You lost the deal yesterday. The lead emailed you at 5:40pm, politely saying that "for this stage" they're going with a more established vendor. They didn't say who and now you're wondering which of the bigger players got your deal.
Even though it might seem as if you got rejected because of your size (ouch), it's probably not really the problem. Instead, there was probably one of the three major issues that go against you when you compete with bigger players that have been in the game for longer:
- They already cleared procurement. This is a tough one to swallow, but when you work with enterprises you usually have to go through a certification process and when another company offers a solution to the same problem, they will get priority if they are already approved.
- Their brand is recognisable, so it's easier to accept. Imagine you're the person you're having calls with that goes to their boss and says "we need to buy from this company, they have a solution for problem X" and the boss responds "yeah, but Salesforce also has a solution for problem X". This becomes a tough discussion and obviously people don't want to take the blame if going with your solution ends up a mistake, so they go for the obvious choice.
- You don't position yourself in a unique way so people just think you're the weaker, cheaper or uglier version of the tool they know. That's the problem of playing the game on your competitor's field instead of setting up your own and it will partly help with the two problems above, because people will stop comparing you to the incumbents.
Why fighting the Goliath is a bit ridiculous
If you are not the first player in your category, you probably think about your product as superior in a lot of ways. You're probably faster, more flexible, more user-friendly ecc. That's all amazing, I'm all for it (not sarcastically, I promise!)
The thing is most people don't care enough about these things to actually change or take risks for you. You might be selling to a VP of a big company who needs to invest hundreds of thousands if not millions in your solution or a founder with a really tight budget who might lose the investor's trust if he wastes too much money. Both of these people don't want to risk the money too much for some uncertain return.
If you come in and say "we're faster, cheaper and more flexible", they don't really see clear ROI and it's not even that certain that you're actually faster, cheaper and more flexible. So if they have an established player and a new comer, they would be stupid to choose you.
So what should you do? You should get out of explicit and direct comparisons. Don't try to say you're doing the same thing a bit better, say you fix a specific problem in a new way.
Look at Linear vs Jira. Linear never positioned itself as a faster Jira or a cheaper Jira. They didn't walk into the market saying "we do what Jira does, but better." They looked at everything Jira couldn't do well (clean UX, speed, an opinionated workflow designed for lean engineering teams that don't need seventeen levels of configuration) and they packaged that into a completely different product category. Linear became the tool for teams that were dissatisfied with Jira's bloat. They created a home for the people who had already mentally left Jira but didn't have anywhere to go.
That's why Linear never needed to compete on price or speed. They weren't offering a better Jira, but an alternative solution to how issue tracking should work. The comparison to Jira happens in the buyer's head naturally, but Linear never invites it on their own terms.
If you're a startup competing against an incumbent, your positioning work starts with one question: what can't they do well because of how they're built? That's your territory.
Why big companies don't take the whole market
There's a common misconception that incumbents "own" the market and you need to steal customers from them. The reality is more complex than that. Big companies leave gaps in the market constantly, and they do it for reasons that have nothing to do with product quality or their marketing capabilities.
Some deals, they don't want. A sales rep at an enterprise company has a quota that pushes them toward large contracts. A $15K/year deal is nothing to someone who needs to close $800K this quarter.
Other deals, they can't take even when they'd want to. Their process is so heavy that mid-market buyers give up before the contract is signed.
And that's without even considering the legacy architecture problem incumbents have. They've built their product around things that made sense ten years ago, and serving the new segment would require too much effort for the money they would earn.
Your job in this is to find the scraps the incumbent leaves and start building your entire business from a solid base where nobody will disturb you and the prospects will be happy somebody is finally listening to them.
How to win the deals incumbents can't or won't take
These are teams too small for the incumbent's sales motion or too lean for their implementation process. They might also be teams that are simply much more advanced when it comes to their stack and implementing a legacy-focused solution doesn't sit well with the team (again, Linear vs Jira).
You win these deals by default IF your positioning makes it obvious you exist for them. The problem is that most startups try to look bigger than they are in the wrong way. They mimic enterprise language, hide their pricing, add "contact sales" buttons, and generally make themselves look like a smaller version of the incumbent. This actively repels the exact buyers who would choose them.
Be the obvious choice for their specific situation instead. Speak about the problem and your solution for it. Let your positioning cut your sales cycle from 5 calls to 2. You have a huge advantage here, because your sales process is most likely still led by one of the founders, which is an amazing thing. You don't even realise how much passion for the problem you should exude during these calls. Make the day of these bored managers who just want to finish their job, be the expert on the call and show them they are in good hands.
How to win deals the incumbent actually wants
Now this is the harder part. As I've said before, sometimes you're going after a deal where the incumbent is already pre-approved by procurement. They're in the vendor system. Even with an inferior solution, the incumbent gets preferred because choosing them is frictionless for the buyer.
Going into these situations is difficult, but if your positioning is right and you've clearly articulated why your approach solves a problem the incumbent can't, it creates enough internal pressure to make the buyer consider the switch.
A champion inside the organization might start pushing for you because they've felt the pain of the incumbent's limitations personally. If you position yourself in a good way, it becomes much easier for that person to push internally, because if the boss asks "why don't we just use Salesforce", they can respond "Salesforce doesn't do what they do" and that's an easier game to win.
But remember that the buyer is really afraid of making a mistake. If they choose the incumbent and it doesn't work great, nobody blames them, it was the obvious choice and it didn't go well, it happens. If they choose you and something goes wrong, people will ask why they didn't go with the more obvious choice. They could genuinely lose their job if they choose you and it doesn't go well.
So your job is to reduce the perceived risk for that specific person AND make the incumbent less of an obvious choice.
Use the incumbent's weak points to define your strengths
If you understand the structural weaknesses of the incumbent in your space, you've already done half the positioning work. The next step is putting that knowledge on your website.
You don't name the competitor. You don't say "unlike [Company X], we do Y." That looks desperate. Instead, you frame your strengths as solutions to industry problems. You describe the pain that the incumbent causes without mentioning them by name, and then you explain how your product was built specifically to avoid that pain.
The reader recognizes the competitor's weakness immediately because they have to suffer through them everyday. They don't need you to say the name. They're nodding along. And when your copy makes them feel understood at that level, they start trusting.
Be explicit about what you do well and why you built it that way. Don't be vague about your strengths hoping that the reader connects the dots to the competitor's weakness. Spell it out in concrete terms. "Built from day one for X" is better than "we also do X" because it signals intent behind the product. It's easy to trust a project full of passionate freaks. Specificity beats superiority claims every time.
Real example: Sembu AI
Sembu AI is a client of Qubo Studio that operates in healthcare insurance which isn't really a sector where risks are happily and easily taken. Misclassifications in medical coding could lead to a lot of money lost, audit flags triggered, and some compliance checks.
For a healthcare insurer comparing classification tools, a misjudgment could cost a lot of time and money, so heads are on the line. While the incumbents are bolting AI capabilities onto systems that were designed for general document processing, Sembu is positioned as the AI precision layer for insurers. It takes care of the chaos humans can't process, it compares all the data a human would miss and when a case is simple, it can even accept it on its own.
Sembu also works as an additional layer on top of existing systems and doesn't require a full replacement. For a buyer at a large insurer, this means they're not made to rip out their claims processing infrastructure to try a new tool. Incumbents can't replicate this approach easily because their architecture assumes they're part of the primary system.
See how this positioning isn't just better, faster and cheaper? It tells the customer that Sembu cannot be directly compared to the competitors because those don't really offer this precision advantage without disrupting the original system, they just do document processing.
Common questions
What if the incumbent is also a potential partner or integration? This is common in enterprise software. You can position against their weakness in one area while building an integration with them in another. Many successful startups exist as a complement to the incumbent rather than a replacement. Partnership and competition aren't mutually exclusive in B2B.
How do I know which structural gap to target? Look at your closed deals from the last six months. Specifically, look at why those customers chose you over the alternative (including doing nothing). The pattern in those reasons is probably the gap you are already filling, try to think about what exactly connects all those deals and see if the gap is bigger than you might believe now. If you don't have enough closed deals yet, look at where the incumbent's users complain publicly, so things like G2 reviews, Reddit threads or community forums. The recurring frustrations point you toward the gap.
Should I mention competitors by name on my website? Almost never. Comparison pages can work for SEO and GEO ("Alternative to X") but on your core positioning pages, describe the problem without naming the source. Your buyer knows exactly who you're talking about and you maintain a cleaner brand position. The exception is if the competitor is so dominant that the category is defined by their name (like "Jira alternative"). In that case, use it strategically in SEO-focused content.
What if my product genuinely is better at the same things the incumbent does? You might be right, but "better at the same thing" is the hardest positioning to sell because the buyer has to believe you over the incumbent's claims and they are already questioning whether to trust you. Instead, find the angle where you're different. "Better project management" loses to "project management built for teams under 50 people who ship weekly." Specificity beats superiority claims every time.
