Rethinking Playbooks and GTM in AI Times

Peter Grant is the Chief Revenue Officer at You.com, the AI search and productivity platform reshaping how people find and create information. A veteran GTM leader, Peter has built and scaled revenue engines at some of tech’s most iconic companies — from Siebel Systems to Salesforce to C3.ai — working directly under legends like Tom Siebel and Marc Benioff. Today, he’s leading You.com’s charge against giants like OpenAI and Google, bringing precision, storytelling, and speed to the most transformative era in technology.

Discussed in this episode

• How Peter defines “the biggest opportunity of our lifetime” in AI
• Lessons from working under Tom Siebel, Marc Benioff, and Rishi Khosla
• How to hire SEAL-Team-Six-level GTM talent
• Why belief and speed are non-negotiables when competing with giants
• You.com’s differentiation strategy against OpenAI and Google
• How to operationalize AI literacy and agentic workflows
• The ROI gap in generative AI adoption, and how to fix it
• Building products that stand on truth

Episode Highlights

00:14 — The biggest opportunity in technology this century

05:25 — Lessons from working directly with Thomas Siebel

06:41 — How to hire “SEAL Team Six” sales talent

10:24 — Why “train hard, fight easy” defines great enablement

20:08 — The new sophistication bar for AI literacy in sales

25:14 — How You.com differentiates against OpenAI & Google

30:00 — Peter’s personal AI productivity system: 40 agents

40:12 — Speed, truth, and trust: You.com’s go-to-market culture

48:30 — The “war room” story: building a sales plan overnight

59:45 — No easy days: why startup life mirrors special forces

This episode is brought to you by our sponsor: BoomPop

A quick pause to spotlight a partner that helps GTM teams actually connect—BoomPop.

Your next big unlock might not come from another meeting… it’s from getting your team in the same room. BoomPop makes that happen with end-to-end offsite planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

And as a listener of GTMfund, you’re eligible for full-service event planning for just $99 per person (terms apply).

Head to boompop.com/gtmfund to start planning your offsite.

Guest Links

• LinkedIn: linkedin.com/in/peterkgrant
• Company: you.com

Recommended Books

• The Hard Thing About Hard Things by Ben Horowitz
• Elephants Can’t Dance by Louis V. Gerstner Jr.
• The Master Algorithm by Pedro Domingos
• No Easy Day by Mark Owen — a favorite for its lessons on grit and resilience

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.