Road to $1M ARR day 33/60: digital sales will die

Dec 4, 2025

Road to $1M ARR day 33/60: digital sales will die

(at least how 90% of people want it to be)

Day 33 of the $1M ARR sprint.

Today I sat in a founder’s office (with quite a nice view), drinking coffee while he told me he burned 20 hours last week doing what we automate in minutes.

20 hours of manual GTM work that’s half a work week gone on tasks a properly configured Clay table could handle in 15 minutes.

Think about the opportunity cost here.

20 hours could’ve been spent talking to his power users about expansion features. Or aligning with his CTO on the technical roadmap.

Or testing asymmetric growth channels that could 10x his pipeline.

Instead? Researching each prospect by hand. Copy pasting LinkedIn messages and updating CRM fields like it’s 2019.

He knew it was inefficient. He just didn’t know the alternative existed until I showed him our orchestration layer live, right there on his conference room screen.

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This meeting only happened because of a calculated digital to physical strategy.

I outreached him on LinkedIn last Tuesday. Not with some generic “we help B2B SaaS scale” pitch.

I referenced his seed announcement from 3 months ago, mentioned his CTO’s post about hiring challenges, and suggested their GTM bottleneck was probably manual prospecting eating into product velocity.

3 years ago, adding {{first_name}} and {{company}} to your sequences was enough. Now everyone runs that playbook. The bar moved from personalization to intelligence.

Showing you understand their specific operational pain before the first call.

Digital sophistication got me the meeting. But showing up at their office (conveniently 12 minutes from my apartment) that’s what moved us from “pitch slap” to “potential partner.”

Perfect timing too.

They were already evaluating GTM standardization services/tools. Sometimes you walk into the right room at exactly the right moment.

But only if you’ve orchestrated enough at-bats.

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Second opportunity heating up. The prospect from last week’s pipeline called back. Says he’ll confirm within 48 hours.

Two deals in active negotiation. Both found through different channels (LinkedIn vs. warm intro).

Both solving the same core problem: founders doing $20/hour tasks instead of $20,000/hour decisions.

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Kicked off this morning with a full team call. Everyone on screen together.

Funny realizing “we” now means actual humans executing actual campaigns, not just me and ChatGPT debating growth at 2am.

Grateful for where we’re at.

The compound effect of daily prospecting + in-person meetings + systematic follow-up is starting to show.