By Dan Contento, Chief Commercial Officer, Yieldmo
The open internet remains riddled with structural flaws, from signal manipulation and brand safety concerns to a lack of transparency. Advertisers are still navigating an ecosystem that has long stopped serving their best interests. Based on what I’m hearing from my friends in the industry, and the direction I believe is the right path, contextual targeting has become an ideal way forward.
You’re going to see a lot of contextual ad systems launch in the next 12 months. Anyone with an engineer and access to an LLM can churn something out in 2 weeks that, on the surface, looks like contextually relevant advertising. This method falls far short of the sophistication required to ensure that an ad not only appears on a relevant page but also resonates with the audience, aligns with brand suitability, and delivers measurable performance.
Legitimate contextual advertising must go beyond just words on a page. It must consider the totality of the ad experience, how it fits within the content, how it appears visually, and how effectively it engages users.
To properly evaluate contextual targeting, there are six crucial elements that will shine a light towards a more sustainable way forward.
Relevance:
Relevance is the cornerstone of any contextual ad system, but it’s often misunderstood. Too many solutions stop at basic keyword matching, failing to account for content, sentiment, and intent nuance.
For example, an article about “running shoes” might attract an ad for a marathon, but what if the article is actually about foot injuries caused by improper footwear? Running only keywords would result in an ad placement that’s not just ineffective, it could hurt a brand’s image.
By contrast, advertisers should have a deeper understanding of content and language. They should analyze not just the words on a page but also the meaning behind them, ensuring that ad placements align with user intent and brand objectives.
Appropriateness:
It’s no longer enough just to block content deemed “unsafe.” Today’s advertisers must think about brand suitability, a more nuanced approach that ensures ads appear in contexts that complement the brand’s messaging, tone, and values.
For example, an ad for luxury watches might be brand-safe on a news site covering economic downturns, but it certainly wouldn’t be suitable.
Aesthetic Connection:
An overlooked aspect of contextual advertising is how an ad looks on the page. Context should be more than just words, it should also be about the vibe it gives the intended audience. This means the ad’s visual look, layout, and the viewer’s experience must be considered.
A well-placed ad should feel like it naturally belongs within the content. Factors such as ad slot size, page composition, and even color palette affect whether an ad disrupts the user experience and becomes considered intrusive.
If you look at walled gardens, like Instagram or TikTok, ads blend seamlessly with the content. The open web must pursue a similar approach, ensuring contextual placements account for the aesthetic and flow of the content they accompany.
Granularity:
All ad placements should not be treated the same way. A proper ad system must allow advertisers to make decisions at the most meaningful level—whether that’s choosing specific content types, adjusting pricing based on engagement levels, or dynamically scaling granularity based on available data.
For example, an advertiser might want to set parameters around what is controlled manually compared to what is controlled by automation. This could mean they may want manual control over placements in high-value sites, like premium news or long-form editorial, while allowing more automated optimization in lower-priority segments. A strong contextual system should offer this flexibility and enable advertisers to make informed, data-driven decisions.
Ease of Use:
One of the biggest challenges with contextual adoption is ease of use. Many advertisers are used to buying through programmatic platforms with specific formats and pricing models, and any contextual solution must fit seamlessly into these workflows.
A useful contextual system offers flexible buying models, including cost-per-click (CPC) and cost-per-thousand-impressions (CPM), allowing advertisers to choose what best aligns with their goals. Additionally, it should work with standard creative assets, ensuring that brands don’t have to overhaul their creative process just to participate.
If contextual advertising is to scale, it must be frictionless. Advertisers should be able to activate campaigns with the same ease they expect from traditional programmatic channels.
Effectiveness:
Contextual advertising isn’t just about placement, it’s about performance. If a contextual system can’t measure and optimize toward advertisers’ ultimate KPIs, such as conversions or brand lift, then it’s just another black box.
Advertisers need solutions that track the effectiveness of their contextual campaigns in real time. It could be through AI-driven optimization, predictive analytics, or automated A/B testing, contextual systems must continuously tweak placements to maximize impact.
This is also where the emergence of AI plays a key role. With generative AI becoming more common, advertisers need guidance on how to deploy properly. A system that understands which creative performs best in specific contexts, rather than randomly rotating variations, can dramatically improve outcomes.
As privacy regulations continue to reshape digital advertising, contextual targeting is poised for a resurgence. However, the industry must move beyond the outdated notion that contextual means simple keyword matching.
I believe that by embracing these pillars, advertisers can ensure that contextual strategies aren’t just an alternative to behavioral targeting, but a stronger approach to deliver meaningful engagement and measurable performance.
The open web has a chance to enhance itself. The question is, will advertisers demand a contextual solution that’s built for the future, or settle for one muddling in the past?
