My Best Worst Marketing Mistake

By Ginger Conlon

There were five of us. Four award-winning marketing professionals and me, their host. We were enjoying a celebratory cocktail after the awards ceremony when one of them asked the others, “What was your biggest mistake? You know, the one you could very well have gotten fired for but didn’t.”


Without skipping a beat, the head of analytics strategy for a large bank said, “Oh, that’s easy.” He went on to tell the story of losing about $5 million many years earlier when he was first an analytics VP by giving in to his team’s request to leave early on a summer Friday and not complete a test they were running. They contended that they’d gotten enough data to base a specific decision on, and after a brief deliberation, he relented. Unfortunately, they hadn’t run the test long enough. Bad data led to a bad decision. Never again would he run an incomplete test.


But the story wasn’t about a process change.


This executive realized in that moment the significance of the impact data had on decision making, on marketing performance, and on revenue. As a marketing analytics professional and a proponent of data-driven marketing, if he didn’t advocate for using data correctly and ensuring its quality, who would? From that moment on, he would be that advocate. So much so, that it ultimately led him to become the bank’s head of analytics strategy.


Learning opportunities

We all make mistakes. Hopefully, we learn from them, make changes, and move forward. But we all also have That Story. The game changer mistake.


Maybe your plans went awry, or the unexpected happened, or a risk wasn’t so calculated after all; but, hey, you lived — and, most important, you learned — and when you look back you can laugh (well, maybe you grimace) because you’re actually better off having had the experience.


Successes are great. They're invaluable. We can certainly learn from our own and others’ success stories. But there’s no learning quite so impactful as the learning from a big ass mistake.


Inspired by the enthusiasm with which the analytics executive shared his game-changing gaffe, I asked my network to be bold and share a mistake that changed the way they do marketing today, and what they’re doing differently as a result. Six marketing executives enthusiastically agreed to tell their tales and share what they learned.


Here are their stories, in their words.

6 Bold Marketers

MJ Crabbe-Barberis, Senior Principal Business Transformation Architect, Salesforce

My mistake was that I didn’t even think about [the customer's perception].  More...

Jeff Rohrs, CMO, Yext

I missed out because I made the fundamental mistake of not building a deeper set of relationships. More...

Celeste Giampetro, VP of Marketing, PebblePost

I made the rookie mistake of not insisting on testing the platform from day one. More...

Justin Thomas-Copeland, President, RAPP New York

The biggest misstep was not integrating the teams. More...

Daniel Incandela, CMO, Return Path

I ended up “panic hiring” for a particular role. It turned out to be a catastrophic mistake. More...

Chris Sojka, Cofounder and Chief Creative Officer, Madwell

Our creative was vibrant, but our strategic framework was underdeveloped. More...

Their Stories in Their Words

MJ Crabbe-Barberis, Senior Principal Business Transformation Architect, Salesforce

The backstory

I was a marketing manager at a global enterprise bank working out of Chicago in the late ’80s. There was a lot of acquisition going on at that time, and our company was actively acquiring many smaller local and regional banks in the Chicago metropolitan area.

My responsibility at the time was to handle to customer transition communications. Once a deal closed, we had to alert the customers of the acquired bank that there was a new owner, there would be a transition, their account numbers might change or not, and the like. I diligently worked to get all the communications drafted and approved. I got all the direct mail packages out on time for the first acquisition communication I worked on; no issues. And I thought everything was great. It wasn’t.


We started to get feedback at the local branches that customers were angry. Initially, I thought it might be customers thinking, “Here’s this big company coming in to take over and everything’s going to change.” But the complaint was, “Why did you send me nine of the same letters?”


That hit hard for me. I was horrified, because Marketing 101 is to dedupe. But that wasn’t the problem at all.


The problem was that legally we had to send a letter to each named account. So, if there’s a husband and a wife in a household, for example, you could easily have four unique named accounts: one for each individual, one where one spouse is listed first and the other second, and vice versa.


My mistake was that I didn’t even think about it. I sent the letters without concerning myself about what the customer’s perception might be. I think these customers were angry because they were thinking, “This behemoth company is coming to take over and doesn’t care about costs. They don’t have to be efficient. They don’t have to put in any effort to do the right thing.”


Also, I inconvenienced a lot of people. They opened all nine of those letters only to see, even if they noticed, that the one difference was the name at the top of the letter.

The big change

All I really had to do to solve the problem was add language into the letter to say, “Hey, we know you’re getting the same letter multiple times. But legally, we’re obligated to send this same mailing for every single account ownership combination that you have within the bank.” So, I worked with legal to craft the appropriate verbiage and included it in all the future acquisitions-related communications.


Now, that doesn’t necessarily make the transition easier, but it does avoid adding to any initial negative perception that these customers might have had.

But the whole thing goes deeper than fixing a process. I was pretty young, and I had a lot of anxiety over this because I certainly didn’t want to cause pain for other people or get criticized. I took that to heart and used it as a lesson. The lesson I learned was to always take the customer’s perspective.

The go-forward strategy

I became a champion of what I call plain-language messaging, combined with segmentation and customization. So, before you send communications, put yourself in the customer’s shoes. That means don’t send them anything they don’t need or won’t have a remote interest in.


As a result of taking this perspective, I was eventually moved to marketing for mortgages and home loans. I routinely saw conversion rates of 30 percent or more. Conversion in this case means somebody actually applied for a loan. And I didn’t get any negative customer responses.


My new approach also led me into predictive modeling. I wanted to better predict customers’ needs and then respond with customized offerings. Over time that transitioned into real-time decisioning; to look not just at demographics, but also at what was happening right then and there — for example, the actions that someone took in an IVR or on a website — and present information to them, or sometimes not present anything to them. I might never have gone into real-time analytics had I not gone through that error early on in my career.

The sage advice

Marketers overuse terms like customized or relevant. But to me, it’s not really relevant just because I buy a pair of gym shoes that now you’re going to offer me socks. There’s so much more that we can do as marketers if your put yourself into the customer’s shoes and don’t offer something just to offer it.


The emails we receive for the most part today are really advertisements. I get emails from one retailer regularly and the bottom of the email says, “If only you had our ABC Retailer credit card, we’d do this for you.” Well, I’ve had your credit card for 10 years. So, you’ve wasted my time; you’ve irritated me.


So, my advice is to pause before sending to take the customer’s perspective. You don’t need a master’s in analytics to “personalize” communications. Just use the information you have available to try to do a better job.     Back to Contributors list

Jeff Rohrs, CMO, Yext


The backstory

When I was president of digital agency Optiem, about 12 or 13 years ago, I had a terrific client in cookware brand Calphalon. I was born and raised in Toledo and they had a factory there. I had a longstanding desire to work with Calphalon and got the opportunity to do their search and some other marketing. We were a small digital agency, and this was pre-social media, pre-iPhone. There was just the iPod in its old, clunky iteration.

I wanted to build a campaign around the iPod for Calphalon’s new stainless cooking set. I had this strange recollection of my youth — because at the time I had young kids — that the first instruments anybody ever learns to play are the pots and pans in their parent’s kitchen.



I thought, what if we sampled those sounds and turned that into songs. And better yet, what if we turned it into an interactive tool and had a contest for people to mix their own songs? Making music with Calphalon products.

I started to riff on that a little bit more. Again, this was about 2004-2005, so blogging was the hot thing at the time and would have been considered the social media of the moment. I came up with this idea of a blog about the intersection of food and music called Food Groove. I even registered the URL.

It was all this fun idea that we could do for about the cost of one or two print ads. It would have been so viral and connected people with the brand in a new way—and made the brand accessible to a new generation that was coming up. We built a huge dossier pitch that I was going to give to my client contact at Calphalon, whom I liked a great deal. 

I flew to Chicago; I was all excited. As I was in the cab heading there to present I noticed — on my flip phone — that I had a message. My client was sick and wouldn’t be able to make the presentation. She was hoping that her boss and some other folks would attend.

Well, of course, once your primary advocate isn’t in the room, the boss doesn’t have an incentive to be there. I ended up presenting to two interns, which was really demoralizing. I went home with my binder between my legs and licked my wounds and we never got the shot again to pitch.

I missed out because I made the fundamental mistake of not building a deeper set of relationships within that customer such that I could go there and not only make sure the right people were at the table, but also ensure that there would be multiple people involved in case one of them fell by the wayside.

I’d invested all this sweat equity, only to see it crash and burn. I had that binder as a stark reminder up until my move from Cleveland to the New York City area just a couple of years ago. Then I finally let it go. That mistake remains pretty much emblazoned in my mind.

The big change

That meeting broke my spirit to be in the agency world. So, when Scott Dorsey, cofounder and then CEO of ExactTarget, approached me about six months later at a conference and said, “Hey, would you ever consider working for us?” I said, “Sure,” in part, because I realized that pitching these ideas, which are, effectively, your children, and seeing them crash on the rocks was very difficult. I wanted to go in-house and be able to control a bit of my own destiny.

I was fortunate to have that happen at ExactTarget and to get my fingerprints on a lot of different creative. That’s not to say that everything I proposed got the green light, but I was emotionally invested in the success of that company and the people around me. And I could see the fruits of my labor, as opposed to going into a dog-and-pony show and maybe have a chance of getting something green lit.

That Calphalon pitch pivoted my career, but it also impacted how I think about marketing and selling and that you need to get the right folks around the table. It also got me thinking a lot about what you invest your sweat equity into. I became a much more discerning provider of that extra effort, because if you do that all the time, you’re just going to burn out.


The go-forward strategy​

Now, as CMO of Yext, we talk a lot about “the buying pods,” borrowing that language from SiriusDecisions. The idea is that it’s not a single buyer that you’re working to sell to; there are multiple people involved. In our case today, if we don’t get multiple people within one client from search, digital, brand, legal, facilities, procurement on the contracting side, and IT, so they understand how to leverage this technology, we miss out on valuable advocates, as well as some key people who’ll want to sign off.

We’d all love to always have the hero sale, where we have the champion and they are the buyer and the signatory and you’ve got the sale. But that’s so rare that to build your processes around it is foolhardy. You need to have a broader conversation and invest in relationships — especially in B2B. As I often say, the B2B sale is a much more emotional sale than B2C because, “My job is on the line when I’m buying from you. I want to know that I like you, that I trust you, that I want to work with you.” That’s not true of just one person. Today it’s usually multiple people.

The sage advice

Don’t be afraid to take risks and bet big. But be sure to set up the circumstances so that success has a greater chance than failure. That means it’s not just about the idea, it’s also about the process, the relationships, and the opportunity.

I think creatives can get ahead of themselves. The balloons start rising and they want to go with them. As a manager, you don’t want to stick a pin in the balloons, but there has to be some sort of business outcome. So, also with having the idea, you need to ensure that they’re thinking about the way they want to execute the idea and thinking about, strategically, what’s the right time and the right audience from the client and how do we get them in the room. Those are all parts of a greater chance of success.


Also, make sure to build relationships with all the people who need to be in the room, because sometimes it’s the quietest person who has the greatest amount of power. You really need to know your audience, what credibility you have with them, what additional people you should have in your corner saying, “Yeah, this is good idea.” Build some consensus or momentum behind an idea with multiple client stakeholders before you go and pitch it.

That’s not to say that in every instance you’re going have all that. There will be times when you just need to strike when the iron is hot.     Back to Contributors list

Celeste Giampetro, VP of Marketing, PebblePost


The backstory

Early in my career, back in 2000, I took a big risk and left my five-year tenure at Forbes to join a Swiss-owned HR software startup. I was their first and only marketing hire at the time, but there were lots of great people around me who were telling me about the platform and what it could do. The platform was a 360-performance management tool. My role was to evangelize this platform to a target audience of HR professionals and senior decision makers.

I made the rookie mistake of not insisting on testing the platform from day one. Actually, I never saw the platform except in sketches and maybe one demo. I never got to put my hands on the keyboard to learn as much as possible about the tool and its user experience.



Instead, I was listening closely to the two founders and their dream of what the platform would be, rather than understanding where it was that day. As a result, I was writing grandiose statements that were often kicked to the curb by the product team.

There was this real disconnect. It was incredibly frustrating because I didn’t have someone else in marketing to guide me at that point. Other senior leaders tried to make up for that communication breakdown, but it wasn’t the same as insisting I steep myself in the platform.


The big change

Unfortunately, I didn’t get a chance to fix that situation. About a year into the job I took another big risk and left the company after a pivot in their business case. I was there long enough to realize that the product had stalled and was never going catch up to the founders’ dream.

I resigned without having another job, which was terrifying. Fortunately, I got a new job not too long after. The startup folded a few months later, so leaving turned out to be a good risk.

That first startup experience taught me to always do your due diligence, get your hands on the keyboard, go to product trainings, take notes, ask questions, make the product your new best friend. If you don’t understand how something works,
how can you develop marketing communications explaining why it matters, or why it’s going to move the needle for your
target audience?

Now, at PebblePost, I log in to the platform regularly. I also work closely with the product team to improve fluency in our offering and help guide those translations from something very technical to a benefit.

The go-forward strategy

Since that first startup experience I’ve grown more curious and hungry to stretch beyond just my scope as a marketer. For example, at PebblePost we have this great new sales enablement training program that launched several months ago. They’re churning out courses on our product and our platform weekly. My goal is to take as many of those courses as I can and absorb as much as possible. The opportunity to learn, learn, learn and develop fluency in how the product and platform work is definitely going benefit me as a marketer. And because PebblePost is a marketing technology platform, in some sense,
I’m the customer.

Sometimes in marketing you can feel divorced from the product. It’s critical to, literally or figuratively, get your hands on the keyboard, see how the platform is supposed to work and understand firsthand what the actual user experience is. You might find nuggets that you as a marketer see as a benefit that others don’t necessarily see the same way.

The sage advice

Feed your curiosity. It’s too easy to get into your marketing box and rinse and repeat. Get close to the product team. And, if you have access to the engineering team, get to know them as well, so you really understand what they’re up against.


My marketing team is close with a few engineers. Those relationships have created a deeper appreciation of the scale of work they have on their plates and all their accomplishments to date. It’s daunting and impressive.

There are other benefits of building these relationships for the business. For instance, we’re experimenting with agile methodology in how marketing attacks projects, mimicking what the engineering team does on a much smaller scale. It’s one example of how teams can learn from each other. It makes for a much richer experience.      Back to Contributors list

Justin Thomas-Copeland, President, RAPP New York


The backstory

I was chief digital officer at Novartis Consumer Health in Europe, around 2012. I had to retrain all of marketing across the region. The kickoff to catalyze that change was going to be a conference. All of the CMOs and their marketing teams, including GMs — about 200 to 250 people — were flying in so that I, my team, and our agencies could brief them on transforming to digital and taking a more digital-first approach.

Perhaps it was my overexuberance. Or that the company had been planning this event on a lesser scale before my arrival only three weeks prior, but I turned it into a what would be a big, inspiring conference and significant investment. Whatever the root, my mistake was all in


the preparation. As the adage goes, “Perfect preparation guarantees perfect performance.” Well, I thought I had that under control, but the day before the conference, I found out clearly that I did not. And small inconsistencies became big issues quickly.

The biggest misstep was not integrating the teams, especially the agency teams. I had three agencies working for me to get
the content right and had separate development streams for each of the content tracks. That was OK. The problem was not kicking off a simultaneous briefing. I had tried to divide and conquer to get everything ready in time but had overlooked
bringing together all key parties at kickoff to ensure that we were all laddering back up to the same key objectives and vision
for the workshop.

This mistake became clear to me the night before the event, when I looked at all of the content streams. It was the first opportunity I’d had to put them together, take a step back and review for coherency. Don’t get me wrong — we’d had check-ins with each individual partner and aligned on components that needed to evolve. But the key word is individual — after each agency check-in, I was on to the next, and then the next, going through them rigorously but individually.

I had overlooked pausing at critical moments to review the bigger picture perspective in advance — and when I did, the night before, I saw we weren’t ready. We had to regroup.

The content was there, it just needed refining. It needed to be actionable, which is what we promised. We weren’t going to be talking at people for two days. We were developing training programs, and the teams would actually be working on dummy briefs, walking the digital walk while they were at the conference.

So, it was a case of: You have less than 24 hours to go, make sure you get to where you need to. I pulled in some extra help and got us laser-focused. We made the necessary updates to the content and the event was a success.

The go-forward strategy

There are key tenants I learned through that experience that I use to this day.

Learning number one: Get all stakeholders together when you’re working on a major initiative. It’s too easy to say, “I’ll talk to one person, Skype with another, and email the third. It’ll all come together.” Getting people together and having a conversation at the outset of a major initiative is priceless. It saves time. It creates and cements a common understanding of goals and eliminates any misinterpretations of what we’re trying to achieve. And it’s now something I do no matter what.


Learning number two: Where you have clear goals, repeat them. With so much coming at people today, make sure you repeatedly review your plans against your goals. I now do this methodically; it takes only 10 or 15 minutes. I often underscore to my leadership team the importance of repetition.

Learning number three: Embrace the good and the bad. I’ve always been one to embrace accountability, but this experience took it to another level. It was a lesson in, “This is on me, so own it.” I didn’t look left or right, I didn’t ask why or why not. I just embraced it and moved on. Accountability is an essential skill to develop since so much is constantly changing in marketing and we don’t always know the answers because we’re going into new territories. Being accountable is a great leadership skill that you can never become too good at.

Learning number four: Take a time out. Pause to let the energy dissipate and have a cold look at where you are versus where you need to be. Make sure everything is covered and that stakeholders are clear on their roles and responsibilities. This is critical because we’re all moving so fast.

Learning number five: Don’t be the lonely man or woman up front. Make sure your team is right beside you and that you’re not speeding ahead of everyone.

The sage advice

Always be excited. Always have high energy. But never let that enthusiasm overshadow laying down the basics. And never let it allow you to speed ahead without checking in with those around you to ensure that you have support from, and alignment with, everyone involved.

There’s a lot of speed in business today. There’s a lot we can all get wrapped up in. So, make sure that whatever initiative you’re planning, you’re doing it for the right reason and it’s going to deliver the value it’s meant to.     Back to Contributors list


Daniel Incandela, CMO, Return Path


The backstory

I was in my first management role in the software industry and had to build my team while managing one of the biggest projects I’ve ever led in my career. It was a massive website relaunch in seven languages, with a new site map, new infrastructure, new content, and a deadline that was shrinking by the day — and I had to hire people to get the job done.

Typically, I’m methodical and patient around hiring because I strongly believe there are no shortcuts when it comes to hiring good people. But I was under so much pressure to hire quickly that I ended up “panic hiring” for a particular role. It turned out to be a catastrophic mistake.


I brought in someone who was not a good culture fit, was not particularly good at their role, and ended up being pretty toxic. There were also the unintended consequences of personality clashes and damage to team morale and team dynamics.

I ended up having to let this person go and then go through the hiring process again, so it was a total waste of time and resources for the company. The project got completed and was very successful without this person, which actually was the
best decision.

The big change

I learned a lesson from that bad hire that I have made sure not to repeat. Since then I've gone into other roles where I’ve had to either build teams or reorganize and add headcount, and now I absolutely respect the process. It’s too big of a risk to not be careful when it comes to selecting the right person.

Also, having to separate with an employee or tell them that they no longer have a job is one of the worst things you can go through as a professional. I can’t even imagine what it’s like for someone receiving that news. So, I can’t stress enough that as a leader you should invest in all of the research and work needed before making a hire because the last thing you want to do is let anyone go. It’s awful.

The go-forward strategy

Since that hire, I’ve learned to trust the process, be patient, and trust my intuition because, ultimately, I’m the one who knows the culture. One thing I’ve shifted slightly since then is relying on feedback from others across the organization as a gut check and a second opinion on the candidates I’m considering.

It’s impossible to get every hire correct. I know that. But what I try to do is hire in a way that increases the probability that the person will be a good hire and a good culture fit.

The sage advice

My advice to other marketing leaders is to trust your instincts when it comes to building a team. As a leader, it’s on you to build a team that’s going to operate well within the company and across departments — and, that will generate successful work. You shouldn’t rush hiring because the results won’t be as good. Plus, it’s a lot less expensive to take a little extra time to do due diligence and research, and really get to know candidates instead of just rushing through.

But if you have made a bad hire or inherited a team where it’s clear that someone’s not up to performance or they’re causing toxic issues, make the decision to part with them quickly. It’s better for the company, and, often, the individual isn’t happy either. So, it’s usually the best decision for everyone.      Back to Contributors list

Chris Sojka, Cofounder and Chief Creative Officer, Madwell

The backstory

About four years ago a well-known CPG brand chose us as their marketing agency. We were just a few years old at the time, and I believe we won the business because of our creative energy and enthusiasm. Although we hadn’t yet expanded to the variety of disciplines we have today, we rarely failed to throw our heart and soul into a pitch. This was no different.

Since cofounding Madwell we’ve continuously tried to live up to our full-service mission. But back when this particular client hired us, we hadn’t perfected what is now our structure and approach. Our strategy team — today a hybrid of UX and account planning theory — was little like it is now. Eighteen months after we started working with that brand, it was acquired.


We were put in review and lost the business. It was heartbreaking.


The big change

While painful, the loss wasn’t a mystery. Our creative was vibrant, but our strategic framework was underdeveloped, which made it hard to protect our thinking.


It was the consequence of losing that client that made me decide to work with my cofounder and the entire team to completely reevaluate how we wanted to operate our company to serve our clients more cohesively. Out of that loss was born the strategic apparatus and philosophy that now governs our entire business infrastructure. Every department and its operations now fit into that apparatus, with accounts and production operating as the flywheels that keep it all moving.


The go-forward strategy

Instead of looking away from our failure, we confronted it, ultimately restructuring the agency over the past three years to match our robust new strategic philosophy and approach.


The first and biggest change was developing and formalizing our strategy team, which we call Insights and Experience. I’d had concerns with traditional account planning, which is not always as rooted in strategy or consumers’ needs as it should be. To address those concerns, our Insights and Experience team combines user design and analytics. The team maps consumer journeys across all media and dimensionalizes them based on behavior.


Then, over time, we complemented that by rethinking the function and responsibility of our accounts team. That meant moving our account managers into more formal strategic partnerships with our clients. After all, clients want progress — and results — not martini lunches. Socializing is a bonus you get after you’ve met their goals.


The sage advice

If there’s one thing this experience has taught me, it’s that failure is the single most important educational tool we will ever have.


Failure is final. It’s not a mistake. It’s not an “oops.” It’s consequential. Our loss had consequences. And because of how we chose to respond, a lot of those consequences were positive. I’d go so far as to say that we wouldn’t be the company we are today — strengths-wise, client roster-wise, personnel-wise — if it wasn’t for losing such a lovely brand run by such lovely people.


So, my advice is this: Play to your weaknesses, not your strengths. Playing to your strengths is the easy way out. Search for your weaknesses and play to them. Build your business around addressing them constantly. Don’t let them get you down. Let them be an engine of creative, personal, and moral evolution.


And, don’t ever get comfortable with what you believe you’re an expert in, because the world is always changing. There’s a quote from Heraclitus I love: “No man stands in the same river twice.” The updated version is: “The only constant is change.” I think that’s truer than it’s ever been.      Back to Contributors list

About the Author

Ginger Conlon, chief editor and marketing alchemist at MKTGinsight, catalyzes change in marketing organizations. She is a frequent speaker on marketing and customer experience, and serves in advisory or leadership roles for several industry organizations. Ginger was honored with a Silver Apple lifetime achievement award for her contributions to the marketing industry.

Find her at @customeralchemy and on LinkedIn.