I remember co-hosting a webinar with a knowledge management thought leader several years ago.
We were making small talk before the event, and when I told him I was doing well, he said “it’s nice when you’re working for the market leader, isn’t it?”
According to Gartner, we were the market leader—but we still lost deals and severely struggled in certain markets.
Where I work now, things are different. There are big, established names with a huge advantage in the enterprise market. The safe, familiar options—the choices that never got anyone fired.
But we wouldn’t be doing business if we didn’t have an edge. And while the pragmatic majority might not be ready for us yet, there’s enough market share out there to gobble up.
In this article, we’ll discuss how to embrace your role as the underdog and carve out opportunities to use it in your favour.
This is the art of asymmetric positioning—how to win when you’re not the biggest name in the room.
Embrace being the underdog
There’s a temptation to posture when you're going up against a giant. You want to look bigger than you are. You’re desperate to show feature parity, even when it’s not there.
But buyers can smell the spin.
Great positioning starts with radical self-awareness. You’re not the market leader—and that’s exactly your advantage. You can move faster. You can be more focused. You can take a bold stance. And unlike the giant, you don’t need to win everyone—you just need to win someone.
As April Dunford writes in Obviously Awesome, positioning is about framing your product in a context that makes its value obvious. That context shouldn’t be your competitor’s home turf.
So before you make your next battlecard, take a moment to reframe the game.
Reframe the playing field
The biggest mistake underdogs make is trying to beat the leader at their own game. If they own the "full-featured platform" story, don’t try to prove you’re more full-featured. If they’re the safe, compliant, enterprise-grade choice, don’t try to be safer.
Instead, shift the debate.
You win by changing what matters.
- If the leader is bloated, you position around simplicity.
- If they’re complex, you emphasize time-to-value.
- If they sell to CIOs, you sell to product managers.
- If they talk about scale, you talk about agility.
In war rooms, this is often called "changing the axis of competition." You’re not denying the leader’s strengths—you’re declaring they’re irrelevant to your ideal customer.
Think of how Webflow positioned against WordPress. It wasn’t about being more powerful, but about being visual-first and developer-optional. Or how Linear went after JIRA—not by saying they had more features, but by focusing on speed and elegance.
You’re not playing on their field. You’re building your own.
Find the customer who hates the leader
Every market giant has a trail of unhappy customers and alienated prospects behind them. Maybe it’s because of price. Or complexity. Or support. Maybe it’s just the feeling of using something that was clearly designed in 2012.
Find those people.
The fastest way to wedge into a market is to channel dissatisfaction. Not through petty competitor bashing—but by speaking directly to the frustrations your prospect already has.
This is where voice-of-customer work becomes priceless. Talk to people who’ve churned from the incumbent. Search review sites for patterns. Comb through Reddit threads. Ask your sales team, "What pain points come up unprompted when people mention [giant’s name]?"
Then, build your positioning around solving the things they gave up on.
One of the best examples is how Canva initially positioned against Adobe: not by trying to be Photoshop in the browser, but by helping non-designers create beautiful content quickly. They didn’t win the creative director—they won the social media manager with five minutes and no design degree.
Make a statement that can’t be disputed
Category leaders often stretch their messaging thin to please everyone. This is your chance to own something specific and emotionally resonant.
It could be:
- “The easiest way to go live in 2 weeks”
- “Built for teams who hate red tape”
- “All the power. None of the bloat.”
What matters is that your message is believable. Avoid vague claims like "AI-powered" or "intuitive UI" unless you can back them up. And don’t try to sound more enterprise than the enterprise player—you’ll lose on believability every time.
Instead, ground your positioning in one thing your target audience can feel. Something they can see in your demo and experience in week one.
As Andy Raskin suggests in his strategic narrative framework, your messaging should center around a shift in the world—an undeniable change that your product is uniquely suited for. When that story lands, the category leader starts to feel like old news.
Compete on momentum, not features
Underdogs often get pulled into feature comparison traps. The giant has ten integrations—you have five. They have a roadmap 50 engineers deep—you’re shipping updates with a lean team.
But here's what buyers actually care about:
- Are you building fast?
- Are customers like me getting value?
- Do you listen and respond to feedback?
So tell that story.
Highlight release velocity. Show customer logos—especially ones that resemble your ICP. Share case studies where someone switched from the leader and won. Be transparent about what’s coming next.
Momentum is magnetic. It makes buyers feel like they’re joining something, not just buying something.
Even if you’re behind on features, you can win on belief.
Turn constraints into talking points
Your weaknesses are only weaknesses if you try to hide them.
- No sales team? You're easier to buy.
- No legacy codebase? You’re faster to adapt.
- No 100-page RFP response? You’re focused on building, not bureaucracy.
What feels like a limitation to you might feel like relief to your customer.
Remember when Mailchimp used to brag about being for "people who hate marketing"? Or when Basecamp embraced its lack of integrations as a way to reduce distraction? That wasn’t a bug, it was a brand.
You don’t need to be everything to everyone. You just need to be obviously better for someone.
Focus your competitive playbook on fit
Sales doesn’t need a war chest of objections and rebuttals. They need a way to guide the prospect to clarity.
- Who are we right for?
- Who are we not for?
- Why do our happiest customers choose us?
- What triggers make us a better fit than the leader?
The best competitive enablement is not a list of traps to set. It’s a lens. One that helps your rep—and your buyer—see the comparison in a new light.
When someone says, “How do you compare to [giant]?”, the goal isn’t to go line by line. It’s to say, “Let me explain how we’re different, and why that matters for teams like yours.”
That’s how you shift the conversation from defense to offense.
Make it easy to switch
If you’re replacing the leader, switching is your battleground. The biggest fear isn’t that you’re worse—it’s that the migration will be hell.
Make this part of your pitch. Show a clear plan. Offer migration services or one-time onboarding support. Provide templates, importers, and a named point of contact.
On the other hand, if you’re entering the market further downstream—winning net-new customers—then your job is to reduce decision friction. Kill the jargon. Simplify the trial. Eliminate excuses.
Every click, every page, every sentence on your site should help a prospect feel like this will be easier than I thought.
That’s how underdogs win.
Have confidence in who you are
You’re not trying to become them. You’re trying to offer an alternative.
And that means your energy, your message, your posture—it all has to signal confidence in who you are. Not mimicry of what they are.
The most successful challengers don’t win by being louder. They win by being clearer.
So own your difference. Celebrate your strengths. And remember: being the underdog is only a disadvantage if you try to play by the giant’s rules.