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.

Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step.

We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring.

Your operational partner in crime. An extension of the CEO across the entire organization.

The Thesis

Harper is a deeply founder-led, operationally intense company. The CEO is the connective tissue between sales, ops, growth, and engineering—in the details on submissions, strategy, partnerships, and how we build our AI systems. That intensity is a feature, not a bug. It’s how we scaled 100x in a year.

But as we grow, one person can’t be everywhere at once. The Chief of Staff operates the way the CEO does—fast, direct, in the details—and extends his reach across the organization. You’re the person he thinks out loud with, the person who can walk into any room at Harper and drive things forward with the same intensity and context he would.

This is an 18–24 month tour of duty. If you crush it, the natural next step is a functional leadership role inside Harper—Head of Ops, Head of Strategy, GM of a new vertical. We promote from within and path people toward P&L ownership.

The Role

This is not a program management role. This is not an EA role. This is a high-autonomy, high-ambiguity operating role for someone who wants to build a generational company from the inside.

You will sit at the center of Harper’s most important constraint at any given moment (people, throughput, quality, speed, execution). Your job is to turn chaos into an operating system—without slowing the company down.

What You’ll Do

Be an extension of the CEO across the org — Walk into any function (sales, ops, engineering, growth) and drive alignment, remove roadblocks, and push things forward with the same context and urgency
Build our operating system from scratch — Leadership meetings, OKR tracking, quarterly planning. None of this exists yet. You create the rhythms that let a 25-person company operate like a 100-person one
Own board materials, investor updates, and cap table management end-to-end
Drive the highest-priority cross-functional initiative at any given time — M&A (target ID, diligence, integration), new vertical expansion, or standing up operational playbooks as we scale
Turn tribal knowledge into systems — A lot of how Harper operates lives in people’s heads. You map it, document it, and build the processes that let us scale without losing what makes us great
Plug functional gaps — We’re building the exec team in real time. Until every seat is filled, you step into whatever leadership role the company needs
Fix things that are broken before anyone notices they’re broken

What this actually means at Harper (real examples):

Install an execution cadence that forces clarity: top 3 priorities, owners, deadlines, weekly scoreboards
Build repeatable runbooks for messy operational workflows, then push them into automation (human <> AI handoffs)
Make sure high-stakes operational surfaces don’t degrade quietly (submission quality, underwriting throughput, quoting speed, customer response time)
Increase CEO leverage: fewer “CEO has to touch it” loops, more “it ships anyway”

You Might Be a Fit If…

You’re 4–7 years in—IB, PE, MBB, startup BizOps, or you built something yourself
You actually understand finance—cap tables, driver-based models, unit economics. Not “familiar with,” fluent
You’ve owned outcomes, not just advised on them. You stick around to see the results of what you build
You can draft a board memo, run a leadership meeting, handle a hard conversation with a senior hire, and negotiate with a wholesale broker—same week
High empathy, low ego—teams actively want to work with you, not around you
Comfortable in AI-native environments—you don’t write code, but you understand how AI creates leverage and you use it in your own workflows
You work at whatever intensity the situation requires. Some weeks that’s 60+ hours. If that energizes you, keep reading

Requirements

4–7 years of experience in high-intensity environments (banking, consulting, PE, startup ops, or founding)
Strong financial modeling and analytical skills
Exceptional written and verbal communication
Based in San Francisco or willing to relocate immediately

Nice to Have

Insurance, E&S, or financial services background
M&A experience (sourcing, diligence, or integration)
Previous Chief of Staff or BizOps role at a Series A–C company
You’ve been part of scaling a team from <50 to 100+

Not a Fit If…

You need rigid structure or defined swim lanes to feel grounded
You’re “strategic” but don’t want to do the work yourself
You need external validation or constant direction to stay motivated
You optimize for process over outcomes

Compensation

Salary: $175,000–$250,000 (depending on experience) + performance bonuses & equity
Location: San Francisco, in-office

Benefits

Health, dental, and vision insurance
Housing stipend
Daily meals ($60/day)
Commuter benefits (Uber covered)
Team meals and snacks

To Apply

This is a launching pad—into leadership within Harper, or to build your own thing someday. If you want an operational partner role with a founder who will push you harder than you’ve been pushed before—send your resume and a few sentences on why Harper.

Optional (but strongly encouraged): include a 1-page memo answering: “What’s one bottleneck you’d expect to exist inside a hyper-scaling, AI-native insurance brokerage—and what would your first 30 days do about it?”

Carpenter

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