Coconut Software: Building a Consistent Sales Motion and Doubling Win Rates
Client: Coconut Software
Industry: SaaS (Financial Services Technology)
Role Interviewed: Denise — VP of Sales
The Challenge
When Denise joined Coconut Software, the company was scaling quickly but the sales organization was going through significant transition.
The leadership team was new. Many of the BDRs and sales reps were new. And different teams were operating with different approaches to selling.
There was no consistent framework for discovery, qualification, or prospecting.
At the same time, Denise was responsible for onboarding new reps, preparing for revenue kickoff, evaluating pricing and competition, and aligning sales with marketing.
“We had a lot of change happening at once — new leadership, new reps, and different teams operating in different ways. We needed one songbook everyone could work from.”
The Objective
Create a consistent sales motion that would:
- Align BDRs and AEs around a shared sales framework
- Improve discovery and qualification discipline
- Strengthen outbound and pipeline quality
- Enable more consistent onboarding and coaching
- Increase pipeline velocity and win rates
The Approach
Tom worked directly with Denise and the revenue leadership team to design a tailored enablement program for Coconut.
The focus was not just training, but building systems the team could execute every day.
Key elements included:
- Sales Framework Development
- Defined a consistent discovery and qualification framework
- Introduced shared language for sales conversations
- Eliminated “micro-pitching” during discovery
- Training + Reinforcement
- Hands-on sales training for BDRs and AEs
- Call coaching and practice sessions
- Ongoing reinforcement instead of one-time training
- Playbooks and Scorecards
- Created structured sales playbooks
- Implemented call scorecards for discovery and qualification
- Enabled consistent coaching across the organization
- AI-Driven Coaching
Coconut later integrated the scorecards into an internal AI tool that allows reps to score their own calls and improve continuously.
“It wasn’t just training. It was the follow-up, the practice, and the accountability that made it stick.”
The Results
Within the following sales cycle, Coconut saw measurable improvements across the pipeline.
Key outcomes included:
- 75% reduction in time spent in the qualification stage
- 2× increase in mid-market win rates
- Improved pipeline velocity across every stage
- Higher quality pipeline overall
The behavioral changes inside the team were equally important.
Reps began focusing on discovery rather than pitching early.
“We saw a real shift in how our team sold — more active listening, less micro-pitching, and stronger discovery.”
Coaching also became more collaborative.
“Reps started coming to me asking for coaching. It became a pull instead of a push.”
Leadership Impact
The engagement also helped Denise scale the organization more effectively.
With consistent frameworks in place, onboarding improved and coaching became more targeted.
“Having a consistent playbook made it easier for me to focus on developing each rep instead of trying to train everyone at once.”
The Bottom Line
By introducing structured discovery, consistent training, and a unified sales framework, Coconut Software significantly improved pipeline performance while building a stronger foundation for continued growth.
“We doubled our win rate in mid-market and improved pipeline velocity across every stage.”
