Before you approve a new role or a small batch of hires, write down the outcome that must improve, why a person is the right fix, who will coach the new hire, the full cost and time to productivity, what success looks like at day 30 and day 90, and what you will stop doing if the hire slips. Paste the hiring request, the data behind the problem, the manager's current team, compensation and runway figures, and any alternatives already considered into one request. Instruct Pingpong to test whether the evidence points to a staffing gap or to a process, product, or tooling gap, and to flag missing success measures. Review your written answers in a second round.
This page is for chief executives, finance leaders, and department heads deciding on a specific role before it opens. Executive starting points live under Pingpong for executives.
Write the role case in two sentences
Fill in this sentence before anything else: We need this person because [measure] has moved from [number] to [number], and by day 90 they will have [result]. Then add a second: If we cannot hire by [date], we will [what stops or changes]. A request that cannot complete both sentences is not ready.
Rule out the alternatives
- A process change: would fixing how work moves through the team close the gap?
- A product or tool change: is the work caused by something the product should do itself?
- A contractor or agency: is the need temporary or uncertain?
- An existing employee: could someone move into the work, with the role backfilled later if needed?
Check the manager and the money
A new hire needs coaching, and a manager with a full team gives less of it. Count the manager's direct reports after the hire. Then price the role fully loaded, with salary, benefits, taxes, equipment, and recruiting, and set it against the months before the person is fully productive and the company's runway.
A worked example
This example is illustrative and does not describe a customer. A 120-person software company with 26 months of runway is asked to approve three customer success managers. Gross revenue retention has fallen from 92% to 86% over four quarters, and the head of customer success argues that each manager carries too many accounts. Each role costs about $130,000 a year fully loaded, so the request totals $390,000 a year.
The chief executive pastes the request, the churn analysis by account, the customer success team structure, ramp data from past hires, and the finance plan.
A useful pass finds that about 70% of lost revenue came from accounts that never finished onboarding, a pattern that more account coverage may not fix. Onboarding is handled ad hoc by whichever customer success manager has time. The head of customer success already has nine direct reports, and three more would make twelve with no team lead. Past hires took four months to carry a full set of accounts, so the new coverage would arrive around month five. The request sets no measure for day 90 and says nothing about what happens if hiring takes longer than planned.
The chief executive approves one onboarding specialist, at about $115,000 fully loaded, instead of three customer success managers. At day 30, the specialist runs onboarding for every new account. Success at day 90 is 80% of new accounts completing onboarding within 30 days. Engineering adds an in-product setup checklist this quarter. A senior customer success manager becomes team lead, taking four direct reports from the department head. If the specialist is not hired within 60 days, the team pauses quarterly reviews for the smallest accounts to free time for onboarding. The customer success manager roles come back for review next quarter if retention has not recovered above 89%.
For a plan covering many roles at once, see war-game a hiring plan before the board approves it.
A request you can copy
Below are a hiring request, the data behind the problem it addresses, the hiring manager's current team, compensation and runway figures, and alternatives we considered. Test whether the evidence points to a staffing gap or to a process, product, or tooling gap. Check the manager's capacity to coach. Calculate the fully loaded cost and when the hire would be productive. Flag missing success measures for day 30 and day 90, and any missing plan for a slow hire. Stop there so we can answer in writing, then review our answers.
How Pingpong runs the review
The web review app sends your request through several models in order. Each later model receives the original request and every earlier answer, with instructions to assess the work so far. For the steps inside the app, see running your first review.
What a model can't review
A model does not know your team's workload beyond the data you paste, the local hiring market, or the candidates. HR owns compensation bands and hiring practice, and you own the decision.
When headcount changes go to the board, see war-game a decision before the board meeting. More guides live under work decisions before you commit.