Road to $1M ARR day 56/60: deal cycles

how to shorten them

Day 56 of the $1M ARR sprint.

No new signature today. But i’ve been thinking about something that might be worth more than any single deal.

After 55 days of intense selling, i’ve learned more about shortening deal cycles than in the previous 2 years combined. So today i’m sharing the playbook.

- - - - - - - - - - - - - - - -

The first thing that changed everything was stopping selling services like services.

For years i pitched Earleads the standard agency way. Case studies, process explanations, deliverables breakdown, slide decks.

The whole song and dance every agency does.

Then one day i tried something different. i pitched our service like a software product. Screen sharing. Live walkthrough. Personalized to their exact situation.

Showed them what we’d build for them specifically, not what we did for someone else.

The reaction was immediate. Prospects didn’t just understand what we do. They saw themselves using it. They felt ownership before signing anything.

i’ve demoed software hundreds of times as chief of staff. Why wasn’t i applying that to services?

The moment i made that switch, conversion rates jumped and cycles shortened. People don’t need 3 follow-up calls to “think about it” when they’ve already seen their future.

- - - - - - - - - - - - - - - -

Second learning: digital gets you the meeting, human closes the deal.

i tracked this obsessively over the past months. In-person meetings close at 60%. Zoom calls close at 20%. Same prospects. Same offer. Same me.

Three times the conversion just by showing up physically.

There’s something about sitting across from someone, reading their micro-reactions, adjusting in real-time. You can’t replicate that through a screen.

The founders who complain about long sales cycles are often the same ones refusing to get on a plane (or just a cab drive lmfao).

- - - - - - - - - - - - - - - -

Third: stop pitching the how. Sell the outcome and let them pull the details.

Prospects don’t want “GTM engineering.” They want pipeline. They want meetings booked. They want revenue.

When i started breaking down our services into hyper-specific outcomes instead of capability descriptions, something shifted. i sent 10 messages to dormant CRM prospects with a specific value prop. No fluff. Just “here’s exactly what we’d build for you.”

3 booked calls immediately. 30% conversion on cold reactivation.

The vaguer your offer, the longer your sales cycle. Specificity creates urgency.

- - - - - - - - - - - - - - - -

Fourth: sell the vision, not the service.

i’ve been testing a new outreach angle in NYC. Instead of pitching what we do, i tell founders i’m scaling to $1M and want to challenge my vision with people in their space.

Coffee next to their office. No ask. Just conversation.

The conversion to meeting is insane. And here’s what happens in those meetings: they buy into where we’re going, not what we’re selling today.

When someone aligns with your vision, the service becomes obvious. They’re not comparing you to other vendors. They’re joining a direction.

That changes the entire dynamic. Price conversations disappear. Scope discussions become collaborative. Cycles shorten because there’s nothing to negotiate.

- - - - - - - - - - - - - - - -

None of this is complicated. But most people never systematize it.

Demo like software. Show up in person. Be specific about outcomes. Time your outreach to buying signals. Sell vision over service.

Each one alone shortens cycles by 5-10%. Stack all five and you’re operating in a different reality than your competitors.

55 days in and this is probably the most valuable thing i’ve learned. More than any single deal. Because this compounds forever.

ARR: $928K → Target: $1M | Days remaining: 4

See you tomorrow 👊

O.

Subscribe to Othmane Khadri

accidentally built a million ARR GTM agency by refusing to spray & pray. now racing to $1M just to prove cold emails gurus wrong.

Subscribe