Creative Marketing: Pete DiMaio on Finding Brilliance
With over 20 years of experience wielding both traditional and digital hospitality marketing, Pete DiMaio's data-driven approach generates real results. He's a proven powerhouse, crafting performance-based web design, paid marketing, and SEO campaigns that drive occupancy, increase RevPAR, and skyrocket direct bookings.
He's the host of the Hotel Marketing Podcast, keeping you informed on the latest trends, and actively collaborates with HSMAI, ensuring you benefit from the best practices in the business.
LBB> What does creativity mean to your brand?
Pete> In digital hotel marketing, creativity goes beyond visual design. It’s about discovering innovative ways to connect with potential guests through channels that competitors haven’t explored, all while maximising efficiency. At TravelBoom, we blend creative thinking with strategic execution to optimise the entire conversion funnel, from initial engagement to post-stay experience. While the visual aspect may not be the primary focus, our approach leads to more bookings and record-breaking returns.
LBB> And more broadly what does creativity mean to you - outside of work, outside of the sphere of advertising and marketing?
Pete> Creativity, in my view, involves looking at the world through a lens beyond the ordinary. It starts with an insatiable thirst for knowledge and a curiosity that sparks new connections. I've realised that true creativity requires pushing beyond the boundaries of the workplace. For instance, an art director who only creates print ads in a cubicle will soon find their work becoming stale and formulaic.
However, if that same art director takes up sailing, engine repair, beekeeping, or any other activity outside their expertise, they’ll discover fresh inspiration and develop creative masterpieces by connecting previously unrelated ideas.
For me, this means setting a yearly resolution to learn something entirely new, outside my current knowledge base. This approach helps me grow as a person and enables me to develop creative solutions that would otherwise be unattainable.
LBB> What was the moment or experience in your career that really helped ferment the importance of creativity in marketing?
Pete> Reflecting on my early days in marketing as an agency account coordinator. I was working with Myrtle Beach Golf Holiday, a destination marketing organisation (DMO) focused on driving demand for golf in the Myrtle Beach area. Creativity was integral to our strategy, not only in the design aspect of advertising but also in the innovative use of mediums and tactics. What stood out most to me was the out-of-the-box thinking that went into developing partnerships and promotions.
As with many DMOs, funding was often tight, but our account and media teams consistently found ways to create amazing opportunities that went beyond the standard rate cards.
One event that truly underscored the importance of creativity was GolfApalooza, part of a larger media partnership with Golf Digest. This event was a collaborative effort from the entire team, relying on strategic media spending, excellent creative execution, and the combined expertise of Golf Digest, Myrtle Beach Golf Holiday, Brandon, entertainers, and industry professionals.
A personal highlight for me is still having my framed and signed Edwin McCain GolfApalooza poster—it's a great reminder of the power of creativity in bringing such events to life.
LBB> What have you learned is the key to nurturing fruitful relationships with your creative partners?
Pete> Building a successful relationship with creative partners hinges on effective communication. In my experience, investing time upfront to clearly articulate the objectives and define the key performance indicators (KPIs) leads to significantly better outcomes and fosters a stronger, more collaborative relationship. Often, frustration between clients and creatives stems from unclear goals and ambiguous direction.
The solution lies in overcommunicating—ensuring that all parties have a comprehensive understanding of the project’s objectives, expectations, and key data points.
By setting clear expectations from the outset and maintaining open lines of communication throughout the project, you can minimise misunderstandings and keep the creative process aligned with the desired outcomes. This proactive approach not only improves the quality of the work but also strengthens the trust and rapport between the client and the creative team, making the collaboration more productive and enjoyable for everyone involved.
LBB> Which creative campaigns from other brands (past or present) have inspired you most in your career and why?
Pete> I absolutely love what Red Bull has done with their brand and creative. I don’t think I’ve ever seen someone actually drinking a Red Bull in their commercials (aside from the cartoon character), yet they’ve seamlessly integrated themselves into everything cool in the world. Jumping from space? Check. Landing a plane on a skyscraper? Check. Creating a whole new sport with Red Bull Flugtag? Done.
What I admire most about Red Bull’s approach is how they built their empire by serving as a conduit for their audience to achieve their ambitions. They authentically support their audience in pursuing what they value. I firmly believe in being a conduit and servant to your customer, and this really resonates with me. As a hotel marketer, this is where the most successful hotels connect with their guests—by serving as the gateway to an extraordinary experience.
LBB> What campaign that you’ve worked on has been the most creatively satisfying and why?
Pete> This is a tough question because each campaign has its own satisfying and memorable elements. One that stands out, however, was a video production campaign we created for a major amateur golf tournament in partnership with the Golf Channel. The budget was tight, and as the account manager, I had to pull a lot of strings to get everything done on time and within budget. We used Golf Channel production assets along with talent we flew in for the shoot in Orlando.
The final spot was fantastic, but what really sticks with me was the complexity of turning a creative vision into a finished product. As someone who came up through the account side, getting hands-on experience with the shoot and the creative process was invaluable. It was a great reminder of how much work goes into bringing a creative concept to life.
LBB> Of all of the puzzles facing marketers right now, what’s the topic that’s perplexing your team the most right now?
Pete> Personalisation, when done right, remains a significant challenge in the hospitality industry, especially for independent properties. While large hotel chains often have access to extensive resources, sophisticated data analytics, and advanced technology platforms to create tailored guest experiences, independent properties frequently struggle to achieve the same level of personalisation. Even large chains often fall short in this area.
This challenge isn’t unique to hospitality; marketers across all industries face similar issues. We operate in a world with nearly limitless touchpoints—desktop, mobile, apps, print, OTT, social media, and more.
Additionally, most marketers manage countless outbound touchpoints and automations. Combined with increasing restrictions on personal data, creating a truly one-to-one marketing experience is no easy task. While we’re making great strides, marketers—and hoteliers in particular—are still working to solve this complex issue.
LBB> What areas of marketing are you seeing most exciting potential for creativity?
Pete> It’s almost cliché to say that AI is shaking the foundations of marketing, but it’s true. Despite its immense potential to revolutionise the creative process, AI remains largely underutilised in many agencies. Striking the right balance in leveraging AI continues to be a challenge for marketers, both large and small.
AI is no longer just about automating tasks or analysing data—it’s increasingly becoming a creative partner. This shift can be unsettling for those with a traditional creative mindset, but it’s important to recognise how AI tools can enhance the creative process while preserving the essential human touch.
For marketers, AI offers better access to hidden trends, data-driven insights, and the ability to extract actionable items from vast data sets. Beyond data analysis, AI can transform the creative process—from research and briefing to concept development and the final product. However, one of the biggest challenges lies in overcoming the mental “turf war” of allowing AI to interfere with the creative process. Embracing AI doesn’t mean corrupting creativity; it means evolving it.
LBB> You must see so many ideas pitched to you - and have had to sell in so many ideas to the rest of your company. So what’s the key to selling a great idea?
Pete> As someone responsible for the bottom line, I greatly appreciate when a creative pitch clearly connects to improving key performance indicators (KPIs). As we navigate budget season, every line item must be justified in terms of a KPI. While revenue is often the focus, KPIs can also include awareness metrics, cost savings, engagement, and more. However, creativity for its own sake isn’t a metric I can base decisions on.
I would ask anyone pitching a creative concept to justify their decisions in terms of return, however that may be defined. For instance, in the hotel industry, when pitching creative ideas for a website, we typically include a prominent “book now” button or a booking widget that allows users to enter their arrival and departure dates.
These elements may not always result in the most aesthetically pleasing design, but they are supported by data showing a measurable increase in conversion rates for a given consumer segment. Including or omitting these overt conversion elements then becomes a logical decision, backed by clear, data-driven reasoning.
Presenting a broad creative campaign that spans multiple channels may be more challenging, but if the campaign is backed by consumer research and studies, you can clearly connect the dots between great creative work and its market impact. Demonstrating how well-crafted creative resonates with the target audience can effectively show its potential to drive higher conversion rates when deployed across various platforms.
LBB> In your experience how can marketing teams drive creativity throughout the rest of an organisation?
Pete> Marketing teams can significantly enhance creativity across an organisation by involving a broader range of team members early in the process. While agencies and brands may sometimes face resistance when including analysts, operations, production, or other departments in creative discussions, expanding the pool of contributors can be incredibly valuable. Bringing diverse perspectives to the table fosters an environment where new and innovative ideas can emerge.
Involving different departments not only broadens the creative thinking but also ensures that the ideas generated are more well-rounded and practical, considering insights from various facets of the organisation. This collaborative approach can lead to more effective and innovative solutions, as it taps into the unique strengths and knowledge of each team member, ultimately driving greater creativity and success in marketing initiatives.
LBB> How do you encourage creative excellence among your team?
Pete> To encourage creative excellence among my team, the first priority is creating a culture where everyone feels safe to share any and all ideas. Some of the world’s best ideas initially seemed outlandish, so it’s crucial for leadership to actively defend and encourage even the most unconventional concepts. These ideas should be heard and rigorously tested, often using the Five Whys method.
'The Five Whys Theory', developed by Sakichi Toyoda, is a powerful problem-solving tool that can be applied to virtually any challenge, including creative development. By asking why five times—or as many times as necessary—you can dig down to the root cause of an issue, addressing it at its core rather than just treating its symptoms.
In the context of creative development, the 'Five Whys' can be incredibly useful. For instance, if a campaign isn’t resonating with the target audience, asking why repeatedly can help uncover the underlying reasons. Is it due to a misunderstanding of the audience’s needs? Is the messaging off target? Or perhaps the chosen medium isn’t the most effective for reaching the desired demographic? By systematically breaking down the problem, creative teams can refine their approach, leading to more effective and impactful solutions.
LBB> The big question. We know creativity is effective but when you’re assessing an idea that’s totally original and new, how do you figure out if it’s brilliant or indulgent?
Pete> Creativity is essential—it’s what transforms background noise into a message that truly resonates. But how do you assess whether an idea that’s entirely original is brilliant or simply indulgent? The distinction is crucial.
Indulgent creative is fairly straightforward to identify. It comes down to one key question: How will this creative help achieve my marketing objectives? If the creative is genuinely designed to advance the client’s goals, it’s not indulgent. However, when an agency prioritises winning awards such as ADDYs or Clios over delivering results for their clients, they’re missing the mark.
Determining whether creative is “brilliant,” however, is more complex. It involves assessing the idea against three critical criteria:
- Goal alignment: Is the creative specifically designed to achieve the stated objectives?
- Research support: Does market research validate the creative direction?
- Performance: Does the creative meet or exceed the goals once it’s launched?
If an idea can satisfy these three criteria, it’s likely more than just original—it’s brilliant. Creative excellence isn’t just about being different; it’s about being different in a way that drives meaningful results.
LBB> Tell us about a time you’ve really had to fight for a creative idea - what was the idea, what was the obstacle and why was it worth it?
Pete> Nearly all of my responses in this interview focus on conversion optimisation, which has presented unique challenges when presenting creative to clients. Several years ago, I was involved in pitching creative for a new destination site, with the primary goal of driving conversions through a specific request form. Our creative approach was intentionally clean and engaging, designed to achieve one objective: maximise request form submissions.
However, during a review with a large group of stakeholders, we received feedback suggesting the addition of elements such as a “Learn More” button, links to FAQs, and videos. While I’ve always supported offering users multiple conversion opportunities, these should ideally align with the same conversion goal. After some thoughtful conversations and discussions about how the creative would ultimately be evaluated, the client agreed with our focused direction, and the campaign proved successful.
This experience taught me the crucial lesson of securing signoff on the creative brief and goals before moving into design and development. By doing so, the client essentially agreed with themselves, reinforcing the importance of creating a campaign that excels at a single, well-defined objective.
LBB> What one piece of advice do you have for marketers at the beginning of their careers who are still figuring out how to drive impactful creative marketing?
Pete> The best advice for anyone starting out in marketing—or even those who have been in the business for years is you don’t know anything! You may have educated assumptions and preconceived notions of what will work, but the data reveals the true story.
After 25 years in marketing, it’s easy to fall into the trap of thinking I know what needs to be done. However, the best marketers approach their work like scientists—constantly analysing data and striving to learn something new.
While your past experiences are invaluable, it’s essential to continually validate them against the insights you’re gaining and the data you’re collecting.
