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Harper (YC W25) · 22 hours ago

Founding Content Lead

San Francisco

Full-time

Onsite

Mid Level

$80K/yr - $110K/yr

3+ years exp

Harperinsure is an innovative company aiming to transform the small business insurance market by building an AI-native brokerage. They are seeking a Founding Content Lead to develop and execute a comprehensive content strategy that captures the voice of small business owners through various media formats and platforms.

Artificial Intelligence (AI)FinTechInsurance

Responsibilities

Own the entire content strategy

Develop Harper's content vision across all formats: short-form (TikTok/Reels/Shorts), long-form (YouTube), LinkedIn, X, and whatever's next

Build the editorial calendar, content pillars, and distribution playbook

Make Harper the voice of small business owners—not just an insurance company with a social presence

Run founder-led production: direct shoots, manage recording blocks, turn raw footage into polished content

Get in the field—shoot with real business owners, capture their stories, show the human side of what we do

Create content that shows how AI and humans blend seamlessly at Harper

Record, edit on the fly, post, iterate—you can do the whole thing yourself

Know the creator ecosystem: tools, trends, formats, what's working right now

Set up contractors/editors as needed, but never lose the ability to ship solo

As this grows, you'll build a team

Create the systems, playbooks, and standards that let Harper's content operation scale without losing quality or voice

Tie content to outcomes: recruiting inbound, investor/operator engagement, brand perception, and eventually demand

Weekly review rhythm: what worked, why, what we double down on

Shipping daily across platforms

Content strategy documented: pillars, formats, cadence, distribution plan

First field content captured with real business owners

Recording + publishing rhythm locked in

Harper is consistently shipping 5-10 shorts/week + regular long-form content

Clear format winners emerging—repeatable, high-performing templates

Recruiting pipeline noticeably improves ("I found you through your content")

Brand perception shifting: Harper is the one people pay attention to

YouTube strategy in motion

Harper is recognized as the voice of small business insurance

Content is a meaningful driver of recruiting, credibility, and demand

You're leading a team and the function runs without founder dependency

Qualification

Content strategy developmentContent productionStorytellingSocial media proficiencyVideo editingDirecting talentUnderstanding creator ecosystemFast executionTeam leadershipAdaptability