2026 DX Trends Report, Vol. 2
The top challenges facing enterprise brands
In the second installment of Contentstack’s series on digital experience trends, 15 marketing and digital leaders give their take on the toughest challenges that enterprise businesses will have to overcome in 2026.
I think it's the same challenge we saw in 2025, which is they struggle with what to do with all the disparate data sources. AI should surely help here but companies still need the vision and roadmap of what they want to achieve and what it will take.
I have to say, the biggest challenge is likely about maintaining brand momentum in a cautious economy.
Recent Fed announcement patterns signal a continued climate of uncertainty, where every rate adjustment triggers ripple effects on marketing budgets and brand investments. Budgets tighten, priorities shift overnight and yet creative expectations stay high.
If brands keep operating with static, campaign-based mindsets, they’ll struggle to keep up. The next era requires modular, adaptive brand systems that can scale up or down without losing continuity.
The brands that win will treat creative not as a cost center but as a system of ongoing momentum, built to flex with economic conditions.
In terms of marketing; trust. Old ways of measuring performance are being disrupted, and it's uncovering a lot of rot in the machines.
If marketers want to get buy-in for digital experiences that actually work, they must focus on building trust with their teams and with audiences. Doing what's right in an environment full of disruption often requires investing in projects with uncertain outcomes, and sometimes counter-intuitive strategies.
Reaching across silos to build trust, allies, and believers, will be critical work. And of course, knowing what the heck you're doing so those strategies pay off.
AI councils, responsible AI boards, and compliance teams are becoming gatekeepers — but often without enough technical grounding or urgency. This can lead to:
- Fragmented accountability: no clear ownership between IT, Legal, and individual business units.
- Innovation fatigue: front-line teams stop proposing ideas because approval seems impossible.
AI councils have been slowing everything down. Governance without velocity is a top enterprise risk now.
Connecting the actual value and long-term advantage of their product to the VERY REAL HUMANS who buy it, and are responsible for the outcome of shelling out lots of dosh for these solutions.
Enterprise brands can and need to think big but act "small." By that, I mean keeping the human (aka your buyer and customer) at the center of everything you do; the human touch, the human interaction and the human connection you get with smaller orgs that Enterprises seem to totally ignore once their ACV gets chonky enough.
Getting noticed! It's a crowded market, and there's always consolidation with the biggest players just getting bigger so you have to find a way to differentiate your brand.
Rising SaaS costs due to:
1) Margins thinning and boards getting more aggressive, which puts pressure on enterprise SaaS teams to do more with less, and ultimately the customer suffers.
2) Embedded AI features that no one asked for, but the rising cost of AI token usage is real. And companies feel the pressure from...again...their boards to add needless AI features that add no real value to the customer.
The toughest challenge isn’t upgrading the tech — though that requires focus, skill and a clear plan — it’s changing how teams work.
Enterprises need to modernize fast enough to stay competitive, but that means rethinking operations, not just systems. Building adaptive, AI-assisted workflows takes new tools and new habits, and habits can be much harder to switch.
The biggest challenge facing enterprise brands in 2026 isn't technology. It's internal alignment in a world where AI is completely reshaping how we measure marketing's value.
The marketing team can be deep into GEO and AEO while the C-suite is still stuck asking about click-through rates and MQLs — all while the product team and engineering are doing their thing. It's a recipe for strategic paralysis.
The real battle is translation. How do you convince a traditional leadership team that being the top result in an AI-generated answer is more valuable than a thousand random website clicks? How do you quantify the impact of being the definitive source that AI trusts?
This means building a new language of marketing metrics that speaks directly to revenue to:
- Prove how AI citations translate to market credibility
- Show how brand trust in AI engines drives actual pipeline velocity
- Connect seemingly abstract "AI visibility" to concrete business outcomes
The enterprise brands that crack this code will completely redefine their market position.
And cracking it requires more strategic storytelling than any marketing campaign, as it's a communication problem — not a technology one.
2026 digital experience challenges: 3 top takeaways
From a lack of brand relevancy and trust to an inability to turn data into meaningful stories and experiences, our experts shared their candid takes on the new (and not-so-new) pitfalls that are facing enterprises in 2026. Here are three recurring points that came up in our participants’ responses:
1. Internal alignment and speed-to-market continue to stand in the way of enterprise growth
The biggest barriers to innovation are not technological, but internal. Enterprise brands struggle with the complexity of their internal processes, requiring a focus on rethinking operations and governance to improve agility. Key friction points include misaligned priorities between leadership and frontline teams, and slow-moving AI review councils.
We believe that the way companies work has to change. Adopting new habits, tools, performance and evaluation cycles — that’s the real challenge that businesses must crack in order to get ahead.
2. The fight for brand resilience: Earning trust and differentiation in a skeptical market
In an increasingly crowded business environment where many brands look and sound the same, the core challenge is establishing differentiation while maintaining (or regaining) buyer trust. That’s a difficult tightrope to walk, especially when ongoing economic caution poses a discouraging effect to anything that’s not “safe.”
Brands must shift to being more human-centric to stand out, adapting their systems to flex with economic uncertainty and connecting their product value directly to the real needs of the skeptical human buyer.
3. The operational imperative: Unifying data and modernizing workflows for velocity
The biggest internal barrier to success is no longer the technology itself, but the enterprise's ability to unify disparate data sources, change ingrained work habits and operationalize new strategies (like personalization) at scale without sacrificing speed.
In short, modernization requires more than just system upgrades; there needs to be a fundamental rethinking of how we approach internal operations and workflows.
For more digital experience industry trends, predictions and insights, visit contentstack.com/resources.
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