At the heart of modern sales enablement is a question we all face: How do we scale impactful coaching while staying ahead of what our reps need? Coaching at scale is no longer optional—it’s essential. For us, the answer lies in moving beyond reactive training toward predictive enablement, an approach grounded in data, automation, and continuous development.
Our implementation with artificial intelligence (AI) tooling at Justworks has been a game-changer in building what we call our AI-First Revenue Engine. It’s not about replacing the human touch—it’s about augmenting our enablement efforts to be more timely, relevant, and scalable. Here’s how we did it:
1. Start with intentional design. We began by mapping our core revenue motions to the competencies needed for success at each stage. This gave us a clear view of where to embed AI coaching and automate repetitive tasks such as follow-up nudges, session recaps, and calendar invites for peer learning.
2. Automate the admin, amplify the coaching. Our AI tooling system syncs with our customer relationship management (CRM) system and rep calendars to identify key opportunities for coaching intervention—whether it’s after a deal stalls or when new product messaging rolls out. From there, it automatically delivers personalized AI coaching nudges that simulate manager feedback and reinforce key skills.
3. Shift from lagging indicators to leading ones. Reactive enablement waits for the pipeline to slip. Predictive enablement anticipates it. Our AI tool’s insights allow us to track knowledge gaps before they show up in lost revenue. We proactively analyze trends across team performance and deal progression to offer content, reinforcement, or live coaching. It’s like having an enablement radar constantly scanning for potential headwinds.
4. Stay rooted in your mission. By empowering our reps to show up sharper, faster, and more prepared, we’re ultimately serving our customers better. We don’t just track AI usage—we measure impact. AI is making us more human where it counts.
5. Keep iterating. We are building for adoption, not just implementation. AI isn’t static—and neither is coaching. We have taken a rep-first approach: embedding AI insights into weekly coaching rhythms, manager one-on-ones, and pipeline reviews. We regularly review the data with our AI tooling partner to fine-tune models and refine coaching prompts based on what’s driving real results.
With the right tools and mindset, you, too, can turn data into action and coaching into a growth engine.