2026 is the moment of truth for go-to-market (GTM) organizations.
After two years of experimenting, it’s clear that AI has the potential to transform sales enablement. The organizations that succeed in turning that potential into concrete performance improvements will be the ones that race ahead this year.
To get the most out of AI, it needs to be woven into everything you do. From identifying high-value prospects and personalizing outreach to handling objections and closing the deal, AI belongs in every part of the sales process. Fragmented tools won’t get the job done. Instead, you need a continuous performance system: a virtuous loop in which every human action is prepared, analyzed, and improved by AI.
Going all in on AI means thinking about your role in a new way, even if you’ve already been experimenting with the tools. Here are five habits that will help you build an AI-first mindset and win more deals than ever before in 2026.
1. Never miss a signal
In sales conversations, subtle signals can sometimes be the most valuable. A buyer who mentions an upcoming deadline might need to place an order soon to stay on schedule. On the other hand, prospects without a clear timeline are probably not ready to take action.
contain messages hidden between the lines. But when you’re managing multiple deals at the same time, those indirect messages can be easy to miss. As a result, you risk moving too fast and damaging trust or waiting too long and losing the deal to a more aggressive competitor.
With Highspot Deal Agent, sellers stay on top of signals across your communication channels and content. Deal Agent draws on information from your CRM and buyer interactions to turn signals into informed next steps. Supported by AI insights, you’ll have the confidence to press ahead with urgent deals or move an opportunity to the back burner.
2. Make practice personal
Generic, one-size-fits-all practice won’t prepare you for every sales scenario. To manage distinct buyer personas and address their pain points, you need to personalize your approach. Your skill set is also unique — for training to be effective, it should be tailored to your role and current capabilities.
With AI role play, you can practice high-stakes conversations in a low-pressure environment, working through objections specific to the sale. Highspot Role Play takes personalization even further, connecting to your team’s content, messaging, and training to fine-tune exercises.
Successful sellers know feedback is key to improving performance. Highspot Role Play evaluates your practice sessions and provides instant feedback that maps to your team’s coaching and competency frameworks. This targeted approach helps you focus on improving the skills that matter most and accelerates sales readiness.
3. Train, execute, train again
Waiting weeks or months before putting training into practice is no longer an option for sales teams. AI is accelerating the pace of change, and what you learn today might be outdated just a few weeks from now.
By minimizing the time between training and execution, you can make sure you’re always working on relevant skills and sales plays. Highspot Role Play allows you to run through the sales conversations you’ll have later that day or week, as many times as you need. With instant AI feedback, you can keep polishing your performance right up until it’s time to take the stage.
Evaluation and feedback aren’t limited to your practice sessions. Meeting Intelligence helps you understand how well you applied what you learned during role play to real customer conversations and identify areas to work on before your next interaction.
To succeed in sales in 2026, learning and development need to be a continuous process. That loop is only achievable with a unified AI infrastructure. Today’s practice and tomorrow’s execution both provide valuable data for your AI system, leading to improved coaching and stronger results going forward. Sales leaders can see how reps are progressing and keep their teams on track with Highspot’s AI-powered scorecards and coaching analytics.
4. Trust in the data
Successful sales reps recognize that selling is more science than art. Intuition can’t compete with today’s machine learning algorithms that can turn large quantities of sales data into actionable insights.
Customers are also setting the bar higher. Your product might perfectly solve a customer’s needs, but they won’t just take your word for it. Buyers want proof that what you’re offering is the best solution, and they expect that proof in real-time. Failure to meet customer expectations and deliver accurate data can damage trust and cause deals to slip away.
When AI models are trained on your sales assets and conversational intelligence, they can surface the right data at the right time. Imagine pitching a medical device, and the buyer asks to see clinical trial data not included in your sales deck. An AI agent can quickly comb through your documentation and find the relevant materials without interrupting your flow.
5. Keep the human touch
AI is a valuable companion, but buying and selling is still a human pursuit. A seller who has a poor relationship with the customer will struggle to close the deal, even if their product is a good fit. In 2026, success in sales will depend on your ability to apply the technology with a human touch.
Empathy, storytelling, and building trust remain essential skills for sellers. AI coaching for sales shows you how to deploy these skills in conversations and calibrate them according to the buyer persona. AI can also help you create narratives that resonate with customers and clarify your value proposition.
Today’s B2B buyers expect personalized sales experiences. Highspot AutoDocs lets you create tailored pitches and custom proposals that address each buyer’s pain points directly with personalized text, charts, and images. Buyers feel valued and understood, and sellers get time back to focus on building relationships and closing deals.
Is your sales team ready to enter its Performance Era? Read our new eBook, The Future-Ready Seller’s Playbook: Turning Preparation into Performance.
