Over the last three months, I've spoken to 80+ sales enablement & Sales leaders across India and the US.
And one thing keeps coming up.
Coaching is important. But somehow, it gets treated as an afterthought.
For years, sales coaching has largely followed the same model.
A manager gets the team together.
Share some feedback.
Runs a training session.
Everyone goes back to selling.
But there's a bigger problem.
A lot of coaching happens after something has already gone wrong.
A rep isn't performing.
So we go back and start analysing calls.
Was it a skill issue?
A talent issue?
A motivation issue?
A coaching issue?
By the time we are asking these questions, the deal may already be lost.
That has always felt a little strange to me.
Because sales don't stand still.
Every quarter, the product narrative changes. New competitors show up. Customer objections change. Messaging evolves.
So why do we expect coaching to happen once in a while?
And there's another question I keep thinking about.
What happens to the top performer?
If someone is having a great quarter, does that mean they don't need coaching?
When I was at LinkedIn, I was fortunate to be one of the high-performing reps.
But I still wanted feedback.
I wanted someone to listen to my calls and tell me:
"What could I have done better?"
I used to think about something else too.
What if I could get that feedback while I was actually on the call?
Not tomorrow.
Not at the end of the quarter.
Right there, when it could actually make a difference.
How powerful would that be?
Today, that idea has become a reality.
We recently launched Sunnyside Live Call Assist — built to give salespeople intelligent support and guidance while the conversation is actually happening.
And honestly, this isn't just another product launch for me.
It feels personal.
Because something I used to imagine as a rep is now something our team has actually built.
I couldn't be more proud of the team that made it happen.
Maybe the future of sales coaching isn't about looking back at what went wrong.
Maybe it's about helping the rep get better while they're actually selling.
Moving coaching from post-mortem to real-time.