Chief of Staff

Company overview:

vQuip is redefining risk management for adventure sports and recreational rental businesses—helping operators of boats, ATVs, snowmobiles, and other adventure sports outfitters protect their business, lower risk, and access better commercial insurance solutions.

Our mission is to deliver an exceptional customer experience, comprehensive coverage, and affordable rates through the use of loss control, data and technology- driven efficiency. vQuip is built on the belief that as technology transforms the world, so do the opportunities to solve age- old challenges within specialty insurance. Technology enables vQuip to deeply understand risk in curated niche verticals, giving us unique insights that unlock defensible underwriting advantages.

Role Overview:

We’re seeking an entrepreneurial, highly organized Chief of Staff to act as an operational right-hand to the CEO. This is a mission-critical role responsible for driving operational efficiency, supporting high-value strategic initiatives, managing critical investor and partner deliverables, and ensuring organizational alignment as we scale rapidly.

The Chief of Staff will blend start-up agility with disciplined operational execution. You will act as a force multiplier—amplifying the CEO’s bandwidth, enabling cross-functional progress, and ensuring our priorities are executed at speed and to standard.

The role reports directly to the CEO.

Key Responsibilities:

Operational Leadership

Own and optimize company-wide operational rhythms, OKRs, and strategic planning processes.
Coordinate cross-functional initiatives, removing bottlenecks and ensuring alignment.
Lead special projects that span multiple teams (e.g., product launches, operational improvements, strategic partnerships).
Create frameworks, processes, and dashboards to drive accountability, leadership alignment and decision-making.

Investor &Partner Relations

Manage ongoing communication and reporting with investors, including board meeting prep, KPI tracking, and fundraising materials.
Prepare executive-level presentations, memos, and strategic updates.
Support and take a lead role in the preparation of investor analyses and deliverables

Organizational Excellence

Serve as the CEO’s proxy in meetings and decision-making forums when required.
Develop and maintain internal communication channels to ensure the team is aligned and informed.
Proactively identify and resolve operational gaps, inefficiencies, and risks before they impact execution.
Ensure strategic initiatives are on track, escalating and course-correcting as needed.

Qualifications:

4+ years’ experience in high-growth startups, top-tier consulting, investing, and/or operational roles
Proven ability to operate tactically in early stage environment —comfortable in the weeds but able to think big picture.
Exceptional organizational skills with a bias toward action and a track record of delivering results in fast-paced settings.
Strong financial acumen and comfort working with P&L, KPIs, and investor reporting.
Experience in investor relations or operational leadership.
Excellent communication skills—able to synthesize complex information into concise, compelling narratives.
High EQ, discretion, and ability to manage sensitive information.

What Success Looks Like:

The CEO and leadership team can trust you to seamlessly execute and prioritize high-value, strategic activities. Investors and partners receive proactive, well-structured communication and see vQuip as a disciplined, high-performance organization.
Strategic initiatives move from concept to execution with speed, precision, and measurable outcomes.
The organization becomes more aligned, efficient, and adaptable without losing entrepreneurial agility.

Compensation & Benefits: