by Cheryl Fosberry
Sales isn’t slowly changing. It already changed. In 2026, the most effective salespeople won’t just be good closers. They will be the ones who know how to adapt, prioritize, and build trust in an environment where attention is limited, and expectations are higher than ever.
At Jacaruso, we’ve been working remotely for nearly two decades and operating across several brands and hundreds of properties. This vantage point makes sales patterns apparent. The gap between average and high-performing salespeople is less about effort than about how they think, how they use technology, and how consistently they execute.
Here’s what actually separates the top performers.
Adaptability isn’t optional anymore
The sales landscape shifts constantly. Tools change, buyer behavior evolves, and demand fluctuates. The best salespeople don’t wait for stability. They adjust quickly, test new approaches, and move forward without getting stuck in how things used to work.
Resistance to change is one of the fastest ways to fall behind. What’s catching people off guard isn’t AI or automation, it’s the expectation that sales teams can be more strategic, more efficient, and more human at the same time.
Relationships still close deals
AI and automation speed up outreach, but real interaction creates trust. Deals move forward when buyers feel understood. The strongest salespeople are intentional about how they show up digitally. Their outreach is relevant, their follow-up is timely, and their communication reflects an understanding of the client’s business needs and goals.
Poor prioritization and generic messaging weaken relationships. The sellers who stand out treat every interaction as a chance to build credibility, even when it’s a short email or a quick check-in.
Data only matters if it drives action
Most sales teams have access to more data than they know what to do with. The top sales performers show restraint. They don’t chase every metric. They focus on the data points that actually move revenue: response times, conversion rates, segment performance, and pipeline health.
Instead of reacting at the end of the month, they adjust early. They notice patterns forming and make changes before results suffer. Data becomes a tool for decision-making rather than report card after the fact.
Strategic thinking beats chasing deals
Transactional selling is easy to spot and easy to ignore. The best salespeople approach their role differently. They think in terms of accounts, not just opportunities. They understand how decisions get made on the client side and provide solutions that align with longer-term objectives.
This approach takes more thought up front, but it pays off in stronger relationships, better retention, and more predictable revenue. Especially in uncertain markets, strategy outperforms speed.
Emotional intelligence shows up under pressure
Longer sales cycles, tighter budgets, and more competition mean pressure is part of the job. The salespeople who stand out are those who stay composed, listen carefully, and adjust with empathy. They don’t disappear after a setback. They stay engaged, consistent, and professional. Those skills matter more now than ever.
Technology should support sales, not replace it
Technology only helps when it’s applied with intention. Teams struggle when tools are layered on without a clear purpose or when automation replaces judgment. The strongest salespeople use technology to remove friction, not create distance.
AI works best when it handles the repetitive work and surfaces better information, allowing sellers to focus on conversations and decisions that require experience and context. When technology supports focus instead of noise, performance improves.
Remote-first is an advantage when done right
Relationships are maintained through consistency, not proximity. In fact, we often see remote-first sellers outperform because they’re forced to be more focused. Without the distractions of an on-site office or the illusion of productivity that comes with being visible, performance comes down to execution. Outreach happens on time. Follow-up doesn’t get delayed.
Remote and hybrid work aren’t trends anymore; they’re the baseline. What separates high-performing salespeople in this environment is discipline. The sellers who succeed remotely are organized, responsive, and intentional about how they manage their time. They don’t rely on being in the same building to stay accountable or productive.
At Jacaruso, this isn’t theory. It’s what we see every day. Remote-first works when it’s done with structure, focus, and accountability. Those are the teams that continue to perform as the industry evolves.
For owners and leadership teams, these traits are a clear signal of who can deliver consistent results in a market that doesn’t slow down. There is no single skill that defines salespeople who will succeed in 2026. It will be the ones who can balance strategy, insight, and human connection, supported by technology that helps them work smarter.
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Cheryl Fosberry is the Vice President of Sales for Jacaruso Enterprises. With 10+ years of experience, Cheryl helps hoteliers build sales strategies that increase revenue, expand market share, and deliver consistent results.