Senior Member of Technical 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.

You'll be one of the most senior engineers at Harper. That means you own systems end-to-end.

The Thesis

The difference between MTS and Senior MTS: you own outcomes, not tasks. You look at a business problem-"we need to 10x our quoting capacity"-and figure out what to build, build it, and make sure it works. You architect systems AND implement them. You mentor by building alongside people, not by reviewing PRs from a distance.

The Role

This isn't a "tech lead who attends meetings" role. You make architectural decisions that stick, and ship code that directly generates revenue. No waiting for consensus-we don't have time for consensus.

What You'll Do

• Own core AI infrastructure - LLM orchestration, prompt management, retrieval systems, structured output parsing
• Design agent architecture - Define abstractions that let us ship new agents in days
• Build evaluation that works - Systems that measure whether agents are getting better at closing deals
• Architect decision trace capture - Make every AI judgment traceable
• Own platform scale - Thousands of concurrent conversations, sub-second response times

You Might Be a Fit If...

• You've owned production systems (not contributed to-owned; you got paged when it broke)
• You architect AND implement-the best architecture comes from people who live with what they build
• You've built AI systems in production (LLM applications, agent frameworks, RAG, voice AI)
• You write code with AI (Cursor, Claude Code) and manage multiple sessions
• You're 3-6 years into your career

Requirements

• 3-6 years software engineering experience
• Production experience with LLM applications and AI systems
• Strong architectural skills with hands-on implementation
• Track record of owning systems end-to-end
• Based in San Francisco or willing to relocate

Nice to Have

• Voice AI or real-time systems experience
• Experience building agent frameworks or evaluation systems
• Prior startup experience

Compensation

• Salary: $160,000-$230,000 + performance bonuses & equity
• Location: San Francisco, in-office

Benefits

• Health, dental, and vision insurance
• Commuter benefits
• Team meals and snacks

The Process

1. 15-min founder call - Alignment on mission and pace
2. If in SF: Super Day on-site
3. If outside SF: Technical phone screen, then on-site

To Apply

If you want to own systems that run a real business and work with founders who will actually listen to you-send your resume and tell us about a system you've owned.