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.