Home » The First 90 Days — A Fractional CRO’s Playbook for Turning Around a Stalled Sales Team

The First 90 Days —

A Fractional CRO’s Playbook for Turning Around a Stalled Sales Team

Most companies don’t need more tools. They need a turnaround. When I walk into a new client as a Fractional CRO, I’m not just fixing a pipeline—I’m rebooting culture, structure, and confidence.

The first 90 days are make-or-break. Here’s what they look like when done right.

Day 1–30: Assess and Diagnose

Pipeline Health Audit: What’s real, what’s fluff, and what’s missing?
Sales Process Review: Do we have one? Is it followed?
Win/Loss Analysis: Who are we winning and losing to—and why?
Team Interviews: What do the reps, managers, and execs really think?
CRM Usage Analysis: Is it a system or a spreadsheet graveyard?

Outputs: A gap analysis report, initial quick wins, and a baseline sales capacity model.

Day 31–60: Stabilize and Rebuild

Install Core Playbook Components:
- ICPs, buyer personas
- Qualification frameworks (BANT, MEDDIC)
- Discovery call and demo structure
Sales Meeting Revamp: We move from update meetings to accountability and coaching forums.
Forecasting Overhaul: Define stages, exit criteria, and roll up forecasts bottom-up.
Rep Enablement: Quick-start kits, objection libraries, and micro-learning via AI tools.

Outputs: Sales Playbook v1, new meeting rhythms, and initial forecast accuracy lift.

Day 61–90: Activate and Accelerate

Outbound Launch: Persona-driven cadences with AI-assisted personalization
Manager Coaching: Weekly call reviews, objection coaching, deal strategy support
Performance Dashboards: Real-time metrics tied to activities and outcomes
Celebrating Early Wins: Showcase small wins to drive morale and adoption

Outputs: Faster cycle times, improved close rates, and rising team confidence.

Why It Works

Because it’s not theoretical. It’s practical, field-tested, and adapted to your culture. It blends structure with flexibility. And it builds trust at every level—from rep to boardroom.