Hospitality is a high-touch business, where every operational choice directly affects the guest experience. From front desk check-ins to housekeeping coordination and service recovery, the industry depends on people responding quickly and empathetically.
Technology has increasingly become the piece that helps teams deliver consistency at scale, and makes moments more personalized and predictable, helping operators better anticipate needs. Great go-to-market execution is where technology, people, and customer value intersect. In hospitality tech, that intersection is uniquely demanding, because the buyers’ risk tolerance is shaped by real-time operations and real-time guests.
When an enterprise hotel group replaces its property management system to Cloudbeds, it is not swapping out a tool. It is changing the operating system that runs the front desk, reservations, housekeeping coordination, billing, and the data that informs nearly every guest interaction.
“Credibility in hospitality isn’t just built through a great pitch or a great product. It’s more built through empathy and care with the properties and understanding their operations,” says Marta Perez, Head of Sales, Americas at Cloudbeds.
The operational reality behind every enterprise deal
Perez began her career at SiteMinder, a global hotel distribution and revenue platform, as a sales executive in London before relocating to the U.S. to help in the company’s effort to build a market from the ground up.
What made it especially formative is that it wasn’t “just” a sales job. When you’re starting a market from scratch, everything is sales and everything supports sales: your partnerships become brand awareness, your events are pipeline creation, your product feedback becomes win-rate improvement, and your customer success stories become the proof that unlocks the next tier of buyers. You’re building the playbook while you’re executing it.
That experience helped sharpen a point she still returns to today as a Head of Sales at Cloudbeds: hospitality buyers are never just buying software. They are committing to change, and in a business that operates 24/7, change is inherently disruptive.
“You’re selling into businesses that run 24/7 with very thin margins,” Perez says. “Any technology decisions that they make carry a lot of operational risk.”
Selling to a stakeholder map
Enterprise hospitality sales has grown more complex as ownership models, brand standards, and specialized teams have multiplied the number of decision-makers. “The buyer landscape has become a lot more complex,” Perez says, outlining the cast of stakeholders that can influence an enterprise purchase: ownership groups, management companies, brand standards, asset managers, revenue teams, IT, and finance.
That means the modern sales leader has to orchestrate alignment across stakeholders who measure value differently. Revenue teams may prioritize ADR and distribution performance, while finance pushes for cost controls and procurement discipline. IT focuses on security and integration while operations cares about uptime, workflows, and training. Brand teams may impose constraints that override local preferences.
Hospitality has been asked to modernize while still absorbing the aftershocks of disruption. Operators are expected to digitize processes, use data more intelligently, improve guest experience and explore AI, all while managing staffing instability and tight margins. That combination can breed skepticism about new platforms, even when the business case is strong.
Resilience that treats “no” as intelligence
Perez describes enterprise selling as an emotional endurance sport, one that starts with mindset. “The first one is real optimism, dealing with rejection, treating no as information, not as an identity,” she says.
Enterprise deals are full of non-linear setbacks: budget cycles slip, priorities shift, stakeholders change, and brand constraints appear late in the process. For top performers, rejection becomes diagnostic.
“No becomes more of what has changed, what risk are they seeing, who else do we need to get involved? What would it need to be true to move this forward,” Perez says. That framing keeps teams focused on learning rather than spiraling. It also creates space to re-enter accounts later with sharper insight into risk, timing, and internal dynamics.
Discipline that scales beyond individual talent
If optimism keeps reps in the game, discipline is what wins it. “In complex deals and in all sorts of deals in reality, the difference between average and excellent is often follow up,” she says. In her view, excellent sellers “ are relentless about next steps, timelines, and mutual accountability” That means stakeholder mapping, strong account plans, explicit next steps, realistic timelines, and recap emails that prevent drift. The goal is to reduce variance. Enterprise deals do not reliably close because someone delivered a charismatic demo. They close because the process is managed tightly enough to keep momentum through inevitable friction.
“My job as a leader is to build a system where great execution isn’t dependent on one heroic rep; qualification, account plans, and stakeholder alignment happen in a similar way every time” Perez says, calling it a non-negotiable. Scaling matters because hospitality GTM teams are often selling across geographies and ownership structures, where a consistent operating model is the only way to ensure forecast accuracy and repeatability.
Humility that earns trust in high-stakes transformations
The third pillar is humility, which Perez frames as a practical advantage. In the hospitality industry, trust is earned by listening well. “Not making it about the seller, but about the buyer,” she says. “When people are buying a product, they can smell ego instantly.” Good sellers “listen more than they talk, they ask better questions, they adapt to what the customer actually needs.”
That posture also invites the kind of candid feedback that helps teams surface objections early, navigate internal politics, and build a more credible implementation plan.
The shift to platforms, and what AI changes for leaders
Looking ahead, Perez believes enterprise hospitality is moving away from point solutions and toward platforms and interconnected ecosystems. “Our clients used to want the best-in-class for every stage of the guest journey,” she says. “Now they’re prioritizing fewer vendors, stronger integration across their stack, and a clearer ROI.” It’s a shift she sees firsthand at Cloudbeds, where groups increasingly favor consolidation, seamless connectivity, and measurable business impact.
Those expectations raise the bar for both vendors and sales teams: faster deployments, stronger support, more data transparency, and proof that the technology changes outcomes, not just workflows.
AI accelerates that shift on both sides of the table. For buyers, it raises the baseline for decision-making through forecasting, personalization, and automation, which means software is increasingly judged by measurable business outcomes. For sellers, it changes the mechanics of work. “We can do better research in seconds, we can better prioritize accounts, improve coaching, and use conversational intelligence to move faster” Perez says. At Cloudbeds, she sees AI working best when it helps with personalization and coaching.
Still, she does not buy the idea that AI can replace the most valuable part of hospitality selling. “I don’t think AI will replace the most valuable part of selling in hospitality because that goes back to a personalized journey, the trust and the relationship,” she says.
Her takeaway is that the industry must build AI-fluent teams that use automation to remove friction, while holding humans accountable for decision-making and trust. “Reinforce the fundamentals, qualification plans, stakeholder clarity, and then use AI for consistency and coaching and keep humans accountable for the judgment and the trust part of it.”
Follow Marta Perez on LinkedIn for more insights.
