Five lessons from Pyramid Global’s VP of Marketing, Evan Crawford, on standing out, building trust, and booking more business in the age of AI.
The group sales landscape is changing faster than it has in years.
AI can draft proposals in minutes. Meeting planners are doing more research before ever contacting a hotel. RFP response times are shrinking. Meanwhile, every property claims exceptional service, beautiful meeting space, and luxury accommodations.
So how do hotel sales teams stand out when every competitor sounds the same?
That question was at the heart of a recent InnSync Show conversation between Cory Falter and Evan Crawford, Vice President of Marketing for Pyramid Global Hospitality, who oversees marketing strategy for Benchmark Resorts & Hotels, the company’s independent collection.
While the discussion covered everything from AI to marketing attribution, one theme surfaced repeatedly: Hotels that know exactly who they are—and communicate it authentically—will outperform those trying to appeal to everyone.
Here are five lessons every hotel group seller can take from the conversation.
1. Stop Trying to Be Everything to Everyone
Every hotel wants more business. The temptation is to cast the widest net possible.
The problem? Generic messaging creates generic results.
“The ones that have a clear voice,” Crawford said. “They know who they are. They know what they need to be for the customer. They know who their customer is.”
That doesn’t mean turning away potential business.
It means leading with what makes your property different instead of trying to check every possible box.
Crawford shared an example of one of Pyramid’s resorts that welcomes families but doesn’t market itself as a family resort.
“We have a resort that is family-friendly,” he explained, “but I wouldn’t describe it as a family resort.”
That distinction matters.
Meeting planners aren’t simply comparing square footage and sleeping rooms anymore. They’re looking for venues that fit the personality of their event. Leadership retreats, incentive trips, executive meetings, association conferences, and creative off-sites all have different goals.
The clearer your hotel’s identity, the easier it becomes for planners to picture their event succeeding there.
As Crawford put it: “You can be present for every consumer without trying to be for every consumer.”
2. AI Can Write the Proposal. Your Sales Team Still Has to Win the Business.
AI is changing hospitality sales.
Tools are emerging that can pull rates, availability, meeting space, and proposal content together in minutes. Soon, responding to an RFP may take five minutes instead of forty-five.
That’s exciting—but it also creates a new challenge.
If every hotel is using the same technology, proposals begin looking remarkably similar.
Crawford doesn’t see AI as replacing salespeople. He sees it creating more time for them to do what technology can’t.
“Maybe you use your AI fulfillment as a starting point,” he said, “but then you add something personal to it.”
That extra layer could be:
- A personalized note addressing the planner’s priorities.
- A short video introduction.
- Recommendations based on similar events.
- Local insights the planner won’t find in a template.
AI should eliminate repetitive administrative work.
It should never eliminate relationships.
As automation handles more of the mechanics, the human touch becomes even more valuable.
3. Your Salespeople Are Part of the Product
Hotels spend enormous effort showcasing guest rooms, restaurants, pools, spas, and meeting space.
Many spend very little showcasing the people who actually make events successful.
That’s a missed opportunity.
Falter noted that planners don’t just want to know whether the ballroom looks beautiful. They want to know who’s going to help them execute the event.
“I want to know who’s gonna help fulfill that for me,” he said.
Crawford agreed, pointing out that personal branding has become just as important as property branding. “There’s nothing worse than a salesperson who is phony.”
Today’s buyers build trust long before the first site visit. They visit LinkedIn, watch videos, consume thought leadership content, and pay attention to whether a salesperson consistently provides value instead of constantly promoting their property.
The strongest sellers become trusted advisors ... not brochure distributors.
In many cases, Crawford observed, successful salespeople could change companies and bring much of their business with them.
Why? “It’s their relationship.”
That relationship often becomes the deciding factor when several hotels offer comparable products.
4. Every Extra Click Costs You Business
One of the most practical takeaways from the conversation had nothing to do with AI.
It had to do with forms.
Too many hotel websites make it surprisingly difficult to start a conversation requiring lengthy RFP forms that ask for dozens of details before a planner has even spoken with someone.
Crawford joked about requiring “a meeting planner’s blood type” before allowing them to submit an inquiry.
Instead, he suggested a much simpler approach. “Have an RFP? Attach it here.” That’s it.
Experienced planners can upload their documents immediately. First-time planners—or executive assistants tasked with finding a venue—can simply ask a question without feeling overwhelmed.
Reducing friction matters because planners have choices.
If your website feels like work, they’ll move on to another property or submit through a sourcing platform instead.
As Crawford summed it up: “Reducing friction should be the target.” Sometimes the fastest way to generate more leads isn’t spending more on marketing. It’s making it easier for prospects to raise their hand.
5. Relationships Are Becoming More Valuable—Not Less
With so much attention on AI, it’s easy to assume technology is becoming the competitive advantage.
Crawford sees it differently. “The core of what you’re trying to do is relationship building.”
That principle hasn’t changed. Only the tools have.
The best hotel sales teams will use AI to handle repetitive work so they can spend more time prospecting, networking, creating content, visiting clients, and strengthening relationships.
That’s especially important as inbound business evolves; more planners are researching independently, more buying decisions are influenced before an inquiry is ever submitted.
Sales teams can no longer afford to wait passively for RFPs to appear. They need to become visible experts by sharing insights, offering advice and answering questions.
It's about building trust before someone is actively shopping. Because when the opportunity finally arrives, the relationship already exists.
The Bottom Line
AI will change how hotels respond to RFPs, qualify leads, and support sales teams.
It won’t replace what has always closed the biggest deals: authenticity, relationships and trust.
As Crawford reminded us throughout the conversation, success starts with knowing who you are and communicating it consistently.
The hotels that win the next generation of group business won’t simply have faster technology.
They’ll have clearer positioning, more visible salespeople, fewer barriers between a planner’s first question and a real conversation—and the confidence to stop trying to be everything to everyone.
