Customer Experience Leaders Share Their Top Challenges in 2026

Published Mar 27, 2026

11 min read

For customer experience (CX) leaders, digital experience drives business metrics like retention, cost-to-serve, and customer lifetime value. However, CX teams often inherit complex workflows and fragmented systems that weren’t designed with the customer or the frontline CX agent in mind.

Explore the challenges facing CX leaders and how Intelligent Agreement Management (IAM) can help CX organizations reduce friction, improve compliance, and scale experiences. Throughout this eBook, we incorporate real-world perspectives from CX executives managing onboarding, compliance, content resources, document workflows, and omnichannel customer journeys.

Here are the key takeaways we found:

Complexity and unclear navigation create friction
Balancing security and customer experience is top of mind
Legacy processes, lack of integration, and content sprawl make it difficult to scale
AI and automation unlock better CX experiences

Read on for more details and insights from CX leaders.

CX leaders must navigate an increasing number of complexities in today’s fast-changing environment. Rising customer expectations, rapid advances in technology, data overload, and pressure to demonstrate measurable business impact all demand constant adaptation.

Balancing personalization with privacy, aligning teams around the customer, and delivering consistent experiences across channels have become important priorities for modern CX leaders. The CX journey has many owners across various teams and departments, reinforcing the fact that CX leaders must often orchestrate—and not solely own—the journey.

"I really look at digital as a piece of the journey—not the whole journey. The most important thing is understanding all the customer touchpoints, how they fit together, and what people are actually saying about the experience across channels."
Director, Customer Experience, insurance industry

Let’s take a look at some of the challenges CX leaders and teams face.

From a customer success standpoint, onboarding friction doesn’t just impact conversion; it sets the tone for the entire relationship between a business and its customers. Industry data shows that 66% of people say they’d abandon an interaction entirely if a form is too hard to complete Opens in a new tab. Yet many onboarding experiences remain overly complex.

Customers are often asked to manage lengthy, confusing navigation structures, re-enter data, wait on manual steps, or determine which user journey pathway applies to them, often across multiple channels.

As a director of digital experience and content strategy at a financial services company shared:

“A lot of the core actions are actually just getting users into their accounts. You can be a plan member, a sponsor, or an advisor—and a huge part of our content work is figuring out who’s who and routing them to the right place.”
Director, Digital Experience Strategy, Wealth management

Another CX leader described the reality this way:

“Taking clients through our agreements can be anywhere from 20 minutes for someone really savvy to several hours over multiple phone calls. And a lot of drop-off comes down to the complexity of what they’re being asked to sign.”
Senior Director, Product Management, Debt settlement company

When onboarding becomes a barrier instead of a jumping-off point, customers disengage.

Specifically, one leader shared this insight:

“A lot of our focus was on simplifying the experience and anticipating the need in the moment. People don’t always trust that you’re telling them the right thing, so they leave the platform to Google answers. We had to bring trusted information into the experience so they didn’t feel the need to go somewhere else.”
Director, Customer Experience, Insurance

Disengaging creates churn risk before customers have a chance to experience the product or service.

One of the most underestimated sources of CX friction is poor navigation and labeling. Internal teams often default to internal language, with wording that makes sense organizationally but not experientially.

As explained by a director of digital experience strategy in wealth management:

“Our marketing teams took a stab at writing navigation labels, and in user testing, it did not resonate at all. We think of it so much internally, but it just didn’t work for customers.”

User testing consistently revealed that customers were getting stuck early in their journeys, often at the very first click.

“Across all of our websites, people told us they couldn’t find what they were looking for. That’s not an end-user problem—that’s a content and navigation problem.”

On the internal side, having too much content can result in operational inefficiencies:

“A lot of the sites we’re moving have been around for five-plus years. The hygiene of that content is not great. We have to decide: Do we remove it, move it as is, or completely overhaul it?”

At scale, these decisions become operational bottlenecks. Without centralized systems and reusable components, teams are forced to rebuild the same tools repeatedly.

“We were building the same features on 17 different websites. The real win now is building once and letting everyone benefit.”

There is an organizational cost of this fragmentation, according to one leader:

“We have a lot of people executing, but not necessarily an in-sync experience. No unified digital strategy, no on-brand execution. That’s not unusual in an immature digital organization, but it slows everything down.”
Director, Customer Experience, Insurance

Poor content creates problems for both customers and internal teammates. For CX leaders, this reinforces a key lesson: Information architecture is experience design, not just a content exercise.

Balancing security and customer experience is top of mind

CX teams operate at the intersection of experience and risk management. They are responsible for guiding customers through secure, compliant processes—sometimes involving sensitive data—without overwhelming them.

Two CX leaders from the insurance sector highlighted the importance of intentional friction in these moments:

“I know security adds friction, but the question is whether it’s healthy friction. You can convince people to do more, like multi-factor authentication, if they understand it’s to their benefit.”
—Director, Customer Experience, Insurance

“We handle a lot of personally identifiable information—Social Security numbers, credit card information. Our goal is to keep both agents and end users inside secure systems, because once information lives outside the core platform, risk increases fast.”
—Senior Director, Product Management, Debt Settlement

At the same time, 58% of organizations fear that stronger fraud prevention will increase abandonment, creating tension between security and CX.

Without embedded identity verification and automated compliance, audit readiness suffers, errors surface late in the lifecycle, and trust erodes when customers are asked to repeat or re-verify information.

Lack of integration, legacy processes and content sprawl make it difficult to scale

CX and support teams frequently juggle multiple systems and browser tabs, manual document parsing, quality assurance, and context switching while chatting live with customers.

“It’s a lot of searching, a lot of context switching. You might be on the phone with a client while also pulling up creditor information, payment schedules, and documents across different parts of the system.”
—Senior Director, Product Management, Debt Settlement

This complexity slows resolution times and increases error rates. Legacy digital environments often reflect years of incremental growth rather than intentional design. As a result, CX teams and customers alike must navigate outdated content and duplicated experiences.

83% of CX leaders with more advanced agreement management solutions believe it helps them achieve their customer support and digital self-service goals. Operational efficiency is foundational to CX success.

As organizations grow, onboarding and document workflows often become harder to manage.

A CX leader shared their experience:

“We’ve made our processes more difficult than they need to be. Every time there’s a regulatory change, it’s a chain reaction—legal, design, engineering, QA, republishing.”
—Senior Director, Product Management, Debt Settlement

Hard-coded workflows and static documents make it difficult to respond quickly to regulatory updates, launch new programs or markets and maintain consistency across hundreds of document variations.

CX teams feel this pain most acutely when process delays prevent customers from moving forward with their onboarding or troubleshooting needs.

Examining the right metrics with regard to operational efficiency is crucial too. According to one CX leader:

“One of the best shifts I’ve seen is moving away from measuring call duration and focusing instead on problem resolution—did we actually solve the customer’s issue, and did we do it the first time?”
—Director, Customer Experience, Insurance

The solution: how AI and automation can help

AI and automation are transforming how organizations deliver customer experiences. Together, these capabilities enable faster, more personalized, and more secure interactions by streamlining processes, reducing friction, and ensuring the right access at the right time. When applied strategically, AI and automation help organizations not only meet rising customer expectations but also unlock more consistent, efficient, and trusted CX outcomes.

AI and automation unlock better CX experiences

CX leaders are increasingly focused on self-service, speed, and proactive insight. As one CX leader from the financial services space shared:

“Our clients manage their financial wellness after hours. Giving them the ability to self-serve is both a better experience and a cost reduction for us.”
—Senior Director, Product Management, Debt Settlement

When thoughtfully applied, AI and automation are transforming how organizations deliver customer experiences. For CX leaders, the value lies not in novelty but in removing friction and scaling consistency.

Here’s how one team is using AI behind the scenes:

“We piloted an AI publishing assistant that gets us about 50–60% of the way there when migrating webpages. That alone helped us meet extremely tight 90-day timelines.”
—Director, Digital Experience Strategy, Wealth Management

On the front end, AI improves discoverability and comprehension:

“We’ve embedded AI-generated summaries, read time, and even an AI glossary because financial terms can be intimidating, especially for first-time retirement users.”
—Director, Digital Experience Strategy, Wealth Management

AI-powered tools, personalization, and content intelligence reduce cognitive load for customers while helping CX teams guide next-best actions more effectively. Another CX leader expressed appreciation:

“AI saves an insane amount of time. I’m in it almost every day—competitive research, CX research, informing big initiatives. You still have to be careful and source everything, but the efficiencies are incredible.”
—Director, Customer Experience, Insurance

According to recent Deloitte research, 49% of organizations with advanced CX capabilities outperform their strategic goals, driven by automation, real-time data, and personalization.

Speed and conversion acceleration: reducing drop-off in onboarding

Automated onboarding reduces friction by pre-filling forms with known data, embedding identity verification directly into workflows, and enabling e-signature without channel switching.

Organizations that minimize friction see 31% lower deal abandonment and 83% faster account opening.

From a CX lens, faster onboarding means faster time-to-value and fewer stalled customers who require manual follow-up.

Security, compliance, and auditability by design

Rather than adding security and compliance features as an afterthought, modern IAM embeds security and compliance into every step of the journey. One CX leader shared:

“If it’s outside of our core CRM, it’s not readily visible. Bringing everything in-house gives us visibility across the entire client lifecycle.”
—Senior Director, Product Management, Debt Settlement

Building this thinking into systems from the beginning reduces audit risk for businesses while simultaneously creating trust and transparency for customers.

Operational efficiency through integration and frictionless omnichannel experiences

For CX teams, integration is not a technical luxury; it’s an experience multiplier. Results of integrated systems include fewer errors, faster activation, and more time for CX team members to focus on outcomes.

Additionally, adaptive, mobile-friendly workflows allow customers to complete actions without switching channels or waiting for an agent.

IAM-powered omnichannel journeys ensure consistency, accessibility, and professionalism across every interaction.

So, how can CX organizations get started implementing solutions to the challenges they face? Let’s take a look at some next steps.

Next steps for CX and digital experience leaders

Shadow frontline teams. Assess both top performers and new hires to uncover friction in real-world processes.
Audit onboarding and agreement workflows for manual steps, handoffs, and compliance gaps.
Enable self-service tools to reduce support load while improving CX.
Invest in configurable IAM to support AI, automation, and rapid change. Specifically, leverage Docusign IAM for CX to unify identity, agreements, and customer journeys.

Docusign IAM for CX

Streamlines application processes with prefilled data, conditional logic, and reusable templates
Reduces fraud and simplifies compliance with built-in identity verification
Speeds execution with mobile agreement review and signing
Aligns teams with collaborative agreement workflows and version control
Automates next steps across connected systems with no-code workflows and extension apps

To learn more, visit our Customer Experience solutions page.