Breaking into GTM

What does a good first sales hire actually look like, and what should I not fall for?

The short answer

You want someone who will do their own button clicking. The single most common mistake is overshooting seniority: hiring a person whose last three years were spent managing a territory handed to them by a marketing team you do not have. Look for grit, coachability, and genuine curiosity about the product, and be suspicious of a resume that is only big brand logos, because hitting quota at a company with brand pull rarely transfers. Two useful filters: would you buy from this person, and have they carried a bag at a company under 50 people. Hire two, not one, so you can tell whether a miss is the rep or the playbook.

Go deeper, your way

5 hand-picked resources, 1 India-specific, 5 link-checked. Pick how you want to dig in.

The same ground, at another level

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

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 5 resources → How many reps should I hire next quarter, and in what order? Do the arithmetic backwards from the number. Take next year's new ARR target, divide by realistic per rep yield, then divide again by the attainmen... Leading a GTM team 4 resources → How did Freshworks build a global sales team out of Chennai when that talent did not exist yet? They stopped looking for the resume and started looking for the raw material. Girish Mathrubootham's rule was bet on people, not pedigree, so they ... How the best do it 4 resources →

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 5 resources → I have been offered the first sales hire job at a startup. What should I check before I say yes? 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, ... 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 5 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.

Do I actually need a co-founder, or can I go solo? You don't strictly need one, but the data says teams outlast solos: complementary skills, shared load, and someone to argue you out of bad calls al... 3 resources → How should co-founders split equity fairly? For most early teams, split close to equal, an even split signals you see each other as true partners, and long-term contribution rarely matches wh... 3 resources →
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