Chief of Staff at Harper

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. 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 th