Case Study

Enterprise Sales Team Transformation

A PE-backed marketing technology company transformed an underperforming Enterprise sales team through bold talent decisions, strategic recruiting, and structured onboarding to achieve breakthrough quota performance.

113%

Q1 FY25 quota achievement

50%

Team replaced with value sellers

12 to 22

Team scaling capacity built

6 months

Complete transformation timeline

The Challenge

A PE-backed marketing technology company's Enterprise sales team was systematically underperforming with several critical issues.

Multiple Account Executives performing at less than 50% of quota for consecutive quarters.
Reps defaulting to feature-based selling rather than articulating business value and ROI.
Team culture normalizing mediocrity with limited accountability for performance.
Lack of differentiation in competitive situations leading to discount-driven conversations.
Complex enterprise sales cycles treated like transactional product sales.

Solution

Bold Talent Transformation Program (timeline: 6 months).

Rigorous performance assessment of each Enterprise AE's skills, methodology, and improvement potential.
Strategic decision to terminate 50% of Enterprise team unable to adapt to value-based selling.
Developed detailed hiring profiles for value sellers with proven enterprise SaaS track records.
Personally led first-round candidate screens assessing discovery skills and business acumen.
Implemented comprehensive 30-60-90 day plans with clear milestones and coaching checkpoints.

Results & Impact

Team achieved 113% of Q1 FY25 quota (up from ~40% Q4 FY24 previous attainment) following transformation.
New sellers demonstrated stronger business acumen and value-articulation skills.
Shifted conversations from feature comparisons to business outcome discussions.
Built foundation for scaling team from 12 to 22 reports.
Established performance-driven culture with clear accountability standards.

Reflections

"When I analyzed the Enterprise team's performance data, multiple AEs were stuck below 50% of quota for consecutive quarters due to feature-based selling. When reps treat $1M+ enterprise deals like transactional product sales, training won't fix the fundamental gap. I made the call to rebuild, replacing 50% of the team with value-driven sellers who could navigate complex enterprise cycles. The result: 113% of Q1 quota and a transformed enterprise motion."