SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 140,000 - 220,000 / annual
WithCoverage is redefining insurance brokerage through AI-supercharged risk management for high-growth companies. Founded by JD Ross (Opendoor co-founder) and Max Brenner (Bain, Compound), the company has raised over $50M from Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. WithCoverage serves hundreds of category-defining clients including GoPuff, Eight Sleep, Bombas, and Blank Street Coffee, operating a proprietary Agency Management System that provides visibility into policies, exposures, claims, billing, and commissions.
As a Member of Technical Staff - Automation Specialist, you will join the R&D organization to build systems serving clients' complex risk needs. You'll work directly inside real insurance servicing workflows, learn how they operate in practice, and systematically automate them. For each workflow you own, you will execute the work, identify decisions and edge cases, help design automation, and operate remaining exceptions as automation improves. Once a workflow becomes effectively zero-touch, you'll move to the next high-value problem.
Key responsibilities include: owning workflows end-to-end from request receipt through final delivery; using technical tools (spreadsheets, scripts, APIs, internal tools, AI systems) to solve operational problems; identifying repeatable steps and reducing manual work over time; understanding where automation breaks down and designing for edge cases; translating operational knowledge into clear requirements for product and engineering teams; and measuring success by workflow automation rather than personal activity volume.
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. The ideal candidate has experience with Python, SAS, MATLAB, SQL, or similar tools; has built models or analyses; has automated parts of their own workflow; or has developed a reputation for figuring out how systems work and making them better. Candidates from analytical, technical, or quantitative environments—such as economic consulting, quantitative research, analytics, and technical operations—are particularly well-suited.
The core operating principle is simple: create efficiency, automate the work, and move on to the next problem.
QUALIFICATIONS & REQUIREMENTS:
- Exceptionally strong analytical problem-solving skills; ability to break messy, ambiguous processes into underlying rules, decisions, and edge cases
- High technical fluency; ability to quickly learn new systems and understand how different tools fit together
- Experience with analytical or technical tools such as Python, SQL, SAS, MATLAB, R, advanced Excel, or similar
- Highly precise and detail-oriented; able to operate complex workflows accurately while redesigning them
- Clear communication with both technical and non-technical teams
- Comfort with a continually changing role as parts become automated
- Background in analytical, technical, or quantitative environments preferred (economic consulting, quantitative research, analytics, technical operations)
- Open to a wide range of levels for this role
