Empowering the underdog: Q&A with Tom Klein, CMO at Mailchimp


Visibility isn’t easy. Especially when you consider the sheer volume of options that customers have today. Searching “water bottle” on Amazon returns 60,000 results. “iPhone case” returns 50,000. Even “gold birthday balloons” gives us 9,000. To make their brand known, businesses are turning to Instagram ads, sponsored content, Google AdWords, influencers, Snapchat filters and more. Yet, there is one channel that has stood the test of Internet time, still bearing the scars to prove it. That channel is email.

The criteria for an organization to make it into Fast Company’s Most Innovative Companies requires them to: “… demonstrate how their innovations from the past year have impacted their business, their industry and the broader culture.” Apple’s found a home on that list. Tencent, Marvel Studios, Patagonia and a host of other recognizable brands, too. One brand that made it to 2017’s list was email marketing service, Mailchimp, and justifiably so. For them to build a successful business in a time where email is no longer the go-to channel highlights how much of a juggernaut they are in the SMB world. The importance of brand in the B2B space is typically understated, but Mailchimp’s dedication to building a strong and hyper-relevant brand certainly de-mystifies that claim. In 2018: Forbes valued the company at $4.2 billion, 450 million e-commerce orders were made through Mailchimp-generated campaigns and they generated $600 million in revenue. As of this year, they’re aiming to become a full marketing platform. Tom Klein is the CMO of Mailchimp and, in many ways, has helped the organization turn little Freddie (the capwearing, winking monkey logo) into what Fast Company called “an 800-pound gorilla.” Klein shares his learnings on customer centricity, how data powers their communication and what it takes to empower SMB underdogs.

Mailchimp has empowered a new generation of brands and it’s easier to start companies now because of you. Tell us about Mailchimp’s role and how you’ve built an incredible brand.

From the beginning, we’ve set a high bar for ourselves at Mailchimp. It’s always been important to us to push the boundaries of creativity and focus on helping small companies grow their business. Mailchimp built a great brand because of our core mission to be customer centric. We try to model the behavior that will inspire brand builders and their customers. It’s important to remember that everyone is still a person, and we focus on talking to customers and putting people first in everything we do. Just like with our customers and the products they’re selling, we want customers to fall in love with Mailchimp, and the best way to do that is to inspire them to find their greatness.

How does the company’s desire to stand out instigate the Mailchimp brand? From your perspective, what does this mean to you as a brand from a commercial sense?

Sometimes people are mystified about why it’s important to think about and invest in a brand, as it can sometimes feel like a dark art. Commercially, there’s a lot of love for Mailchimp in the world – about 15,000 people sign up every day. A large part of that is because we aim to guide our customers in everything we do. For example, in our business, it’s important to know when the right time is for someone to sign up, use, and pay for Mailchimp. That’s why we came out with a podcast called Going Through It. where we really speak to the emotional elements of the entrepreneurial journey – when to quit vs. when to keep going. We believe the brand is the placeholder for trust and education.

In a world full of data, we can often struggle with the ability to extrapolate meaningful, scalable insights. How does the company work with customers to deliver on their needs?

Our motto is to ‘listen hard, change fast’ and we really do put it to work. From the moment I started at Mailchimp, I’ve been impressed with how we engage with customers every day in every way imaginable about product, experience, etc. The largest function at Mailchimp is the support organization. We have special teams set up to interpret what’s coming in and support chats so we can fix and improve quickly. The other part is listening to customers outside of our business and looking at what larger enterprise customers are doing. We observe the larger corporations and democratize what’s happening for smaller businesses. What do sophisticated CMOs want and how do we transfer that as value for our customers (mostly SMBs)?

We’ve addressed that with the launch of our all-in-one marketing platform, which includes landing pages, marketing CRM, etc. All that comes from our customers’ requirements to reduce the complexity in the enterprise space, as well as our desire to make our own customers’ data more accessible and understandable. Data powers on many levels and it’s our job to help our customers use their own data to target and communicate with their own customers in a more compelling way.

You consider yourself to be a learning organization. How do you deal with risk in the business?

In the software business, not changing feels risky. Standing still is risky because it’s a fast-moving business, and in many ways, the consumerization of IT raises the bar for everyone. I have a teenage daughter who lives inside of social media and Instagram, and in many ways she’s learning the elements of marketing and interaction of software. Consumers learn to create and share content that their peers want to see and, in turn, increase engagement. A lot of the marketing elements are not that different. Instagram is a creative domain but also mindful of the audience; am I winning my audience over with this photo I post? Because people experience more software as a consumer, it’s made to be very easy to use, and beautifully made. That notion has extended to inside of a business so everyone expects everything to be easy and beautiful. Businesses are targeting dreamy photos on Instagram. One of the exciting things is the explosion of creativity, and we want to help our customers – whether a 1-person company or 1000-person company – achieve this. We want to liberate customers to communicate expressively, make things weird and give small businesses the data to figure out what’s the best approach from a commercial perspective.

Does the requirement to innovate often take businesses away from core business values? What guides your decision-making around what are the right decisions and KPIs versus innovating?

Our purpose is to empower the underdog, but our approach has always been different. In an ad-driven business, leveraging consumer data to sell ads can put you in a compromising situation. The same people that pay us are the people we’re focused on. We maintain our focus on small businesses and we’re a privately held company. This gives us the luxury to focus on the customer, and it gives us freedom as a brand builder. Everyone at Mailchimp is focused on asking, are we the most inspiring we can be? Are we the most loved brand? When that’s the vision, that gives you the liberty to what we and Ben Chestnut refers to as “burning a few pancakes.” We’ll make mistakes and that’s perfectly fine. However, what’s not fine is being risk-averse, not being expressive, and not connecting with customers at an emotional level. Or what we call, being a robot. We strive to keep things lighthearted and be inspirational. There’s a reason why certain brands persist over time and it’s because of a great deal of focus on the customer and the long-term goal of meeting their needs.

What keeps you up at night and what keeps you going?

I’m always asking, are we being creative enough? I still have to grow and manage things, but from a creative perspective we embrace chaos. Also, things have to make sense. A good example is updating Freddie and identity and brand system last year. Our theme for that launch was to create a container for our chaos. And when I say chaos, I mean intentionally creative and expressive content. I needed it in a container so it doesn’t drive everyone crazy, and I can contemplate how I can create chaos in other languages. There are things that come with being a global company that we’re growing up to be. I want to create wonderful opportunities for customers, but also create a wonderful experience for them that makes sense; that’s cohesive and helps them be successful.


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