Question

You are interviewing for an Account Executive role at OpenAI. Describe a meaningful deal you lost in the last 90 days involving a product such as ChatGPT Enterprise, the OpenAI API, or OpenAI’s enterprise platform. Focus on what happened, why the deal was lost, and what you changed in your sales process afterward.

What to cover

1. Deal context: Briefly explain the customer, the use case, deal size or strategic importance, and the stage where the deal was lost.
2. What changed: Identify the specific event, stakeholder shift, competitive move, procurement issue, security concern, or discovery gap that changed the outcome.
3. Your diagnosis: Separate factors within your control from those outside your control. Be explicit about where your process broke down.
4. Process changes: Explain the concrete changes you made after the loss. Examples include earlier multithreading, stronger qualification, tighter mutual action plans, deeper technical validation with a Solutions Architect, earlier security review, or clearer executive alignment.
5. Evidence of learning: Share how you applied the new process on a later opportunity and what improved as a result.

Interviewer guidance

A strong answer is specific, recent, and accountable. The candidate should not blame pricing, product gaps, or the buyer without showing self-awareness. Look for structured reflection, strong customer-facing judgment, and changes that are operationalized rather than vague.

Example framing

For example, a candidate might describe losing a ChatGPT Enterprise expansion because they were single-threaded with an innovation lead, missed InfoSec concerns until late stage, and then changed their process to require technical, security, and executive stakeholders to be engaged before forecasting commit.