WithCoverage · 1 day ago
Chief of Staff + GTM Lead
New York
Full-time
Hybrid
Mid, Senior Level
$150K/yr - $200K/yr
2+ years expWithCoverage is an innovative company redefining risk management through AI technology. The Chief of Staff & Sales Lead will support the CEO in driving revenue growth, overseeing cross-functional initiatives, and ensuring a seamless experience for early customers.
Business DevelopmentInsuranceInsurTech
Responsibilities
Act as an extension of the CEO to drive alignment, follow-through, and execution across the company
Lead project management for cross-functional initiatives (launches, implementations, partnerships) to keep the company operating smoothly
Support and eventually lead sales activities—including joining discovery calls, managing the pipeline, handling follow-ups, and driving deals toward close
Manage CEO priorities, prepare materials for key meetings, and ensure decisions translate into actionable plans
Qualification
Required
2–6 years of experience across operations, chief of staff, sales, consulting, or other generalist roles
A strong communicator who can represent the CEO internally and externally with clarity and polish
Comfortable in sales calls - can ask thoughtful questions, handle objections, and drive next steps
A builder of processes and systems, especially in zero-to-one environments
Highly organized with exceptional follow-through and attention to detail
Thrives in ambiguity and enjoys switching between strategic planning and hands-on execution
High ownership mindset - proactive, resourceful, and able to work with minimal direction
Comfortable with data, dashboards, CRM tools, and basic GTM metrics
Trustworthy and discreet, with the judgment to handle sensitive information and represent leadership effectively
Benefits
Competitive compensation that may include equity
Flexible paid time off
Comprehensive benefit plans for medical, dental, vision, life, and disability
Flexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA
Commuter Savings Account
Human Interest: 401(k) provider
Time Off: Sick Leave, Family and Medical Leave, Flexible Time Off
Paid Holidays: Observance of all major national holidays
A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers
Collaborative, transparent, and fun culture
Company
WithCoverage
WithCoverage operates as a modern risk management and insurance broking platform targeting fast-growing businesses.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$42M2026-01-13Series B· $42M
Leadership Team
Max Brenner
Co-Founder & CEO
JD Ross
Co-Founder
Recent News
alleywatch.com
2026-01-20
2026-01-16
Company data provided by crunchbase