The Setup: Testing My Upper Limit
I usually send anywhere between 40 to 50 business proposals a day on Upwork. That's my baseline — the number I'd built a rhythm around and knew I could sustain without burning out.
But I wanted to test my upper limit. Not just nudge past it — exhaust it. I decided one day to push through every boundary I'd set for myself and see where the tipping point was.
As the day went by and more proposals kept going out, I kept going. Teacup after teacup. I finally stopped and decided to count.
The Conversation I Hadn't Dreamt Of
That 40% extra volume got me into a conversation I genuinely hadn't anticipated. One of the 82 proposals landed with a company whose average order value was $20,000.
I'll be honest — that number took me back a bit. This wasn't a typical Upwork engagement. The stakes were higher, the buyer was more senior, and the wrong move would have ended the conversation immediately.
What followed was tactful, deliberate communication. Not a pitch. A meaningful conversation — asking the right questions, listening carefully, and responding with substance rather than eagerness. I focused on understanding their problem before talking about solutions.
How I approached the conversation
Acknowledged their problem in their own language — not agency speak
Asked questions that showed I understood their business model and AOV
Focused on building trust through the conversation, not rushing to a close
Secured the meeting — and handed off to the senior sales executive to close
The Close: $10K Retainer — Then Another $6K
The senior sales executive closed the client for a $10K retainer. That deal alone exceeded what I'd set out to accomplish when I started sending proposals that morning.
But the story didn't end there. This opening paved the way for Daniel Budai to secure another client from the same pipeline — closing out 2023 with a $6K deal at the end of Q4.
Total value generated from that one day of pushing the limit: $17,000.
The Lesson: Refining What Works
This wasn't luck. It was the Law of Averages, applied deliberately. When you stay true to your process and remain alert enough to keep refining it, you've understood the key to achieving your desired outcome.
What refining means in practice
- High-volume, consistent outreach
- Personalised, problem-first messaging
- Tracking what gets replies
- Testing your limits systematically
- Generic "we are a team of experts" openers
- Pitching before understanding the problem
- Arbitrary daily limits you've never tested
- Skipping follow-up
For others, this kind of output may seem like hard work. But when you've built the process, internalised the framework, and committed to the reps — it becomes as natural as breathing.
What Daniel Said
"Shivraj has been a great team member to work with, he helps our team generate more qualified leads, so our salesperson can close them. He's not only great in communication and a team player but he's highly reliable and able to figure things out by himself. This helps our team grow faster. I hope we can work together for a long-time in the future and improve each other's game further."
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