Ishan Chhabra
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Post performance
Likes + comments per post, last 6 months
Top posts
- 2/11/2025textView →
I am so jealous of software engineers. I began my dev career 15 years ago. Back when sleepless nights debugging errors and racing deadlines were just part of the job. AI writing even a basic “Hello, World” was a pi…
♥ 42💬 115↗ 0157 total - 3/12/2025mediaView →
My Biggest Founder Mistake Took 6 Years to Fix. 🫢 This week marks six years since I took on two of life’s hardest journeys at once: Starting my family and starting a company. I got married around the same time I f…
♥ 121💬 9↗ 0130 total - 2/4/2025textView →
I wrote 1,000 lines of code without touching my keyboard. For months, I pictured a script that checks every 20 minutes to see if I'm actually working. Then I did something crazy, I went to GPT and ranted a big prompt,…
♥ 53💬 49↗ 0102 total - 2/21/2025textView →
I let my entire sales team go—and it was 100% my fault. Here's the BIG mistake you must avoid as an early-stage founder. 🏃🏻 BACKGROUND: On Christmas day last December, I found myself staring at terrible sales numbers…
♥ 39💬 42↗ 081 total - 11mo agomediaView →
"The second I signed with Gong, I wanted to leave." I just got off a call with a CMO who said this to me. He wasn't talking about a gym membership. He was talking about a 5-figure annual contract he signed with Gong.…
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Recent posts
All posts in the feed →- 2mo agotextView →
"Can your AI find X in a transcript?" is the wrong question to ask me in a demo. Because what I tell every VP that's asked me that is: Yes, it can. But so can you with a custom-built agent you spend 2 hours creating…
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Are you evaluating AI sales tools right now? Here's a small thing you should know that predicts adoption better than the features you were offered: How that vendor named the agents. A lot of them ship a whole cast of…
♥ 23💬 2↗ 025 total - 8mo agomediaView →
The founding team is now complete. 👶🏽✅ 2 weeks ago, my son Veer arrived and immediately took the #1 spot on our org chart. Everyone's doing great, and I'm currently operating on a sophisticated revenue stack made of…
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"The second I signed with Gong, I wanted to leave." I just got off a call with a CMO who said this to me. He wasn't talking about a gym membership. He was talking about a 5-figure annual contract he signed with Gong.…
♥ 68💬 12↗ 080 total - 11mo agomediaView →
Dreamforce 2025 had a lot of hard truths. As much fun as I had — we’re still a long way from where we need to be. AI only matters when it disappears. When agents quietly handle the busywork — and teams just sell, lead…
♥ 70💬 9↗ 079 total - 12mo agomediaView →
I’ll be at Dreamforce this year! Excited to be back where AI agents are on the verge of reshaping GTM, Sales and RevOps. But let’s be honest—there’s still a long way to go before these agents are truly “agentic.” I’m…
♥ 57💬 1↗ 058 total - 9/25/2025mediaView →
The biggest thing I took away from the Alliance Summits? People aren’t just buying new tools — they’re rebuilding systems. Across sales, CS, RevOps, and enablement, everyone’s asking the same questions: → How do we ma…
♥ 71💬 3↗ 074 total - 5/19/2025mediaView →
“I think it will be incredibly annoying to get a call from an AI asking about my day.” That’s what an Account Executive said the last time I pitched Oliv’s AI voice agent. Fair point. But let’s be honest - You know wh…
♥ 69💬 10↗ 079 total - 3/28/2025textView →
I have a question for everyone in sales. 🙋🏻♂️ Do you think confidence is the key to nailing a sales demo? Here’s my take: Confidence helps, but it’s not the whole story. Sure, mindset matters. A lack of confidence…
♥ 44💬 1↗ 045 total - 3/24/2025textView →
Stop tracking closed-lost reasons. 🛑 All through 2024, I was obsessed with fixing our closed-lost data. I’d meet with my sales team every quarter, wave new picklists in their faces, and beg them: “Please, just fill t…
♥ 13💬 1↗ 014 total - 3/20/2025mediaView →
The battle between sales management and reps is FINALLY over. For years, there’s been a silent battle between sales management and reps. 🚩 Managers want visibility into the pipeline: How are deals progressing? Where…
♥ 25💬 4↗ 029 total - 3/13/2025textView →
In my last post, I shared the biggest mistake I’ve made as a founder in the last six years. Today, I want to show you how we operationalize that lesson at Oliv—where we launch a new version of our product every two month…
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My Biggest Founder Mistake Took 6 Years to Fix. 🫢 This week marks six years since I took on two of life’s hardest journeys at once: Starting my family and starting a company. I got married around the same time I f…
♥ 121💬 9↗ 0130 total - 3/11/2025textView →
The SE - AE boundary. Where do you draw the line? Last week, I spoke with a manager of a Sales Engineering team. He mentioned that his team had a new mandate this year: "Get SEs involved from the very first discovery…
♥ 10💬 0↗ 010 total - 3/4/2025textView →
Yesterday, I lost a deal to AI 🤖 I thought I had this deal on lock. I did everything by the book—discovery calls, demos, follow-ups—and the prospect was 𝗲𝗻𝗴𝗮𝗴𝗲𝗱. But then they compared me to a competitor (a…
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