Chief of Staff - GTM | InsurTech | Hybrid NYC

$120,000 - $150,000/Year

Location
New York, NY, USA
Job Type
Permanent
Industry
Sales
Remote/Onsite
Must Be Onsite
Experience Required
3 - 8 Years
Education Required
Higher Education
Job Summary

We are partnering with a high-growth, venture-backed organization that is modernizing a legacy, trillion-dollar industry through a technology-enabled, advisory-led model. The company works with fast-scaling, category-defining businesses across consumer, manufacturing, hospitality, and emerging technology sectors, helping them manage complex operational and financial risk as they scale.


Rather than operating as a traditional services firm, this organization has built proprietary internal technology to automate workflows, improve efficiency, and enable a more data-driven, consultative go-to-market motion. The business has scaled rapidly while remaining capital-efficient and is backed by well-known institutional investors.


This is a company at a true inflection point — combining strong product-market fit, meaningful revenue growth, and a clear path to continued vertical expansion.


Sector: B2B Services / Technology-Enabled Professional Services

Stage: Series-A, VC-backed

Size: ~50 Employees

Role Focus: New logo acquisition, enterprise expansion, multi-stakeholder sales motions


The Role


As Chief of Staff & Sales Lead, you will act as a direct force multiplier to the CEO while helping drive the company’s early revenue engine. This is a hybrid strategic + customer-facing role designed for someone who thrives in fast-moving environments, loves solving ambiguous problems, and is excited to help build a company from the ground up.


You’ll play a pivotal part in aligning the organization, accelerating decision-making, supporting sales conversations, and ensuring early customers have a seamless, high-value experience. If you want a seat at the table and enjoy wearing multiple hats, from operations to GTM to customer success, this role is uniquely high-impact and high-visibility.


This is ideal for a leader who wants:


  • Ownership over outcomes
  • Exposure to sophisticated buyers
  • A seat close to strategy and decision-making
  • The opportunity to grow into a deeper leadership & strategy role over time


What You’ll Do:


  • You’ll be 100% focused on growing as quickly and efficiently as possible.
  • You’ll directly own the most important initiatives to get this done.
  • 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.


What We’re Looking For:


  • 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.


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