Drillbit
Automating Office Work for Residential Contractors.
Operations Lead
About the role
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 at a $50 million valuation. Mason, our AI employee, has generated over $100M 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 $68M ARR sales pipeline.
The Role
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. (https://www.redfin.com/blog/reasons-to-move-to-austin/)
What You’ll Do
- Own customer relationships post-sales to ensure smooth onboarding, gather feedback, and surface insights to engineering.
- Translate complex customer needs into clear, actionable product and engineering requirements.
- 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.
You Might Be a Fit If You:
- Have 2-6 years of experience in consulting, operations, or a product-facing role ideally at a fast-paced startup.
- Are technical enough to speak engineering’s language, with familiarity in tools and concepts like TypeScript, React, and SQL, and can dig into systems without getting lost.
- Are experienced with Excel and Notion, using relations, rollups, and database formulas to organize and connect data efficiently.
- Enjoy talking to customers, finding patterns in their feedback, and driving solutions forward.
- Are a self-starter who thrives on autonomy and momentum.
- Get things done quickly and with high quality, even when the path isn’t clear.
Compensation and Benefits
- Early-stage equity
- Catered lunch
- Competitive top-of-market salary
- $100/month gym reimbursement
About Drillbit
Mission: Drillbit’s mission is to make housing more affordable. Contractors needlessly waste hours every day on office work resulting in inflated costs. Drillbit automates all of it so that businesses can get back to the work they were hired for.
Stage: Drillbit is a YC startup that has raised $4.1 million at a $50 million valuation. Mason, our AI employee, has generated over $46M in GMV for our customers across over 65k 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 30% month-over-month growth, building a $16M ARR sales pipeline.
