Technical founders selling for the first time: a first-year sales routine

You shipped the product and told yourself you would start selling once the next release was out. Three releases later, the list of prospects is still in your head. A technical founder's first sales year can run as a fixed weekly routine in four blocks: finding people, reaching them, talking to them and writing up what they said. Keep the blocks small and on the calendar like a customer meeting, and use the notes to build the pitch a future salesperson will inherit.

Why does selling fail when the product is good?

A founder from an engineering background may treat selling as a launch event: build, announce, wait. It is closer to maintenance. Enquiries come when someone reminds the right person at the right moment, and that takes repetition more than brilliance.

The other trap is explaining. A founder describes the architecture because it is what they know. Buyers want to know whether their problem goes away. Much of selling is listening until you hear the problem in their words, then describing your product in those words.

What does a weekly routine look like?

Here is a layout for a founder who can spare roughly a day in total. Adjust the hours to your week, but fix the blocks.

Put the notes on one page per conversation with the same headings: the person's role, what they do today, what went wrong last, what they tried, who else decides, and what happens next. Do this on the same day, because a call remembered on Friday is a different call by Monday.

Who do you talk to first?

Start with people you can reach without a stranger's introduction: former colleagues now in operations or IT, clients from earlier jobs, members of a community you already belong to. Ask them for conversations, not orders. "I am building something for X; could I ask how you handle it today?" asks for less than a pitch does, so it is easier to say yes to.

Aim in the first months for learning, not volume. Twenty honest conversations teach you the wording of the problem, the real price a buyer will accept, and the objections you must answer. Our post on the two-minute sales pitch shows how to turn that wording into a short pitch.

Case: a Chennai founder and an invoice-matching tool

Imagine an invented former finance-systems engineer in Chennai who builds a tool that matches supplier invoices to purchase orders for mid-sized distributors. For four months the founder codes and plans to sell after launch. Launch day brings silence.

Selling had to start before the product did, so the founder reverses the order. Tuesday morning is for naming ten finance heads at distributors. Wednesday is messages. Thursday and Friday afternoons are calls. Within two months the notes show a pattern: few finance heads say "invoice matching". Most of them say "the month-end pile". The homepage and pitch take on that phrase. The notes also show that two prospects would pay for a pilot only if their ERP exports worked, so the export feature moves to the top of the build list. By then only three of the forty people contacted have booked a pilot, and the founder is still behind on the build, which suffers from the weekly blocks. That is the trade.

A hired salesperson would not have heard either of those things first-hand, which is an advantage a founder has in year one.

What do you ask when the call comes?

Four questions carry a first conversation, and none is about your product. How do you handle this today? When did it last go wrong, and what did it cost you? What have you tried? Who else would have to agree to change it? Write the answers down in the buyer's words before you say anything about what you have built. If you catch yourself describing the architecture, stop and ask the next question instead.

What should you keep a record of?

Four things, in a sheet rather than your head.

1. People contacted, with dates, so no one is chased twice by accident.
2. Conversations held, and which stage each reached.
3. Objections, copied in the buyer's own words.
4. Prices mentioned and what the buyer said back.

At the end of each quarter read the objections list aloud. If the same one appears in six of ten calls, look at the product or the messaging before blaming the selling.

When is it time to hand over to a salesperson?

Not by the calendar and not because you are tired. Hand over when you have closed several buyers yourself, you can write the pitch, price, qualifying questions and top objections on two pages, and a newcomer could follow them. Before that point a hire would be guessing at what you have not yet learned. Our note on hiring salespeople when your firm is not a known name deals with the hire itself.

Skip this routine if you have an inbound-only model that already brings a steady stream of buyers, or if your product is bought through a partner, where the routine belongs to the partner. And if a block keeps getting cancelled for building work, the problem is priority, not time.

Block out the next four weeks

Put the four blocks in your calendar for the coming month. List the first thirty people by name. Handing the routine over later is the subject of founder-to-sales-team transition, and other work for software and IT firms is under technology. When you want a second view on your plan, tell us what you need.