Harper
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 founders@harperinsue.com
Your portfolio
A video telling me why you’re the person to bring this to life
#J-18808-Ljbffr
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 founders@harperinsue.com
Your portfolio
A video telling me why you’re the person to bring this to life
#J-18808-Ljbffr