How to Build Your First Sales Team: From Founder-Led Sales to Your First Sales Hire

One day in the mid-1880s, Joseph H. Crane got off the train in Findlay, Ohio, at around 4.30 in the morning. He could not find a room at the hotel and spent the night in a barber's chair. The next day he took half of the hotel parlour and set out the five cash registers he had brought with him. By Friday evening he had shown the machine to sixteen merchants. Not one of them signed.

Crane was the brother-in-law of John H. Patterson, head of the National Cash Register Company in Dayton. According to Samuel Crowther's 1923 biography of Patterson, he was known as the best wallpaper salesman in Ohio. After each merchant left, he wrote down on the back of a statement slip the points he had forgotten to explain. That evening he won over a restaurant owner, and the next day he closed three of the sixteen. He revised his note from time to time, after a while stopped needing to look at it, and tore it up. At the end of ninety days he realised he was saying the same thing to everyone, in almost the same words.

One day Patterson called him into his office and asked: "How do you sell? What is your method?" Crane sat him down as if he were a grocer in a country town and went through his whole talk. Patterson called in a stenographer, had the text taken down and sent it to the company's twelve salesmen: "Crane sells more machines than any of you fellows, and he sells them this way." The text first went round as "How I Sell National Cash Registers, by J. H. Crane". Then, because there was "too much Crane about it", it was renamed the Primer. According to Crowther, the first Primer came out in June 1887 and was the first attempt to make selling something more than an individual knack.

The story has two curious details. Crowther writes that there is no record of Patterson ever selling anything himself; his contribution was asking the question. Nor did the salesmen take to the text straight away. When they were told at the 1887 convention to learn the Primer, they received the news without enthusiasm and mostly carried on as they pleased. Years later a salesman in Newark would tell Patterson: "I'm not a parrot."

From founder-led sales to your first sales hire

In most startups today the founder still makes the first sales. The real question is when to hand that work over, and to whom. Meka Asonye, who spent about four years leading sales at Stripe, took on this question in a 2021 piece for First Round Review, together with leaders from Stripe, Figma, Coda and Front.

Learn to sell before you hand it over

Stripe's chief operating officer Claire Hughes Johnson argues that founders should not skip the period of finding out for themselves who the buyer is, who makes the decision and who controls the budget; those three roles do not always sit with one person. Asonye's warning points the same way: hand sales over too early and you will not know whom you need, nor what to tell that person to do once they arrive. The usual result is a hire that does not work out and months lost.

Check whether you are the bottleneck

The other extreme is costly too. Asonye's first test is simple: are you still giving your newest customer the attention you gave customer one or customer two? The second is a count: if five companies squarely in your target profile are deeply engaged with you, you are probably the bottleneck and it is time to hire. Matt Hudson of Coda says that, looking back, the answer was always hiring, and that he brought some roles in too slowly.

Write down what you know, then work side by side

Crane's note on the back of a statement slip is the draft of what you will hand your first salesperson. Before hiring, Asonye suggests writing down the target customer's stage, industry, buyer, current solution and the events that trigger a purchase, along with how many prospects enter the funnel each month and how many steps and how long it takes to reach a paying customer. Writing is not enough. Andrew Berger of Front says he spent months at the side of co-founder Mathilde Colin to replicate how she sold Front; the team's repeatable process came out of those months.

Your first salesperson must cope with ambiguity

For Kenny Mendes of Coda, the baseline requirement for a first sales hire is the ability to deal with ambiguity; that first phase calls for a particular kind of person. A big name is often the wrong choice. Jeanne DeWitt Grosser of Stripe says most leaders cannot scale back more than one order of magnitude in team size: if you are building a team of ten, look for someone who has run a hundred people, not a thousand. Keep the commission plan simple too. Asonye recalls that in Stripe's first year a sales team of around ten worked with no variable pay.

To give, and not be able to tell

The English word sell comes from Old English sellan, whose first recorded sense is "to give", and then "to give up for money". At its root, a sale is a handing over. Handing over sales is a transfer too, and the hard part is passing on not the product but the knowledge.

The Hungarian-born thinker Michael Polanyi put it in one sentence in The Tacit Dimension, published in 1966: we can know more than we can tell. We recognise a face in a crowd, yet cannot explain how. Polanyi called this tacit knowledge. Each note Crane drew from sixteen failed meetings was a piece moving from tacit to explicit knowledge. What never reaches the page can only be passed on by working side by side, which is why Berger's months were not time lost.

In later years Patterson made salesmen memorise the Primer word for word and dealt harshly with those who objected. Even so, the Newark salesman's protest showed something: a written method works as a starting point, not as a cage.

"For the mind does not require filling like a bottle, but rather, like wood, it only requires kindling."

Plutarch, On Listening to Lectures

If your salesperson started tomorrow, what could you hand them: a note on the back of a statement slip, or only a feeling that lives in your own head?

For choosing the right people as you build your first team, Hiring Your First Employees: How Do You Choose the Right Person? is worth a read.