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Doing the work

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 get their qualification questions right. By week ten they should be creating pipeline at a rate that, extrapolated, clears quota, and their calls should sound like your best call, not like a generic discovery script. The strongest early signal is coachability: give one specific correction, then check the next call for it. If you have to give the same correction three times, the problem is not knowledge.

Go deeper

4 resources, 4 link-checked.

📖 Book
✓ Link checked Free Intermediate

Names the two ways founders get the timing wrong, scaling too early and scaling too late, and walks the progression from founder selling to pods to a real team. Useful precisely when you are deciding whether it is time.

Founding Sales, Chapter 10: Early Sales Management and Scaling Concepts

From Founding Sales by Peter Kazanjy 35 min read

  • A good B2B win rate is 15 to 30 percent, and hitting it is the signal you can add reps.
  • Sales cost should stay at 20 to 25 percent of the revenue closed; a 100K rep needs to bring in about 500K.
  • A dedicated sales ops hire pays for itself around 10 reps, adding roughly 50K in bookings per rep.
  • Metrics-driven management moves manager ratios from 1 per 5 reps to 1 per 8, cutting cost of sales by about 40 percent.
  • Baseline SDR output is about 10 new qualified meetings a week.
Open foundingsales.com
📄 Article
✓ Link checked Free Intermediate

Stripe's Chief Business Officer on building a written sales operating model (leads, conversion, deal size, win rate, cycle) so you can diagnose whether a miss is the rep or the model. The missing step in most handoffs.

How to train and measure your startup's early sales hires

From SignalFire by Sadasia McCutchen with Jeanne DeWitt Grosser 14 min read

  • Building a working outbound capability takes a minimum of two years, and the median SaaS startup needs 33 months to reach 1M ARR.
  • A rep averages about 4.4 real customer conversations a day, so plan pipeline math off that.
  • Stripe paid early sellers higher equity with lower bonus and OTE, against a shared team quota.
  • The bar for product depth: a PM or engineer should need 10 minutes to notice the person is not on the product team.
  • Early sales hires are part revenue and part R&D, so treat them as a product insight channel.
Open signalfire.com

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