Hiring your first field sales team

I have built a field sales organisation twice: once at Uber Eats in Paris, taking a restaurant portfolio from 1,200 to 1,600 partners with a team of ten, and once at Beanstock, running city expansion with ten field operations staff and full P&L responsibility. Both times, the hardest part was not finding people. It was knowing what I was hiring them to do.

Most founders reach for field sales at roughly the same moment. The product works, a few customers found you without help, and the obvious next move is to put people on the street. So you hire two reps, give them a target, and wait.

Three months later the pipeline looks busy and nothing has closed. The instinct is to blame the hires. It is almost never the hires.

Sell it yourself first, properly

You cannot hand over a motion you have not run. Not because founders sell better — they usually do, but that is not the point — but because until you have done it, you do not know what the job is.

Before the first rep, you should be able to answer, from memory:

• How many conversations it takes to get one signature.
• How long that takes, from first contact to live account.
• Which objection kills the deal, and what actually answers it.
• Which customers churn within ninety days, and what they had in common at signature.

If you cannot answer those, a rep will not discover them for you. They will just burn through your market while you find out.

The first hire is not a closer

Founders tend to hire for charisma. The first rep in a young company spends most of their week on work that has nothing to do with charm: building a target list, keeping records straight, noticing that half the wins came from one particular kind of account.

Hire for organisation and resilience. A well-organised average closer will outperform a brilliant one with no system, because the brilliant one cannot tell you why they won and you cannot copy it.

And hire two, not one. A single rep gives you no signal: if they miss, you cannot tell whether the problem is the person, the territory or the product. Two reps in comparable territories give you an answer within a quarter.

Territory beats talent

Nothing demoralises a new team faster than uneven ground. If one rep has the dense city centre and the other has everything else, you have not built a team, you have built a grievance.

Split by geography where density allows, and keep the split explicit and written down. Rotate nothing for at least two quarters — relationships in field sales are slow, and a rep who loses an account they nurtured for four months will not trust the next plan you announce.

Pay simply

The best compensation plan is one a rep can calculate in their head on the way to a meeting. Base plus commission on signed, live accounts. One accelerator above target if you want one.

Every additional clause — quality modifiers, clawbacks, team multipliers, quarterly gates — buys you a marginal behavioural correction and costs you something far more valuable: the rep's ability to know, on any given Tuesday, whether they are winning. Complexity in a comp plan is almost always a sign that the underlying metric is wrong. Fix the metric.

The cadence is the management

This is the part that gets skipped, and it is the part that works.

• Daily, fifteen minutes, standing. What closed, what is stuck, what one thing do you need from me.
• Weekly, one hour, one to one. Pipeline reviewed account by account. Not a status update — a decision about each deal.
• Monthly, the number. Against target, in front of the team, without drama in either direction.

Ride along on visits for the first two months. Not to supervise — to hear what your market actually says when you are not the one asking. Founders who stop doing field visits lose contact with their own product within a year, and they are always the last to know it.

Know what you are buying

A field team is not a growth lever you pull once. It is a fixed cost with a ramp: roughly a quarter before a rep is useful, two before they are profitable. If your runway cannot absorb two quarters of an unprofitable team, you are not ready, and hiring anyway converts a cash problem into a cash problem plus a redundancy conversation.

When it works, though, it is the most durable advantage a young company can build. Product features get copied in a quarter. A team that knows every operator in a city by name, and is trusted by them, takes years — and your competitor has to spend those years too.

If you are building this now

We back founders in food, sports, logistics and the software that serves them, and this is the work we most often do alongside them after investing: scoping the role, sitting in on the first interviews, designing quota and territory, and sitting in the weekly review until the cadence holds on its own.

If you are at that point, tell us what you are building.