Chris Reising, a five-time CRO at early-stage tech companies, shares insights on scaling sales at startups, including finding product-market fit, hiring sales reps, and understanding pain points. In the early stages, wearing multiple hats is crucial, and effective communication with product teams is key. Investor relations play a significant role in understanding market signals. Recognizing patterns in sales discussions is a sign of scalability. Founders must overcome the challenge of letting go of day-to-day selling to focus on building the right team.