A playbook
Sell and prospect with AI
Find leads, personalize outreach, and run better sales calls.
3 steps, 31 questions, laid out in the order you'll hit them
Each step is a topic with the real questions founders ask; open whichever one you're stuck on for the answer and the resources on it.
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1
Sales ProspectingWhy use AI to find and qualify leads (Clay, Apollo + AI workflows)? 20 → How do founders personalize cold outreach at scale without being creepy? 20 → What does an AI-assisted founder-led sales motion look like end to end? 19 → How do I define my ICP and build my first lead list with AI? 19 → Should I buy an AI SDR, or keep prospecting human? 16 → All 13 questions in Sales Prospecting →
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2
CRM & Sales CallsHow do founders use AI notetakers and call analysis (Granola, Fireflies, Gong-style tools) to close more deals? 20 → Why let AI update the CRM, draft follow-ups, and forecast pipeline? 23 → Which AI notetaker should I actually pick: Granola, Fathom, Fireflies, or Otter, and what will it cost? 18 → Do I need a CRM at the pre-seed stage, and should I pick an AI-native CRM like Attio over HubSpot or Zoho? 18 → How are founders using AI tools like Clay and Apollo to run outbound prospecting and personalized cold email? 20 → All 12 questions in CRM & Sales Calls →
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3
Customer SupportWhy can AI now handle most support tickets, and should it? 13 → How do startups set up AI support (Intercom Fin, Decagon, custom bots) in a week? 12 → How do founders use support conversations as product research with AI? 11 → What does AI support actually cost, and how should a founder think about the ROI? 12 → How do you stop an AI support agent from hallucinating and breaking customer trust? 12 → All 6 questions in Customer Support →