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Chris Balestras
Chris Balestras

The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, @ Tennr

The Vibescaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives on all things GTM + AI + startups

Chris Balestras
Feb 11, 2026
The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, @ Tennr

The 2x2 Matrix That Determines How You Get Paid In GTM

Ability to sell larger deals + ability sell to technical personas = $$$

Chris Balestras
Feb 10, 2026
The 2x2 Matrix That Determines How You Get Paid In GTM

Why You Should Join Cursor Over OpenAI and Anthropic W/ Tomer Chernia, VP of GTM @ Cursor

The Vibescaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives on all things GTM + AI + startups

Chris Balestras
Feb 5, 2026
Why You Should Join Cursor Over OpenAI and Anthropic W/ Tomer Chernia, VP of GTM @ Cursor

Jack Dorsey Hired Me From My Dorm Room As Employee 100 @ Square | Mike Donohue, CRO @ Maven AGI

The Vibescaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives/SaaS companies on all things GTM + AI + startups

Chris Balestras
Jan 28, 2026
Jack Dorsey Hired Me From My Dorm Room As Employee 100 @ Square | Mike Donohue, CRO @ Maven AGI

It's A Privilege To Be An Order Taker In Sales

The term everyone uses as an insult is actually the goal we should all be striving for (initially)

Chris Balestras
Jan 27, 2026
It's A Privilege To Be An Order Taker In Sales

How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP of Global Revenue @ Legora

The Vibescaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives/SaaS companies on all things GTM + AI + startups

Chris Balestras
Jan 22, 2026
How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP of Global Revenue @ Legora

How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins

The Vibescaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives/SaaS companies on all things GTM + AI + startups

Chris Balestras
Jan 15, 2026
How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins

$2M to $950M ARR: How Kyle Parrish Built Figma's Sales Machine

The Vibescaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives/SaaS companies on all things GTM + AI + startups

Chris Balestras
Jan 8, 2026
$2M to $950M ARR: How Kyle Parrish Built Figma's Sales Machine

This Week In GTM - Episode 2 (ft. Brendan Short of The Signal)

Brendan Short joins to riff on Jeanne DeWitt Grosser's (CRO @ Vercel) appearance on Lenny's pod, the new rules for hiring your first rep, why LinkedIn > cold email, and why Ramp shut down their outbound automation team

Chris Balestras
Dec 19, 2025
This Week In GTM - Episode 2 (ft. Brendan Short of The Signal)

5 Takeaways From Our "Selling To Developers" Event With Clay on 12/10

Our fall event series in NYC with Manhattan-based AI darling Clay on all things "selling to developers", including GTM executives @ Cursor, Kleiner Perkins, Clay, & (former) Mongo

Chris Balestras
Dec 17, 2025
5 Takeaways From Our "Selling To Developers" Event With Clay on 12/10

This Week In GTM - Episode 1

The first of our weekly "This Week In GTM" podcast/video series, where we call out tweets we saw from the week + jam out on different sales + startups + AI topics

Chris Balestras
Dec 10, 2025
This Week In GTM - Episode 1

How Raphael Parker Built Segment's GTM Machine From 0 to $100M in ARR

The VibeScaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives/SaaS companies on all things GTM + AI + startups

Chris Balestras
Dec 3, 2025
How Raphael Parker Built Segment's GTM Machine From 0 to $100M in ARR

How We're Building A GTM Media Engine @ VibeScaling

A breakdown of using content to drive our other efforts (advisory, recruiting, fund)

Chris Balestras
Nov 26, 2025
How We're Building A GTM Media Engine @ VibeScaling

5 Takeaways From Our VibeScaling x Factory Event in SF on 11/5

Our fall event series in SF with our portfolio company Factory on all things "selling to developers", including GTM executives @ Factory, Modal, LiveKit, & Fireworks AI

Chris Balestras
Nov 10, 2025
5 Takeaways From Our VibeScaling x Factory Event in SF on 11/5

VibeScaling Podcast Episode 1: Todd Busler, CEO @ Champify

Announcing The VibeScaling Podcast: a weekly podcast where we interview the top GTM leaders @ the fastest-growing AI-natives on all things GTM + AI + startups

Chris Balestras
Nov 3, 2025
VibeScaling Podcast Episode 1: Todd Busler, CEO @ Champify

10 Takeaways From How Snowflake Scaled GTM

Where I agree and disagree with "Make It Snow: From Zero to Billions: How Snowflake Scaled Its Go-to-Market Organization"

Chris Balestras
Oct 30, 2025
10 Takeaways From How Snowflake Scaled GTM

7 Things Top GTM Interviewers Are Doing In 2025 To Land Offers

A new list of what we're seeing behind the scenes, working with hundreds of candidates/hiring managers @ VibeScaling

Chris Balestras
Oct 20, 2025
7 Things Top GTM Interviewers Are Doing In 2025 To Land Offers

Find Your GTM Renaissance: Why NYC and SF Are Still Worth the Move

The Medici effect & why moving to these cities early to mid in your career is worth it

Chris Balestras
Oct 9, 2025
Find Your GTM Renaissance: Why NYC and SF Are Still Worth the Move

The Best GTM Teams Hire For Spikes

What we can learn from Enron (lol), McKinsey, Plaid, Palantir, and others on hiring top talent

Chris Balestras
Sep 30, 2025
The Best GTM Teams Hire For Spikes

Clay is the Most Undervalued Startup in AI @ a $3B Valuation

Why Clay is eating the GTM world + 3 takeaways from VibeScaling's time @ Sculpt, their first conference, in SF this week

Chris Balestras
Sep 19, 2025
Clay is the Most Undervalued Startup in AI @ a $3B Valuation

Why I left big tech for startups in 2021

The navy vs the pirates and a legendary tale from Steve Jobs

Chris Balestras
Sep 11, 2025
Why I left big tech for startups in 2021

11 Tips to Ensure Your Next GTM Opp in AI is the Right One

Takeaways from our SF event on 8/24 with Pylon on how to choose your next homerun GTM opp in AI

Chris Balestras
Sep 4, 2025
11 Tips to Ensure Your Next GTM Opp in AI is the Right One

6 Takeaways From Our VibeScaling x Clay Event on 8/14

First NYC spin of our GTM + AI panel series last week, which is the second of many private GTM events we're throwing in NYC and SF

Chris Balestras
Aug 25, 2025
6 Takeaways From Our VibeScaling x Clay Event on 8/14

CRM of the Future: Clarify

Almost like if Apple/Superhuman/Equinox made a CRM

Chris Balestras
Aug 13, 2025
CRM of the Future: Clarify

The Mafias of GTM

Why humans are driven toward "talent vortexes" and a list of the current mafias in AI-native GTM

Chris Balestras
Aug 7, 2025
The Mafias of GTM
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Vibescaling Blog

Weekly insights and narratives on the intersection of GTM + AI + startups, written by former/current operators.

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