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Why this grade This listing scored 31/100, which is an F. It lost the most ground on freshness. See the breakdown
- Description depth 20 / 20 How much the posting actually says about the work, measured in characters of real text.
- Pay transparency 12 / 25 A published salary range, worth more than any other single factor because it is what a candidate cannot find out without applying.
- Role specificity 6 / 10 Whether the listing is tagged well enough to tell what the role actually is.
- Corroboration 5 / 10 Whether more than one source carries this listing.
- Remote clarity 3 / 15 Whether "remote" means anywhere, or is quietly restricted to one country.
- Freshness 0 / 15 How recently it was posted. Older postings are likelier to be filled or abandoned.
-15 Ghost-job penalty — Deducted for signals that this posting may not be a real, currently-open role — staleness, repeated relisting, or talent-pool language.
Every figure above is arithmetic over the posting itself — its salary field, its text, its age, its tags and how many sources carry it. How the grades work →
yc-startup vc-backed
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
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Own core AI infrastructure — LLM orchestration, prompt management, retrieval systems, structured output parsing
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Design agent architecture — Define abstractions that let us ship new agents in days
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Build evaluation that works — Systems that measure whether agents are getting better at closing deals
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Architect decision trace capture — Make every AI judgment traceable
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Own platform scale — Thousands of concurrent conversations, sub-second response times
You Might Be a Fit If…
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You’ve owned production systems (not contributed to—owned; you got paged when it broke)
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You architect AND implement—the best architecture comes from people who live with what they build
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You’ve built AI systems in production (LLM applications, agent frameworks, RAG, voice AI)
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You write code with AI (Cursor, Claude Code) and manage multiple sessions
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You’re 3-6 years into your career
Requirements
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3-6 years software engineering experience
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Production experience with LLM applications and AI systems
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Strong architectural skills with hands-on implementation
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Track record of owning systems end-to-end
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Based in San Francisco or willing to relocate
Nice to Have
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Voice AI or real-time systems experience
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Experience building agent frameworks or evaluation systems
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Prior startup experience
Compensation
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Salary: $160,000–$230,000 + performance bonuses & equity
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Location: San Francisco, in-office
Benefits
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Health, dental, and vision insurance
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Commuter benefits
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Team meals and snacks
The Process
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15-min founder call — Alignment on mission and pace
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If in SF: Super Day on-site
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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.
Apply for this role Opens ycombinator.com — the link as listed; we have not yet verified it is the employer's own page
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Where this listing came from
- 21 Sep 2026 Y Combinator first sighting
Seen on 1 board over 0 days.