The Challenge
A sales team originally built to sell low-ticket SaaS was now selling high-value managed services, and still defaulting to transactional habits. Deals landed under $20K against a $150K target, and close rates hovered near 10% with forecasted deals regularly slipping.
- Surface-level discovery: reps rarely probed into buyer pain or business impact.
- Inadequate qualification: "happy ears" kept dead deals in the forecast and bloated the pipeline.
- Feature messaging, not value: conversations framed around the product rather than business outcomes.
- No multithreading: little champion development or access to executive decision-makers.
What Caliber Did
- Role-based skill paths: separate programs for AEs and presales engineers, mapped to the managed-services motion.
- Embedded enablement: a dedicated enablement manager owned rollout and reinforcement, so Jacci stopped facilitating every session herself.
- Discovery and qualification rigor: root-cause questioning and honest deal inspection in place of "happy ears."
- Value messaging and account strategy: frameworks the leadership team used to rebuild decks, messaging, and inspection cadences.
The Results
"I've never heard a sales team rave more about a sales training before. It's practical. It's useful. It's really all the things."