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Rounds/Menlo Insurance/Founding Engineer·#50617
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Insurance·Pre-Seed·San Francisco, California

Founding Engineer

at Menlo Insurance — Insurance
Location
San Francisco, California
Salary
$100,000 - $160,000
Type
Full-Time
TL;DR
  • Strong GitHub is the #1 screen
  • Keeps AI tools on a tight leash
  • Next.js/Python/Playwright; agent harnesses + automation
  • New grad–early career
About Menlo Insurance
Menlo is an AI-powered insurance brokerage that has fully automated the back office of a traditional brokerage using proprietary models fine-tuned continuously in production. It's handling $1M+ in premium and growing fast — projecting ~$1M ARR within ~3 months — in a huge, fragmented, dinosaur-era industry still run on email, phone calls, and paper. The wedge came from a real pain: founder Guido Trevisan (University of Chicago grad) started ~6 months ago helping friends insure fertilizer shipments from Mexico to China, discovered how brutally hard it is to find carriers and build compliant policies for niche commercial risks, and realized the only way this gets solved is a technical founder building it from scratch.
Pre-Seed • 1 – 10
Stage & size
Insurance
Industry
2026
Founded
About This Role

Menlo is hiring its founding engineer — effectively a second technical founder — to help build and scale the platform as it explodes. Menlo is drowning in inbound (too many customers, not enough capacity to service them), systems break easily under load, and this person keeps the rocket ship flying while helping rebuild it mid-flight. The work is heavy on agent harnesses and automation — Next.js, Python, web scraping / browser automation (Playwright/Puppeteer), and a lot of fine-tuning (Guido handles most of the fine-tuning himself; it's a plus, not a requirement). The immediate challenge is scaling the current architecture from ~$1M annualized premium to the next order of magnitude.

The single most important filter is a strong GitHub / evidence of building — Guido is explicit that if someone's never built something end to end, it's a hard no; a great GitHub (a real agent, cool research, something shipped) is basically sufficient to move forward. Equally important: they must actually understand the code, not just vibe-code it. He needs someone who knows data structures and algorithms well enough to keep AI tools (Codex/Claude) "on a tight leash" and know exactly what's being built — his nightmare is a "slop-grenade" PR that breaks 20 things (he's lived it with interns). New grads are welcome (he's a new grad himself); it's not about seniority, it's about being genuinely technical with projects to show, action bias, and willingness to grind.

What You'll Own

  • Scale the platform architecture from ~$1M annualized premium to the next order of magnitude
  • Build and maintain agent harnesses and automation across the insurance back office
  • Web scraping / browser automation (Playwright/Puppeteer) against fragmented carrier systems
  • Keep inbound-demand systems from breaking; fix fast and rebuild for scale
  • Own features idea → deployment; use AI coding tools while fully understanding/reviewing/testing output
  • (Plus) fine-tuning work alongside the founder

Requirements

  • A strong GitHub / proven building — shipped something substantial end to end (an agent, research, a real project). The #1 screen; no building experience = hard no
  • Strong programming fundamentals (CS degree; real DS&A) — can "nudge" AI tools and keep them on a tight leash, not learn-to-code-via-AI
  • TypeScript, React/Next.js, Python, databases
  • Web scraping / browser automation (Playwright or Puppeteer ideal)
  • Good Git workflows: clear commits, PRs, code review, CI/CD
  • Plus: fine-tuning / ML background (harder to find; founder covers most)

Who Will Thrive Here

  • A builder with a standout GitHub who wants to be employee #1 and operate like a co-founder
  • Someone who keeps AI tools on a tight leash and ships clean, understood code fast
  • High action bias, high ownership, ready to grind 996 on a rocket ship
  • New grad or early-career, deeply technical, talkative/edgy-SF energy
  • Excited to automate a massive, broken, un-sexy industry that won't get market-corrected away
Job Details
Experience
0-3 Years
Salary
$100,000 - $160,000
Equity
1% - 3%
Visa Sponsorship
Limited
Employment Type
Full-Time
Work Arrangement
In office
Work Intensity
9-9-6
Benefits & Perks
Founder-arranged Housing
Green Flags
A GitHub with a real agent, automation project, or cool research shipped
Fine-tuning / ML experience (bonus)
Founding/early-engineer or serious side-project builder
Red Flags
No building evidence / weak GitHub (hard no)
Learned to code via AI; can't understand/debug the output ("slop-grenade" PRs)
Needs a spec; low agency / low ownership

Candidate scorecard

· 4 criteria
Strong GitHub / proven end-to-end building
Real programming fundamentals (CS, DS&A)
Action bias, immense ownership
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