Nick Stein (CMO at Top Hat) has a wealth of knowledge about start-ups, scaleups, and mega corporations.

In this episode of the Supermanagers podcast, we’ll dive into Nick’s experience with Rypple, Top Hat, and Salesforce. 

Listen to this episode (or read the transcript below) to learn about how remaining curious and maintaining a growth mindset led Nick from a career in journalism to marketing. 

1 Who has been your favorite person to report to and why? 

I’ve been fortunate to work for some incredibly smart founders including the founder and CEO of Top Hat. I think what successful founders have in common is just relentless all-consuming focus on the business. They don’t work to live; they live to work. I would have a really hard time working for someone that didn’t care about the growth and success of the business as much as I do. 

Daniel Debow, my friend and mentor who was the co-founder and co-CEO of Rypple who I worked with at Salesforce gave me my start in marketing and I’ll always be grateful for that. We were able to work really well together to create a brand and a level of awareness at Rypple that really outweighed the size and scale of the business. 

2 What’s something you used to do early in your career that you stopped doing? 

The biggest lesson I learned was the importance of talent. I think early on in your career, especially when you have a small team, it’s tempting to keep someone on your team who you know in your gut may not be the right person for the job. For one thing, you know that when they leave, you’ll have to pick up the slack yourself and when you’re working in a startup you know there are never enough hours in a day.

The other thing is that firing people is really hard, especially when you were responsible for hiring them. 

The lesson that I learned is that moving the wrong person out of your team actually ends up being what’s best for them, and the entire team. If someone’s 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.

3 What is your hiring process? 

I actually spend a few hours on LinkedIn every week reaching out to people who are interesting. It’s all about building a pipeline of really great people so when an opening does come up, you’re not scrambling. 

4 When you’re searching for people, what are you connecting with them on? 

Typically, it’s a role that I know I’m going to have come up in the near future. It’s really just reaching out and saying “Hi, I would love to talk to you about an exciting opportunity”. Or sometimes just saying that I don’t currently have a role available on my team, but I find their background and experience really impressive. 

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5 What have you learned in terms of hiring someone that’s actually really great? 

One of the things that I’ve learned is that the best candidates always embody the values and leadership principles of your organization. At Top Hat we spend a lot of time as an executive team honing in on our values. 

6 Has your leadership style changed as your career has progressed? 

What has remained consistent across small companies all the way to big is my strong belief in delivering feedback in the moment, both in terms of recognition as well as constructive feedback. 

I think what has been really different is the amount of process that you need to introduce into the equation in a small startup versus a large company. When you’re working in a startup the whole team shares the same brain, so you don’t have to spend a lot of time building a process or shared context. 

7 How do you know if you have a high-performing team? 

I spend a lot of time thinking about this and I like to ask myself if the people on my team have a performance or growth mindset all the time.

Are they the types of people that are always asking what they can do next? I often get asked how I went from being a journalist to a CMO because they seem really different but it’s my curiosity and growth mindset that has driven me to both. 

Secondly, you need to have a team that focuses on outcomes, not activity. What I mean by that is focusing on the outcomes we want to achieve rather than the next 10 tasks we need to complete. 

8 Any final tips for managers and leaders who are looking to get better at their craft? 

The biggest tip that I can give is to surround yourself with people who don’t just tell you you’re right.

You’re only as strong as your weakest link so I think that’s an important mindset for leaders to develop. 

Secondly, I think it’s really important to be open to feedback. If you don’t foster an environment where your team feels comfortable sharing feedback with you, and they can’t be honest with you, you won’t grow, and you’ll limit your trajectory.

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