Operations Lead (Manager)

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

Interview Breakdown

• Recruiter screen
• Screening with Head of Commercial Strategy
• Take home assignment
• Technical Interview
• Meet the team
• Offer