Letterhead

Letterhead provides an agentic newsletter execution platform enabling customers to manage their entire newsletter workflow - from content creation and scheduling to monetization and reporting - with greater efficiency and increased automation, driving superior engagement and increased revenue.

Entrepreneur(s)

• Christopher Sopher
• Rebekah Monson
• Bruce Pinchbeck

Sector(s)

• Go-to-Market Technology

Investment Team

• Matt Melymuka
• Andrew Bartusiak
• Charlie Reinkemeyer

Investment Location

• Miami, FL

Status

• Active

Partnership

• FOUNDED 2020
• Partnered 2025, $34M Series A

IMPACT & VALUE CREATION

ICP Refinement

Narrowed focus and unified messaging

Worked closely with management to narrow focus, tightly define ICP and architect a product roadmap to drive clear positioning and differentiation in market.

Executive Hiring

Supporting key management team hires

Assisted in the evaluation and hiring process for key leadership team members to bolster the management bench for the next phase of growth and development.

INSIGHTS & PRESS

Partnership News

We’ve raised $34m to power the Newsletter Operating System

Explore this Resource
October 22, 2025