When Founders Should Hire Salespeople

Timestamps:

(00:00) Intros

(04:00) Vercel's AI SDR: Replacing a 10-Person Team with One GTM Engineer

(08:00) When Should Founders Hire Their First Salesperson

(11:00) "Sales Teams Should Be Indistinguishable from Product Managers"

(14:00) What Does "Consultative Selling" Actually Mean?

(18:00) The YC Founder GTM Playbook: LinkedIn-First Outbound

(20:00) Why LinkedIn Content Beats Cold Email

(26:00) Network-Led Growth: Why Warm Intros Still Win

(30:00) "Climbing Cringe Mountain" - Why Posting on LinkedIn Works

(34:00) Content as a Recruiting Superpower

(38:00) Why Is Everyone Calling Sales "GTM" Now?

(44:00) Ramp Shut Down Their Outbound Automation Team - Here's Why

Episode Description:

In this episode of "This Week in GTM," Chris, Cailen, and special guest Brendan Short (The Signal newsletter) break down the tweets they've been texting each other all week and share unfiltered takes on the evolving state of go-to-market.

Discussed in this episode:

• Vercel's viral AI SDR story: why context matters (ACV, target accounts, and what actually scales)
• The new playbook for when founders should hire their first salesperson
• Why Stripe and Dropbox hired salespeople who "didn't feel salesy" - and what that actually means
• The death of cold email and the rise of LinkedIn-first outbound
• How Brendan landed Slack and Notion as customers through content alone
• Network-led growth: why your investors and advisors should be your first pipeline source
• "Everything good is on the other side of cringe" - why founders need to post
• The "GTM" rebrand of sales: status play or legitimate evolution?
• Why Ramp shut down their Outbound Automation Team and what comes next
• Content as a recruiting superpower

Host Links:

Cailen DSa

Chris Balestras

Brendan Short

About VibeScaling Podcast:

The VibeScaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

Every week, host Chris Balestras, partner @ ⁠VibeScaling⁠ (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About VibeScaling:

⁠VibeScaling⁠ is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

Where to Find VibeScaling:

LinkedIn Company Page - ⁠  / vibescaling  ⁠

YouTube - ⁠   / @vibescaling  ⁠

Newsletter - GTMBA - ⁠https://www.gtmba.ai/

Website - ⁠https://www.vibescaling.ai/