Hire and ramp your first rep

Stop being the only person who can sell it, without setting fire to a year of runway.

4 steps, 64 questions underneath

1. 1
   Hiring and ramping GTM people

   Your first sales hire, the interview loop, the ramp plan, and knowing early when someone is not going to make it.

   When do I stop selling myself and hire my first salesperson?

   The gist Not when you are tired of selling. When you can predict it. The honest test is whether you can write down who buys, what makes them buy now, the three objections you always get, and roughly how long a deal takes, and then have that be true for the next five deals. Most founders get there somewhere between 10 and 30 closed customers, and Jason Lemkin's line is that you should have done it yourself first or you will not be able to tell a good rep from a bad one. If you hire before the pattern exists, you are paying someone to discover your product market fit, which is your job, not theirs.

   🎧 SaaStr Podcast #379: The Top 10 Mistakes Founders Make When Hiring Their First Sales Team Ten specific, named mistakes rather than principles, including hiring a VP of Sales too early and letting a bad rep linger past one sales cycle. It... 16 questions on hiring and ramping gtm people →
2. 2
   Comp, quotas and territory

   Comp plans, quotas, OTE and accelerators, territory and segment design, in dollars and in rupees.

   I have been handed a comp plan. How do I work out what I will actually earn?

   The gist Ignore the OTE headline and find four things: the base, the quota, what percentage of a deal you get, and when you get paid. Multiply your realistic bookings by the commission rate and add the base, because OTE assumes you hit 100 percent and most teams do not. Then read the fine print that decides whether the plan is honest: does commission pay on booking or on cash collected, is there a clawback if the customer churns in 90 days, is there a cap, and what happens during ramp. If quota is more than about five times your OTE, or the ramp period pays nothing, negotiate now rather than discover it in month four.

   📋 Sales Compensation Structure: The Guide With Role-Based Templates Worked examples with real numbers for an SDR at 70:30, a CS role at 75:25 and a presales engineer at 80:20, each with quota, metric and payout. Cop... 16 questions on comp, quotas and territory →
3. 3
   Running a sales process and closing

   Discovery, demos, qualification, champions, procurement and the last mile to a signature.

   I have a call booked with a real prospect tomorrow. What do I do on it?

   The gist Ask questions and shut up. Gong's analysis of more than half a million calls found the sweet spot is somewhere around eleven to fourteen questions, spread through the call rather than fired off at the start, and the best calls surface three or four real business problems. Aim for a talk to listen ratio near forty six to fifty four, which will feel like you are barely talking. Open by stating the purpose of the call, the benefit to them and a check that it works for them, then dig into what happens today and what it costs. Do not demo until you know what to demo, and end with a specific next step and a date, not "I will send something over".

   📄 Effective strategies for successful sales discovery calls Gives you numbers to aim at on your next call instead of vague advice: roughly 11 to 14 questions, spread through the call rather than front-loaded... 16 questions on running a sales process and closing →
4. 4
   Forecasting and GTM metrics

   Pipeline coverage, stage conversion, CAC payback, magic number, and calling a number you can defend to a board.

   What is pipeline coverage and how much pipeline do I actually need to hit my number?

   The gist Pipeline coverage is qualified open pipeline divided by the target for the period, and the honest answer to how much you need is one over your win rate. The famous 3x rule comes from a time when good B2B teams closed about a third of qualified pipeline. If you close twenty percent, you need five times coverage, not three, and using the rule of thumb instead of your own number is how teams cheerfully walk into a miss. Two cautions: only count opportunities with a real buyer, a real need, and a date, because inflating the numerator is the easiest way to feel safe and be wrong. And measure coverage at the start of the period, not at the end, since coverage is only useful as a leading indicator you can still act on.

   📄 Pipeline Coverage Ratio: What Your Number Actually Means Explains why the 3x rule of thumb is wrong for most teams and shows how to derive your own coverage number from your actual win rate. Weighted vers... 16 questions on forecasting and gtm metrics →