AI marketing has a timing problem.
By the time you finally, finally settle on messaging, the product has already evolved and buyers have their shortlists.
(Kind of like sending holiday cards out in February. Nice gesture, but trust… your readers have moved on.)
It’s a tough cycle:
- AI products evolve quickly.
- When customers see value in one workflow, they immediately push for more.
- Product decisions follow.
- Positioning shifts.
- And messaging has little time to settle before the cycle repeats.
It leaves many marketing teams stuck in response mode, updating messaging after roadmap decisions are made, chasing clarity instead of leading with it.
To make matters worse, buyers are narrowing their options faster than sales and marketing teams anticipate. G2’s 2025 Buyer Behavior Report found that active testing of AI tools was common throughout 2025, but this exploratory phase has an expiration date. Once testing stops, only the tools already under consideration have a real chance of being adopted into a company’s tech stack.
The doorway is the testing window. The hat is your AI product. You’re Indiana Jones.
But there’s good news in all this. Sydney Sloan can help.
In her work as CMO advisor to G2, Sydney watches how buyers research, compare, shortlist, and select software across more than 100 million decisions a year. An important pattern she’s noticed: once buyers narrow their shortlist, they almost never reopen it.
The pressure’s definitely on. Here’s how not to get cooked.
Key takeaways: What actually determines who makes the shortlist?
- AI positioning changes faster than traditional SaaS because customer success quickly leads to expansion, and that forces frequent product and messaging changes.
- In 2025 and early 2026, AI buyers are in an active testing phase, but that window is closing. By mid-2026, most will have selected their core AI platforms.
- The teams that make the final lineup keep four decisions aligned on a regular cadence: positioning, build-vs.-partner choices, the buying committee, and messaging for business, IT, and practitioners.
Lead the change instead of reacting to it
Right now, buyers are experimenting.
Contracts are short.
Switching is easy.
Platforms are being tested side by side.
“People will switch. We’re not loyal,” Sydney says. “We’re in the playground right now, but by this time next year, people will pick their platforms of choice.”
Over the next 6–9 months, buyers will narrow their options and lock in the platforms they plan to build on. And once those decisions are made, they rarely change.
G2 found that this consolidation is already underway. Shortlists with just 2–3 vendors grew from 28% in 2023 to 38% in 2025. Single-vendor shortlists doubled over the same period. And a growing share of buyers choosing just one platform to evaluate at all. “8% of buyers now shortlist a single vendor,” Sydney notes.
Once buyers form that shortlist, the outcome is usually decided. In fact, 95% go on to select their initial top choice.
The lesson here: Timing determines outcomes more than polish does.
The teams that stay relevant don’t try to freeze their messaging while the product evolves. They expect change and plan for it.
More specifically, they align four decisions at the same time—positioning, build-vs.-partner choices, the buying committee, and messaging—so product, marketing, and go-to-market teams move together instead of in sequence.
That coordination is what keeps a platform in the conversation while buyers are still choosing.
A 4-step system for staying on the shortlist
Step 1: Define the swim lane you own and the one buyers want next
Start with one question: Which workflow stage do you clearly own today?
Be explicit about the result customers get there. This isn’t a one-time exercise; revisit it monthly. As your product evolves, the answer will too. But you have to be specific, Sydney notes:
You can’t just lead with ‘AI’ or ‘agent,’ because everybody does that.
When positioning keeps shifting, it’s often because teams skip this step or only do it once. In AI markets, that’s not enough.
Sydney consistently pushes teams back to the same discipline. “It comes back to outcomes,” she says. “What are the 3? What promises are you making? What outcomes are you actually designing for?”
Limit your answer to three outcomes. Fewer forces focus. More creates noise.
One useful exercise is to state each outcome as, “We will [specific action] by [specific multiple].” For example:
- We will convert inbound demand 5× faster than legacy workflows
- We will cut time to opportunity creation in half without adding headcount
Avoid abstract claims like “improve efficiency.” Buyers need to understand exactly what changes when they use your product.
Once you’ve wrapped your head around your swim lane, document where customers are pulling you next. Expansion requests are signals.
For example, in 2023, Box shifted its positioning from “document management” to the “content cloud” as demand for AI functionality increased.
Over time, patterns emerge that show which adjacent swim lanes buyers expect you to enter. Capturing both sides—the swim lane you’ve already proven and the one buyers want next—creates a stable anchor in a fast-moving cycle.
Step 2: Include “build or partner” decisions in your messaging
Every expansion request (aka, every “it would be cool if you could add…”) from customers forces a product decision. That decision shapes what marketing can credibly promise.
If you build, you own a larger swim lane and the outcomes that come with it. You’re also committing to ongoing maintenance, security, performance, and support.
If you partner, your integrations and partner products become part of how buyers evaluate your platform. It means you’re tying your promise to someone else’s roadmap, reliability, and user experience.
In both cases, marketing is responsible for setting expectations buyers will hold the product to. That’s why Sydney pushes teams to engage at the decision stage, not after the work is already underway.
“If you build it, you have to manage and maintain it,” she says. “Most teams haven’t fully quantified what that actually means.”
Those costs compound over time. When products or integrations fall short of the promises marketing makes, positioning loses credibility fast and buyers notice. 1 in 4 buyers won’t even consider a vendor without pre-built integrations. Another half use integrations to break ties.
Marketing teams that participate early in build-or-partner decisions avoid gaps between roadmap choices and buyer expectations.
Step 3: Talk to your new buying committee, IT
In traditional SaaS, marketers had a rough rulebook. Company size, industry, and revenue were usually reliable indicators of buying behavior. Qualification criteria followed familiar patterns, and business stakeholders (operations, finance, business unit heads) typically led the decision.
Not so with AI. Sydney explains:
In SaaS, business buyers had control. With agentic systems, IT is back in the driver’s seat.
In other words, the AI boom means that IT organizations control much of the decision-making power. They hold the line on security and compliance, but also on whether a platform can even be seriously evaluated. G2 found that by spring 2025, IT departments controlled more than half of AI software funding.
As a result, strong marketing teams today are the ones who can craft messaging around technical alignment, rather than company demographics. They’re considering new rules, like:
- Which foundational LLM the IT organization supports
- Whether buyers are actively testing multiple AI tools
- How well the existing stack aligns with your integrations
“Does the IT organization support the foundational LLM your models rely on?” Sydney asks. Your job is to be able to answer that question—for yourself, and your prospects.
Step 4: Build layered positioning that speaks to your committee
Once teams align on what they’ve built, how they’re expanding, and who’s involved in the buying decision, they don’t try to say everything at once.
They build 3 layers of positioning:
- Business leaders: Care about clear outcomes tied to the swim lane
- IT: Need to understand explicit LLM foundations, security posture, and governance
- Practitioners: Interested in workflow fit, integrations, and day-to-day value
Each layer reinforces the same core story without relying on another stakeholder to interpret or explain it.
Layered messaging lets teams update a specific layer of their positioning—like IT-facing technical language, integration messaging, or practitioner workflows—without rewriting their entire narrative every time the product evolves. That flexibility matters when expansion is continuous, not occasional.
When clarity actually matters
Buyers are giving fewer companies a real shot and more of them are skipping comparison altogether. They used to explore options side by side. Now they’re committing faster and reopening the door far less often.
Simply put, in 2026, the "evaluation" stage is really going to be “confirmation.” So you’ve gotta get on that shortlist early.
The teams that make the list will be the ones who align four decisions on a regular cadence: positioning, build-vs.-partner choices, the buying committee, and messaging. They present a clear, consistent story across every touchpoint.
Those teams design for change as a constant. They’re assessing expansion requests deliberately. They’re updating messaging in weeks, not quarters.
FAQ
How often should AI teams revisit positioning?
Monthly. AI markets don’t sit still, so your positioning can’t either. It’s not a one-time exercise. A regular cadence helps teams stay aligned as customer requests, product decisions, and buyer dynamics evolve, without rewriting everything from scratch.
Does frequent change signal weak strategy?
No. In AI markets, change is a signal of traction, not confusion. What creates instability isn’t change itself, but teams making product, marketing, and go-to-market decisions in isolation.
What matters more: creative messaging or consistency?
Consistency. Buyers reward clear, coherent stories across business leaders, IT, and practitioners, especially as shortlists shrink and decisions harden. Clever messaging can attract attention, but coherence builds trust.
When should marketing join product expansion decisions?
Early. Build-vs.-partner choices shape what marketing can credibly promise long before messaging is updated. When marketing participates upstream, teams avoid gaps between roadmap decisions and buyer expectations.
