Earn the Next Year Before You Ask Buyers to Sign for It

A buyer agreeing to evaluate your product, a buyer approving an annual budget, and a buyer accepting three years of contractual obligation are making three different decisions. I would not ask a sales team to treat those decisions as interchangeable.

That is where I land on SaaStr’s “When Should We Start Pushing For Multi-Year Contracts?”. The supplied snippet advises most vendors to stop pushing for them in the age of AI. It describes shorter contracts as the norm across B2B and AI, framing that preference as rational buyer behavior rather than something sellers should fight.

That is SaaStr’s position. My view is narrower: keep multi-year agreements available, but stop making contract length a substitute for understanding the buying decision.

Separate the market claim from the sales decision

The source snippet does not provide contract-duration data, renewal comparisons, or a breakdown by product category. I would not use it to declare that every buyer now wants a shorter term, or that every multi-year proposal is misguided.

I do think it presents a useful challenge to a familiar sales instinct: if a longer agreement benefits our planning, we should push harder for it.

At Leads.biz, our editorial position is that a seller’s preference for predictable revenue is not, by itself, a buyer-facing reason to accept a longer obligation. The proposal needs a specific answer to a specific question: what does the buyer receive in exchange for surrendering flexibility?

“Better pricing” is a starting point, not a complete answer. The buyer still has to weigh the discount against the duration, scope, payment schedule, and consequences of changing direction.

Ask what the longer term actually buys

Before I would recommend presenting a multi-year option, I would want the account team to document four things:

• The durable need: Which workflow does the buyer expect to retain throughout the proposed term?
• The agreed scope: Which users, teams, or capabilities are covered, and what happens if that scope changes?
• The buyer’s consideration: Is the buyer receiving a price commitment, defined implementation support, or another concrete contractual benefit?
• The change provisions: What do the proposed terms say about expansion, reduction, renewal, and exit?

These are my recommended qualification questions, not findings reported in the source.

Their purpose is to distinguish a considered agreement from a longer version of the same sales pitch. If the account team cannot explain the exchange without referring to its own quota or forecast, I would take the multi-year push out of the conversation.

A longer term can remain an option. It does not have to become the test of whether a prospect is serious.

Do not make the discount do all the work

I would present term length and payment timing as separate choices. An annual commitment, an annual upfront payment, and a multi-year commitment are not the same commercial arrangement.

For each proposed option, show the actual duration, total obligation, billing schedule, included scope, and relevant change provisions. Avoid letting a prominent monthly-equivalent price obscure what the buyer must approve.

My preferred sales question would be: “Which part of this commitment is hardest to approve: duration, total spend, scope, or payment timing?”

That is suggested language, not a customer quote. It gives the seller a more precise problem to address than a general objection to commitment. A budget-timing issue calls for a different discussion from uncertainty about whether the product will still fit the workflow two years from now.

Carry the same discipline into prospecting

For B2B marketers, I would bring this distinction upstream. Campaign messaging should identify the problem the product addresses before emphasizing the length of the relationship the vendor wants.

I would start audience planning with a defined account profile and relevant buying roles. Then I would use discovery—not an assumed preference attached to an industry or job title—to establish budget timing, evaluation criteria, and acceptable commitment.

If your team is revisiting that starting point, build a prospect audience around the accounts and roles relevant to your offer. Treat that audience as the beginning of qualification, not evidence that its members want a particular contract term.

The handoff to sales should preserve that distinction. “Fits our target profile” and “ready for a three-year agreement” are separate statements requiring separate support.

Make the next decision easier to understand

I would judge a contract proposal by how clearly it answers the buyer’s decision, not by how many years appear on its first page.

That means recording why buyers accept or reject longer terms, distinguishing duration objections from pricing objections, and reviewing those reasons before changing the offer. It also means resisting the temptation to interpret every shorter-term preference as weak intent.

SaaStr’s recommendation is to stop pushing. My recommendation is to stop pushing by default. Offer a longer agreement when you can explain the buyer’s benefit, define the obligation, and address the uncertainty honestly. Otherwise, focus on earning the next commitment rather than stretching the current one.