Scaling Strategic Alignment Across 1,200+ Reps at Kaseya

When GTM Scales, Complexities Scale

Kaseya’s GTM org included over 1,200 professionals—account managers, technical account managers, SEs, and specialists—spread across geographies and business units. With so many moving parts, the challenge wasn’t talent or effort—it was alignment.

Kaseya’s leadership team saw an opportunity to simplify execution and reinforce the strategy across the board.

Challenges included:

• Low Visibility into Rep Activity
  Managers couldn’t see how GTM processes were being executed in practice.
  
• Siloed Data
  Key details were missing from systems, slowing down handovers and reducing visibility.
  
• Coaching and Enablement Gaps
  Traditional training methods didn’t scale well, making it hard to implement change.

“We weren’t short on strategy—we just needed a way to operationalize it consistently across the field.”

Omar Chanouha SVP GTM Strategy & Operations, Kaseya

AI-Enabled GTM Execution Across Every Layer

Kaseya implemented WINN.AI to build a consistent, real-time layer of execution across the sales org. One that will not slow down reps or add friction for managers.

Here’s how they rolled it out:

• Live Guidance for Customer-Facing Calls
  WINN.AI guided reps live with Kaseya’s playbooks during customer calls—ensuring consistency and better alignment to their sales methodologies.
  
• Automated CRM Updates
  Key call details were captured and structured instantly, sent through Kaseya’s API directly to their BI systems – providing real-time visibility into their pipeline, playbook execution, and rep’s efficiency.

• Enabling Front-Line Managers in Real-Time
  Live AI guidance was then expanded to support internal meetings. deploying AI-powered playbooks for 1:1s and deal reviews. This gave frontline managers structured prompts and data-driven insights to coach more effectively.

Change Management, Reinforced in Real Time

Kaseya operationalized the way they implement change into their revenue strategy. By embedding live playbooks into calls, the team could roll out new messaging, new processes, and new GTM priorities – having all of them adopted in the field immediately. 

Managers gained real-time insight into execution, while reps received in-the-moment guidance. The result: faster change deployment, better visibility, and a scalable way to turn strategy into action.

• Clear Visibility into Execution
  Frontline managers and leadership can now track how GTM initiatives are adopted and executed across teams and regions.
  
• Meeting Data in Just 46 Seconds
  CRM fields are auto-filled seconds after each call, saving reps time while ensuring data is clean and consistent.
  
• Live Strategic Reinforcement
  Reps receive live prompts that reflect the latest priorities, ensuring strategy is reinforced, not just announced.

Bottom line:
Kaseya’s approach goes beyond automation. It’s a blueprint for how AI can turn strategy into process and process into habit, by empowering every layer of the revenue organization, from reps to managers to leadership.