DealDrill

DealDrill is a web app (with optional mobile companion) that forces strategy to prove itself against reality: pipeline, win/loss, pricing, and customer segments. It connects to your CRM (Salesforce/HubSpot) and billing (Stripe/NetSuite exports) to auto-generate a “Strategy Scorecard” that highlights where your stated positioning and target ICP don’t match actual closed-won behavior. Teams run lightweight quarterly “strategy drills”: pick a hypothesis (e.g., mid-market healthcare is core), the app pulls supporting/contradicting evidence, then guides a decision log with owners, dates, and measurable bets. It includes a simple competitor tracker fed by sales notes and win/loss tags—no fantasy market maps. This is a combination traditional + AI app: traditional dashboards and workflows, plus AI to summarize patterns, flag inconsistencies, and draft decision memos. It’s built for companies tired of slide-deck strategy that never changes execution.