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Founder-Led Sales: A Journey Through Cold Calling

In the early days of SimplifiMed, a startup I founded and which later got acquired by TeleVox in 2020, I stood at a peculiar juncture. Here I was, a Product Manager turned founder, diving into the unfamiliar world of direct sales. The challenge? We were venturing into the healthcare domain, notorious for its difficult entry barriers. In an industry where executives treat LinkedIn requests as white noise and outbound emails as potential security threats (thanks to rigorous HIPAA guidelines), breaking in seemed like a Herculean task.


Cold calling emerged as the reluctant hero of the hour. However, as a newbie with a distinct Indian accent, my early attempts sounded something like this:

Me: “Hi, this is Chinmay from SimplifiMed. We partner with Epic App Orchard, helping hospitals like yours engage patients through SMS.”

Prospect: “Thanks, but we already have a solution in place. Not interested.”


I wasn't oblivious to the fact that their 'solution' was outdated, constraining messages to a mere 160 characters and lacking self-service capabilities. So, I modified my pitch:

Me: “Hi, this is Chinmay from SimplifiMed. I noticed you're using a platform that restricts you to 160 characters. With us, you can send more extensive messages.”

Prospect: “Our analyst has mastered the art of concise communication. We're fine, thanks.”

Throughout these interactions, several insights emerged:

  • The Undeniable Need for Cold Calling: No matter the traction, as a startup, cold calling is invaluable.

  • Cold Calls Are, Well, Cold: Intrusive by nature, cold calls aren't the recipient's favorite activity. An unfamiliar name like “Chinmay” can sometimes add to the challenge.

  • Ease Into the Pitch: No one appreciates a hard sell. Engage your prospect first before diving into your pitch.

Recently, I stumbled upon the “Mic Drop” cold-calling method. While it aligned with my experiences, I believe that had I discovered it during SimplifiMed's early days, I still might have struggled. There was simply no room for practice in our lean setup, especially as I was the only US-based employee until 2019.

However, today's founders have an ace up their sleeves: AI-driven role-playing. With tools like iWish AI, startups can simulate cold calling scenarios and role-play without burdening their lean teams. Practice makes perfect, or in this case, helps book more meetings.

For those of you scaling your startup, especially if you're backed by YCombinator, TechStarts, or 500 Global and are diving into the cold-calling arena, I have something special. Connect with me at chinmay@iwish.ai for an exclusive offer.


Chinmay Singh

Founder (iWish.ai)

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