playbook
Challenger Sale
Commercial teaching pitch delivered, stakeholder-specific messages tailored, deal momentum created through constructive tension
The prospect knows the market.
How it runs
- research-company + prospect-audit → deep prospect research, understand their industry, competitive position, and current approach
- decision-maker-mapper → map buying committee with role-specific priorities and likely objections per stakeholder
- Review teaching pitch — validate that the insight is new, reframes the problem, and leads uniquely to your solution
- consultative-selling → tailor the teaching pitch for each stakeholder: create role-specific versions addressing their priorities, language, proof needs, and likely objections
- Deliver the teaching pitch to primary contact or buying committee
- meeting-intelligence → extract stakeholder reactions, objections raised, consensus gaps, and next steps
- consultative-selling → develop Take Control strategy: constructive pushback scripts for objections, stall tactics, discount requests, and consensus-building approaches
- Review deal momentum — assess if teaching landed, adjust approach for stakeholders not yet convinced, plan next engagement
What it needs
- Prospect company and stakeholder details
- Current sales stage and prior discovery outputs
- Service line being proposed (to select relevant commercial insight)
- Industry data and benchmarks for teaching pitch
- Known competitor activity (who else is being evaluated)
What you get
- Prospect Dossier.md
- Stakeholder Map.md
- Teaching Pitch.md
- Pitch Variants.md
- Objection Scripts.md
