Challenges

Complex, Rapidly Evolving Product Portfolio: Cloudflare’s 30+ solutions required sales reps to stay constantly updated on technical specs and value messaging, which was overwhelming without structured support.

Inefficient Coaching & Enablement: Sales leaders struggled to reinforce training and replicate top-performer behavior across a large, globally distributed team.‍

Fragmented Content Delivery: Previous vendors failed to deliver relevant, timely insights in-meeting, leading to missed opportunities and inconsistent messaging.

‍

Solutions

Real-Time Conversation Intelligence: Aircover delivered contextual content mid-call based on live dialogue, helping reps respond to objections, surface value points, and pivot based on buyer cues.

Role-Based Dynamic Playbooks: Tailored content views for Solution Engineers, AEs, BDRs, and CS reps enabled precise support across functions, aligned to sales methodologies.

Integrated Insights & Automation: Post-call recaps, auto-sharing, and Salesforce auto-field mapping and data sync created a custom system to track what messaging and content impacted pipeline outcomes – and why that messaging won.

‍

Outcomes

Positive Sales Milestones: A mid-market team using Aircover hit their LOP target for the first time in 18 months.

Massive Rep Efficiency Gains: AI-assisted enablement drove $2M in rep productivity gains in a single month.

High Messaging Adoption Across Teams: 5,000+ in-meeting content views within the first month; internal demand surged from previously hesitant teams.

‍

Case Study Highlights

1. In-Meeting Enablement Drove Immediate Engagement

Cloudflare logged over 5,000 real-time content views within the first month, showing rapid adoption and active rep engagement during live customer conversations.

“As they’re talking, when a subject is mentioned in one of the cards that we've loaded, that card shows up in that window… and it’s auto-generated. They don’t have to do anything. It’s completely seamless. And it has really changed how we do business in the particular groups that we've rolled it out to.”
– Tracye Shaw, Head of Enablement Strategy & Operations, Cloudflare

2. Rep Productivity Surged by $2M in One Month

With Aircover’s in-call guidance and automated post-call workflows, Cloudflare saw $2 million in rep efficiency gains – a clear signal that deploying real-time enablement isn’t just a nice-to-have, it's a must-have on the path to maximizing revenue.

“The rep efficiency gain last month was $2 million. They’re spending less time searching for answers and more time selling. We’ve seen a huge shift in how fast they can respond, how confident they are in conversations, and how consistently they follow up – it’s made a tangible difference in productivity.”
– Tracye Shaw, Head of Enablement Strategy & Operations, Cloudflare

3. Sales Milestones Achieved for the First Time in 18 Months

After implementing Aircover, a sales team that had missed targets for 18 months straight finally hit their line of product (LOP) goal, demonstrating the tangible impact of AI-driven enablement on sales outcomes.

“For the first time in a year and a half, that particular team hit their product, their LOP target. That was the first ever for them. We had tried other vendors before, but nothing gave them what they needed in the moment. This wasn’t just a small win – it was a breakthrough moment that proved how much the right tool can change performance.”
– Tracye Shaw, Head of Enablement Strategy & Operations, Cloudflare

‍

Key Takeaways

• Just-in-Time Enablement Beats One-and-Done Training: AI-delivered content during live conversations reinforces learning and improves performance where it matters most – in front of customers.
• Role-Specific Intelligence Increases Adoption: Customizing content by team function and methodology accelerates rep ramp and improves usability.
• AI Isn’t About Replacement – It’s About Amplification: Cloudflare’s approach focused on enhancing reps, not replacing them, leading to scalable, repeatable success.