I once closed a deal on a Sunday.
Not later in my career.
Not as a founder.
In my first year on quota as a newly promoted AE at Salesforce.
I was obsessed with one thing - being at the top of the dashboard.
There was a startup CEO evaluating Salesforce vs. SugarCRM.
Competitive deal. Real stakes. No way I was losing it.
He signed up for a free trial.
Then, on a Sunday afternoon, an email hit my inbox:
Do you have a few minutes to help me understand how to build a report?
I replied immediately.
Offered to talk - TODAY
We spent an hour on the phone.
I walked him through the product.
Answered every question.
Removed every doubt.
I sent the paperwork that evening.
He signed that night.
Proud.
✈️ The Insight: Pride Can Hide Fragility
At the time, I told myself:
“This is what top performers do.”
“This is how deals get done.”
“I want more.”
And I did.
But there was another feeling I didn’t expect.
I was annoyed.
No recognition.
No acknowledgment.
No signal from management that this extra effort mattered.
Over time, a more uncomfortable realization set in:
That deal closed because I showed up on a Sunday.
Not because the sales motion carried it.
And that distinction matters.
🧭 Why This Matters for Founders
Early-stage founders live in this moment.
You:
Take calls nights and weekends
Personally unblock late-stage deals
Step in when momentum wobbles
That’s part of the job early on.
But here’s where founders need to be careful:
When someone on your team does the same thing—
it doesn’t feel the same to them as it does to you.
They don’t own 50% of the company.
Or 10%.
Or 5%.
Or even 1%.
They won’t experience the upside of a $1B outcome the way you will.
So when they show founder-level commitment anyway,
that behavior deserves to be seen.
🧠 The Leadership Lesson Most Founders Miss
When you see someone:
Working on a weekend or late at night to help a customer
Going above and beyond to save a deal
Carrying responsibility they don’t technically own
Celebrate it. Publicly. Specifically. Immediately.
Because effort without acknowledgment turns into resentment.
And ego—the “this is just expected” kind—is how you quietly train great people to stop caring.
Don’t be like my Salesforce VPs who assumed the number on the dashboard was reward enough.
For you, it might be.
For them, it isn’t.
🧭 The Sales Lesson Still Holds
That Sunday deal taught me two things at once:
As a seller:
If a deal only moves when you intervene, you don’t have momentum—you have dependency.
As a leader:
If someone carries a deal across the line for you, recognize it, or you may not get that effort twice.
Both lessons matter.
I’m still proud of that Sunday deal. It wasn’t the only one I’ve closed on a weekend, but it’s definitely the most memorable.
Remember to celebrate the wins. ✈️
– Justin
Founder, Revenue Pilot
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