Scale it Up with Ishan

For Challengers, Deal Design Is Where the Game Is Won

I have been thinking a lot about how deals are won, especially when you are a perceived challenger in the category versus a leader.

Jan 28 • Ishan Gupta

3

Customer Success Is a System, Not a Team

Earlier this week, I spent time in San Francisco with customer success and post sales leaders from across the ecosystem.

Jan 23 • Ishan Gupta

4

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November 2025

Part 2- Building a Customer Success Strategy at a Fast-Growing Startup

Your First Six Months as a CS Leader: From Foundation to Scale

Nov 18, 2025 • Ishan Gupta

Part 1- Building a Customer Success Strategy at a Fast-Growing Company

While growth is hard, sustaining it is just as hard.

Nov 7, 2025 • Ishan Gupta

1

October 2025

Joining a New Team? Lead with Presence, Not Pressure

Taking over a team is one of the most important transitions a leader can go through.

Oct 3, 2025 • Ishan Gupta

September 2025

Closed-Won Isn’t Done

There’s a great saying that “good fences make good neighbors.” It applies perfectly to sales and post-sales.

Sep 19, 2025 • Ishan Gupta

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Scaling Up With AI: Why the Human Edge Still Wins

I wasn't at Hubspot INBOUND 2025 earlier this week in person, but I was impatiently waiting for Hubspot CTO Dharmesh Shah’s keynote.

Sep 6, 2025 • Ishan Gupta

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May 2025

What Lean AI Startups Teach Us About Scaling It Up, but Smartly

AI-native startups are breaking all the old rules of building companies—and doing it with shockingly small teams.

May 31, 2025 • Ishan Gupta

BizOps: Your Hidden Advantage in Scaling with Clarity

At the recent Operator Guild Summit, I had the chance to hear Rachel Nazhand speak on a topic that doesn’t get nearly enough credit—Business Operations.

May 27, 2025 • Ishan Gupta

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The New Customer Success Playbook: Designed for Scale, Built for Outcomes

(Published by my AI Avatar, using tools from Heygen.)

May 2, 2025 • Ishan Gupta

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2:56

April 2025

Scaling Yourself to Scale It Up

When we talk about scale, the conversation usually jumps to teams, revenue, and market share.

Apr 24, 2025 • Ishan Gupta

1:37

March 2025

Solving Customer Challenges with First Principles Thinking

As leaders, especially in GTM and customer-facing roles, we constantly encounter challenges that seem insurmountable.

Mar 13, 2025 • Ishan Gupta