Member of Technical Staff – Automation Specialist

Location: New York, NY

About WithCoverage:

WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy. 

We partner with hundreds of high-growth, category-defining companies, including GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clients span iconic consumer brands, hospitality leaders, GCs, advanced manufacturers, and next-generation defense contractors. They operate in complex risk environments and need a partner that can move at their speed.

Instead of a fragmented, manual brokerage stack, we have built a new category: elite risk advisors operating on top of proprietary technology. Our in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions. This platform enables deep automation, better decisions, and a fundamentally higher standard of service.

WithCoverage was founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound). We have raised over $50M from leading investors including Sequoia, 8VC, Khosla Ventures and Crystal Venture Partners. 

Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the economy.

Why join us:

• Grow faster – We’re scaling quickly, giving you significant opportunities to learn, lead, and shape your career and the company's future.
• Work that matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.
• Redefine an industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.
• Financial rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and excellent benefits. We believe strongly in internal promotion and lay out a plan for everyone's career growth.

About The Role:

We are open to a wide range of levels for this role.

As a member of our R&D organization, you’ll help build the systems that serve our clients’ complex risk needs. You’ll work directly inside real insurance servicing workflows, learn how they operate in practice, and then systematically automate them.

For every workflow you own, you’ll execute the work, identify the decisions and edge cases involved, help design the automation, and operate the remaining exceptions as automation improves. Once a workflow becomes effectively zero-touch, you’ll move on to the next one.

This role sits at the intersection of operations, analytics, and technology. You should be exceptionally comfortable with computers, structured problem solving, data, and technical tools. You might have used Python, SAS, MATLAB, SQL, or similar tools in prior work; built models or analyses; automated parts of your own workflow; or developed a reputation for being the person who figures out how systems work and makes them better.

What You’ll Do:

• Own workflows end to end. Take responsibility for real servicing workflows, from receiving a request through delivering the final result. Learn the process by doing the work yourself and develop a detailed understanding of the inputs, decisions, dependencies, and exceptions involved.
• Use technical tools to solve operational problems. Work with structured and unstructured data, spreadsheets, scripts, APIs, internal tools, and AI systems to investigate problems, improve workflows, and create leverage.
• Automate and improve continuously. Identify repeatable steps, codify decision-making, and reduce the amount of manual work required over time. As one workflow becomes increasingly automated, move on to the next high-value problem.
• Design for the edge cases. Understand where automation breaks down and why. Identify exceptions, decision rules, escalation paths, and feedback loops that make each workflow more reliable over time.
• Work alongside product and engineering. Translate operational knowledge into clear requirements for automation. Test new capabilities against real work, provide rapid feedback, and help determine when a system is ready to take on more responsibility.
• Measure automation, not activity. Success is not defined by how many requests you personally process. It is defined by how quickly a workflow becomes faster, more reliable, and less dependent on manual work.

Who You Are:

• You are an exceptionally strong analytical problem solver. You can take a messy, ambiguous process and break it into its underlying rules, decisions, and edge cases.
• You are highly technically fluent. You easily learn new systems quickly and figure out how different tools fit together. You have experience with analytical or technical tools such as Python, SQL, SAS, MATLAB, R, advanced Excel, or similar.
• You are highly precise and detail-oriented. You can operate complex workflows accurately while simultaneously thinking about how to redesign them.
• You communicate clearly with both technical and non-technical teams and can turn what you learn from operating a workflow into precise requirements for how it should be automated.
• You are comfortable with a role that continually changes. As one part of your job becomes automated, you expect to take on the next unsolved problem.

Candidates from analytical, technical, or quantitative environments may be particularly well suited for this role, including economic consulting, quantitative research, analytics, and technical operations.

The core operating principle of this role is simple: create efficiency, automate the work, and move on to the next problem.

This role is on-site in our New York office. The expected cash compensation range for this position at the start of employment is $140,000–$220,000 a year. In addition, WithCoverage offers generous equity and equity refreshers.

What We Offer:

• Competitive compensation that includes equity
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Pre-tax accounts (FSA, HSAs, dependent care FSAs, 401(k), commuter savings)
• Time Off: Flexible time off, sick leave, family and medical leave, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture