Five rungs, five questions
Each hire answers one question about your sales motion and leads the rung below. Don’t hire the next rung until the current question is a yes and the rung below has more than one person.
- 01Account ExecutivesCan someone besides me sell this?Leads no one. Carries a quota.~$0.5–1.5M ARR
- 02Sales ManagerDoes it work without me in the deal?Leads AEs.~$2–6M ARR
- 03Director of SalesDoes it work across teams?Leads managers.~$8–12M ARR
- 04VP of SalesCan we double capacity on plan?Leads directors.~$15–20M ARR
- 05Chief Revenue OfficerShould one person own all revenue?Leads VPs.~$30M+ ARR
Before the ladder: founder-led sales. You close the first deals and learn why customers buy. No hire replaces this.
ARR ranges are rough. The signals below decide timing.
A leader needs a team of the rung below. Several AEs need a manager. Several managers need a director. One manager doesn’t.
Hire on signals
If any “not yet” is true, fix it before you hire.
| Rung | Hire when | Not yet | Hire for |
|---|---|---|---|
| 01 Account Executives | You’ve closed 10–20 customers and can name why they bought. Your own selling hours are now the growth constraint. | Every deal closes for a different reason, or you can’t say why customers buy in one sentence. | An AE who has sold without a brand, enablement or a playbook, and writes down what works. Hire two so you can tell the rep from the motion. |
| 02 Sales Manager | At least one AE consistently hits quota, and it’s time to scale to 4+ reps. | AEs still rely heavily on founder touches to close, or you don’t have the money to scale the team. | A player-coach who carried a bag recently, coaches from call recordings, and runs a tight pipeline review. |
| 03 Director of Sales | Two or more managers, usually because the team has split: BDRs and AEs, or SMB and enterprise. The work shifts from coaching reps to building comp, territories and a forecast the board trusts. | You have one manager. A director over one manager is an expensive layer. Coach or replace the manager first. | A systems builder: comp plans, territory design, a repeatable hiring engine, and a forecast cadence managers actually run. |
| 04 VP of Sales | Two or more directors, a written playbook, win rates that hold quarter to quarter, and a plan that doubles sales capacity. | You have one director, or you want someone to “figure out sales.” A VP scales a motion. They rarely invent one. | Someone who has led directors through the next doubling at your ACV and sales cycle, not only at a bigger logo. |
| 05 Chief Revenue Officer | Two or more VPs across sales, CS and marketing need one revenue owner, handoffs between them are losing revenue, and expansion is a real share of growth. | One VP can still run all of revenue, or the founder needs to stay close to the business. | An operator who has led VPs across the full customer lifecycle. Finance-literate, comfortable with the board, and fluent in NRR as well as bookings. |
Managing reps, managers, directors and VPs are four different jobs
Coaches deals
Call reviews, deal strategy, ramp. Wins when reps get better.
Builds systems
Comp, territories, hiring, forecast. Wins when managers coach well.
Designs the org
Headcount plan, segment strategy, a seat on the exec team. Wins when directors run their systems.
Aligns functions
Sales, CS and marketing on one number. Wins when each VP owns their function.
Being great at one level doesn’t predict the next. Hire for the level this person will actually lead on day one.
On titles: the job matters more than the title. If the right person will do the manager or director job but needs a bigger title to join, a bigger title can work, as long as you’re fine with title inflation. Write down the actual job first: who they lead, what they own, and how you’ll judge them. Then hire the person who will do that work, whatever it says on their card.
Three expensive mistakes
Hiring the VP first
Without a playbook, a VP has nothing to scale. Hire two AEs and keep selling.
Promoting your best closer
Closing and coaching are different jobs. Promote the rep others already ask for help.
Hiring one AE
If one rep misses, you can’t tell whether the rep or the motion failed. Hire two.
Before your next sales hire
- Name the rung you’re on today.
- Review the next rung’s signals with your board each month.
- Count who this hire will lead. If it’s one person, wait.
- Write the scorecard, then start the search. Use the Who Method.