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“To avoid burnout, work on what you love and are passionate about” with Constant Contact CMO John Orlando

Ihad the pleasure to interview John Orlando. As CMO, John oversees marketing at Constant Contact, an established leader in online marketing for small businesses, built to simplify the complex and confusing task of marketing an idea. A strategic and creative marketing executive with more than 20 years of experience in marketing technology, mobile entertainment and […]

Ihad the pleasure to interview John Orlando. As CMO, John oversees marketing at Constant Contact, an established leader in online marketing for small businesses, built to simplify the complex and confusing task of marketing an idea. A strategic and creative marketing executive with more than 20 years of experience in marketing technology, mobile entertainment and marketing services, John has been instrumental in the creation of new businesses, the establishment and enhancement of corporate brands, and the conception and launch of new products.


Thank you so much for doing this with us! Before we dig in, or readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Myjourney to CMO did not follow a traditional path and was sort of accidental! I believe that was beneficial for me in the long run because it allowed me to develop a unique perspective on the marketing industry and understand the role it plays for businesses of all sizes. My background is actually in engineering and I began my career working on missiles at Raytheon Missile Systems. I kind of joke with people that I started my career as a rocket scientist! During my time there, it always felt like I had a natural North Star pulling me forward in terms of career development. I moved up quickly from engineering roles to project management positions and became fascinated by the buyer/seller relationship. This relationship, to put it simply, is when the buyer has a problem, and, in their mind, they have a value equation that they’re looking for a seller to offer. There’s a real seam between buyer expectation and seller value proposition. Time has proven over and over that companies that get this equation right, who understand what the customer wants and needs, have a much higher success rate than those that don’t.

Over the years, I held roles in several startups which are great environments to figure this equation out. Startups are looking to solve a problem with a specific target customer and work to define the right offer that meets that need. This curiosity and passion, which tends to drive the way I approach marketing, has ultimately driven me to where I am today as a CMO. On the way, I held a number of different roles, from developing product roadmaps to brand building, but it has always naturally tied back to the consumer marketplace and translating what this means for businesses.

Can you share a story about the funniest marketing mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Although it was somewhat serious at the time, I can look back now and laugh about an experience I had at NMS Communications when we acquired a strategic company in India. I went over as one of the welcoming senior executives and did some local press to announce the news. Naturally I had a local translator who helped me understand the questions and then translate my responses back to the media. The next day, to my dismay, a news story came out in the local market that was something along the lines of “NMS Communications exiting marketing to do XYZ,” which was not something I had meant to say at all.

Unable to get this statement retracted, I had to call my CEO and let him know the situation. Thankfully, he understood the complexities of global language barriers and saw the humor in the mix-up. From this, I learned the importance of being extremely careful when speaking publicly and being cognizant of factors that could result in a misconstrued message.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

When I was at NMS Communications earlier in my career, we worked on moving the business from a supplier of technology to a supplier of complete solutions. We made embedded cards that were used in systems like voicemail and other types of telecom systems. Well, it turns out that one of our customers wanted us to help them eliminate the “ring ring sound” you hear making a mobile phone call. They wanted to insert music that was selected by the person receiving the call. The customer was SK Telecom and it turns out we made one of the first instances of “Ringback Tones.” We decided that this would be our complete solution and I was lucky enough to be on the team that was defining and marketing this to mobile operators. At the end of the day, we battled hard and won the Vodafone Group Award in Europe. That win redefined our company. As I said earlier, it was a great example of understanding the customer and developing a service that delivered an exceptional experience.

This was the point in my career that I entered marketing full-time. This period taught me many things: how to launch a product in a market you did not compete in, how to position your company as being the best possible provider of a service and how to compete and not give up in a complex competitive gridiron. This ultimately set me on a path to become a first-time CMO.

What do you think makes your company stand out? Can you share a story?

In the market we’re in, there is a lot of yelling and selling that can create an overwhelming sense of noise for small business owners. Our customers tell us this all the time. SMBs are time-starved and digital marketing can be very confusing. There is so much frustration and let down after a small business buys an online product, especially when there is little support to guide them through using it successfully. As a brand, Constant Contact has always been a helpful and authentic advocate for our customers. We truly care about their success. Getting the sale is always important but seeing our customers engaged with our product and actually hearing from customers how they have been able to easily leverage our products to grow their business is very rewarding.

Another strong advantage we have as a brand is our emphasis on customer service. Help is always just a phone call, or a chat, away and our support and sales teams are very knowledgeable and enjoy talking to, and helping, those businesses that contact us. Also, when a business first contacts us, our teams spend a good amount of time getting to know them and suggesting strategies on how to best leverage our products. This really helps jumpstart their success.

Are you working on any exciting new projects now? How do you think that will help people?

Through research we have done, we know that small businesses are typically time-starved. They also have a long learning curve to understand the complexities of digital marketing. In response to this we developed a program called Marketing Advisor. At the core of this program are real marketing experts that our small businesses can leverage to help them understand how to do digital marketing. Since businesses are all different, we have vertical specialists who work on specific industries, like retail, real estate nonprofits, etc. We are also offering varying levels of help depending on what they need, from offering advice to actually doing their marketing for them. So far, the response has been very positive. We are helping a lot of businesses who otherwise would need to figure out a different way to learn and execute their marketing — or even ignore it altogether.

What advice would you give to other marketers to thrive and avoid burnout?

My advice is pretty simple. Work on what you love and are passionate about. We all get busy and have to put in a lot of hours, that’s just the way it is today. If you don’t like what you are doing, that can really drag you down. Alternatively, if you like what you’re working on, the customers you serve and the industry you’re in, that can really help put wind in your sails. I’ve been very lucky to have worked in two areas I love. As I mentioned previously, earlier in my career I worked in mobile music. As a musician, it couldn’t have been any better, I was able to do what I loved all day long. These days I am working with small businesses. For anyone who has spent time with them, they are amazing. They are the dreamers and those who dare. They are typically driven by a passion for what they do, and they are crucial to our economy. So that’s my advice, find what you love and stick to it. It will help you get out of bed every morning with energy and purpose.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I was an engineer when I originally entered NMS Communications. I entered that business as part of an acquisition of a very small startup doing voice over the internet. When I ultimately left the company 10 years later, I was CMO. My CEO through all of this, Bob Schechter, provided a lot of coaching and guidance that I still remember today. Through a series of events he gave me an opportunity to prove myself and grow in the role of VP of Marketing, which ultimately led to my first job as CMO. This was a big deal for me because on paper, I wasn’t the typical candidate for a VP of Marketing role, especially since I was an engineer by trade.

I still remember something that Bob said to me, “In life, everyone wants to climb the corporate ladder and be something. You find two types of people: those who just want to be on the next level but aren’t actually talented enough to be there, and the people who just keep climbing and don’t even know why they’re climbing.”

After you have been around for a while you realize that everything comes down to the opportunities you are given, and I am grateful that Bob gave me a chance — it changed the trajectory of my career.

Ok super. Let’s now shift to the main part of our discussion. There are hundreds of memorable marketing campaigns that have become part of the lexicon of our culture. What is your favorite marketing or branding campaign from history? Can you explain why you like that so much?

I’d say Flo from Progressive stands out as a personal favorite. The reason being how much this fictional character has transformed the entire company’s brand awareness and market perception. Before Flo, Progressive was constantly being confused with the canned foods company, Progresso. They had little brand awareness, and nobody knew who they were, let alone that they offered insurance. Then Progressive had the idea to make insurance a fun experience by adding in a character to make it more personable. This character, who we now know as Flo, has essentially become the brand’s entire image. They’ve added other characters over time for other products, but something about her has stood the test of time (over 10 years!) and has driven such growth for their business. This is so interesting to me because in advertising or marketing we only have 30 seconds to connect with an audience and incite some form of emotion and they were able to nail that on the head. Whether you like her or not, you know her.

If you could break down a very successful campaign into a “blueprint”, what would that blueprint look like? Please share some stories or examples of your ideas.

The blueprint begins by finding the right target audience, identifying the ways they speak and listening to what they value. When you approach a campaign, it’s critical to have the consumer mindset guiding every decision. From the medium, to visuals and words that will resonate, all of this has to be done right or you end up wasting a lot of time in the process.

Companies like Google and Facebook have totally disrupted how companies’ market over the past 15 years. At the same time, consumers have become more jaded and resistant to anything “salesy”. In your industry, where do you see the future of marketing going?

I believe that consumers have become more demanding and their expectations have changed dramatically. There is also a big difference between how Millennial and Gen Z audiences consume content. More and more, I see that brands have to develop an emotional connection with their prospects and customers. And to do this involves well-executed content strategies, specifically storytelling. Obviously, video has become such an important medium but also being able to stand out from competitors, the ability to translate to mobile, and understanding consumption patterns on various destinations, are now requirements to make that connection.

Brands need to connect with consumers early in the buying process. They really need to work their upper funnel and develop engaging content that can land that brand impression with some emotional engagement. If done right, it doesn’t feel salesy, and it can be the first step in getting into a prospect’s consideration set.

Can you please tell us the 5 things you wish someone told you before you started? Can you please share a story or example for each.

  1. Getting something right takes a lot of persistence and testing. If you think you’re going to get it right on the first try, you’re sadly mistaken… or incredibly lucky!
  2. Positioning and messaging are an art form that far too many people pass off as unimportant or ends up being overlooked, or even worse, something that is jammed in at the end. You need to understand your product and why it matters first.
  3. Providing vision and leadership for your marketing team is harder than it looks. You need to spend real time communicating and sharing your vision and then allow your teams to ask questions and internalize it. It’s amazing what a team that really gets it can do!
  4. Hire the absolute best talent you can find. Many times, you settle for someone that has been with the company, or someone who is available, but at the end of the day, you need the best talent to execute the best marketing.
  5. Be data driven to a fault. And hug and believe what your data is telling you. Sometimes your gut instinct and emotions want to guide you in a direction, but the data may be telling you a different story. It’s important to have a marketing team with a culture that is data driven.

Can you share a few examples of marketing tools or marketing technology that you think can dramatically empower small business owners to become more effective marketers?

Marketing tools ultimately are a vessel to deliver content. And when you look at the landscape, there are common marketing tools available to small business owners. How these small business owners use these marketing tools is a different story. First, I believe that marketing guidance and recommendations done in-product can dramatically increase the marketing proficiency and speed up the learning curve for a small business owner. Offering tailored marketing guidance integrated within the tool will be a next level of technology that will deliver significant benefit.

Secondly, I believe that data-driven tools that offer insights, either automation or other artificial intelligence, can greatly improve the marketing results for business owners. Without these automated insights, businesses would not be able to figure it out on their own. I believe that this type of technology, specifically around the area of ecommerce marketing, will become a requirement for any marketing tool provider in the coming years.

What books, podcasts, documentaries or other resources do you use to sharpen your marketing skills?

I spend a lot of time using the same digital channels that our customers do. So, I spend a lot of time on social media channels (and there are lots of them!). Looking at who is developing compelling content that is driving engagement. I obviously meet with many partners, such as Google and Facebook, for example, and understand what they are seeing in terms of best practices, engagement and trends. I also spend a lot of time looking at my competitors and watching what they are doing, what channels they are leveraging, content they are producing, how they are messaging, and brand programs. I also talk to my daughter who is a sophomore communications major at Marist College. She likes to give me lots of advice!

On a leadership level, I find myself constantly referring back to the lessons from the national best-seller, “The Advantage: Why Organizational Health Trumps Everything Else in Business” by Patrick Lencioni. The takeaways can be applied to every aspect of leadership — no marketing campaign can be successful if the core health of the business is being overlooked.

Who is your hero? Can you explain or share a story about why that person resonates with you?

My grandfather is the first person that comes to mind as a personal hero to me. In addition to being a talented pianist and a dedicated family man, he also worked at the Revere Iron Works for many years. He was known for always having a smile on his face and the positive energy he brought to every conversation, so much so that he actually became President of the Optimist Club in his hometown of Rome, New York. His love of life and strong work ethic left a lasting impression on me, as well as our shared passion for music and getting involved in the community. Coincidentally, my family constantly reminds me how much we look alike, so I might be biased in my opinion towards him.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

As a father, I’d want any movement I could theoretically inspire to benefit my children. My youngest daughter is high-functioning autistic and as a parent of a child with a disability, I’ve been completely exposed to the struggles they face every day. She’s going off to school now and in the search process, we found only a few schools across the U.S. that have specific programs to help autistic students get prepared for college. That being said, if I could inspire a movement it would be to increase awareness of the needs of people affected by disabilities and how to inspire others to be more considerate and kind. With more kindness and understanding around the world, we would all be happier.

How can our readers follow you online?

LinkedIn: https://www.linkedin.com/in/johnorlandoeig/

Twitter: @John Orlando

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