A 30-60-90 Day Plan for Onboarding a New Sales Rep

Half of a good ramp happens before the rep starts. Prepare:

• Accounts for the CRM, email, calendar, call recording tool and team chat, with permissions set.
• A written sales playbook, or at least the process and discovery sections.
• A folder of recent wins, losses, proposals and call recordings to study.
• A list of starter accounts or a territory, so nobody waits for an assignment.
• A schedule for week one that includes time with product, customer success and the founder.
• A named buddy for questions that a manager shouldn't have to answer.

Agree the compensation plan and the ramp treatment in writing beforehand, too. See the commission plan guide for how ramp affects quota and pay.

The first month is for learning how you sell and how customers buy. Aim for:

1. Product fluency: they can explain what you do and who it's for without slides, and they've used the product themselves.
2. Customer knowledge: they've listened to a set of recorded calls and joined live ones, and met a few customers.
3. Process knowledge: they can describe your pipeline stages and what evidence moves a deal between them.
4. Shadowing: they've observed several discovery calls and demos, and debriefed each with the manager or buddy.
5. A first practice run: a role-played discovery call and demo, with feedback.

Judge readiness by observation. If a rep can't run a mock discovery call using your structure, keep them in learning mode a bit longer instead of pushing them into live calls.

In the second month the rep starts selling, with a manager's safety net. Typical milestones:

• They run discovery calls on their own, with the manager listening in on a sample and giving feedback within a day.
• They build their own pipeline from the starter accounts, and their CRM notes follow a fixed discovery notes structure.
• They send their first proposals, with the manager reviewing before they go.
• They bring at least one deal to the weekly pipeline review and defend its stage and next step.
• They practice handling your top objections in role-play.

Set activity and pipeline expectations from what your past reps or your own founder-led sales achieved at this point. If you have no history, state the expectation as a first estimate and revisit it after a month.

By the third month the rep should work like an owner of their patch. Look for:

• A pipeline they can explain deal by deal, with dated next steps and buyer evidence for each stage.
• Independent run of demos, proposals and negotiations within the pricing rules you've set.
• Accurate forecast calls, meaning their category calls match what happens.
• Use of the CRM without reminders.
• A short written reflection on what's working, what isn't and what help they need.

Hold a formal review at day 90 with the rep. Compare results with the plan, agree the strengths to build on and the gaps to fix, and set goals for the next quarter. If it isn't working, this is the time for an honest conversation, not month six.

Keep a weekly one-to-one with a fixed format: what went well, what's blocked, what to practice this week. At days 30 and 60, hold a short review against the milestones above, and record it.

Measure a mix of inputs and outputs. Inputs include calls held, discovery quality and pipeline created. Outputs, such as closed revenue, come later in a long sales cycle, so don't judge the rep on them in month two if your cycle is longer than that. The average B2B new-logo win rate is 19 percent¹, so expect to need a decent volume of qualified opportunities before wins appear.

An enablement tool like Highspot or Showpad can serve as the learning path, with content, quizzes and tracked completion. Weigh that against the comparison of enablement platforms if you're choosing one. Before you buy, make sure the plan works on paper first.