Asked and answered
In the ever-evolving world of marketing, taking calculated risks can lead to remarkable rewards. We've gathered insights from eighteen Chief Marketing Officers, CEOs, and other top executives on the gambles they've taken that have reaped benefits. From a successful paid attendance conference to an innovative LinkedIn strategy that surpassed the competition, discover the daring moves that paid off for these industry leaders.
At the desk
In a startup, you don't always know when the right time is to hold the first conference to invite both existing customers and prospects, so it is often a risk to go ahead with the decision based on intuition. In retrospect, I have come to realize that this is one of those risks that has paid off for us. When we decided to organize a conference, we were coming out of the pandemic and did not have enough data to understand whether we would be able to get enough participants into the venue. In addition, we also decided to make attendance at the conference a paid ticket. The general intuition here was that people were hungry to be back to in-person learning, and if they paid for the ticket, they were more likely to attend.
Both of these risks paid off when we ended up getting about 1,000 attendees for our conference. This also validated the product-centric strategy for any marketing campaign. If the product is good, in this case, the content and the experience of the conference, then getting that product into the hands of the users as quickly as possible is the shortest path to growth.
I was at an ad agency, and we decided to target an entirely new market segment. It was very risky, for the client had never ventured out of its 'comfort zone' in its history. I convinced them that it was worth the risk to test this new segment based on industry research and our own data. After a slow start, the new market segment exploded and validated my idea, and eventually became part of their overall buyer personas.
One example of a risk we took in our marketing strategy that paid off immensely was securing the trademark "Committed to the Community." This wasn't just a slogan for us, but a profound movement and initiative that every staff member at Berman Law Group actively participates in. Each week, we engage in various community service activities—whether it's bringing food to local companies and those who serve and protect, or offering staff paid time off to volunteer at local charities that are dear to their hearts.
By embedding this commitment into our company culture, we've transformed it into a core part of our identity. The initiative not only enhanced our brand reputation but also fostered a stronger, more united team. Our consistent, genuine involvement in the community has resonated deeply with our clients and partners, allowing us to become one of the biggest companies that give back and make a tangible difference to people and nonprofits around us.
This risk of dedicating resources and time to community service, while initially daunting, has paid off by significantly boosting our brand’s credibility and establishing Berman Law Group as a trusted and valued community partner.
Matt GehringChief Marketing Officer · DutchOne risk we took that paid off was experimenting with a new email marketing approach by testing different subject lines and content formats on a small segment of our audience. While it was uncertain whether these changes would improve our results, the test revealed that personalized, interactive content significantly increased open rates and engagement. Based on these insights, we rolled out the updated approach across our entire email list, leading to improved campaign performance and better overall customer response. This small-scale experiment demonstrated the value of data-driven adjustments and iterative testing in refining marketing strategies.
One risk that paid off significantly for us was producing a feature-length documentary titled "6 Years to Launch," which chronicled the milestone of our first satellite launch.
On paper, the idea of a lean marketing team of just four people producing a full-length documentary might sound ambitious. It's not a traditional marketing tactic. However, we saw an opportunity to capture a pivotal moment in our company's journey—the launch of our first satellite—in a way that could deeply resonate with our audience.
We decided to go all-in, documenting everything from the founders' initial meetings to the moment we watched the rockets take off. Despite the challenges and our limited resources, we believed in the power of authentic storytelling.
The results have been outstanding. The documentary provided us with exceptional content to share across various platforms and opened doors we never anticipated. It has been featured on major movie websites, discussed by video professionals, and sparked conversations about our brand in entirely new circles.
This experience reinforced the importance of taking calculated risks in marketing. Sometimes, stepping away from the traditional playbook and creating something unique can yield game-changing results when it aligns with your brand and resonates with your audience.
Historically, our team hasn't run online advertisements. We put a few Google Ads up, but our team didn't have much experience in that field, so they never returned great results, and it wasn't something we pursued. That said, on the suggestion of one of our advisors, we decided to try a risky experiment: saturating the pay-per-click search market for one of our core product lines. Our market is competitive, and while our product is high-quality with unique features, standing out from other brands has been a challenge. So, we set aside a significant budget and launched a campaign designed to bid as much as it took to always show our brand on top.
We weren't sure if it would work at all, and we had a lot of other tried-and-true ways to get a positive ROI on that ad spend. Fortunately, our campaign paid off, and in that week, we collected as many new customers as we'd normally get in a full quarter! Naturally, it wasn't sustainable to run the ads permanently at such a high spend, so we turned them off, but the loyal customers we gained made that campaign a huge success and easily justified the cost.
darwin liuCEO · X AgencyOne of the most significant risks we've taken in our marketing strategy is choosing to go against the grain.
In an industry where many agencies offer similar programs, we've made it a point to do the opposite of what everyone else is doing. This unconventional approach has not only set us apart but has also become a cornerstone of our success.
By challenging the status quo, we've been able to offer unique solutions that resonate more deeply with our clients, ultimately driving greater engagement and results.
Brian JacobCMO · McCready LawTurning down TV and doubling down on social media.
We consume content on devices more than TV these days. In fact, most people consume content on a device while they watch TV shows or even movies. It's easier... quick nuggets to learn from, to be entertained by, and to share with others.
The content that we create can be positioned to exactly the right person we want viewing it. Added engagements—liking, sharing, and saving—give us insights other display advertising simply cannot.
We can also track the leads we generate and attribute them accurately. This is important when you want to determine advertising spend on each property. It's a risk, but it can work for the right type of businesses.
Investments in brand-building and relaunches, particularly within B2B organizations, are often high-risk, high-reward endeavors. Unlike consumer marketing, where budgets are dedicated to establishing brand differentiation, B2B companies typically prioritize product marketing and pipeline growth. Even with a well-defined strategy and a carefully considered ROI thesis, securing buy-in from the board, executive leadership, and the broader organization can be challenging. However, the risks are often justified by the potential rewards—creating clear differentiation that makes a brand memorable and unique within its category.
Shafqat IslamPresident · OptimizelyPeople often view out-of-home (OOH) advertising as a risky relic of the past—it's costly, unmeasurable, and unwieldy. Yet, after spearheading three of Optimizely's first-ever OOH campaigns in the last year, I've discovered it's quite the opposite. OOH marketing can be a potent tool in a modern CMO's arsenal, particularly for B2B marketing when executed correctly. By tailoring our homepage to reflect the campaign cities, we created a cohesive visual narrative, enhancing brand messaging and enabling precise measurement of engagement spikes from those areas.
Following the launch of each campaign, we could track an uptick in engagement from our target accounts as they moved through the ABM funnel, providing another layer of measurable impact. We also witnessed a surge in social media engagement, a buzz of excitement within our team, and even garnered some inbound leads, which validated the effectiveness of our OOH ads in driving meaningful interactions. For a campaign aimed at raising awareness, that's a significant win, if you ask me.
When I was the co-founder and CMO of .CLUB Domains (sold to GoDaddy in 2021), we spent a large sum on a co-promotion with the rapper 50 Cent. He was (and is still) well-known for the hit song, "In Da Club," and I thought that would be a memorable tie-in with the .CLUB domain, which we were launching. In addition to being able to use his name and likeness in promotion for our launch, we had a big (and expensive) party at Tao, a hot club in NY.
We invited (and paid for) registrars and domain industry bigwigs from all over the world to attend (and, of course, 50 Cent was also there). Nothing like this had ever been done for the launch of a domain extension, and many thought we were insane to spend so much on such an idea. But it put us on the map and got the attention of the entire industry, and helped support a very successful launch of .CLUB (and a decade later, people still talk about it). It was definitely a risk, and it paid off, in da .club and beyond.
Nickalaus PatrockyFounder · Coldoutreach.comGiving away all of our strategy secrets with the hopes that enough prospects would still want to hire us because they didn't have the time to do it themselves paid off big time, and we got better clients than we could have hoped for. Giving away all of your 'sauce' proves your competence to other people. We realized the 'DIY' people were never going to hire us anyway.
Ginger LiuCEO · GMEI think getting your prices right is a risky business. Do we go too high to chase that one client who may hire us? Or do we go too low, which means there's too much work with little reward? I have taken a risk with both of these strategies, marketing to large B2B and small businesses. The greatest risk is jumping out of your comfort zone. Staying at the same level with the same clients and the same offerings can lead to stagnation because businesses must always evolve with the markets. Taking risks to showcase new services that may hit or miss is a great way to test the waters and stay vital.
The Houston Livestock Show and Rodeo is one of the largest events in the country, including a world-class rodeo and concerts, the world's largest livestock show, carnival, wine garden, and educational exhibits. With our core offering being rodeo and primarily country concerts, our demographic heavily skewed Caucasian. However, Houston’s demographics have changed considerably over the past few decades and are continuing to change, as Houston is now considered the most diverse city in the US and has no ethnic majority.
While our core offering will always remain focused on our Western heritage, several years ago we began targeting a more diverse fan base, namely Hispanics and African Americans. Greater Houston is more than 40% Hispanic, so having representation within our fan base is important to maintaining our place in the community, both now and in the future. This strategy has paid off significantly, as our 2024 attendees almost perfectly aligned with the demographics of Greater Houston.
Patrick BeltranMarketing Director · Ardoz DigitalIn one of our digital marketing campaigns, we really went out on a limb and made a bold commitment to our clients. We promised something major, like "we'll never raise our rates" or "you'll see results within three months, guaranteed." This was a high-risk, high-reward move that put a lot on the line for our marketing agency.
We adopted this daring strategy to stand out from our competitors and build trust with our clients. We thought that by making such a bold promise, it would not only set us apart but also show our confidence in our ability to deliver outstanding results. It was certainly risky, as basing our reputation on these promises in our digital marketing campaigns could have backfired and been costly if we failed to deliver or execute properly.
Fortunately, we were able to follow through on our promise, which greatly enhanced our reputation. Our clients could see that we weren't just talk; we walked the walk by living up to our bold claims. However, it's a tactic we would consider carefully before using again. Such promises carry a lot of risks because if they're not carried out or delivered effectively, they could lead to major setbacks and harm our credibility.
Omër GüvenCo-Founder & CEO · FintalentLaunching a podcast aimed at a niche audience was a risk that paid off for us. By focusing on unique industry topics, we connected with listeners who craved specialized content. This strategy boosted our brand visibility and conversion rates.
It helped us stand out in a crowded market and build strong, lasting relationships with our audience, proving that targeting a specific group with tailored content can be highly effective.
Azam Mohamed NisamdeenFounder · Convert ChatOne notable risk we took in our marketing strategy was shifting a significant portion of our budget to influencer marketing. Initially, we were uncertain about its effectiveness compared to traditional advertising channels. We partnered with a handful of micro-influencers whose values and audiences aligned closely with our brand.
The result was phenomenal. These influencers created authentic, engaging content that resonated deeply with their followers, leading to a substantial increase in brand awareness and sales. This move not only expanded our reach but also built stronger trust and credibility with our target audience. The success of this strategy underscored the importance of taking calculated risks and exploring new avenues in marketing.
When it comes to social media marketing, the path well-traveled is not always the wisest. For our interior design firm client, we saw competitors flocking to Instagram and Pinterest to inspire potential clients. The beautiful photos and trendy designs attracted attention, without a doubt.
After carefully analyzing who the clients were that we were targeting, we realized LinkedIn represented a blue ocean of opportunity. While other firms focused on metrics like growing followers, likes, shares, etc., we dove headfirst into thought-leadership content on LinkedIn.
And it paid off big time.
By creating unique and valuable content for LinkedIn's professional audience, our client stood out from the crowd. We established them as credible experts, generated high-quality leads, and even began converting customers from day 1 of our LinkedIn strategy!
The key was honing in on our target customers and meeting them where the competition wasn't. Embracing an unconventional social media strategy provided the edge they needed to grow and establish their brand.
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