What to write down before you hire your first sales rep

Why a count of closed deals is not enough

Founders often decide when to hire from deal volume: enough closed deals, so it is time to add a rep. The count says the motion works. It does not say why it works, and that is what a new rep needs.

The founder won some deals through a relationship, some through knowing the product to the last detail, some through a call that went a certain way. None of that is written anywhere. When the first rep cannot match the founder's results in the first month, the usual conclusion is that the hire was wrong. Often the real gap is that the way the founder sells never left the founder's head.

The three things to record

One row per deal, past and present. Three columns carry most of the value.

1. Where the deal came from: a referral, an inbound request, cold outreach, an introduction. Pick three or four categories and stick to them.
2. How long it stayed in each stage: discovery, proposal, negotiation, close, or whatever matches how you sell today. The total sales cycle matters, and so does the time in each stage.
3. How it ended: won or lost, and when you lost, the reason as best you know it. An imperfect reason still beats none.

How to keep it going without a project

A spreadsheet is enough while you are the only seller. You will move to a CRM when the team grows, and the columns carry over. What matters is consistency: a record that takes ten minutes a week survives, and one that needs an afternoon does not.

Add the row when a deal enters the pipeline, update the stage when it moves, and set aside half an hour on Friday to fill the gaps. After a couple of months you have patterns to look at: which sources close, where deals wait, where they drop off.

What the new rep does with it

The record gives a rep benchmarks. If proposals usually take two weeks to turn into a decision and a rep's deal has sat for four, that deal needs a conversation. If a stage is where most losses happen, the rep can prepare for it early instead of finding out on their own.

It also changes what you tell the rep in the first month. With a six-week sales cycle, nobody should judge a new rep on closed deals in week four. They should be judged on whether their deals move the way yours did.

What the record cannot show

Columns tell you what happened and when. They do not tell you what you did between the rows: who you pushed to meet, which deals you dropped early, what you asked for at the end of a call. That reasoning is the part that does not copy by itself.

So add one line to each row: what you did on the deal and why. Write it in a sentence or two, close to the moment. Over time those lines become the first draft of how your company sells.

An example at Halden Freight

Take a founder who has closed eight deals and lost five. In the record, four of the five losses stop at the same point: a proposal above 50,000 USD that never reached the person who approves it.

Halden Freight is one of them. The contact, Maya Lindqvist, was friendly, the quote was 86,000 USD, and nobody on the seller's side had met Tom, the CFO. The founder never needed a rule for this because they always asked for that meeting. A new rep did not know to.

Once the pattern is written down, the rule is simple to state: before a proposal above 50,000 USD goes out, get time with whoever approves it. A new rep can apply that on their own deals from the first week.

Mistakes to avoid

• Waiting for a perfect tool. A spreadsheet started today is worth more than a CRM configured next quarter.
• Logging outcomes without reasons. A lost deal with no reason teaches nothing.
• Recording only the wins. The losses show where a new rep is most likely to get stuck.
• Handing over the spreadsheet and nothing else. The record shows the pattern, and the founder's reasoning explains it.
• Treating the first month as a test of closed deals. Judge a new rep on whether their deals move as yours did.