Job Description

Chief of Staff at XILO

XILO, a rapidly growing Vertical AI company backed by recent Series A financing, seeks an experienced and versatile Chief of Staff to serve as the CEO’s strategic partner and operational leader. This is a dynamic, multi-faceted role, ideal for a driven professional ready to impact the company’s strategic direction and operational excellence in a high-growth startup.

About XILO

Founded in 2019 by two best friends, Jon and Eli, XILO was created to transform the insurance industry through cutting-edge technology. Starting as a vertical SaaS solution addressing core quoting challenges, XILO has evolved into an innovative Vertical AI company, leveraging advanced AI capabilities layered onto our platform. Our recent Series A funding underscores our momentum and ambition as we scale our impact across the industry.

About the Role

The Chief of Staff will serve as the CEO’s trusted right-hand, managing strategic initiatives, operational processes, and cross-functional projects to drive XILO’s growth and effectiveness. Your role will include strategic planning, performance reporting, investor communications, and operational alignment across teams. You’ll play a critical role in turning strategic goals into executable actions and ensuring key initiatives stay on track.

Key Responsibilities:

• Oversee strategic planning processes, including preparing financial reports and aligning SaaS metrics with financial performance.
• Craft compelling board materials, investor updates, and financial reports, clearly articulating company performance and strategic initiatives.
• Lead data-driven analysis and KPI tracking across Sales and Customer Success teams, ensuring accurate and timely reporting.
• Facilitate internal coordination and alignment, running team meetings and stand-ups to maintain operational effectiveness.
• Act as a direct liaison between the CEO and internal teams, translating high-level strategic guidance into actionable plans.
• Drive process improvements, proactively identifying operational bottlenecks and executing solutions.
• Support recruiting and people operations, helping to scale the team by sourcing talent, managing interviews, and supporting onboarding processes.
• Oversee administrative and office management tasks as needed, ensuring smooth day-to-day operations.
• Manage financial operations, including basic treasury functions, payroll coordination, and cash flow monitoring.

What We're Looking For:

• Approximately 5-10 years of relevant experience in operations, strategy, consulting, or finance, preferably in high-growth tech or SaaS startups.
• Strong analytical and strategic planning capabilities with proven experience managing cross-functional projects.
• Exceptional organizational, communication, and presentation skills.
• High emotional intelligence (EQ), with proven ability to build relationships and influence without formal authority.
• Strong numerical proficiency with experience creating financial reports and tracking operational KPIs.
• Demonstrated flexibility and problem-solving ability, capable of handling strategic initiatives and tactical operational details.
• High discretion, professionalism, and reliability as a trusted advisor to senior leadership.
• Bachelor’s degree required; advanced degree (MBA or similar) strongly preferred.

Why Join XILO?

At XILO, you'll be a central figure in a collaborative, high-impact team dedicated to redefining the future of insurance through innovative AI solutions. We offer a supportive yet fast-paced environment where your strategic insights and operational expertise will directly shape our trajectory and success.

If you are ready to significantly influence the strategy and operations of a pioneering startup, we’d love to connect with you.

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