How Deel Increased Win Rates by 33% by Reinforcing MEDDICC in Real Time
About the Company Deel is the global leader in HR and payroll for distributed teams, empowering companies in over 150 countries. In just six years, Deel reached $1 billion in annual recurring revenue, making it one of the fastest-growing SaaS companies in history.
Strong Reps, Lacking Alignment
Deel’s sales team had world-class talent but lacked consistency. Reps weren’t following the sales methodology, CRM fields were empty – making pipeline reviews and strategic planning difficult. Despite robust enablement programs and a strong playbook (including MEDDICC), frontline sellers often reverted to their own habits.
This resulted in:
- Gaps in discovery and qualification
Reps weren’t consistently executing on discovery and qualification, pleading to weaker deal strategies. - Incomplete CRM data
Managers lacked the context needed to understand and support active deals. - Low visibility into deal health and MEDDICC alignment
It was difficult to assess whether deals were truly qualified or where they stood in the buying process. - Low forecasting confidence
With inconsistent methodology usage and unreliable data, predicting pipeline outcomes became more guesswork than science.
Frank van der Vinden, Senior Enablement Manager at Deel, saw an opportunity to unify the team’s approach and close key execution gaps in real-time.
“Our methodology was solid—but without real-time reinforcement, it just wasn’t showing up in the calls or our CRM.”
Operationalizing MEDDICC at Scale
Rather than relying on more training or dashboards, Deel took a systematic approach to driving better sales execution and partnered with WINN.AI to implement live sales coaching and automated CRM updates.
- Embedded MEDDICC into the daily workflow
Deel’s Enablement team implemented their MEDDICC playbooks directly into WINN.AI, ensuring every stage and question reps were expected to cover was clearly defined and embedded in real-time guidance. This meant reps were constantly reinforced on MEDDICC live throughout their actual sales calls.
- Eliminated dependency on reps for CRM data
Deel mapped each MEDDICC element in their WINN playbook to the relevant fields in their CRM. With that structure in place, WINN.AI could automatically populate Salesforce with the exact information needed, eliminating manual updates and ensuring clean, consistent data after every call.
- Leverage CRM data for deal visibility and enablement visibility
With the CRM now reflecting what was actually happening in conversations, Deel didn’t just gain visibility—they gained control. Sales managers could now use MEDDICC fields to evaluate deal quality, track playbook adherence across teams, and identify coaching gaps based on real performance signals—not gut feel.
Better MEDDICC Adherence, More Wins
By implementing real-time AI, Deel saw measurable improvements across their revenue organization:
- MEDDICC adherence increased by 31%, as reps followed the methodology in real time
- Win rates improved by 33% for WINN users, compared to non-WINN users
- CRM fill rate jumped from 1.1% to 73%, unlocking visibility for managers
- Zero time spent on CRM admin, freeing reps to focus on selling
Bottom Line:
This transformation helped Deel turn their sales methodology into a daily discipline—and gave revenue leaders the clarity they needed to forecast and prioritize with confidence.
“WINN.AI turned our sales qualification framework from a training deck into something reps actually use and follow.”
