How to Sell

Bosmeny says founders should sell before hiring a sales team, because talking to customers helps them understand what to build. At Clever, he took responsibility for sales while his co-founders focused on the product. He points to founders’ product passion and industry knowledge as advantages.

Bosmeny says early prospecting takes persistence: he estimates only 2.5% of companies may consider buying from an unproven startup. He recommends starting with your network, attending industry conferences, and sending short, personalized cold emails. For conferences, identify attendees in advance and book meetings before arriving.

Bosmeny calls listening the core of sales. He suggests asking about a prospect’s problem, current approach, and ideal solution, and says strong salespeople let customers do most of the talking. Deals may also require many follow-ups: one early Clever sale took about two months and closed at $100,000 per year.

For enterprise sales, Bosmeny recommends having a contract ready and keeping revisions moving, while getting legal advice on proposed terms. He warns that requests for one more feature can lead to endless custom work, and suggests tying development to a commitment or waiting for other customers to ask for it. Instead of a free trial, Clever offered an annual agreement with a 30-day cancellation option.

Bosmeny says the sales motion must fit the price and number of customers a business needs. High-touch sales, including travel and conferences, may not work for a low-priced product that needs millions of customers. In the Q&A, he advises founders to sell themselves before hiring, then look for early sales reps who can learn and figure things out without a detailed playbook.