Sharan Jhangiani on Winning at Enterprise Sales in 2025

Sharan helps run go-to-market at Yoodli, a Series A startup that does AI roleplays for sales teams. He's run deals from SMB → mid-market → enterprise. Sharan also connects founders + investors through OnePager and does part-time GTM consulting.

You can feel his genuine, thoughtful nature, then watch a razor-sharp realist take over when it's time to cut through the noise.

He sat down with Luke to riff on the evolving landscape of go-to-market strategy and share hard-won lessons from the trenches.

On brand being your sustainable moat

Brand is everything now. The more powerful your brand, the more implicit trust you can build, and the easier your sales conversations become.

We're seeing competitors pop up everywhere because you can just code a tool. The challenge has shifted from building enterprise-grade software to getting in front of customers at the right time and convincing them to trust you over hundreds of other options.

There's going to be way more competitive software out there. The winners will be the ones with the right brand momentum who are genuinely loved, with an emotional reason for people to choose them.

On building emotional connection through content

Bringing people along for your journey makes them feel like active participants in your story.

I'll buy a $100 sweatshirt from Minted in New York over a random Gap hoodie because I've watched the founder's YouTube videos, seen him on runs, and felt connected to his craft. When he vlogs about picking materials for hoodies I'll wear months later, I feel like I'm part of the process.

The same principles apply to software. If you're regularly sharing your struggles, your wins, your product development journey, prospects develop genuine trust. When they're in a trial between you and a competitor, they'll remember watching you work through problems honestly.

On multithreading to survive enterprise chaos

One of the hardest lessons in enterprise sales is how quickly deals can die when you're single-threaded.

I had a deal that was deep in one department with executive buy-in and allocated budget. Then the company went sideways at the board level and everything got paused. My deal died overnight.

Meanwhile, other reps had built relationships across sister organizations within the same company. Different use cases, different budgets, different org structures. When one thread dies because priorities shift or people leave, you still have backup options running in parallel.

On using intent signals for warm outbound

Signals are the most important thing if you're doing outbound. If someone's looking at your pricing page, then case studies, then terms of service, they're basically pre-qualified already.

Use tools like Syft for website de-anonymization, see what pages they're visiting, send those data points to GPT to understand what's happening in their buying journey. Then reach out with a relevant 3 line email.

On the land-and-expand enterprise play

Getting into large enterprises is painful - IT, procurement, compliance can drag deals for months. But once you're in their vendor system with an MSA, expansion becomes dramatically easier.

Even at tiny ACV, if you can get someone senior enough to champion you through the initial process, you've unlocked the door for future growth within that organization.

The land-and-expand strategy at large enterprises is phenomenal because once you're approved, additional purchases become internal processes rather than full vendor evaluations.