Raising Prices Is Easy. Closing Bigger Deals Is Not.

Founders love the idea of going upmarket. Fewer deals. Bigger checks. Easier math.

Until they try it.

Moving upmarket isn’t just about raising prices. It’s about changing how you sell. Which is hard.

All the sudden, you’re not pitching to just users anymore.

You’re also pitching to directors. VPs. Cross-functional committees. They don’t care about your UI. They care about risk. ROI. Budget. Security.

And that changes the game.

Bigger buyers expect more. More proof. More support. More professionalism.

They won’t buy if you still look like a small vendor with weak messaging, no process, and no credibility.

On top, enterprise buyers follow the herd. They check who your customers are. How your team shows up. Whether you can actually scale.

Closing bigger deals isn’t just about raising pricing or hiring better reps. You need to rebuild the whole motion.

Which means:

• Your pitch needs to shift from features to business impact: Time saved, revenue protected, risk reduced.

• Your website needs to speak to decision-makers, not power users.

• Your onboarding needs to feel consultative, not self-serve.

• Your security posture needs to hold up.

• Your support model needs to match the price.

• Your sales reps need to manage multi-threaded, high-stakes deals.

In summary, going upmarket isn’t just a pricing tweak. It’s a company shift.

Big deals don’t just pay more. They expect more. If you can’t deliver, they won’t close.

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Enjoyed reading this?

Then check out my conversation about this on the focal podcast with Russ Thau, a seasoned sales leader who helped scale Intercom, Box, and Envoy through every stage of growth plus has advised and worked with companies such as Airtable and LaunchDarkly since they were sub $1M in ARR.

Youtube | Apple Podcast | Spotify

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We lead their first round at the very start with up to $1M. Often before they even write their first line of code.

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