Founding Content Lead - San Francisco - Harper General Contractors

Description

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. Its a sea of samenesscommoditized, forgettable, invisible.

36 million businesses in America need insurance. Most of them feel ignored, confused, or ripped off by an industry that hasnt evolved in decades. Nobody speaks for them.

Harper is building an AI-native brokerage that actually works. But were not trying to be another basic insurance company. We want to become the voice of small business in Americaand 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 dont 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 motionit compounds, its defensible, and it filters for the exact candidates and customers who belong here.

But this isnt just about the founder talking to a camera. Were going to be in the field with business owners. Were going to show what AI-powered service actually looks like from the inside. Were going to build something people watch, share, and remember.

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

The Role

Youll build Harpers content engine from zero. Strategy, production, distributionall of it. Youre not managing a process; youre creating a media arm for a company that wants to define a category.

Own the entire content strategy

• Develop Harpers content vision across all formats: short-form (TikTok/Reels/Shorts), long-form (YouTube), LinkedIn, X, and whatevers next
• Build the editorial calendar, content pillars, and distribution playbook
• Make Harper the voice of small business ownersnot 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 fieldshoot 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, iterateyou can do the whole thing yourself
• Know the creator ecosystem: tools, trends, formats, whats working right now
• Set up contractors/editors as needed, but never lose the ability to ship solo

Build toward scale

• As this grows, youll build a team
• Create the systems, playbooks, and standards that let Harpers 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 emergingrepeatable, 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
• Youre leading a team and the function runs without founder dependency

Who You Are

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

• Youve built content that actually performednot 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 posttoday, 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 doesnt 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

• Your portfolio
• A video telling me why youre the person to bring this to life