Staff Software Engineer, AI

Why Drillbit

Mission: Drillbit’s mission is to make housing more affordable

How: Residential contractors spend exorbitant amounts on customer acquisition due to wasteful human-driven administrative practices. This inefficiency inflates the cost of basic services, hurting everyone in America. Drillbit provides AI office workers to eliminate that waste, and allow businesses to get back to the work they were hired for.

Stage: Drillbit is a YC startup that has raised $4.4 million. Mason, our AI employee, has generated over $95M in GMV for our customers across over 90k opportunities. He is booking jobs at a rate 3x greater than the best human CSRs at a small fraction of their cost. In the past 12 months, Drillbit has sustained 42% month-over-month growth, building a $98M ARR sales pipeline.

Role Overview

We’re looking for a sharp, highly technical AI Engineer to join our 7-person engineering team in Austin, TX. You’ll be on the frontlines designing and deploying cutting-edge AI systems that power Mason and the next generation of Drillbit products. This is an in-person role (9 to 7, Monday to Friday), perfect for a relentless self-starter who thrives in fast-paced startup energy and wants to ship real impact every day.

On top of working with a world-class team of engineers from Apple, Microsoft, SpaceX, and more, you’ll have access to a bustling city with BBQ, trails, and affordable rent.

What You’ll Do

• Own the architecture of Mason’s AI systems across natural language, reasoning, and voice.

• Design and deliver high-impact AI features that are robust, scalable, and measurably improve customer outcomes.

• Lead cross-functional initiatives (Design, Ops, Sales) to tightly align Mason’s product direction with customer needs and engineering execution.

• Evaluate and operationalize cutting-edge AI/LLM techniques, ensuring Mason stays ahead of the industry and ships real, defensible advancements.

• Mentor and level-up the eng team, creating reusable patterns, libraries, and tooling that increase velocity across the entire engineering team.

  What You Have

• Passion about making housing more affordable

• BS/MS/PhD in Computer Science, a related scientific field, or equivalent experience

• 5+ years of full-stack experience with proficiency in TypeScript, React, Next.js, and relational databases

• Experience with audio processing, livekit, and ASR systems (nice to have)

• Production experience with LLMs (OpenAI, Anthropic, etc.) and RAG architectures

• Bonus points if experienced with PostgreSQL, Node.js ecosystem tools (NPM, Jest, ESLint), docker, and styling libraries like Tailwind CSS

Life at Drillbit

Daily Catered Lunch

Competitive Top-of-Market Salary

Early-Stage Equity

$100/Month Gym Reimbursement

Relocation Assistance

Monthly Team Outings

Medical, Dental & Vision Insurance

Interview Breakdown

• Recruiter screen
• Technical screen with Head of Engineering
• Take home assignment
• Technical Interview
• Meet the team
• Offer