How startups can outmanoeuvre category leaders

When you’re a small fish in a big pond, the instinct is to copy the big fish. 

This may mean matching their features, mirroring their language, and competing on their terms.

That instinct is wrong though, startups don’t beat giants by being cheaper or faster versions of them. 

They win by being different and sharper. They spot the blind spots and go where the incumbents can’t or won’t.

In this post, we’ll show you how to avoid the trap of category mimicry, identify and exploit positioning gaps, and to craft a story that sticks.

This is about clarity, not complexity, and it starts with one uncomfortable truth: if your pitch sounds like theirs, you're invisible.

Don’t compete on their playing field

Big companies want you to believe that size equals legitimacy. That market share is a proxy for quality. 

Category leaders can be slow, burdened by legacy code, bloated messaging, and less agile thinking.  

That’s your advantage.

Instead of trying to compete on scale, ask yourself:

Where are they weak, slow, or silent?

• Under-served segments. Notion ignored enterprise early on, Almanac doubled down on it. 
• User frustrations. For example, Canva’s simplicity was a response to Adobe’s complexity. 
• Old messaging. Duolingo broke language learning’s ‘serious’ tone with humour and gamification. 

Don’t echo their value proposition, try and undermine it. 

Find your wedge, not your tagline

Most early-stage messaging is a mess of buzzwords such as scalable, innovative, cloud-native. It sounds like everyone else.

What you need is a strategic wedge.

A wedge is your way into the market. It’s the narrow, sharp slice of the problem that you solve better than anyone else. It gives you permission to expand later, but traction in the short-term. 

Your wedge should be:

• Solve real pain > offer extra polish. Urgent, not just nice to have.
• Specific > vague. ‘Stripe for marketplaces’ is sharper than ‘the future of payments.’
• Position against something. Be anti-spreadsheet, anti-slow, anti-overengineering, whatever your users hate most.

You don’t need to be all things to all people. You need to be the right thing for the right people.

Punch above your weight with a sharper story

Category leaders play it safe but you can’t afford to. As a startup, you don’t have a decades-old brand to fall back on. 

You do have the advantage of focus though. 

While bigger rivals are busy building roadmaps for five personas and ten verticals, you get to speak directly to one kind of person with one kind of problem. 

Startups punch above their weight by telling sharper, spikier stories.

Here’s how:

• Lead with a villain. Frame your story around what’s broken. It gives your solution urgency. As Andy Raskin says, “The most powerful story you can tell is not about your product, but about a change in the world” 
• Speak to identity. Don’t just promise speed or savings, speak to who your customer wants to become. A builder? A rebel? A fixer?
• Use bold, repeatable lines. Think ‘Show it. Say it. Send it.’ or ‘The tool you’ll actually enjoy using.’ These phrases do more work than entire paragraphs.

“People don’t remember features. They remember feelings. If your story makes someone feel like you ‘get’ them, that’s when they trust you.” - positioning expert April Dunford

Build a story around a mission, not a menu of features. If it wouldn’t fire someone up in a pitch deck, rewrite it.

Make your size a strength

Here’s a common trap: early-stage startups try to look bigger than they are. Corporate language. Big logos. Over-designed websites.

It can backfire as customers don’t want another faceless tech company. They want to know:

• Who’s building this?
• Why do you care about the problem?
• Will you treat me like a number or a partner?

Your small size is your superpower, and here’s how you can use it:

• Be radically transparent. Share your roadmap, your thinking, your team. Open startups like Buffer and SavvyCal earn trust through openness.
• Offer founder access. Early users love to feel close to the source. Founder support and fast iteration are huge assets.
• Move faster than anyone else. Use speed as a USP. Frame it as: ‘We shipped a feature in 48 hours because a customer asked.’

“Startups should act like insurgents, not incumbents. Use speed and focus to do what the giants can’t.” - Ben Horowitz 

Examples of startups positioning smartly

Let’s look at how some breakout startups found their wedge and won:

Linear

Crowded space. Project management (vs. Asana, Jira)
Wedge. Fast, opinionated workflows for modern software teams
Message. ‘The issue tracking tool you'll enjoy using.’
Edge. No fluff. Optimised UX. Built for velocity.

Fathom

Crowded space. Meeting tools (vs. Zoom, Otter, Notion)
Wedge. Automatic, high-quality meeting summaries
Message. ‘Never take notes again.’
Edge. Speed, value, and a free model

SavvyCal

Crowded space. Scheduling (vs Calendly)
Wedge. Scheduling links that feel personal and respectful
Message. ‘A scheduling tool both the sender and recipient will love.’
Edge. UX-first, solo founder with a strong personal brand. 

These startups didn’t outspend the big names, they outpositioned them. Their message was clear, opinionated, and customer-obsessed.

Every category has a blind spot. Your job is to see it, own it, and hammer it home.

Recap: How to position against giants

If you remember just five things. 

1. Don’t copy the category leader. They’re slow, safe, and bloated.
2. Find your wedge. Solve a real, specific problem better than anyone else.
3. Tell a sharper story, one that’s emotional, pointed, and not afraid to alienate.
4. Use your size. Be fast, personal, and accessible.
5. Be memorable. Your message should turn heads, not blend in.

Your next step

Want to sharpen your startup’s positioning? Run a category teardown with your founding team. List out:

• What your bigger rivals are promising
• Where they fall short
• What your best early users rave about

Then distil it into a single, pointed sentence. For
example: ‘We’re the only hiring platform that removes interviews entirely for fast-growing tech startups.’