Question 1

How long should sales onboarding take?

Accepted Answer

Effective sales onboarding for startups takes 30-90 days depending on product complexity and sales cycle length. The first 30 days focus on product knowledge and shadowing. Days 30-60 involve supervised selling with coaching. Days 60-90 transition to independent selling with performance milestones. Rushed onboarding leads to longer ramp times and higher turnover.

Question 2

What should be in a sales playbook?

Accepted Answer

A startup sales playbook should include: your ideal customer profile and qualification criteria, discovery questions and objection handling, demo flow and key talking points, pricing and negotiation guidelines, CRM usage and deal stages, and email/call templates. Keep it practical and update it as you learn. A 10-page playbook that gets used beats a 50-page document that collects dust.

Question 3

How do I know if my sales rep is ramping successfully?

Accepted Answer

Track leading indicators during ramp: number of quality conversations, pipeline generated, and deal progression—not just closed revenue. Set weekly milestones for the first 90 days. A rep ramping well shows increasing activity quality, asks good questions, and improves their pitch each week. Red flags include avoiding prospecting, not following the process, or making the same mistakes repeatedly.

Training & Onboarding

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