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Newsletter Issues

Newsletter Archive

Weekly insights, strategies, and tactics delivered every Tuesday. Each issue is a 5-minute read packed with actionable GTM playbooks.

Issue #10
Strategy7 min readJan 29, 2026

Enterprise Pricing Strategies: How to Price for $1M+ Deals

The pricing frameworks I've used to close $100M+ in enterprise deals. Real examples and strategies that work.

Issue #9
Playbook9 min readJan 22, 2026

Building a Repeatable Sales Process: From Founder-Led to Revenue Machine

How to turn your founder's sales magic into a repeatable process that scales. The exact framework I used at Hortonworks, Cockroach Labs, and StarTree.

Issue #8
Playbook8 min readJan 15, 2026

How to Handle Enterprise Sales Objections: The Playbook That Works

The exact objection-handling framework I've used to close $100M+ in enterprise deals. Real examples from Hortonworks, Cockroach Labs, and StarTree.

Issue #7
Playbook12 min readJan 13, 2026

Enterprise GTM Systems & Tools: The Tech Stack That Scales

Complete tech stack for enterprise GTM teams. CRM, sales enablement, revenue operations, and tools used by companies like Hortonworks and Cockroach Labs.

Issue #6
Playbook15 min readJan 12, 2026

Enterprise GTM Hiring Playbook: Job Descriptions & Hiring Framework

Complete job descriptions and hiring framework for building an enterprise GTM team. Roles, responsibilities, and interview processes for scaling from $0 to $100M+ ARR.

Issue #5
Framework12 min readJan 10, 2026

Org Chart Decisions: Mapping the Enterprise Buying Committee

How to navigate complex enterprise buying committees and identify decision makers. Framework for mapping stakeholders and accelerating deals.

Issue #4
Framework10 min readJan 8, 2026

MEDDIC: The Qualification Framework That Turned 35% Close Rates Into 82%

How to qualify enterprise deals ruthlessly using MEDDIC. Real examples from scaling three companies to $100M+ ARR.

Issue #3
Framework8 min readJan 2, 2026

The HUNT Framework: A Deep Dive into Enterprise Prospecting

How to systematically identify, qualify, and convert enterprise prospects using the battle-tested HUNT methodology.

Issue #2
Strategy6 min readDec 28, 2025

What Changes When You Scale Past $100M ARR

The GTM playbook that got you to $100M won't get you to $500M. Here's what needs to change.

Issue #1
Playbook5 min readDec 21, 2025

Building Enterprise Champions Who Sell For You

The secret to winning $1M+ deals isn't your pitch—it's the champions who advocate for you internally.

Two Bear Capital operates where innovation thrives: Menlo Park · New York · San Diego · Boston · Whitefish, MT