StrategyLeadershipFive lessons learned from conversations with brilliant CMOs

Five lessons learned from conversations with brilliant CMOs

I talked with five super smart CMOs. Here are the five main takeaways we can learn from their experience as leaders in marketing and marketing technology.

It’s not unusual for me to work with well-known CMOs on a daily basis. Having a front row seat to their strategic leadership is always fascinating to me. Not only does it reinforce the fact that there is not one singular path to success, but it also reminds me that there are some truly brilliant people leading marketing today. And a few things get me more excited than that.

Not everything in our conversations or work together is mind-blowing, but there are often some golden nuggets I hear that stick with me. No matter where you are in your career, from a marketing intern to a CMO yourself, I’m firmly in the camp that we can all continue learning. And there’s no better way to do so than to learn from one another.

So, here are five of my favorite insights I’ve gathered from leading CMOs who aren’t afraid to push the envelope and chart their own courses to success.

1. Sarah Kennedy, CMO of Marketo

“There’s unparalleled power in humanizing your brand, and setting up your customers to humanize your brand too.”

One thing I do a lot, which often gets me and my company into hot water, is to call a horse a horse. But I stand by that because not everything is roses; it’s not always “AWESOME!” And Marketo, in 2016, was not awesome. A brand created by marketers, for marketers, had lost all of its marketers. Marketo was having a major identity crisis.

For years, Jon Miller had shored up Marketo’s brand with the transparency of results. If you were a marketer from 2009 through 2013, the chances that you referenced market conversion stats and benchmarked your performance against theirs is huge. In fact, I would go as far as to say that nearly every organization we spoke to during this timeframe wanted to do what Marketo was doing. I would literally see organizations use Marketo’s slides in their strategy decks.

The tides started to shift when Marketo went public, and then was acquired by Vista Equity Partners. The term equity was very appropriate, too, because a lot of folks cashed theirs in and left.

This could have been a big problem, but incoming CMO Sarah Kennedy tackled this challenge in a highly innovative way. She could have stepped in and tried to double down on prior strategies, content to pump out even more of the best practices they had before to prove the validity of their solution.

And don’t get me wrong; they did that — Marketo still owns best practices. But their big transformation came in the form of a completely new direction as they focused instead on humanizing the brand.

They focused on how Marketo made people feel. “How does software make someone feel?” you may ask. Well, it makes people feel fearless. Fearless because marketers had spent years becoming experts on this platform, had carved out niches, built supporting solutions, agencies, and careers. Sarah and her team recognized and amplified this with their ‘’Fearless Marketer” campaigns where they took the humans behind the technology and placed them squarely out front.

Marketo now had a new face, 50 of them to be exact, and those faces looked like us. This was probably the quickest and most effective B2B brand boost I’ve ever been so close to. It’s also a campaign that’s had a huge shelf life because people are innovating and advocating for this technology daily, and recognizing those efforts ensure the brand will stay fresh and connected to their user base. Aspiration is the best place a brand can be, and Marketo has become an aspirational brand for marketers thanks to this humanization.

2. Scott Gainey, CMO of Cherwell

“Activating your team and creating ownership is one of the best ways to transform a marketing organization.”

I’ve found that marketers love to talk about the tactics and technologies they’re using, but don’t always give their people adequate time in the spotlight. Scott Gainey, CMO of Cherwell, is far and away an exception in this regard. He’s all-in on team building, organizational design, and empowering the right people. And it shows.

When he started with Cherwell as CMO, the company was in an environment of true flux. They had just purchased technology that didn’t align well to their business strategy, the marketing department wasn’t well-aligned to the organization’s goals, and Scott was facing what many CMOs are these days: a complete overhaul.

As an incoming CMO who had inherited these problems, Scott recognized the critical nature of this juncture and chose to invest in activating his team and creating ownership.

By fostering the growth of their team, Cherwell created exposure for the organization as well as showcased their employees as visible experts in the space. One great example of this is Ashley Cornella, who has become an advocate for women in marketing and is a technology expert. This strategy permeated the entire marketing department and has resulted in a whole that is truly more than the sum of its parts.

I consider Scott and his team at Cherwell to be a huge success story, and any company can be too if you recognize that your greatest assets walk on two feet every day. By allowing your team the ability to gain expertise through education, training, networking, and certifications, you create a powerful atmosphere of ownership that leads to true transformation. Cherwell is now firing on all cylinders with an aligned organizational strategy to marketing execution and cutting-edge tech stack allowing for repeatable scale.

3. Maria Pergolino, CMO of Anaplan

“Internal marketing needs to be just as strong as your external marketing in order to be successful.”

I’ve worked with Maria, both as a partner and a customer, and it’s clear as day that she considers internal marketing just as much of a priority as influencing the buyer is. This is another facet of marketing often overlooked in today’s fast-moving, hyper-growth environments. And it’s not surprising then, that a huge part of Maria’s success has been achieved by breaking down the barriers between the organizations and the marketing department.

Another one of Maria’s keys to success is true transparency. If something is happening in marketing, the rest of the company needs to know about it. Information is great, but empowerment drives success. By informing her colleagues and counterparts of what’s going on in her realm, she effectively scales her efforts by empowering the company to participate in her messaging and campaigns.

4. Anthony Kennada, CMO of Gainsight

“You’ve got to have a funnel for upselling, cross-selling, and renewing.”

Anthony and the entire Gainsight team have been championing a customer-driven approach to sales and marketing for years now.

The traditional view of marketing requires the buyer to conform to a process outlined by the seller, which is very ineffective. This myopia continues throughout the customer service process and ultimately creates the problems we see today punctuated by customer churn.

But customer marketing and customer success take that notion and turn it on its head. Rather than requiring the buyer to behave in a certain manner, Anthony advocates for a true buyer-driven approach that focuses on the novel idea of listening to the buyer’s wants and needs, and responding accordingly. This changes everything. It’s amazing, too, how many false assumptions you uncover when you lead with the simple desire to understand the buyer’s point of view.

It also requires that marketing, rather than operating at the top of the buying “funnel,” broadens its perspective across the entire buyer journey, making them an advocate for the customer’s voice.

I think of this as an invitation to a party. A lot of marketers lie about what’s going to happen at the party and will say anything to get you into that little get-together, so much so that perhaps it’s advertised as a big get-together. To the extent, it’s even pitched as one that will have celebrity guests, tons of free stuff, prizes you really want, and will actually change your life. But, when you get to the party, it’s just you, and it’s horrible. But, their job was to get you to the party which they did.

It was never considered that most of the people who were showing up to these parties hated the people that invited them, often for life.

Customer marketing changes all of that because it recognizes that if you invite someone to a party, they have to have a good time. And the goal is also to get them to become your friend, and have many more interactions after that. When you stop thinking of marketing like a “bait-and-switch,” and recognize it for what it really is (a means of communicating with the buyer), it changes your charge as a marketer and makes you a much more successful professional.

5. Sydney Sloan, CMO of Salesloft

“Lagging metrics matter, and transparency into those metrics can create unbelievable organizational alignment.”

The first time I met Sydney, Craig Rosenberg introduced us and said, “You need to meet Sydney; she’s nails.” This meant that she was really, really good at her job. You can’t really get a better introduction than that, and I’ve followed her career ever since.

These days, it seems that everyone has jumped head-first into account-based marketing and yet, so few executives have been willing to provide true transparency into the underlying metrics.

Sydney’s approach to this couldn’t be further from the norm and, for this reason, it’s been easy for me to use her as a benchmark for success in, well, benchmarking.

By allowing your organization to take an unfiltered look into your existing demand generation performance, it makes it easier to create buy-in around the need for change. The innovation here takes place by getting ahead of the curve and positioning the change as necessary, and as one whose results will have equal transparency. By focusing on the results, decision-making becomes less emotional, and instead data-driven. Benchmarking also creates alignment among the leadership team, which is absolutely critical for successful ABM execution.

Sydney is also a big proponent of metrics that matter, focusing less on typical “leading” metrics and shifting instead to the “lagging” metrics often relegated to sales. Win rates and contract value, as well as retention and satisfaction on existing customers, are the KPIs she has created organizational alignment around. And it’s really hard to argue with a lift that occurs in those areas versus impressions, clicks, and conversions. This is where most marketing leaders gravitate toward. With all the lip-service ABM receives, Sydney has shown you have to put your money where your mouth is.

If you take anything from these insights, I hope it’s this: Keep your eyes wide open, and never stop learning from others who have gone before you (or are leading the way right now).

These five people have made me better as a marketer and a CEO, and taking cues from each other is how we can all grow, and get better, together.

Justin Gray is CEO of LeadMD.


US Mobile Streaming Behavior

Whitepaper | Mobile US Mobile Streaming Behavior


US Mobile Streaming Behavior

Streaming has become a staple of US media-viewing habits. Streaming video, however, still comes with a variety of pesky frustrations that viewers are ...

View resource
Winning the Data Game: Digital Analytics Tactics for Media Groups

Whitepaper | Actionable Analysis Winning the Data Game: Digital Analytics Tactics for Media Groups


Winning the Data Game: Digital Analytics Tactics f...

Data is the lifeblood of so many companies today. You need more of it, all of which at higher quality, and all the meanwhile being compliant with data...

View resource
Giving a Voice to Your Brand

Whitepaper | AI & Automation Giving a Voice to Your Brand


Giving a Voice to Your Brand

Voice commerce, or conversational commerce, is a major disruptive opportunity in US retail. It opens up the possibility of building deeper relationshi...

View resource
Mobile Messaging Masters

Whitepaper | Mobile Mobile Messaging Masters


Mobile Messaging Masters

Every year the mobile market continues to grow and develop. Cyber Monday 2018 saw $2.2 billion in sales stemming just from smartphones in the United S...

View resource