One clear takeaway from the September conference circuit — highlighted at Dreamforce, Sistas in Sales, SaaStr, and Inbound — was the importance of staying ahead of the AI curve when selling. Sales reps aren’t just riding the AI wave; they’re leading it by engaging directly with customers, understanding where they are in their AI adoption journey, and helping them realize the benefits. Even as some customers are still catching up, these reps are out on the front lines, guiding them through the transition and highlighting the value AI can bring. Clear communication and consistent updates are essential for bridging this gap and ensuring customers understand the value of AI advancements.
Rapid Technological Change in Sales
Sales professionals have never had to absorb information as quickly as they do now. Over the past decade, sales and marketing technologies have grown exponentially. According to Salesforce’s State of Sales, 89% of sales professionals report that they have increased their use of sales technology over the past ten years, with 72% stating that AI tools have significantly enhanced their ability to understand customer needs. This is where embracing advanced technologies can make a significant difference. NVIDIA's executive insights emphasize that adopting AI early leads to big improvements in efficiency and customer satisfaction. This highlights the importance of actively using AI to stay competitive.
Staying Informed on AI and Tech Developments
With AI rapidly changing how we work, missing a key presentation, conference, or product release can feel like falling behind. Staying informed is crucial, especially for sales reps who travel frequently. To maintain an edge, reps can leverage podcasts, bite-sized newsletters (Axios AI is a great resource), and AI-driven content summaries. This challenge applies not only to sales professionals but also to their customers.
Daily Updates to Eliminate Surprises
At TigerEye, our comms team uses PR software and ChatGPT to share daily AI and tech headlines in Slack, keeping everyone updated on the market. This helps the dev team see the latest releases, test new models and make quick decisions while enabling sales teams to stay current on industry trends and emerging technologies, engage customers with up-to-date knowledge and make more strategic, timely decisions.
Sales Leaders’ Role in Product Development
This will vary from company to company, but it’s wise to have sales leaders be part of tech discussions. By engaging with the CTO, developers, and Go-to-Market (GTM) teams, they gain valuable insights into product development and the roadmap. For example, in selling GTM software, having veteran in-house experts guide functionality is a key resource. This allows sales leaders to preview upcoming features, helping customers envision future benefits and positioning the company as an innovator.
Position offerings within the broader market
By combining internal project knowledge with industry news, sales leaders can contextualize their company’s offerings within the broader market. The more informed sales leaders are, the more they can help their teams sell proactively. Leveraging internal insights and industry trends enables them to paint a complete picture for customers, painting future potential. This approach helps customers make informed decisions, building trust and long-term loyalty. The goal is to equip sales leaders with a broad understanding of both the product and the industry, so they can guide customers through AI’s transformative impact.
Stay Focused on Customers Amid AI Hype
It’s important to remember that where a sales professional is at in their AI learning journey may not be where their customers are. They might still be learning about what AI can do, while sales reps are already on to the next big thing. That gap can be tough to navigate, and it makes clear communication essential. Explain concepts in straightforward terms, share regular updates, and never assume customers are already on the same page — because more often than not, they aren’t.
Transparency also plays a huge role in building trust, especially when AI is part of the equation. According to Gartner, by 2028, 60% of seller work will be executed by Generative AI technologies, making transparency even more critical as AI becomes more integrated into sales processes. Customers deserve to know when they’re interacting with AI, as this transparency reduces skepticism and fosters trust, and it is quickly becoming a standard in the industry.
For example, Salesforce has taken a proactive approach: their AI assistant, “AI Agent,” signs outbound emails with a simple message like “Generated by Sophie, Sak’s AI Agent.” This kind of disclosure helps customers feel informed and comfortable, reinforcing trust instead of leaving them with questions. Worth mentioning that TigerEye used ChatGPT 4o with canvas to easily make citations throughout this post, help with headers and grammar review.
Helping Customers Justify the Investment in AI
With emerging technologies like AI, budgeting becomes a new challenge — often requiring a dedicated line item. Establishing a deeper understanding of what these technologies solve, and how they save time, money, or reduce risk (ultimately the only reasons people make purchases) becomes harder to prove because companies are starting from square zero. Unlike mature products where ROI might be well-documented, AI requires careful conversation and education to help customers build a case internally. Sales reps need to connect the dots between what the technology does, how it aligns with customer goals, and why it justifies the investment. This foundational work is critical to getting customers comfortable enough to budget for AI solutions.
In a time when AI can make or break customer relationships, clear communication and transparency are a sales reps best allies. Stay curious, keep learning, and remember — your knowledge is not just for you, it’s for your customers too. Keeping them in the loop builds trust, and trust is the foundation of every strong sales relationship.
Anna Randall is a seasoned sales leader with 15 years of experience in manufacturing and tech. She has excelled in various roles, from inside sales to leading successful teams at companies like Autodesk, Eaton and Oracle. Anna's true passion lies in teamwork, whether it's collaborating cross-departmentally or mentoring others. Outside of work, she dedicates her energy to family, enjoys cold weather, and listens to Taylor Swift.
