How do we position against a much bigger competitor?

You don't beat a much bigger competitor by matching them. You beat them by changing what the buyer is comparing. A giant's size is only an advantage on the axis they picked. Move the buyer to a different axis, one where scale reads as slow, breadth reads as blur, and everything-for-everyone reads as nothing-for-you, and the size you were afraid of becomes the liability you put to work.

Every founder going up against a giant makes the same opening move, and it's the losing one. They build the feature-comparison chart. They tell the buyer, we do everything they do, plus a few things they don't, for less money. That's not a position. That's an audition for the buyer to keep the incumbent and ask for a discount.

Here's the truth nobody running this play wants to hear. When you market on parity, you've agreed to fight on the giant's field, on the giant's terms, with a fraction of the giant's budget. You will lose that fight. Not because your product is worse, but because you let the bigger company define what better means, and they defined it as more of what they already have.

Why does the bigger competitor feel impossible to beat?

Because you're comparing the wrong things. The giant has more features, more logos, more headcount, more analyst coverage. If the buyer's mental scorecard is who has more, you lose before the first call. This is Solution-Focused Marketing wearing a competitive jersey: you get so fixated on out-doing the incumbent's solution that you accept their definition of the game. The buyer never sees a reason to leave the safe, big, default choice, because you handed them a smaller version of it.

April Dunford, who wrote the book on B2B positioning, makes the point that your position is set by the competitive alternative, the thing a buyer would do if you didn't exist. Against a giant, that alternative is just buy the big brand, nobody gets fired for it. If you don't change what you're being compared to, that's the alternative you lose to every single time.

Why is this harder in 2026 than it used to be?

Because the buyer now does the first round of research with an AI, and AI rewards footprint. When a buyer asks ChatGPT or Claude for the best tool in your category, the model reaches for the brand with the biggest, most consistent presence across the internet. That's the incumbent. The giant doesn't just win the deals now. It wins the shortlist before a human ever looks at you. I unpack that shift in The State of B2B Messaging 2026.

There's a second squeeze. AI brought the cost of look-alike copy to zero, so every challenger in your category is now using the same models to generate the same modern-alternative-to-the-giant messaging. You're not just blurred against the giant. You're blurred against every other small company trying to unseat the giant the exact same way. Sameness is the giant's best friend, because it keeps the buyer on the default. The only escape is a position sharp enough that a model, and a human, can attach it to one specific buyer and one specific fight. That's the whole argument behind why every B2B SaaS homepage says all-in-one.

What's the framework for positioning against a bigger competitor?

Six plays. Each one moves the buyer off the giant's axis and onto yours, where the giant's size stops helping and starts hurting. You don't need all six. You need the two or three that fit your truth, run hard.

1. 1Pick a beachhead the giant is structurally too big to serve. Narrow until you're the obvious choice for one specific buyer the incumbent treats as a rounding error. A giant can't optimize for your niche without breaking the thing that makes it work at scale. Their size is exactly what stops them from following you in.
2. 2Make their size the villain. Reframe big as what it actually feels like to the buyer: slow to ship, slow to support, a ticket number in a queue, a roadmap you'll never influence. Name the old way the giant represents and declare war on it. This is villain framing, and the incumbent hands you the villain for free.
3. 3Change the category so their strengths stop counting. Don't be a cheaper version of their category. Name a new one where the thing you do best is the thing that matters most, and the giant's biggest features become beside the point. Play Bigger's research found category kings capture 76 percent of their market's value, and the fastest way to stop losing to one is to stop competing in their category. I make that case in the category that doesn't exist yet.
4. 4Weaponize the things a focused company can do that a giant can't. Speed, intimacy, a founder who answers the phone, a product shaped around one buyer instead of ten thousand. These aren't consolation prizes. They're the buyer's whole experience, and they're structurally impossible for the giant to copy without dismantling itself.
5. 5Name the buyer the giant ignores. Every dominant incumbent has abandoned a segment it used to serve, because it had to chase enterprise, or up-market, or the average. Find the buyer who feels left behind by the giant and build your entire message around them. They're already angry at the incumbent. You just have to say it out loud first.
6. 6Tell the founder story the incumbent structurally can't. A giant can't credibly say we were founded last year because we were furious about this one thing. You can. Lived truth, a real point of view, and a reason you exist that isn't shareholder value are the one thing the giant's size can't manufacture and AI can't fake.

What do we see across 200+ B2B companies?

After running this with more than 200 founder-led B2B companies in the 5 million to 75 million dollar range, the split is stark. The challengers who lose to giants are almost always the ones positioning as the better version of the giant. They lead with parity and price, and they hand the buyer a reason to negotiate, not switch. The ones who win pick a fight the giant can't take. They narrow, name a villain, and stand for one buyer so clearly that the giant looks bloated by comparison.

The pattern underneath is always the same. Size is only a weapon when the buyer is keeping score on size. Change the scorecard and the giant is suddenly carrying its own weight uphill. Positioning is the lever that changes the scorecard, and it's the one move a smaller company can make faster than a bigger one. I argue that positioning is the only moat AI can't copy in Strategic Positioning Is the Only Moat AI Can't Copy.

What does this look like when a challenger actually pulls it off?

Here's a composite from a handful of engagements that ran the same play. A 19 million dollar Series B fintech kept losing to a category giant ten times its size. Their reps led with a feature chart showing parity plus a lower price. Buyers used that chart to go back to the incumbent and ask for a better deal. The challenger was funding its own competitor's renewals.

We didn't add a single feature. We narrowed the company to one buyer the giant had quietly abandoned when it moved up-market, named the exact frustration those buyers felt with the incumbent, and rebuilt the message around a category the giant didn't lead. The giant's size became the proof point for our villain: too big to care, too slow to change, built for somebody you used to be. Within two quarters the challenger stopped showing up in head-to-head feature bake-offs and started winning deals the giant never even got invited to.

The giant's game vs. your game: where does the deal actually get decided?

What should we do about it this week?

You don't need a bigger budget or a longer feature list to start winning these deals. You need to stop fighting on the giant's axis. Three moves you can make this week:

1. 1Pick your beachhead. Name the one buyer you can serve better than any company on earth, including the giant. Write it as a sentence: we are the obvious choice for this specific buyer who has this specific problem the giant handles badly. If it's broad enough to include the giant's whole market, it isn't narrow enough yet.
2. 2Name the villain the giant represents. Write the old way you're declaring war on, in the buyer's words, not yours. Stuck in a ticket queue behind ten thousand other accounts beats legacy incumbent every time. Put it on your homepage and in your deck.
3. 3Run the Three Questions Test on your message against the giant. Who is this for, what problem does it end, what's the point of view, answerable in five seconds by a stranger. If the honest answer is a cheaper version of the giant, you haven't repositioned yet. The standard for what good looks like is in what a strong B2B positioning statement actually looks like.

A bigger competitor isn't an unbeatable competitor. It's a competitor whose greatest strength only works on one battlefield, and you don't have to fight there. Change what the buyer compares, and the size that scared you becomes the weight that slows them down. PitchKitchen builds Magnetic Messaging Frameworks for founder-led B2B companies in the 5 million to 75 million dollar range, fixing the broken messages and look-alike positioning that let bigger competitors win deals on size alone. It was founded by Greg Rosner, author of Story Craft for Disruptors. The Magnetic Messaging Framework (MMF) is built around four anchors: category design, villain framing, an old-way / new-way contrast, and a promised-land outcome, and against a giant, those four anchors are how David picks the ground. If a company ten times your size keeps winning deals your product should take, the fight isn't on the features. It's on the frame, and the frame is the one fight where being smaller is an advantage.