August 28, 2025
August 28, 2025
Selling towards a budget that doesn’t exist
Going upmarket in a new category? Throw out the rip-and-replace enterprise playbook.
pascal's notes

Selling towards a budget that doesn’t exist yet?
It’s an entirely different game with different rules.
Going upmarket in an existing category:
You're not just selling your product. You're selling the risk and pain of change. Inertia / the status quo is your biggest enemy.
Going upmarket in a new category:
You need to convince enterprises that your category should exist at all.
Buyers have no budget line item. There's no RFP process. No competitor comparison charts. No established buying committee.
This creates a paradox:
Enterprises want proven solutions, you're creating something new
There’s no ROI benchmark to measure against
They require executive buy-in for a category that doesn’t yet exist
That requires an entirely different playbook.
You’re only viable path: Land small, expand, consolidate later.
There’s no shortcut.
Here’s how:
Lead with education: You're not selling to pain - you're selling to possibility. Lead with vision and help the buyers understand the category first. Product comes second. Stock the funnel with stories of transformation, not ROI charts.
Design for gradual adoption: Start with a bottom up motion where team workflows kick in naturally.
Sell with honesty: Enterprise buyers are smart, they know you’re still figuring things out. Be transparent about your product roadmap, acknowledge gaps, invite co-creation, and position as an innovation partner, not just vendor.
Unfortunately, a $50 K new-category deal can burn the same calories as a $500 K rip‑and‑replace one in an existing category.
The sales cycles are as long, the education burden is higher, and the risk for buyers is even bigger.
If you succeed, you become the default platform. But the path to get there is a long and difficult one that too many underestimate.
You’re not just selling a product - you're selling a new way of thinking.
Before you go upmarket, make sure to ask yourself: What category do I fall into?
It will determine your GTM motion.
Enjoyed reading this?
Then check out my conversation on the focal podcast with Matt Harmon, a seasoned revenue leader who has successfully moved upmarket from SMB into enterprise many times, including at companies such as Box, Asana and SurveyMonkey.
Youtube | Apple Podcast | Spotify
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