Drillbit

⚡ 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 $120M in GMV for our customers across over 100k 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. 🔎 What We Need We’re looking for an Business Operations Analyst who loves solving ambiguous problems with data, improving internal systems, and partnering closely with engineering to keep Drillbit running efficiently at scale. You will analyze data flows across our product and customer operations, identify bottlenecks, build dashboards, and improve workflows. You’ll help ensure that our internal tools, processes, and metrics are clean, reliable, and scalable as we grow. You should also be a clear, concise communicator who enjoys working directly with customers—supporting onboarding, troubleshooting issues, and helping them get value from Mason. 🚀 What You’ll Do Analyze operational, product, and customer data to identify patterns, bottlenecks, and gaps. Build, maintain, and improve internal dashboards to monitor performance and support decision-making. Guide customers through onboarding and issue resolution, ensuring they feel supported and confident using Mason. Partner with engineering to debug data issues, validate workflows, and improve data quality across systems. Design and document repeatable procedures so the organization can move faster with fewer errors. Operate with urgency, taking ownership of problems end-to-end even when the path is unclear. 🎯 Who You Are Bachelor’s degree in engineering, mathematics, computer science, data science, physics, or another quantitative field. Open to new grads; 1+ years of experience in operations, analytics, consulting, business development, product, or engineering roles preferred. Sales experience is a plus; thrive when owning customer conversations end-to-end; onboarding, diagnosing patterns, and driving the right fixes across the team. Exceptionally organized, is an excellent communicator, and genuinely enjoys bringing order and clarity to fast-moving operational environments. Experienced with SQL, TypeScript/React environments, and API-driven tools. Naturally digs into how systems work under the hood. Fluent with Excel and Notion, using relations, rollups, formulas, and multi-database structures to design dashboards, automate workflows, and standardize processes. A self-starter who thrives on autonomy and momentum, even when the path isn’t clear. 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

⚡ 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 $120M in GMV for our customers across over 100k 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. 🔎 What We Need We’re looking for an Operations Lead who thrives in early-stage chaos and loves being at the intersection of customers, product, and process. You’ll work directly with our founder, customers, and engineering team to help Drillbit run smoothly and scale. You’ll connect what customers need and what engineering builds by translating feedback into product insights, identifying process gaps, and helping us standardize how we operate. 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 customer relationships post-sales to ensure smooth onboarding, gather feedback, and surface insights to engineering. Can translate customer issues into clear technical context for engineers. Able to reason about systems, spot root causes, and debug workflows. Build scalable internal processes across customer success, support, and operations. Propose improvements across everything from documentation to workflows. Partner closely with engineering to triage customer issues, test fixes, and communicate timelines clearly. Create structure where there is none by standardizing tools, metrics, and routines that make the company run better. Be the right hand to the founder on high-priority operational projects. 🎯 Who You Are Exceptionally organized, is an excellent communicator, and genuinely enjoys bringing order and clarity to fast-moving operational environments. Have 3+ years of experience in consulting, operations, product, or adjacent, customer-facing roles, ideally in a fast-paced startup where ambiguity is the norm. Experienced with SQL, TypeScript/React environments, and API-driven tools. Naturally digs into how systems work under the hood. Fluent with Excel and Notion, using relations, rollups, formulas, and multi-database structures to design dashboards, automate workflows, and standardize processes. Thrive when owning customer conversations end-to-end; onboarding, diagnosing patterns, and driving the right fixes across the team. A self-starter who thrives on autonomy and momentum, even when the path isn’t clear. 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

⚡ 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

⚡ 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 Lead development of AI features while ensuring systems are scalable, reliable, and impactful for our customers. Build and optimize real-time AI systems across natural language, reasoning, and voice. Collaborate closely with engineering to design intelligent, human-like AI interactions. Stays current with AI/LLM advancements and knows how to put them into practice Foster a culture of innovation, excellence, and collaboration within the technology team. 🧠 What You Have Passion about making housing more affordable BS/MS/PhD in Computer Science, a related scientific field, or equivalent experience 2+ 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