The Revenue Architect

The Revenue Architect

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The Revenue Architect
The Revenue Architect
How to make your first sales hire
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How to make your first sales hire

Job requirements. Interview questions. Interview project. Pre-start checklist.

Arnie Gullov-Singh's avatar
Arnie Gullov-Singh
Oct 24, 2024
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The Revenue Architect
The Revenue Architect
How to make your first sales hire
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Many early-stage founders excitedly make their first sales hire only to frustratingly make their first sales fire a few months later because it didn’t work out.

It can be a costly mistake, not only in terms of the direct expenses of recruitment and salary but also in terms of the increased management overhead, disruption to team morale, lost momentum, missed revenue opportunities and damage to customer relationships.

This guide lays out how to maximize your chances of making a successful first sales hire and covers the following topics:

  • Common mistakes when making your first sales hire

  • Must-have job requirements for your first sales hire

  • 8 interview questions to ask your first sales hire

  • 3 interview projects for your first sales hire

  • What to document before your first sales hire starts work

Common mistakes in making your first sales hire

  • Overlooking a lack of stage-specific experience. This is by far and away the biggest mistake in sales hiring because a person with extensive later-stage experience very rarely knows what to prioritize when walking into an early-stage startup as the first sales hire. While they may honestly believe their experience is relevant, their frame of reference is a more mature business with a more mature product and more mature go-to-market motion so they will over-engineer and over-complicate your go-to-market, which can get very frustrating for a founder.

  • Chasing the logo dragon. Hiring someone from a hot company will not automatically make your company hot. Most early-stage startup successes are more about having the right product at the right time (i.e. luck) rather than about any particular sales and marketing wizardry, so the sales playbooks are not necessarily transferrable.

  • Hiring someone too senior for what you need. Many founders get advised to make their first sales hire a VP or director of sales, however in most cases this is a recipe for failure because they want (and expect) too much control and autonomy. The initial steps of transitioning out of founder-led sales are much more about the founder delegating away the most repetitive pieces of the sales process than they are about handing over the entire sales process to someone else. Founders still need to drive the sales process and be close to customers

Must-have job requirements for your first sales hire

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