Breaking into GTM

I have been offered the first sales hire job at a startup. What should I check before I say yes?

The short answer

Ask how many customers the founder closed personally and what the last five deals looked like. If the answer is under ten, you are the experiment, not the hire, and you should price that risk into your base. Ask who else is being hired alongside you, because being the only rep means every miss reads as your failure. Get the quota in writing along with how it was calculated, what the ramp period pays, and where the pipeline is expected to come from. And ask what happened to the last person in the seat.

Go deeper, your way

4 hand-picked resources, 1 India-specific, 4 link-checked. Pick how you want to dig in.

✍️ Essay
✓ Link checked Free Intermediate

Why we picked it The clearest arithmetic anywhere on rep economics: the rule of 10 for quota against base, four months to productivity, draws during ramp, and why teams attain about 70 percent of quota capacity so you must plan over capacity.

Simple Math to Set Up a Sales Team

From Craft Ventures by David Sacks 12 min read

Open sacks.substack.com
📄 Article
✓ Link checked India Free Intermediate

Why we picked it Written for Indian SaaS founders by the Everstage CEO, ex Freshworks. It gives the working numbers: quota period must be at least the sales cycle, quota to OTE around 5 to 6x, and two thirds of reps landing between 80 and 100 percent attainment.

Getting the Quotas Right for Your SaaS Sales Teams

From SaaSBoomi by Siva Rajamani 10 min read

Open saasboomi.org

The same ground, at another level

How hiring and ramping gtm people reads from a different seat.

People also ask

When do I stop selling myself and hire my first salesperson? 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 th... Breaking into GTM 4 resources → What does a good first sales hire actually look like, and what should I not fall for? You want someone who will do their own button clicking. The single most common mistake is overshooting seniority: hiring a person whose last three ... Breaking into GTM 4 resources → How do I interview a salesperson when I have never sold for a living? Stop trying to judge charisma and start judging evidence. Write a scorecard first: three or four outcomes you want in twelve months and the handful... Breaking into GTM 3 resources → What should a new rep's first 90 days actually look like? The first 30 days are absorption: product, market, recorded calls, and shadowing you on live deals until they can pitch it back without notes. Days... Doing the work 4 resources → I am the first AE and my founder still runs half the deals. How do we split it? Split by stage, not by account, at least at first. The founder stays on the parts only they can do, the vision framing, the pricing exception, the ... Doing the work 3 resources → How do I know whether a new rep is going to work out before six months have gone by? Watch leading indicators, not bookings, because bookings arrive too late to act on. By week six they should be able to run the demo without you and... Doing the work 4 resources →

Also in Starting Up

The same ground, over in Co-founders, team & legal, our Starting Up track.

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