In this fifth episode of our ‘3 Learnings From...’ video podcast series, we sit down with Anthony Kennada, CMO at Hopin.

Anthony reveals all about how his natural curiosity led him on an unexpected path to becoming a CMO, why joining the right company matters more than a specific role, and what the shape of marketing will look like in the future.

Check out the interview!

‘A B2C marketer trapped in a B2B body’

Like most students graduating from college, Anthony Kennada had no idea what his future had in store with him.

There were clues in his early years that he would become a marketer, like designing t-shirts for his fraternity and hosting high-profile music events on college campus. But at the time, he just couldn’t connect the dots.

What some might call a ‘lack of direction’ after graduating, Anthony would describe as an opportunity to ‘follow your curiosity’. With this open mindset, Anthony found himself in various sales, business development, and product management positions at companies like Box and Symantec, before joining Gainsight in 2013.

As founding CMO at Gainsight, Anthony’s marketing instincts let rip and he led the company’s growth from $0 to over $100M of ARR. He is credited with having created the ‘Customer Success' category—which is helping subscription-based companies achieve sustainable growth by becoming customer obsessed.

His team at Gainsight also dabbled in off-the-wall video campaigns, having created a hilarious 'behind the music' video with over 10,000 views on Youtube for an (actual) hip hop song the company released.

Anthony is now leading marketing efforts as CMO at Hopin—the all-in-one virtual events platform that is optimized for connecting and engaging online. Founded in 2019, the company has since risen to the challenge of helping the event industry adapt and survive during the pandemic.

Anthony has won numerous marketing awards and his book Category Creation: How to Build a Brand that Customers, Employees, and Investors Will Love debuted as a number one new release on Amazon.

Learning #1: Follow your curiosity

For Anthony, it's okay to not have a clear career plan from day one. Stay curious and you will find yourself on the path to your future career:

“I don’t think any of us were growing up as children saying ‘one day we wanna be SaaS marketers’. But there’s a series of things that led me down this path. For me, it was when I was going to university and studying business—but I didn’t know what I actually wanted to do when I graduated, like many students, I think.

An experience I had that meant a lot to me during my college days was studying abroad. I had the chance to study in Florence, Italy. I started thinking through the experiences we had there but also how mobile devices were coming up, and then social networking was coming on.

I said ‘gosh, there has to be a way to help people connect when they travel abroad, who aren’t just the general traveller—but students and young people that have a different agenda.

So I picked up a book about startups, ‘The Art of the Start’ by Guy Kawasaki—now an iconic book for a lot of entrepreneurs—and just started learning, talking to people and asking questions... Long story short, I ended up building a business plan and almost ending up getting funded for a company in the social travel space.

I ended up finding my way to Silicon Valley that way and taking a job—to pay the bills—at what ended up being a big enterprise software company. Ultimately, by following my curiosity, I didn't know exactly what I wanted to do, but I found my path and my career."

Learning #2: Roles are important, but the company you join matters more

If you've found an ambitious company that matches your values, says Anthony, it's worth jumping on the opportunity—even if it's not your ideal role to begin with:

"Staying with the story chronologically... Getting to the Bay Area, needing a job to pay the bills, I didn't necessarily buy into the specific role, because I knew my heart was set on starting this business. So there was this small file-sharing startup in 2009, in Palo Alto, it had about 30 people there—it was called Box.net —and I had applied for a job on the sales floor.

I didn't want to pursue a career in sales necessarily, but this was a company that I really admired. Again, 30 people, it wasn't a major company at that point.

But looking back now, it's been 10, 12 years since my days at Box—my time there as an SDR, entry-level, very young, has come with me throughout my career as part of my brand equity, for my resume, and all these types of things.

So I encourage folks that are thinking about starting a career in tech, or transitioning into tech, that joining the right company matters much more than the specific role that you join for. You might want to be a marketer, a product lead... but SDR, for example, is a great on-ramp into this career, as well as several other on-ramps you can consider.

[Speaking about the criteria for choosing the right company] I think at the highest level, it starts at the top, you need to understand who their leadership are, what they believe, and the type of core principles that they have in mind for starting a company. That turns into the values and culture assessment, which is one of the primary criteria.

The second is the market opportunity. Obviously you want to join a company that is either going after a big market, has the right products, and ultimately, has a mission that has a chance of being realised because the execution and the market is there to go and do it. So I think it's a marriage of those two things."

Learning #3: The future of marketing is human

Anthony insists that it's time for B2B companies to recapture the spirit of B2C marketing and remember they're not just selling to logos, but to people too:

"I think, at least for B2B businesses, for too long we've deprioritized brand for the sake of demand-gen and growth. Because, in our eyes, historically we said 'brand is corporate marketing—it's not part of growth. We need demand-gen, MQLs, SQLs, and we need to go hunting whales'... The language that we've come up with for marketing, has totally dehumanized the marketing process.

When in the the B2C community, they appreciate that behind every purchase is a human, a person. In B2B, we've thought of them as logos, not people.

So a big learning I had during my time at Gainsight was that we could build a brand that could radically serve the people behind the companies that we're trying to sell to—whether through content marketing that helps them solve problems in their business, or events where we can create community and get them to come tother, meet, and network...

These help us build our brand, serve those people and create some value - but also fuel our funnel and grow our business. So we built a $100 million ARR business out of Gainsight by really focusing in on serving the people behind the logos we sell to.

[On the challenge of 'human marketing' during Covid-19] That's why great tools like PlayPlay help us get through this time where video and other ways help us strive to get that connection that we know we can't have in person.

The reality is that we know we want to get back together in person, all of us feel it as humans. I think, more than ever, the world needs great content marketing that's empathetic, that's authentic...

In lieu of being able to get in person, I think it's important. But also, it's a digital world that we're living—so we have to connect in the best way we can."

Thanks Anthony!

With his expertise in ‘human first’ community building, content marketing, and live events, Anthony is bound to see further success in his new role at Hopin.

And you, readers, have you always had a clear idea of your career path? Or did you figure it out along the way? Do you place more value finding the right company or a specific role when applying for jobs?

Tune in for more career learnings in the next episode, where we'll be speaking with Matt Heinz, President of Heinz Marketing!