Harper (YC W25) is hiring: Founding Content Lead in San Francisco

The Problem

36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing.

The Thesis

Commercial insurance is a $100B+ market with zero consumer brand. We want to become the voice of small business in America. Founder-led content is the highest-leverage motion—it compounds, it’s defensible, and it filters for the exact candidates and customers who belong here. In 6-12 months, you’ll have built a content engine that drives recruiting inbound, investor attention, and brand perception.

The Role

You’ll build Harper’s content engine from zero. Strategy, production, distribution—all of it. A builder role, not a manager role. A producer who can also be the talent. You work directly with founders. No committee. No approval chain. You create it, you ship it, you measure the outcome.

What You’ll Do

• Own entire content strategy — Short-form, long-form, LinkedIn, X, YouTube, whatever’s next
• Produce content everywhere — Direct shoots, run recording blocks, get in the field with real business owners
• Execute at every level — Record, edit, post, iterate; set up contractors as needed but never lose ability to ship solo
• Measure what matters — Tie content to recruiting inbound, engagement, and eventually demand

You Might Be a Fit If…

• You’ve built content that actually performed—not just posted, but moved numbers
• You can pick up a camera, record, edit, and post; you work fast without making things feel cheap
• You know the creator ecosystem: platforms, tools, trends, algorithms
• You have strong storytelling instincts and can make insurance interesting
• You thrive in ambiguity and take full ownership

Requirements

• 3+ years in content production or creative ops (or equivalent body of work)
• Portfolio showing range: short-form, long-form, ability to build an audience
• Ability to shoot, edit, and ship content independently
• Strong understanding of platform algorithms and distribution
• Experience directing talent or managing founder-led content
• Based in San Francisco or willing to relocate

Nice to Have

• Built content functions for startups or high-growth companies
• Experience with B2B content that doesn’t feel like B2B
• Understanding of regulated categories (finance/insurance)
• Produced long-form content (YouTube, documentary-style, podcasts)

Compensation

• Salary: $80,000–$110,000 + performance bonuses
• Location: San Francisco, in-office

Benefits

• Health, dental, and vision insurance
• Commuter benefits
• Team meals and snacks

The Process

• Founder screen — Initial fit and alignment
• Portfolio review — Walk us through your best work
• Super day — See how you create in real time

To Apply

Send to founders@harperinsure.com:

• Your portfolio
• A video telling us why you’re the person to bring this to life

Compensation Range: $80K - $110K