Chief of Staff

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, r