In our final #Womenterpise event of the year, we brought together sales leaders from the fastest-growing AI companies in NYC to share their top tactics on the front lines of selling cutting-edge AI products, including:
When asked how selling AI compares to other SaaS products historically, the panelists agreed: it’s both similar and different. Here’s what we learned:
AI products evolve at an unprecedented pace, creating a unique challenge for sales teams.
“The pitch you gave last week might not apply anymore.”
Sales teams must adapt quickly, as products improve under their feet, often influenced by feedback from customers themselves. This dynamic creates a learning curve not just for sellers, but also for buyers, who may struggle to keep up with these rapid advancements.
“We’re learning the product’s limitations from our customers. They’re teaching us what works and what doesn’t. Customers are surprisingly willing to roll up their sleeves and collaborate. They know this space is evolving and are more forgiving than you’d expect.”
This willingness to experiment presents both a challenge and an opportunity: sellers can shape the narrative with early adopters, but they also need to guide buyers through AI's unknowns.
AI sellers often need to meet buyers where they are in their understanding of the technology’s capabilities or ROI.
It’s important to start with clear use cases: “We overcomplicate things when we present AI as a magical solution that can do everything. Start simple. Show what’s possible, then expand.”
The panelists emphasized that selling AI successfully involves tailoring the sales conversation to the buyer's familiarity with the technology to build trust and confidence. Additionally, sales teams must address the cultural shifts AI adoption brings to organizations, such as high levels of change management and new decision makers entering the scene such as chief AI officers.
Despite AI's complexities, the core principles of sales—discovery, multi-threading, close planning, etc.—remain foundational. See all of our sales playbooks on these fundamentals here.
“Ask customers the hard questions…early: What could get in the way of your AI journey? What challenges are you anticipating? These conversations uncover unique needs and obstacles, setting you up for success.”
Balancing traditional sales techniques with AI’s unique challenges ensures sellers don’t lose sight of what traditionally drives deals forward. Most importantly, tailoring the approach to specific sub-verticals and pain points is essential for addressing buyer’s unique needs effectively. A few key tactics:
Automation is a frequent topic in AI sales conversations, but the narrative is shifting.
“Customers see tools like ChatGPT Enterprise as investments in their workforce, not replacements. And employees now expect these tools to augment their jobs and boost productivity…AI is not going to take everyone's job, it is going to take the jobs of those that don't know how to use it.”
The panelists emphasized that companies embracing AI see it as a way to empower their teams rather than eliminate roles and the key is to help customers view AI as an asset for workforce enhancement.
If you’re an early-stage enterprise founder or operator — connect with us directly to chat about anything GTM or check out our events page to stay in the loop on all things happening in the Work-Bench community.
