answer for every question. And every problem I learned from my fellow team members, I learned from the other executives. I learn from my colleagues. What you didn’t learn how to do is how to make decisions without a lot of information and just take risks sometimes. 

And knowing it may not be the right answer, but if we do it quickly, we’re going to figure out whether it’s good or bad, and then we can either do more of that or stop doing it. So it’s a lot more about prioritising and making decisions rather than being the best marketer in the world.


Alex (32:23):

Awesome. I think you’ve shared so much that I think anyone wherever they are in their career that’s looking to move forward, has something to work with. We will make sure that we link to your book in the description and maybe a couple of the other bits and pieces and resources that you mentioned, but thank you. Thanks for joining and for sharing everything so openly.


Maya (32:42):

Yeah. Thank you for having me. And if I could leave everyone was one last thing is that I don’t think there’s ever been a better time to be a marketer, especially in the B2B world. So if you’re excited about this, if this is something you want to do, I would highly recommend that you invest in yourself and you invest in learning and just reaching out to other people and learning from them. If I was starting over, this is exactly what I would be doing.


Alex (33:13):

Perfect, that’s optimistic and a positive note on which to wrap up. So thanks again.


FINITE (33:19):

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