"We Just Signed With Someone Else Three Months Ago" — The Timing You Can Actually Use

A rep on a call I was listening to got the objection every prospector gets eventually. "Appreciate the call, but we just signed with [competitor] three months ago."

He said thanks, asked when the contract was up, heard "three years," and set a task for eleven months out. Polite. Professional. Completely wrong.

He had just walked away from the single best-timed conversation on his list that week and replaced it with a calendar reminder that he will almost certainly not be at that company to action.

Here is what I want to convince you of: when a prospect just signed with a competitor, month three is not the worst time to call. It is close to the best time. And the reason has nothing to do with being aggressive, and everything to do with where the buyer's head is at that specific moment.

What Month Three Actually Feels Like Inside the Account

Think about what happens after a deal closes on the other side.

Month one is the honeymoon. Kickoff call, implementation plan, everybody is polite, the exec sponsor tells the board they solved the problem. Nobody wants your call and nobody should take it.

Month three is different. By month three the implementation has hit whatever it was always going to hit. Data migration was messier than the SOW said. Two integrations that were listed on the website turned out to need professional services. The champion who bought it has discovered that the thing they demoed in a sandbox behaves differently against real records. Adoption is somewhere below what they promised their boss. Somebody on the team has already said out loud, in a meeting, "is this what we paid for?"

And critically, nobody has emotionally committed to renewal yet. The sponsor's identity is not yet fused to the decision. In month twenty-two it will be — by then they have defended the choice in three QBRs, they have built process around it, and asking them to consider an alternative is asking them to admit a mistake in public. In month three, they are still allowed to be disappointed. The receipt is still in the bag.

That is the window. Not to rip the deal out — you almost never will — but to become the name they think of when the disappointment gets big enough to have a name.

Most reps hand that window to nobody. They call at month eleven, when the incumbent's CSM has already booked the renewal review, the sponsor has already rationalised the pain, and your call arrives sounding exactly like what it is: a vendor who checked a date field.

The Trap: Sounding Like a Vulture

The reason reps avoid this play is that the obvious version of it is repulsive.

The obvious version is: "Oh, you went with them? Yeah, we hear a lot of complaints about their support. How's the implementation going, ha ha." Everyone has been on the receiving end of that call. It insults the buyer's judgment in the first thirty seconds, which is a strange strategy given you need that same judgment to eventually pick you.

Here is the rule I hold myself to. You are not allowed to say anything negative about the incumbent. Not one thing. Not a raised eyebrow, not a "interesting choice," not a knowing pause. If they went with a competitor, that competitor won a real evaluation against real criteria, and telling the buyer they were fooled makes you the second person in the room who thinks they are stupid — the first being them, quietly, if things are going badly.

What you are allowed to do is ask questions that let them tell you. That is the whole play. You are not the prosecution. You are the person who happens to be in the room with a notepad when they need somewhere to put the frustration.

So the opening sounds like this:

"Got it — you signed with them in [month]. Honestly that makes this an easier call, because I'm not going to try and unwind something you just bought. Can I ask you two questions about the rollout and then get out of your way?"

That does three things. It acknowledges reality so they stop bracing. It explicitly disclaims the thing they are afraid you want. And it puts a hard, small boundary on the call — two questions — which is much easier to say yes to than "do you have fifteen minutes."

They will almost always give you the two questions. Now make them count.

The Two Questions

Almost every rep I have watched asks some version of "how's it going with them?" That question has one answer: "fine, good, we're happy." It is a social question and it gets a social answer. You learn nothing.

These two are better.

Question one: "Where are you against the original rollout timeline?"

Not "is it going well." Not "are you happy." Against the timeline. Every implementation has a plan with dates on it, and by month three every implementation is either on that plan or it is not, and the buyer knows which one it is without having to form an opinion about the vendor.

This is a factual question, so it gets a factual answer. And the answer is enormously diagnostic. "We're basically where we said we'd be" means the account is healthy, and you should behave accordingly — more on that in a minute. "We were supposed to be live in two regions by now and we're live in one" means something. "Honestly, we paused it" means quite a lot.

The follow-up is one word: "What moved?" Then say nothing. Whatever comes out of that silence is the most valuable thing you will hear all week, because it is the actual shape of the gap between what they were sold and what they got.

Question two: "Who's actually in the tool day to day, versus who you thought would be?"

Adoption is where implementations die quietly. A tool can be technically live and functionally dead. The buyer knows the seat count they bought and they usually know, roughly, how many of those seats log in. If they bought forty seats for the field team and it is being used by the two people in ops who ran the evaluation, that is a renewal conversation waiting to happen and everyone involved already senses it.

Again, this is a factual question. It does not require them to criticise anybody. It just requires them to describe their own organisation, which people are usually happy to do.

Between those two answers you will know within about four minutes whether this account is a real opportunity for month eleven or just a name on a list. And you will know it without having said one bad word about the company that beat you.

"We're Locked In For Three Years"

This is the line that ends most of these calls. It should not.

First, understand what the buyer means when they say it. Sometimes it is literally true. Often it is shorthand for "please stop selling to me, I do not want to reopen this." Occasionally it is a defensive reflex from someone who signed a one-year deal with an auto-renew and has not actually read the term.

Here is roughly what I say:

"Makes sense, and I'm not asking you to break it. Contracts like that usually have a review point somewhere in the middle where you and they sit down and look at whether the original business case landed. All I want is to be a useful data point when you get to that conversation. Nothing to buy, nothing to evaluate. Would you object if I sent you two things a quarter — the kind of thing you'd want in front of you before that review?"

Notice what is not in there. No "just in case things go sideways." No "when you're ready to make a change." No implication of failure. You are offering to help them do a job they already have to do, which is justify or reconsider a purchase at a review point.

And notice the ask. Not a meeting. Not a demo. Permission to send two things a quarter. That is the smallest possible yes and it is the one that matters, because it converts you from a cold caller into someone with standing.

The other thing worth doing, gently, is establishing the actual dates. "Is that three years from signature, and does it auto-renew or does it lapse?" A surprising number of buyers do not know, and the act of finding out — for you, at their desk, while you are on the phone — plants a flag. Now the contract has a shape in their mind. Now there is a date. Dates create urgency later even when they create none now.

Becoming the Documented Alternative

Here is the thing nobody tells new reps about how enterprise renewals actually work.

When a company decides not to renew a piece of software, that decision has to be defended internally. Somebody has to walk into a room and explain why the organisation is going to eat the switching cost, retrain people, and migrate data. "I didn't like it" does not survive that room. What survives that room is a documented alternative — a named vendor, a rough price, a sense of what the migration involves, and evidence that someone did the work.

Most of the time, when the renewal comes around and the buyer is unhappy, there is no documented alternative. So they renew. Not because the incumbent won, but because switching required work that nobody had done, and doing it in the four weeks before a renewal date is not realistic.

Your entire job for the next nine months is to be that documented alternative. Which means the things you send should not be case studies about how great you are. They should be the raw material of an internal business case:

A one-page migration outline. What actually moves, how long it takes, who from their side has to be involved. Buyers are far more afraid of the migration than the price.

A straight pricing structure. Not a quote, not a discount, just how you charge and roughly where a company their size lands. Ambiguity here is what kills you at review time, because "we'd have to get a quote" is a task and tasks do not get done.

Something about the specific problem they described in question one. If they told you the multi-region rollout stalled, the useful thing you can send is how other companies sequenced a multi-region rollout — including, if it is true, where it is hard with your product too. Honesty about your own limitations is the fastest credibility you can buy in this situation, because everything else they are hearing is a sales pitch.

When the review meeting happens, you want your name to be the one already on a page in somebody's drive. That is the whole game.

The Second Use Case

There is a much faster path than waiting for renewal, and most reps miss it entirely.

The incumbent won a specific evaluation for a specific problem. Almost no product covers everything the buyer needed. There is nearly always an adjacent use case, a second team, a region, a workflow that fell out of scope during the evaluation because the buyer had to narrow it to get the deal approved.

That scope cut is your opening, and it does not require anybody to admit the purchase was wrong. It is additive, not competitive.

So somewhere in the call, once the two questions are answered, ask:

"When you scoped it with them, what got cut to make the numbers work?"

Or, if that is too direct for the relationship: "What's the piece the new system doesn't touch?"

I have seen this open doors in the strangest places. A logistics company buys a TMS for their asset-based fleet and the brokerage side is running on spreadsheets for another year — which is why the objection handling in the freight and 3PL cold call script spends so much time on the fact that these buyers have already heard four versions of the same pitch and need you to talk about the part of their operation nobody else asked about. A manufacturer rolls out a system at the flagship plant and the three smaller sites are explicitly phase two, undated, unfunded, and open — the sort of thing that comes up constantly when you actually earn twenty minutes with a plant manager instead of pitching the corporate office. A SaaS company buys a sales engagement platform for the AE team and the SDRs are on something else, which is the split you run into over and over when dialling CROs and RevOps leaders.

A land in the second use case is worth more than the renewal fight, because you are inside the account before the review even happens. You are no longer the documented alternative on paper. You are the vendor they already work with.

The Cadence: Light, Spaced, Useful

The way you lose this account is by treating it like a normal opportunity and running a normal sequence at it. Eight touches in two weeks against a buyer who just signed elsewhere reads as desperation and gets you blocked.

What works is the opposite. Long gaps. Low volume. Every touch carrying something they would have wanted even if you had never called.

Roughly what I run: a short note about a month after the first conversation referencing the specific thing they told me — not a check-in, a piece of substance about that thing. Then something quarterly. A call at whatever the halfway point of the term is, because that is usually when the internal review actually happens, not at the end. Then a genuine re-engagement about ninety days before the renewal date, at which point you are not cold, you have standing, and you have been useful for a year.

Between those, one rule: never send anything that only serves you. No "just circling back." No "wanted to bump this to the top of your inbox." No forwarded webinar invites. Every touch has to survive the test of the buyer reading it and thinking "that was worth thirty seconds." If you cannot pass that test this month, do not send anything this month. The gap costs you nothing. A worthless email costs you the permission you spent a good call earning.

And when the rollout is genuinely going well — because sometimes it is, and the answers to your two questions will tell you plainly — say so and mean it. "Sounds like it's landing properly. I'll leave you alone. If anything changes, or if you end up needing to cover [the second use case], I'm easy to find." Then actually leave them alone for six months. Buyers remember the vendor who took the answer and went away. That memory is worth more than four more emails into a healthy account.

The Reframe

"We just signed with someone else three months ago" is not a rejection. It is the buyer handing you their timeline, their decision criteria, their sponsor, and their pain calendar, all in one sentence — and most reps hear it as a door closing and log a task for eleven months out that nobody will ever action.

Work it as what it is: an account with a live implementation, a known review date, a scope gap, and a sponsor whose ego is not yet welded to the decision. Ask about the timeline. Ask about who is actually logging in. Never say a word against the people who beat you. Be the alternative that is already documented when the review happens.

If this is an objection you are hearing a lot, the fix is not a better email template — it is being able to say the two questions cleanly, at pace, without the little apologetic wobble that tells the buyer you expect to be hung up on. That is the sort of thing I would drill out loud twenty times before your next block, which is exactly why we built DrillCall: to give reps somewhere to run the same awkward objection until it comes out flat and calm instead of hopeful.

The deal is signed. The decision is not finished. Those are two different things, and the gap between them is where a lot of quota gets made.