The first 90 days of business development, week by week
What a new business development function should produce at day 30, 60 and 90, why pipeline is the wrong month-one metric, and the trap of early activity.
Read
Almost every founder asks the question as a revenue question. It is a repeatability question, and the two have different answers.
The first sales hire is the one that founders get wrong most often, and the reason is that they ask the wrong question. The question they ask is "can we afford someone". The question that decides the outcome is "is there anything here for someone to do".
Those come apart more often than you would expect. A company can be comfortably able to pay a salary and still have nothing a new person could pick up, because everything that makes the sale work lives in the founder's head and has never been written down or repeated. Hiring into that produces a rep who spends four months guessing, and a founder who concludes that salespeople do not work.
Below are six tests. They are deliberately checkable. If a test needs a paragraph of explanation about why your situation is different, treat that as a fail.
Ask yourself who buys, and answer without saying the names of your existing customers. If the only available answer is a list of logos, you have customers but you do not yet have a market, and a rep cannot prospect into a list of logos you already closed.
What a rep needs is a description that generates names they have never heard of: the industry, the size band, the job title that feels the problem, and the event that makes it urgent this quarter rather than next year. That last part is the one usually missing. Most founders can describe who has the problem. Far fewer can describe what makes someone act on it.
A new rep should inherit something. Not a full pipeline, but evidence that one can be built: a channel that has produced conversations more than once, and a rough sense of how many attempts it takes to get one.
If the honest answer is that every customer so far came from the founder's personal network, that is worth knowing before hiring rather than after, because a personal network is the one asset a new hire cannot inherit. Our note on where first B2B customers actually come from covers the channels that are transferable and the ones that are not.
Wins teach you less than losses, and losses are what a rep will produce first. If you cannot explain why the last five deals that did not close did not close, you have no coaching material, and coaching is most of what a first rep needs in months one to four.
"They went quiet" is not a reason. It is the absence of one. Deals that go quiet are usually deals that stalled at a specific, identifiable point, and the five places B2B deals actually die are consistent enough to be worth learning before you hire someone to walk into them.
This is the test most commonly waved away, usually with "we will set up a CRM when we hire someone". That gets the order backwards. The rep is not there to build your system. They are there to work inside it.
The good news is that cost is not the obstacle it used to be. HubSpot's published pricing lists a free tier covering up to two users and 1,000 contacts at no cost, with paid seats starting well below what most founders assume. Whatever tool you choose, the point is that the deal history, the contacts and the stage definitions exist somewhere other than your inbox before the new person's first day.
The related question is what happens to reporting once a second person is selling. Pipeline visibility tends to arrive as a weekly spreadsheet that somebody rebuilds by hand, which works until it does not. Rivl has a good piece on getting reporting out of manual spreadsheets without buying a BI platform, which is the right scale of answer at this stage.
A first rep does not produce revenue in month one, and planning as though they might is the most common budgeting error in this decision. They need to learn the product, the buyer and the objections, and in B2B the sales cycle itself sets a floor: a rep cannot close a ninety day cycle faster than ninety days no matter how good they are.
The practical rule is to fund the hire for a period at least as long as one full sales cycle plus the time it takes to build enough pipeline to start one. If that number frightens you, the hire is premature, and the honest alternative is to keep selling yourself for another quarter.
| Signal | Ready to hire | Not yet |
|---|---|---|
| Buyer definition | Generates new names | A list of existing logos |
| Channel | Repeatable, measured | Founder's personal network |
| Losses | Explained by stage | "They went quiet" |
| System | Exists before day one | Planned for after the hire |
| Runway | Funded past one full cycle | Expects revenue in month two |
| Time | Founder available weekly | Hire framed as a handoff |
The reason founders hire is usually that they are out of time. The problem is that a first sales hire consumes time before it returns any, and a founder who disappears at the moment the rep needs the most context is the single most reliable way to waste the salary.
Budget real hours: joint calls in the early weeks, a standing weekly review of live deals, and fast answers when a question comes back from a prospect. If none of that fits in the calendar, the constraint is not headcount, and adding headcount will not relieve it.
It should not be a VP of Sales. A senior sales leader is hired to build and run a team, to design compensation and territories and process, and none of that has anything to attach to when there is no team and no proven motion. The seniority premium buys capability you cannot use yet.
It should also not be someone whose experience is entirely inbound at a company with a known brand. Selling for an unknown company is a different job, and the difference shows up in the willingness to do unglamorous prospecting when nobody has heard of you.
If the tests above mostly fail but the workload is genuinely real, the alternative worth pricing is not a cheaper hire. It is an honest comparison of outsourced business development against hiring, which trades some control for a shorter commitment while the motion is still being figured out.
Two things this cannot tell you. The first is timing against your market: if a competitor is actively taking the accounts you want, waiting a quarter to be more ready may cost more than hiring slightly early. Readiness is a spectrum and the tests above describe one end of it.
The second is that some founders never become good at transferring the sale, and no amount of documentation fixes that. If two competent reps have failed in the same seat, the problem has stopped being the reps. That is usually a sign the underlying issue is structural rather than personnel, which is the argument in treating weak business development as a system problem rather than an effort problem.
The last thing worth saying plainly: passing all six tests does not guarantee the hire works. It only guarantees that if it does not work, you will be able to tell why. That is a smaller promise than most hiring advice makes, and it is the one that holds.
We can run the diagnosis, or run the motion as a service while you decide. Thirty minutes is enough to tell which fits.
Book a Free Consultation