When does a founder stop selling personally, and why do the best ones hire two reps instead of one?
Jason Lemkin's marker is that the founder closes the first batch themselves, roughly the first ten customers, because if you have not done it you will never be able to teach it or diagnose it. Then hire two reps, not one, and his reason is not redundancy, it is that with one rep you learn nothing: if they do well you still have no idea why, and if they fail you cannot tell whether it was the rep or your process. Two also surfaces things you cannot see otherwise. Lemkin's own first rep was strong at consultative deals and his second was strong at volume, and the contrast revealed segments and pricing he had been blind to. After two reps are hitting quota, usually somewhere past 1 to 2 million in annual recurring revenue, you hire a head of sales. Khadim Batti at Whatfix is a good example of the founder doing it first: 500 personalised cold emails in a month, and a first customer signed before the product was built.
Go deeper
4 resources, 3 India-specific, 4 link-checked.
📄 Article
✓ Link checkedFreeIntermediate
The reasoning is better than the headline: with one rep you cannot tell whether success or failure came from the person or the process. Lemkin's own two reps sold in opposite styles and that contrast surfaced new segments.
Founder led selling with the receipts: 500 personalised cold emails in a month, a first customer signed before the product existed, and later a deliberate narrowing from SMB to enterprise CRM teams that took them from 1 million to 10 million in annual recurring revenue in nine quarters.
Practical on the first US sales hire, hiring for adaptability rather than a quota record at a big brand, and on testing localised pricing instead of one global number. Note the publisher sells revenue-based financing, so read the funding section with that in mind.
A ground level account of what Indian founders actually run into when they set up in the US, down to the go to market starter kit on hiring, housing and insurance. Unglamorous and useful.
