🚀 Breathe.



"Moving the wrong person out of your team actually ends up being the best outcome for them, for you, and for the team as a whole. Because if they're in the wrong role, they're not going to be happy, your high-performers on the team will become frustrated, and they actually are at risk of leaving, and the entire dynamic of this team suffers as a result.”

In this episode

In episode 34, Nick Stein sheds light on the people who make up our teams, and the intricacies that come along with leadership.

Nick Stein is the Chief Marketing Officer at Top Hat, a SaaS scale-up that helps professors and students learn more through interactive content. 

Nick is a results-driven marketing leader that has led teams at Vision Critical, as the SVP of Marketing and at Salesforce, as the Senior Director of Marketing. 

In this episode, Nick talks about the importance of being honest as a leader and why letting people know where they stand is a healthy choice for you, them, and your entire team. 

We also explore why hiring should be approached through a relationship lens, rather than a transactional one… and why those who believe in your company’s values and mission are more likely to be great team members. 

Tune in to this episode to explore the characteristics of high performing teams and if your team is on the right track to becoming one.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Successful founders have this in common


Marketing is a team sport


From journalist to marketer


Trust your gut when it comes to talent


Different organizations, different leadership styles


Pivoting your product during the pandemic


Recruiting and marketing are the same things


How to spend your time recruiting on LinkedIn


An outcomes-focused team


Empathy in marketing


Startups are like basketball teams



Aydin Mirzaee 2:23

Nick, welcome to the show.

Nick Stein  2:25  

Thank you. It’s great to be here, Aydin

Aydin Mirzaee  2:27  

Yeah, this is really interesting. I know you and I were both participating in SAS north. And so I heard you speak at the conference. And now we’re doing this. So you become you’re kind of doing like the tour of different shows.

Nick Stein  2:42  

Yeah, it’s it’s interesting. Like I would say I used to do a lot more of this when I was marketing to other marketers. But now in my in my current role, it’s a little more unusual for me to spend time talking about how I think about building teams, leading teams, managing people, and so I really appreciate the opportunity to be here and, and share some of the things I’ve learned over the last number of years.

Aydin Mirzaee  3:10  

Yeah, this is gonna be fun. Before we talk about your leadership, I wanted to ask you going in your past who has been your favorite, or even more memorable might have been favorite in a bad way. But who’s been your most favorite person to report to and why?

Nick Stein  3:27  

Sure. So I’ve been fortunate to work for some incredibly smart founders, including the founder and CEO of top hat. Mike Silagadze, who’s who’s scaled our company, literally from his dorm room at the University of Waterloo to 400 employees today, and I think what successful founders have in common and I’m sure you can appreciate this is just a relentless all-consuming focus on the business. They don’t work to live, they live to work. And I really I share that philosophy and would frankly, have a hard time working for someone who didn’t care about the growth and success of the business as much as I do. If I had to single someone out, though, I would have to single out Daniel Debow, my friend, and mentor who was the co-founder and co-CEO of Rypple, and then later, I worked with him at Salesforce after Salesforce acquired Rypple back at the end of 2011. The reason I single him out is he’s the one who gave me my start in marketing. And I’ll always be grateful for that. Also, in my experience, startup founders either come from a product and engineering background, or a sales and marketing background and he came from a sales and marketing background. So he really understood the power and the value of marketing and I think We just were able to work really well together to create sort of a brand and a level of awareness at Rypple that far outweighed the size and scale of the business. So The other thing I’ll say is, he really understood his strengths. And he understood mine, he was an Idea Factory, he is an Idea Factory, he’s, if you’ve met him or spend time with him, he talks really fast. He’s got a new idea every minute. He loves running experiments and taking risks. But he didn’t always have the patience to see those things through. Whereas I’m more of a systems thinker. And so I’m thinking about which ideas are the ones that are actually worth doubling down on and investing really heavily in? And which ones should we hone further to deliver the biggest impact and as you know, in a startup, the focus is everything and marketing, you can do a million different activities all the time. And the question really comes down to which are the ones you should be putting your limited resources and focus behind. So I would say, between the two of us, we were able to kind of be a bit of a duo really achieving a lot of things together for what was then a small company.

Aydin Mirzaee  6:19  

Yeah, no, that makes a lot of sense. It seems like this, this concept of basically understanding both your own strengths and weaknesses, but also, like, deeply understanding the strengths and weaknesses of your team is an important part of this equation.

Nick Stein  6:34  

It is, I mean, it’s, it’s interesting, because when you work, as as I did, for many years, before going into marketing, I was, I was a journalist, and as a journalist, I was very much dependent on myself. But marketing is a team sport. And I think building successful companies is a team sport. And so being able to identify what your superpower is, what the thing is that you’re really strong at, and then surrounding yourself with others who can kind of fill in the gaps that you yourself have. And being cognizant of that. I think that’s really the key, or at least that has been the key for me too, to building and scaling something successful.

Aydin Mirzaee  7:21  

So, Nick, I have to ask you, because a lot of people do talk about this, you know, knowing your strengths and your weaknesses and surrounding yourself with people who are complimentary. When did you really truly understand what your superpowers are? Because, you know, I gather that it’s not the sort of thing that you just wake up, you know, one day and you know, in your early 20s, and you just know this.

Nick Stein  7:44  

Yeah, I mean, for me, because of the way I came, into marketing, I had had an entire career. Previous to that as an investigative reporter, I moved to New York I, I studied journalism at Columbia, I was working at Fortune magazine. So for me making the transition into content, storytelling, thought leadership, PR, that was very natural, whereas more the metrics-driven side of marketing than the demand generation side was something that I had not been exposed to, at all. Interestingly enough, it’s probably the piece that I’ve gravitated to, I’ve always struggled to figure out what is the thing that I really want to do to such a degree that actually when I was in university, I did all my sciences as electives, just on the off chance that I might go to medical school because I kind of wasn’t sure whether that our more artistic creative side or the more analytical side was the path that I wanted to pursue. And marketing has been great because it’s kind of marries the best of both of those worlds. But I would say like, if I think about my team today, I’m probably playing more of a leadership role on the storytelling side where I’m playing more of a mentorship role on the demand gen side, ensuring that I have really smart analytical people who I can mentor but they can take

Aydin Mirzaee  9:20  

It sounds like you know, at Rypple was when you first started really diving into marketing, although, as you said, like as a journalist, I mean, your storytelling and it’s a lot of the same skills. In your first teams. I assume that was the first team that you managed at Rypple.

Nick Stein  9:37  


Aydin Mirzaee  9:38  

I have to ask you about some of those early mistakes. It’s interesting. Every leader has early mistakes. But it’s interesting that everybody has different mistakes that they learn from. So what was something early on that you did or were doing that you stopped doing later on?

Nick Stein  9:54  

So the biggest lesson that I learned  is the importance of talent. I think there’s there’s a cliche that I’m sure you’ve heard about hiring slow and firing fast. And the way I actually have a cousin who works in HR at Google, who says it a different way, which is better a hole than an asshole. And I think early in your career as a leader, especially when you have a small team, and we had a very small marketing team at Rypple in the beginning, it’s very tempting to keep someone on the team who you know, in your gut is not the right person. Because for one thing, when they leave, you’re going to have to pick up the slack, yourself. And when you’re working in a start-up, as you know, there, there already aren’t enough hours in the day. So the thought that you’re going to have to do even more can sometimes lead you to keep somebody who you just know, isn’t right. And I think the other thing is that firing people is really hard, especially if you’re the one who was responsible for hiring them. I think the lesson I’ve learned, though, is that moving the wrong person out of your team actually ends up being the best outcome for them, for you, and for the team as a whole. Because if they’re in the wrong role, they’re not going to be happy, your high performers on the team will become frustrated, and they actually are at risk, of leaving, and the entire dynamic of this team suffers as a result. So I think definitely as a, in my first experience, managing and leading people, that was a lesson that I probably learned the hard way.

Aydin Mirzaee  11:36  

Yeah, and it’s interesting. And you know, a lot of people put this off, like you said, especially for some managers, because you’re going to take on all this extra work. And, and when you finally do it, a lot of people come and thank you, what took you so long?

Nick Stein  11:50  

Exactly. That’s always been the experience. And again, I think once you know, you probably know what the right decision is in your gut. And so just trusting that, and going with it is probably the best advice that I could give.

Aydin Mirzaee  12:05  

Yeah, so I wanted to maybe dive into some of the different companies that you’ve obviously been at, you’ve been at the startup, which is Rypple, obviously, a scale-up, which is Top Hat, and then a mega Corporation, which is Salesforce, do you feel that your style of leadership needed to be different at each one of these different places?

Nick Stein  12:25  

So great question. So I’ll answer that in two ways. First, what has remained consistent across small companies all the way through to big is, is my strong belief in delivering feedback at the moment, both in terms of recognition as well as constructive feedback. And you’ll appreciate this given what you’re building with Fellow, but with Rypple, really, we had built an application for managers to be able to deliver ongoing feedback coaching and recognition to their team members. And I collaborated during my time there with so many leading thinkers around the world on employee engagement, and motivation, people like Dan Pink and Tony Robbins and, and many others. And the common thread that I heard from all of them about what does it take to be a great manager, a great leader, as you, you always want your people to know where they stand, it goes back to what we were talking about earlier like it’s better to let someone know, things aren’t working out right away, then to have it sort of germinating over time and faster, and to have that small, crack, expand. And so I think that has been consistent. regardless of the size of the team or the size of the organization, I think what has really been different is, is the amount of process that you need to introduce into the equation in a small startup, it’s like the whole team shares the same brain. So you don’t need to spend a lot of time building a process or building a shared context because people just have it naturally already. But as the company that you’re working in gets larger, alignment becomes actually more important being aligned on the thing you’re doing actually matters more than what that thing even is and so that means spending a lot more time thinking about how you create flows of information, feedback loops, not just within your own department, but across the entire organization and, and then once you get into the larger matrix, organizations that cross-functional collaboration becomes even more critical to success and as an as the leader of the marketing function. We literally cannot achieve any of our goals independently. Our success is dependent on building those trusted relationships with what’s Sales with the product and with other teams. And so you know, one of the things I spoke about in my South’s North presentation was was really this idea that as you work in a larger and larger company and manage a larger and larger team, you actually should be spending just as much time optimizing what you’re doing internally as you do optimize what you’re doing, externally. So even just thinking through simple things like how am I structuring my team meetings? How is my organization structured? Those things for me deserve as much or more scrutiny as like, what’s that next email subject line? Or is my landing page, converting the way that it should? And it’s about creating the conditions under which all these people who are working in the company can be successful?

Aydin Mirzaee  15:58  

Yeah, so much unpack there. Let’s start with this. And I’m very curious to dig in more about this particular thing where you said that sometimes it’s much more important for you to get aligned on what specifically you’re going to do versus what the thing actually is. Could you elaborate on that a bit more? And maybe if you have an example?

Nick Stein  16:16  

Yeah, for sure. So I mean, one of the things that the example I’ll give is actually, the last few months with COVID. So Top Hat is an education technology company, and people automatically assume that means online. But actually, the technology that we built was to make the live in-class experience much more engaging and meaningful and motivating for students and for professors for university professors. So March comes along the the COVID, pandemic hits, and all of a sudden, we are in a position where 85% of the courses that are using Top Hat, 1000s, and 1000s of courses now have to be taught online or remotely. And we don’t really have a product that can support that effectively. And so we there were many things that we could have done, there were customers that we had, who were saying top hat is helping me transition more effectively than the courses where I don’t have taught that but we knew we had huge gaps in the product that we have to fill. And so actually just focusing the entire company to say, we’re just going to, we’re going to completely rebuild our platform, so that it is able to support teaching a class regardless of whether it’s happening life or asynchronously whether it’s happening in person, or in a remote context or a combination of the two, it has to work well, no matter what. And then I went back to the marketing team. And I said, Look, this is our one thing, I feel like you always need to have that one thing, you could be working on 100 different things. But the one thing that everyone is clear on, is the difference between success or failure for the team. And we actually change the way we work together as a team, where it was very clear that this was the one thing we were working on, we’re launching this new set of product capabilities. And if you’re not working on this, you, you better have a very good reason why because this is the one thing that’s gonna make the difference.

Aydin Mirzaee  18:30  

Got it? Yeah, so that singular focus. And so it’s not so much you know, the specifics, but as long as it’s aligned on the one focus that the entire company is, is focused on.

Nick Stein  18:42  

Exactly. And again, in this in this circumstance, it wasn’t just marketing. I mean, the product and engineering teams were working on building the new product that we were working with the revenue teams to figure out how are we actually going to position and sell this product to our existing customers and potential customers. And then on the marketing side, we’re thinking about like, how do we completely rebuild our website, the way we talk about what we do our value proposition, everything to be able to support this, this new way of teaching, which is just taken over.

Aydin Mirzaee  19:19  

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Aydin Mirzaee 20:02

So switching gears for a second, I know you care a lot about hiring and you’ve, you know, you’ve said even today that it’s one of the most important things that leaders can do. I wanted to ask you a little bit if you could just tell us what is your hiring process? Like? How do you go about hiring people onto your team?

Nick Stein  20:23  

Absolutely. So earlier, I spoke about obsessing over talent, this actually begins with recruiting. So we have an amazing recruiting function at Top Hat, but I don’t rely on them. So I actually spend a few hours every week on LinkedIn, just reaching out to people who are interesting. I don’t wait until we have an open job rack to me, recruiting and marketing are, are the same thing. It’s about building a pipeline of really great people. So when that opening does come up, you’re not now scrambling to say, who’s the right person to fill this role? So so I think that’s the first thing.

Aydin Mirzaee  21:08  

Okay, so you’re just doing this all the time, a few hours a week, what are you connecting with people on? Is it you know, more just commenting on their work? Or are you actually reaching out and saying, Hi, I’m Nick, I’m not hiring today, but I may be in the future. How does that look?

Nick Stein  21:24  

Typically, it’s a role that I know I’m going to be having coming up in the near future. And so it’s really just reaching out and saying, “Hi, I’d love to talk to you about an exciting opportunity. And then if they agree to meet with me, it’s just telling them about what we’re building at Top Hat, understanding a bit about them, and then saying, you know, would you be interested in exploring a role in the future? Or sometimes it’s just saying, I don’t have a role on my team right now. But your background, and experience are really impressive. And I’d love to just stay in touch with you so that if a role did come up, would you be open to exploring?

Aydin Mirzaee  22:10  

Yeah, that makes a lot of sense. 

Nick Stein  22:12  

And, sometimes it’s years later, like, I’ve hired people who we first had a coffee, I’m sure you’ve had this experience, too, and then a couple of years later, the perfect role comes up for that person, and you just think of them and you reach out to them. And the stars align and you end up hiring.

Aydin Mirzaee  22:32  

Yeah, I think this is a very, very important point because it kind of reflects, you know, people look at scaling companies, and they might think, Oh, yeah, well, you know, they figured out this thing, and then it was growing. And so they just grew, and that was that. And then they were successful. But a lot of work actually goes into this stuff. And I think it makes a huge difference between someone saying, Oh, we need like to hire five people right now, how do we do this and recruiting team please help versus it probably makes a huge difference. because like you said, having the right person on the team can be a huge multiplier.

Nick Stein  23:07  

Yeah, I mean, for me, it’s the difference between a transaction versus building a relationship. If hiring someone is just a transaction, it can very quickly devolve into like, what are you giving me? What’s the compensation? What’s the role, send me the job description. Whereas if it’s a relationship, as one of the biggest challenges in companies is that is growing fast is the role I hire you for today probably looks very little like the role you may be doing next month or the month after that. And so if you’ve created this transactional relationship with a candidate, where suddenly now you have to go to them and say that thing I promised you were going to be your role now looks different. That creates friction. Whereas if you’ve built a relationship first, then it’s about what is in the best interest of the business? And how can I bring my capabilities to bear to help move the business forward? And if that means my role changes? Great, I’m happy to make that change.

Aydin Mirzaee  24:10  

How do you know if someone is you know, so you’re doing this, you’re always building a pipeline of interesting people when it comes down to actually hiring someone? What have you learned in terms of making sure that you hire someone truly great?

Nick Stein  24:24  

Sure. So one of the things I’ve learned is, is the best candidates always embody the values and leadership principles of your organization. So we spent a lot of time as an executive team, at Top Hat, really honing our values, the way we express them, making them feel unique to our company and our culture. And then we have a set of leadership principles which think about them almost as like the operating system for those values. Obviously, companies like Netflix, Amazon, on others have done this very well, as well. And what that means is that you’ve kind of created a blueprint for this is the culture we want to have. And then you’re really looking for is the person coming in going to be a good fit for that, that culture, what I’ve learned about really great people is they do always have to believe in the mission, the values of the organization, a few other things that I’ve learned is hiring them takes convincing, they usually have a great job already. And they’re very thoughtful and methodical about each next step they take in their career, they tend to optimize for learning rather than for a title or, or compensation, especially earlier on if you’re hiring someone more junior. And I would say that they’re not just 10% better than the next candidate. There, they’re 100 times better. And that’s the thing, like putting yourself in a position where you can actually compare and contrast different people and seeing someone is just going to be a step function stronger. And then the last thing I’ll say is they always have a growth mindset. They’re very inquisitive. They ask good questions, they’ve taken the time to actually learn something about you and your business. And they are just naturally curious and self-driven to learn and to, to grow. I think if, if if I get to the end of an interview, and I say, what questions do you have for me, and the candidate is like, well, I don’t really have much to ask for me, that’s a huge red flag.

Aydin Mirzaee  26:44  

Very interesting. And it basically shows you that they’ve done their homework and they are curious, and they’re truly evaluating this versus they’ll just say yes to anything. So we talked about, you know, building the pipeline, hiring the people. Now you have a team or say that you, you took on a team that you know, belong to a different leader before? How do you know if your team is a high performing team? So we all talk about high performing teams, and everybody I feel like it might be one of those things that it’s kind of like driving, everybody thinks they’re better than the average driver. But what are the characteristics that you’ve noticed in teams that you’ve worked with, that you really feel are high performing teams? How do you know if you have a high performing team?

Nick Stein  27:27  

This is a really great question. It’s something I spend a lot of time thinking about and the way I think about it is do they have that performance mindset? Do they have that growth? mindset all the time? And I mean, I’m a huge, huge fan, I talk about all the time of the book, Growth Mindset, by Carol Dweck. And, and for those who haven’t read it, I’d encourage reading it because it really talks about like, inherently, there are people who view life as a learning opportunity where it’s not about putting yourself in a box and saying, you know,  I’m fixed, this is all I am and all I can ever be. It’s what can I do next? And I think that’s a question I often get asked is how did you go from being a journalist to a CMO? Like they seem like such different things, but at their core, it’s there’s an innate, like curiosity and, and growth, my mindset that has to drive both of those activities. So it starts with is it’s about people who don’t just ask what like, what’s the next thing you want me to do? They ask why, why? Why are we doing this thing? Like you just told me to do this? But is this really even the right thing? and help me understand why I would say the second thing is you need a team of people who focus on outcomes, not activity. What I mean by that is, rather than focusing on what are the next set of 10 things I need to do it, what outcomes do we want to achieve? One of the things that I’ve been able to do with my teams, or at least the teams that are successful is I don’t have to tell them what the activities are. I say these are the outcomes. You folks are all probably smarter than me you’re gonna figure out the right activity to drive that outcome. But I want to make sure you’re really clear on what we’re trying to achieve. And then you need metrics to be able to demonstrate that that success and not metrics just to pat pat yourself on the back and, and feel good but really metrics that are aspirational. And then I’d say the last thing is and it sounds strange, but like people who are comfortable with celebrating failure as much as success as long as they’ve learned something from that failure. I mean, one of the things I always say to my team is like make lots of mistakes. Try not to make the same One more than once, because you should be learning from them. But if you’re not making mistakes and breaking things, you probably don’t have a performance mindset and you’re playing it safe. If I had to add one last thing, which which is particularly true for businesses, his obsession with the customer, for some reason, even though they seem like disconnected elements, people who generally really care about performance, it’s not just for the sake of I want, I want to do well, myself, or I want the company to do well, it’s, I want our customers to be successful. That’s the ultimate measure of whether what we’re doing really made a difference.

Aydin Mirzaee  30:46  

Yeah, no, those are all very, very valid points. And, you know, it’s interesting, this other thing that you, you know, you also talked about, which is, you know, customer obsession is, is one thing, but it’s also being aligned with the mission. And when I look at your background, obviously, we talked about you being a journalist, but you know, before getting into marketing, you also spend time teaching, and I can’t help but think that that had something to do with you joining Top Hat.

Nick Stein  31:15  

Before I actually went into journalism, I was considering becoming a professor, I was fortunate that while I was working as a journalist, I got to teach magazine writing at both Columbia and NYU. And I think the biggest thing that helped me with was that creating that sense of customer empathy, because I think, regardless of what role you work in, in a company, but especially as a marketer, who’s trying to figure out how do I communicate the value proposition to a customer, if you can really have empathy for what that person is going through, it’s going to make you more effective at your job, because your success really depends on understanding their pain point, delivering a message that addresses those pain points, and then uniquely positions, what you do in a differentiated way. And, and, and building a narrative that like captures their hearts and their minds. So if you’ve actually literally been in their shoes, you know, what they’re going through in a way that you can’t if you’re just sort of studying it from the outside, so So I would say, knowing that our primary customer, university professors, like have a really difficult job and what that job is, and what those challenges are, was probably the biggest thing for me in terms of my current role at Top Hat. 

Aydin Mirzaee  32:45  

Yeah, that makes a lot of sense. And it kind of ties together in a very practical way, a lot of the things that we talked about, obviously, being mission-oriented, understanding the customer having alignment, I wouldn’t be surprised that if I, you know, went through all the different people who worked at Top Hat that they’ve had a good portion of them would have had some sort of relationship with teaching or academia, or maybe they were a tutor, anything like that. There is one question that we like to ask all of our guests, and that is around just resources, tips, words of wisdom, anything that you would kind of tell people to check out? I mean, you mentioned Carol Dweck, book mindset, which, which I also agree is an amazing book. Is there anything else that you would recommend to people who are actively looking to get better at their craft of management and leadership? 

Nick Stein  33:36  

Absolutely, there are so many good books that I could recommend. But really, I think I’ll focus on sharing two tips. I think the first step and we talked about this a little bit earlier is that the best leaders that I’ve ever seen, and I had the chance when I was a journalist and worked at Fortune magazine to like interview and spend time with like some of the greatest business leaders of this century, folks like Bill Gates and Warren Buffett and others. And what I would say is they don’t surround themselves with people who tell them that they’re right, I think they bring together a team who is better and smarter than they are, particularly in the areas that they know, they’re their weakest. So I know we’ve talked about it a little bit, but I really would reiterate that, for me, that’s the biggest tip I can give. And I think it becomes increasingly important as a company scales. And an analogy I always like to use is when you’re a small startup, you’re a little bit like a basketball team where you could have a LeBron James or Michael Jordan who’s just so superior that you’re able to take a company to that next level just on your own through your own skills. But once you get to become a growth stage, company and beyond As you become more like a soccer team where, where your weakest link is really you’re only as strong as your, your weakest link. And so, so I think that’s, that’s an important mindset for leaders to develop, I think the second piece of feedback, which again, probably goes, goes back to my time a Rypple is as a leader, being open to feedback, even very difficult feedback from people on your team. It’s something I work on relentlessly like I won’t, I won’t lie, like, it’s hard to hear that you’re not doing a good job that you’ve done something wrong. But if you create an environment where your team doesn’t feel comfortable sharing that feedback with you, you and they can’t be honest with you, you won’t learn you won’t grow, and you’ll limit your trajectory. So as hard as it is, you want to make sure you’re constantly letting the people around, you know, I’m, I’m open, like, tell it to me straight tell me the things I need to work on and improve on. It’s got to be a two-way street.

Aydin Mirzaee  36:09  

Those are some incredible tips. And I’ve never heard the analogy about the basketball team and the soccer team in that sense. And I love it because I know I won’t forget it now that you put it in that in that light, Nick is this has been great. Thank you so much for doing this.

Nick Stein  36:25  

Thanks so much. I’ve really enjoyed it. Good luck with everything

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