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Doing the work

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 31 to 60 are supervised reps, they run the call and you sit in silently, then debrief. Days 61 to 90 they own deals and you inspect the pipeline, not the person. Median AE ramp is around four months and enterprise can be nine to twelve, so treat month three as first deal territory, not full quota. Write the milestones down before they join, because a ramp plan you improvise is a ramp plan you cannot hold anyone to.

Go deeper

5 resources, 5 link-checked.

📖 Book
✓ Link checked Free Intermediate

A concrete onboarding curriculum you can copy: cohorts, drilling, peer sparring and shadowing, with the argument that practice matters more than the live calls. Exactly what a first ramp plan should contain.

Founding Sales, Chapter 12: High-Impact Sales Onboarding and Training

From Founding Sales by Peter Kazanjy 30 min read

  • Sales management's traditional expectation is losing 30 to 50 percent of each hiring class within six months.
  • Run a one to two week boot camp, preceded by about ten hours of pre-work spread over two weeks.
  • Onboard in cohorts: it takes about the same effort to onboard four reps as one.
  • The real cost of a slow ramp is opportunity cost, 50K to 200K a month of revenue not being sold.
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
📄 Article
✓ Link checked Free Advanced

The headcount question answered as arithmetic: revenue target divided by revenue per rep and capacity utilisation, with ramp time and attrition built in. Use it before you sign off next quarter's hiring plan.

Sales Capacity Planning

From Everstage 12 min read

  • Reps spend only about 30 percent of the week actually selling, the rest goes to admin and quoting.
  • Capacity formula: revenue target divided by (revenue per rep times utilization), so 5M at 400K and 0.6 needs about 21 reps.
  • Mid-market B2B SaaS reps carry 200K to 500K a year; enterprise reps 500K to 750K.
  • Assume 60 percent capacity utilization and revisit the plan at least quarterly.
Open everstage.com
✍️ Essay
✓ Link checked Free Intermediate

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

  • Rule of 10: an AE's quota is 10x base salary, and the standard SaaS commission rate is 10 percent of ARR.
  • Pay a 50/50 base to variable split, then accelerate to 15 percent commission past quota.
  • Plan for a 4 month ramp and about 70 percent average team attainment, so carry excess quota capacity.
  • Set a manager's quota at 80 percent of their team's capacity; below 400K new ARR per AE, sales-led may not pencil.
Open sacks.substack.com

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