Checkpoints, not contracts
Short answer: a three month outbound pilot is usually too short to prove anything and a twelve month contract is more commitment than most CEOs will approve. The structure that solves both is a twelve month plan authorised one quarter at a time, with defined checkpoints that unlock the next quarter.
You get the planning horizon a real sales cycle needs. Your board gets an exit every ninety days.
Why three months is the wrong unit
The maths is unforgiving. In a market with a six to nine month sales cycle:
- Weeks 1 to 2: lists built, domains warming, scripts written. Nothing is live.
- Week 3: first meetings, from the weakest version of the message.
- Week 6: steady state volume, message tuned.
- Month 3: the first meetings from week three are roughly a third of the way through their cycle.
At the ninety day review, no meeting the program produced has had time to close. The only honest metrics available are pipeline created and conversion rates. If the review asks for closed revenue, the program fails a test it could not have passed.
That is how outbound programs get cancelled while their pipeline is still open. It happens often enough that many revenue leaders now carry it as a general belief that outbound does not work.
Why twelve months is a hard sell
Because it is a leap of faith with an unknown vendor. A CEO who has been burned once will not approve twelve months of spend against a promise, and they are right not to. The objection is rarely about total cost. It is about having no way out if it is not working.
The structure that satisfies both
Plan for twelve months. Authorise in quarters. Gate each quarter on a checkpoint agreed in advance.
| Checkpoint | When | Passing looks like | If it fails |
|---|---|---|---|
| Launch | Day 7 | All channels live, lists and copy approved, domains warm | No invoice. You have paid nothing |
| Volume | Month 3 | The committed monthly meetings held, cost per meeting at target | Exit on 30 days, or reset scope and price |
| Efficiency | Month 6 | Pipeline created tracking to plan, qualification rate holding | Same choice |
| Coverage | Month 9 | Enough pipeline to reach the month twelve number at your close rate | Same choice |
The implementation underneath those gates is deliberate. Days 1 to 14 are onboarding, list building, approvals and launch. Month 1 collects conversations and call data. Month 2 kills losing angles and tightens the ICP. Month 3 is when a documented playbook and a monthly meeting number are ready.
Two details make this work rather than sound good.
The first invoice is tied to launch, not signature. If the agency does not go live in fourteen days, and the delay is theirs, nothing has been paid. That single term removes most of the risk from the decision and costs a competent agency nothing.
The buyer sets the pass criteria. Not the agency. You define what continuing requires, exactly as you would for a new hire, and it goes in the order form.
What each checkpoint should actually measure
Match the metric to what the phase can produce.
Month 3. Qualified meetings held, show rate, cost per meeting, market feedback documented. Not closed revenue. Nothing has cycled.
Month 6. Pipeline created, qualification rate, cost per opportunity. Compare pipeline per dollar against whatever your in house team achieved, which is the fairest available benchmark.
Month 9. Coverage. Is there enough pipeline in the funnel to hit the month twelve number at your historical close rate? This is the checkpoint that predicts the outcome, and the one most programs skip.
Month 12. Closed won influenced, cost per acquisition, and whether the playbook is documented well enough for you to run it yourself.
Do the payback arithmetic before you sign
Take your own numbers: pipeline created, closed won, and the ratio between them. If your close rate on created pipeline is 8 percent and your average contract value is $80,000, then every $1M of closed revenue requires $12.5M of pipeline, which at $80,000 per deal is roughly 156 opportunities.
Work backwards from that to meetings, and you will know within ten minutes whether the volume on offer can reach your payback target. If it cannot, the honest conversation is about scope or expectations, not about whether to sign.
Most disappointment in outbound comes from skipping this ten minutes.
Frequently asked questions
How long should an outbound agency contract be? Long enough to cover your sales cycle plus ramp, which for most B2B software means six to twelve months. Structure it with quarterly exit gates so length does not equal exposure.
Is a three month pilot ever right? Only when the motion is already proven and you are adding volume to a known conversion rate. For an unproven message, three months buys the learning and gives away the return.
What should happen if the agency misses the number? Makegood meetings worked off free the following month, not credit notes. Credits pay you back in money for a problem that costs you pipeline.
Who should set the checkpoint criteria? You. The agency should agree to them in writing before starting. An agency that resists specific pass criteria is telling you it does not expect to pass them.
What if our board only approves quarter by quarter? That is exactly what this structure gives them. The twelve month figure is a plan, not a commitment, and the money is released in quarters against results.
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