Harper

Senior Member of Technical Staff

San Francisco, US Full-time

Join us if you want to change how a $12 Trillion market is serviced and lead the industrial AI revolution.

We are building the first professional services factory in history. For centuries, professional services have operated on a fundamentally human-centric model. We are here to change that.

Commercial insurance is a $1 trillion market serving 36 million businesses in the United States and its broken. Commercial insurance is broken not because of insufficient capital or demand—it's broken because distribution scales linearly and quality differs by the servicer. Traditional brokers need more people, more training, more locations. We're replacing that model with computational systems.

Old model: Hire humans → Train them → Scale linearly

Our model: Build computational systems → Humans teach edge cases → Scale exponentially

Professional services represent a $12 trillion market in the US. Insurance brokering is our entry point to proving that AI-native (business) models can replace human-centric expertise with computational systems that scale exponentially. If we win here, we change how every knowledge work industry operates.

We've grown 100x in 12 months—from $4K to $500K+ monthly ARR. Our sales reps hit 30x the industry average. Not through better training, but through computational systems.

What You'll Do

Build Day 1 AI Native Applications. Define Technical Direction. Build for 100x Scale.

  • Design and architect AI-native applications that fundamentally rethink how business logic operates—moving beyond Web 2.0 patterns to LLM-first, multi-modal experiences.

  • Own critical systems end-to-end: from architecture decisions to production deployment, monitoring, and iteration.

  • Build distributed, fault-tolerant infrastructure using Temporal.io, Kafka, Flink, and other streaming/orchestration platforms that handle millions of events daily.

  • Lead the development of fully autonomous AI agents that take real-world actions - quoting policies, managing workflows, and handling customer interactions.

  • Set technical standards ****for how we build, deploy, and scale AI systems—establishing patterns that other engineers will follow.

  • Bridge AI research and engineering - translating novel research into production-grade systems and providing feedback loops that improve model performance.

  • Drive business-process optimization - identify where changing business operations unlocks 10x improvements in data quality, agent performance, or system scalability.

  • Mentor and elevate junior engineers, establishing engineering culture and raising the bar for technical excellence.

  • Make high-stakes technical decisions under uncertainty - choosing between build vs. buy, monolith vs. microservices, sync vs. async, with real business consequences.

What We're Looking For

Senior Engineers who've architected production AI systems and scaled distributed infrastructure to millions of users. You thrive in 0→1 environments, have strong product instincts, and build technical foundations that scale to billions in revenue. Ex-founders and founding engineers strongly preferred—we want leaders who elevate junior engineers while shipping production code themselves. You own outcomes, not tasks, and know when to mentor and when to move fast.

You'll Thrive Here If You Have:

  • 5+ years shipping production systems in high-growth startups (strong preference for 0→1 experience)

  • Deep expertise building and scaling LLM-powered applications - RAG architectures, prompt engineering, context management, agent orchestration

  • Experience architecting and deploying distributed systems using message queues (Kafka, SQS), workflow orchestration (Temporal, Airflow), and stream processing (Flink, Spark)

  • Experience building full-stack applications using Python backend services (FastAPI, async patterns) + React.js frontends that handle complex state

  • Experience building in AWS with Lambda, ECS/EKS, S3, RDS, DynamoDB at scale

  • Experience designing for failure, reason about consistency vs. availability tradeoffs, and architect for 100x growth

  • Implemented distributed tracing and APM infrastructure using OpenTelemetry and Datadog

  • Technical leadership, mentoring engineers, led technical initiatives, or driven architectural decisions with measurable business impact

  • Been a previous founder, early startup employee, or demonstrated ability to own entire product areas

Nice to Have:

  • Experience fine-tuning LLMs, optimizing inference costs, or building custom ML pipelines

  • Built CDC pipelines (Debezium, Kafka Connect) for real-time data synchronization

  • Shipped data-intensive applications processing millions of records daily

  • Designed and implemented internal developer platforms or tooling

  • Led incident response and built reliable on-call practices

We operate with:

  • Extreme Pace: Ship 80% solutions in days, not weeks

  • Impeccable Taste: Know when simple beats complex and when to optimize

  • Competitive Fire: Here to win, not participate

  • Ownership: Take responsibility for outcomes, not deliverables

  • Day Zero Mindset: Throw away your work if data says it's wrong

The Harper Philosophy

  • "There is no try, there is just do" - Ship fast, iterate. Analysis paralysis is failure.

  • "Actions lead to information" - Do something and measure. Don't wait for perfect data. Actions generate data which help action better.

  • "Strong opinions, loosely held" - Argue passionately, but change completely when data says so.

  • "Software updates, not training updates" - Insights should improve systems automatically.

Why Join Harper

  • Real AI in Production: See how AI actually works at scale (95% of companies never get here). We’re running a real business but AI native.

  • Impact at Scale: Help prove that professional services can be computational. If we win in insurance, we change legal, accounting, HR—every knowledge worker industry.

  • Founder Training Ground: 12 months here = 3-5 years of learning elsewhere. Know what it means to be an operator.

Compensation & Perks

💰 Compensation: Competitive base + equity

🍲 Meals: Lunch / Dinner covered

🏥 Health: Medical, dental, vision

This role is NOT for you If:

  • You want 9-5 hours, clear scope, or work-life balance

  • You need perfect data before taking action

  • You prefer reporting over ownership

  • You're not comfortable with hypergrowth intensity

Interview Process:

  1. 30-min screening call

  2. Take-home coding assessment

  3. On-site

We move fast: Application to offer in 1-2 weeks for the right person.

The Mission

We're building the first professional services factory. Professional services = $12 trillion in US annual labor. The winning model will be AI-native from day 1.

The intelligence you build demonstrates that the Industrial Revolution for knowledge work is possible. If that mission excites you, if you're ready for intensity and opportunity—we should talk.

🚀 Y Combinator Company Info

Y Combinator Batch: W25
Team Size: 8 employees
Industry: Financial Technology and Services -> Insurance
Company Description: AI-native commercial insurance brokerage

💰 Compensation

Salary Range: $160,000 - $230,000
Equity Range: 0.01% - 0.2%

📋 Job Details

Job Type: Full-time
Experience Level: 3+ years