Wingman’s Kushal Saini Kakkar: Psychological Safety Drives Creative Marketing

Perspectives is a weekly series interviewing the best marketing leaders. Subscribe for interviews straight to your inbox.

Humans hate negative feedback. It’s baked into our genes—and for good reason. Positive stimuli like food and water keep you alive for a little while longer. On the other hand, negative stimuli like lions, tigers, and bears bring your life to an abrupt end.

If you’re standing on a melting iceberg, you’re going to think twice before jumping.

Negativity bias (valuing negative stuff more highly than positive) made sense in our hunter-gatherer days. But now? Not so much.

In the workplace, people tend to default to the “freeze” stage of the fight/flight/freeze response. They clam up and keep ideas to themselves for fear of being shot down. They stick to the status quo because it’s safe.

“If you’re standing on a melting iceberg, you’re going to think twice before jumping,” says Kushal Saini Kakkar, director of marketing at Wingman by Clari. “The fear of the unknown and bad outcomes is huge.”

Negativity bias kills creativity… Unless you create a psychologically safe environment.

When you convince people that they won’t be punished or humiliated for speaking up, they tend to speak up. (Surprise, surprise.) Employees who share more ideas improve profitability through innovation.

I caught up with Kushal to discuss how Wingman by Clari created a supportive environment for its employees and how that’s helped their marketing flourish.

You started your career in reality TV. What can B2B marketers learn from the entertainment industry?

There's not enough entertainment in marketing, that’s for sure. We need to dig a little deeper and figure out why B2B content still defaults to safe and boring.

We forget that the customer journey isn’t linear.

I’m falling in love with a term called creative marketing, which I've seen more and more on LinkedIn. It refers to marketing that’s done in a very different spirit from traditional marketing. You can still make an eBook, but what if you included multimedia or VR or 3D? Who’s to say that an eBook like that couldn't work?

The biggest problem is that we, as marketers, forget that the customer journey isn’t linear. People don’t download an eBook and instantly connect with the brand. That's not how it works.

There are so many touchpoints leading to a sale. You need a healthy mix of content. You need to figure out if someone is on a channel for entertainment or education or inspiration. Your content needs to solve that purpose. A blanket approach doesn’t work.

Do you see things differently because you don’t come from a traditional marketing background?

I never formally studied marketing. I don't have an MBA in marketing. I did an extensive six-month masters-level course in digital marketing, but that was my only formal training. Otherwise, I'm a student of literature and journalism. It's all of my varied experiences and roles that helped me understand what it takes to serve up content in different formats.

One way my background helps me is that I have an intuitive understanding of how different types of content formats will work. What’s the staffing requirement? What budget does it need? What timelines are we working to? That puts me in a great place to develop more formats like audio and video. 

Is it tough for marketers to break out of their safe status quo?

Psychological safety is one of my favorite things to think about. It's so key to my work as a marketer. I've been lucky to work with the founding team at Wingman led by our CEO Shruti Kapoor. Now Wingman is part of Clari, and we have an amazing marketing leadership team there as well.

One of the hallmarks of a great founder is that they’re open to trying different ideas. We test ideas in a lightweight sort of way. We’re not always building at scale. We’re trying to make things that make a difference. We're doing it without too many expectations.

If you've just read something, at least 1,000 people have already heard it, learned it, and tried it.

Yes, we're gonna measure the outcomes—how else will we know what’s worked?—but we’re giving the team psychological safety and headspace to experiment.

Marketing is evolving so fast. If you've just read something, at least 1,000 people have already heard it, learned it, and tried it. The best tactics of today will be overdone tomorrow. So how are you going to be different?

How are you innovating at Wingman?

Early on, we decided that we didn't want to follow a laid-down marketing playbook. Our guiding principle was our customers—their needs, their wants, their challenges.

For example, for our On The Flip Side podcast, we interview sales, marketing, and revenue professionals. We’re talking to our customers and letting them be the centerpiece of our marketing.

The other place we've tried to innovate a lot is social media. We've kept it as an extension of our team’s personality and culture. We work in the sales tech space, which is full of amazing companies and diverse people. We're exposed to a lot of different brand tones and personalities on social media, but we've brought our tone, our perspective, and our team to our social media.

Perspectives is a weekly series interviewing the best marketing leaders. Subscribe for interviews straight to your inbox.