Pitching Glean to a chief technology officer: discovery, objections and a pilot plan

You are trying to convince the chief technology officer (CTO) of a prospective customer to adopt Glean, the enterprise search and AI assistant that works across a company's apps and data. How would you sell it to them? ```hint Sell to this buyer A CTO owns the technology stack, the security posture and the decision whether to build or buy. Work out what this person would need to believe before agreeing to a next step. ``` ### Clarifying Questions - What size and kind of company is this, and does the CTO also own internal IT and security, or do other leaders hold those? - Is this a first conversation, or is an evaluation already underway? - Is the CTO also weighing an internal assistant built on the company's own data, or the AI features in tools the company already licenses? - Is the aim of this conversation a pilot or a company-wide agreement? ### What a Strong Answer Covers - Preparation on the company and the CTO's priorities, and a meeting that opens with discovery rather than a feature list. - A value proposition tied to what a CTO cares about: engineering productivity, a governed way to use AI on company data, and tool sprawl. - Direct, accurate answers on security, permissions, data handling and integration effort. - Positioning against the real alternatives, especially building in-house and AI bundled into existing suites. - A concrete next step with agreed success criteria, such as a scoped pilot. ### Follow-up Questions - The CTO says the team could build the same thing with a language model API and a vector database in one quarter. How do you respond? - The security lead joins the next meeting and asks what happens to company data sent to the language model. What do you need to have ready? - The pilot shows heavy use in engineering but little elsewhere. How do you make the case for a company-wide rollout?