Writing · Nº 041065 essays
The writing
Ideas from inside the work. Explore technology, entrepreneurship, and the practice of building things that last.
27 essays found · Page 2 of 3
Clear filtersStrategyHow to Handle the Hallucination Objection in Enterprise SalesWhat if it hallucinates is the objection that kills enterprise AI deals. Here is how to handle the hallucination objection: do not deny it, bound it, and prove the bound.OperatingHow to Scope an Enterprise POC So It Actually EndsAn enterprise POC needs an end date and exit criteria or it runs forever. Here is how to scope a proof of concept that closes into a deal instead of drifting.OperatingHow to Design CRM Pipeline Stages That Match RealityDefault CRM pipeline stages lie to your forecast. Here is how to design pipeline stages that match how you actually sell, so your deals reflect the truth.OperatingHow to Run an Enterprise AI Pilot That ConvertsMost enterprise AI pilots impress everyone and convert no one. Here is how to design a pilot around exit criteria and assurance so it turns into a signed contract.StrategyYou Don't Need a Sales Team to Close Enterprise DealsThe myth that closing enterprise requires a sales team is wrong. A founder who owns the assurance work can close enterprise deals solo. Here is how.StrategyHow to Move an Agency Upmarket From SMB to Mid-MarketMoving an agency upmarket from SMB to mid-market is a positioning and proof change, not a bigger version of the same pitch. Here is what actually changes.StrategyHow Long an Enterprise Security Review Actually TakesHow long does an enterprise security review take for an AI vendor? Weeks to months. Here is what drives the timeline and how to cut it in half with preparation.AICan an Outreach Agent Personalize at Scale Without Faking It?Real personalization at scale is the whole promise of an outreach agent. Here is what separates genuine relevance from merge-tag theater that everyone ignores.OperatingHow to Answer an Enterprise Security Questionnaire for AIAn enterprise security questionnaire is a sales asset, not paperwork. Here is how to answer one for an AI product so the risk team says yes instead of stalling.StrategyHow to Prepare Customer References That Close DealsCustomer references make or break enterprise AI deals. Here is how to prepare references that close, who to pick, how to brief them, and what buyers actually ask.StrategySell a Paid Audit as Your Agency's Front DoorA paid audit is the best agency front-door offer. Here is how it qualifies buyers, funds discovery, and converts to retainers better than a free pitch.StrategyFree POC vs Paid Pilot for Enterprise AIShould you offer a free proof of concept or a paid pilot to enterprise AI buyers? Charge for the pilot. Here is why a paid pilot converts and a free POC stalls.