Founding Content Lead

Location: San Francisco (In-Office)
Reports to: CEO
Compensation: Competitive cash + meaningful equity

The Problem

Commercial insurance is a $100B+ market with zero consumer brand. Geico has a gecko. Progressive has Flo. Small business insurance has... nothing. It's a sea of sameness—commoditized, forgettable, invisible.

36 million businesses in America need insurance. Most of them feel ignored, confused, or ripped off by an industry that hasn't evolved in decades. Nobody speaks for them.

Harper is building an AI-native brokerage that actually works. But we're not trying to be another basic insurance company. We want to become the voice of small business in America—and show the world what happens when AI and humans work together seamlessly.

We have real operational receipts, a sharp point of view, and stories worth telling. What we don't have is someone to bring that to life across every format, everywhere.

The Thesis

The companies that win the next decade will own their narrative. 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.

But this isn't just about the founder talking to a camera. We're going to be in the field with business owners. We're going to show what AI-powered service actually looks like from the inside. We're going to build something people watch, share, and remember.

Short-form. Long-form. YouTube. Whatever the format, wherever the platform—we need someone who can develop the entire strategy and own execution end-to-end.

The Role

You'll build Harper's content engine from zero. Strategy, production, distribution—all of it. You're not managing a process; you're creating a media arm for a company that wants to define a category.

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

Produce content everywhere

• 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

Execute at every level

• 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

Build toward scale

• 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

Measure what matters

• 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

What Success Looks Like

30 Days:

• 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

90 Days:

• 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

12 Months:

• 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

Who You Are

You're a builder, not a manager. A producer who can also be the talent. Someone who thinks in systems but ships like a creator.

• You've built content that actually performed—not just posted, but moved numbers

• You can develop strategy AND execute it yourself

• You know how to direct talent and pull great performances out of busy people

• You can pick up a camera, record, edit, and post—today, not after you hire someone

• You understand the creator ecosystem: platforms, tools, trends, algorithms

• Strong storytelling instincts; you write hooks that stop scroll

• You work fast without making things feel cheap

• You thrive in ambiguity and take full ownership

Bonus:

• Built content functions for startups, creators, or high-growth companies

• Experience with employer brand or B2B content that doesn't feel like B2B

• Understand regulated categories (finance/insurance) and can stay compliant without becoming boring

• Have produced long-form (YouTube, documentary-style, podcasts)

Requirements

• 3+ years in content production / creative ops (or equivalent body of work that speaks for itself)

• Portfolio that shows range: short-form, long-form, ability to build an audience or drive outcomes

• Based in San Francisco or relocating

Working at Harper

Harper runs like a high-performance desk:

• High standards, low ego

• Fast feedback loops

• Direct communication

• Extreme ownership

• Systems > heroics (but we love people who can do both)

How to apply

Send the following to [email protected]

1. Your portfolio

2. A video telling me why you're the person to bring this to life