Harrison Rose has lived the journey most founders only see from the outside.
As Co-Founder of Paddle, he helped scale from zero to $100M+ revenue – without the “overnight success” story everyone loves to tell. Now he’s doing it again with GoodFit, turning the market-mapping and ICP systems Paddle built internally into a product built for modern GTM teams.
In this Making The Grade episode, Harrison breaks down the real inflexion points that unlocked Paddle’s growth, why founder-led sales is often misunderstood, and how teams get trapped at $2–3M ARR when “founder privilege” masks the lack of a scalable playbook.
You’ll also hear Harrison’s clear-eyed take on bootstrapping vs VC, and how AI is moving from “more output” to actually making GTM decisions, including the coming tension over who owns the top of funnel: CRO or CMO.
📚 Episode Chapters:
05:15 – When to hire experienced Sales Leaders
08:45 – A focus on cold outbound
11:25 – Seeing ICP as a spectrum
19:30 – Building true repeatability
25:15 – Funding & the future of AI
🎧 Continue listening…
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