The objective

When we started, there were almost 6,000 hotels in the Hilton portfolio. Today, I believe that number is closer to 8,000. Migrating each individual hotel’s site using a new headless CMS allowed us to reimagine property content as reusable and shareable components.

A massive cross-functional endeavor

The all-hands-on-deck effort took partnership from every corner of the enterprise:

• Agile product team (pod)
• UX, UI and research
• Content operations
• E-commerce, our key stakeholder
• Freelance and contract copywriters
• Project managers

The scope of the project introduced me to people and orgs I wouldn’t have met otherwise, and resulted in lasting connections — so valuable in a global corporate environment.

Content governance, copywriting, and editing

I inventoried and audited the existing website and content sources, looking for areas where we could rely on our property information manager (PIM) to supply content. I facilitated the creation of new descriptive copy where structured data wouldn’t fit. The PIM was full of good info — but since many of the fields were open-text, the data needed to be cleaned up before it could be used.

To create the new descriptions, I led a team of 4 – 6 freelancers (flexing with workload) through a series of sprints. Using our research and my knowledge of best practices, I created writing guidelines and trained them to identify key selling points by using personas and desk research, as shown:

With the help of partners on the content operations team, I edited the copy and packaged it for batch import every other Friday for several months. By my back-of-a-napkin calculation, I oversaw the creation of at least 20,000 pieces of content.

Content lifecycle and stakeholder management

Hotel stakeholders were understandably cautious about all the changes. I communicated regularly and openly with the e-commerce manager and gave her thorough documentation so she could to respond to pushback and help them trust the process. She and her team worked with the hotels to clean up their PIM info and meet requirements for new content. Together, we were able to resolve issues quickly and stay agile.

I hosted workshops at key phases to explain new features and help the teams responsible for maintaining the sites minimize content debt. With access to the data that informed our design decisions, they were able to triage change requests more efficiently and prioritize their backlog.

Bringing bespoke luxury to the web

Our final obstacle to decommissioning legacy Hilton.com was a group of hotels with complex content needs. Once we’d migrated the other 99% of the hotels, I turned my attention to these.

• Luxury hotel content migration

• Refreshing optimizations for hotel website

• Solving hotel booking challenges together

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Objectives

Loyalty is critical to hospitality business and Hilton Honors is one of the biggest hotel loyalty programs in the world. To support evergreen goals of increased member occupancy percentage and revenue, loyalty messaging reaches users at just about every touchpoint, aligned to these themes:

• Acquisition: encouraging users to join for the benefits (both real and perceived)
• Engagement: encouraging members to take advantage of the program
• Recognition: celebrating members and rewarding their engagement

What I did

Writing for this experience took a careful balance of push and pull, and figuring out when to lean into each theme. Conveying those sentiments in a scannable interface, while explaining the complicated algebra of points and miles, was another challenge.

My framework emphasized

• centering the member “choose the benefit that suits your style”
• sensory, active terms designed to excite “Swipe, ride, drive, dine, and fly”
• community and exclusivity “As a Gold member, you get”

Page-by-page

Getting to the Points with content design

Condensing more than a dozen pages of repetitive content into a tidy one-page overview.

Simplifying loyalty program perks

Trying a different way to work with stakeholders helped balance business requirements and user needs.

Helping employees use their benefits

Full-time employees at Hilton get an allotment of discounted room nights to use and share with friends and family. But there are rules. I made them easier to navigate and understand.

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What’s included

• Background explaining what has changed and why
• Objectives for the content and its intended audience
• Content requirements including character count and terms to use or avoid
• Best-in-class examples and examples that don’t meet requirements
• Decision framework for approving and implementing changes
• Rubric for evaluating quality and value

Meetings and events

Golf

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The program covers initating and planning, budgeting and scheduling, and change and risk management, concluding with a capstone project.

The capstone requires learners to manage a real or made-up project and is peer-graded on seven artifacts:

• Project charter
• Work breakdown structure (WBS)
• Sequence
• Schedule
• Budget
• Risk assessment
• Responsibility assignment matrix (RAM)

I created a full-blown Gantt chart, budget spreadsheet, a RACI with dropdowns, plus a WBS and sequencing diagram in Miro for a yearlong celebration of my imaginary company’s 40th anniversary. I may have committed some scope creep with the scale of my submission, but I’m excited to apply what I learned to future content strategy projects.

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While we were optimizing our SCA experience, a product owner on the payments program team reached out with a separate request to review an FAQ page that had been created to explain payment verification emails some years prior. These emails were no longer being sent: Should we do something else with the page or just delete it?

My stance on FAQs has softened over the years because of use cases like this one. Since SCA happens via the user’s credit card provider, our options for clarifying and reassuring within our own UI were limited. Plus, we had recently expanded digital payment methods with more enhancements planned.

When I considered intuitive places to talk about payment security, my next thought was almost always “OK, but who will see it?”

So I redesigned the page with real frequently asked questions.

Why it works

• Translates complex concepts into plain language.
• Content is search-friendly and LLM-friendly.
• Content is legally compliant (after only one round of review!) and consistent with brand tone of voice.
• Anchor navigation and semantic headings allow for further expansion.

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What is the problem you’re trying to solve?

I’ve asked this question so many times, it’s become a catchphrase. But when stakeholders approach with ready-made solutions (and artifacts, sometimes!) getting to the root of the issue can reveal a different approach.

One hotel requested a feature they had on their self-hosted microsite. They wanted to replicate it on their branded site. We knew the problem the hotel was trying to solve: they wanted to make it easier for guests to book ancillary services, like spa treatments and restaurant reservations.

My team wanted to solve the same problem, just not in the same way. We knew at our phase of the journey users are seeking information, so we needed better ways to share it. The hotel’s solution presented a lot of risks: technical complexity, scalability, security, and potential operational challenges at the hotels. There was also another team working on an enterprise initiative to solve the problem.

This was a design opportunity. With our research partner, I hosted a workshop with all kinds of stakeholders: developers, product managers, delivery managers, designers and researchers working on related efforts.

What we wanted to do

• Acknowledge the hotel’s challenges and demonstrate how we are working to address them
• Understand user perceptions and behavior 
• Learn where business and user needs intersect 
• Collaborate and share information with other relevant teams 
• Strengthen relationships with cross-functional partners through shared ownership of design and product decisions

What we accomplished

From interviews our researcher identified some opportunities to improve the user experience. The team was able to create and implement those quickly and focus on big priorities. We got the insights we needed to take to the hotel partner, so the product manager could help them understand why we couldn’t do exactly what they asked. Bonus: they were excited to learn about the upcoming enhancements. These impacts don’t always translate immediately to dollar signs, but building relationships with partners and trust with stakeholders can pay dividends in the long run.

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At a large organization with many teams creating content, consistency can be a challenge. Our team designed the website and app products, but a lot of the words come from systems and from writers on other teams. Sometimes they come from UI/UX or product managers or developers. We needed a home for the style guide that anyone publishing on a digital platform could access, not a collection of forwarded PDFs that would vanish at the whims of the data retention policy.

Inspiration on the run

A guest on Kristina Halvorson’s Content Strategy podcast mentioned that her team used a “white-label Grammarly” to automate their style guide and I knew that was exactly what we needed. Unfortunately, I was on a run so I forgot about it almost immediately. But I later attended the Confab content strategy conference, where WRITER was a vendor! My memory was refreshed.

Making it happen

I’d barely unpacked my bags before I started researching WRITER and comparable products. When I was sure I wanted to proceed, I made the case to my leadership and pitched the product to my peers on other teams. That was the easy part. As a newer manager, I got a crash course in procurement from statements of work to security review.

Soft-launched in late 2022, the style guide

• covers brand and marketing guidelines
• defines industry vocabulary
• sets standards for readable, usable, and accessible content.

Users could submit questions and suggestions via Airtable, and my team and I regularly deliberated on what should be included as products evolved and new programs launched.

Finding new use cases

In 2024, we expanded our relationship with WRITER to include its generative AI features for quicker content ideation, creation, and editing. We also introduced guidelines for internal-facing products that require specialized vocabulary and a more professional tone. These guidelines were socialized with product and business partners to help them better understand our methods.

Successfully scaling style

From June 2024 – June 2025, WRITER scanned more than 2 million words for our teams and offered suggestions for style, clarity, and adherence to brand guidelines. It has generated or rewritten 1.4 million words, saving countless hours.

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Content design is identifying what users need and determining what content best suits that need. Sometimes that content is a PowerPoint presentation. This deck has inspired many “Aha!” moments among partners who are working with content designers for the first time.

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Throughout the website’s booking experience, chips highlight key attributes. One, simply labeled “New,” appeared in hotel search results next to new hotels. Business requirements limited the qualifying criteria to hotels built within a certain timeframe. A search filter for “New Hotels” used the same criteria.

A chance to enhance

Given the portfolio’s recent growth, we recognized that “New” may not be descriptive enough, and qualitative research confirmed our suspicions. Revisiting “New” would be the first step in clarifying these chips and filters for the user.

To start, I mapped out the different types of “new:”

• just-built hotels
• hotels that had been newly converted from other brands
• hotels that had been reflagged within the portfolio
• newly acquired hotels
• and so on.

I pitched “Newly built” as the third variant to test against “New” and “New hotel” (this option was for parity with the aforementioned filter)

Clear language makes a measurable impact

In a win for clear language, the “Newly built” variant increased clickthrough by 2.5% and boosted revenue per visitor by 1.5%. This revealed opportunities to experiment further and find better ways to highlight the many, many other types of “new.”

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The original site for this massive Hawaiian resort merged its official Hilton.com presence with a 128-page “microsite.” After auditing and inventorying the content, I was able to condense the site to about 27 pages. I could have gone even leaner, but wanted to assure the stakeholder that I wasn’t taking anything away — just putting things together where it made sense. 

As the platform grew and alongside it the library of available components, the time came to revisit early adopters to the platform to refresh and enhance. When we had the bandwidth to reevaluate the site’s structure and content, I had the numbers to confirm my suspicions. There were too many subpages, and people weren’t visiting them enough. Eliminating some of the pages would reduce content debt and operational effort. Even better, it would improve the UX.

Using Adobe Analytics, I made a case for better optimizing the site for mobile users, who make up about half the site’s traffic.

Low effort, high-impact optimizations

• Streamlined navigation and reduced clicks by merging five subpages into their parent pages
• Moved the hero images below the introductory copy, so users could find information before scrolling
• Component changes that enabled the use of bulleted lists and icons to make content more skimmable

Presenting these changes with the accompanying data and rationale helped the stakeholder feel like part of the design process, and helped him articulate the decisions and their benefits to his own leadership.

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