Chief of Staff - Benefits Operations

About the Role:

This is a leadership role that will work closely with cross-functional teams to support the execution of high-priority projects, align teams around shared goals, and ensure business continuity. As part of a fast-paced, high-growth environment, the Chief of Staff will have the opportunity to shape and scale a high-performing organization, while directly influencing key outcomes and driving transformational change.

About the Team:

The Chief of Staff to the Head of Benefit Operations will play a pivotal role in driving strategic initiatives, operational excellence, and organizational alignment for the department, ensuring seamless execution across all business functions. This person will be responsible for overseeing the creation and execution of key business strategies, managing OKRs, streamlining workflows, and driving change management initiatives to ensure continuous improvement in customer experience and operational efficiency

Here’s what you’ll do day-to-day:

• Partner with the department head to drive strategic initiatives, ensuring alignment with company goals and cross-functional teams.
• Act as a strategic advisor to leadership, providing guidance on decisions, trends, and growth opportunities.
• Own OKRs, performance reviews, and operational cadence, ensuring alignment and progress across BenOps and leadership.
• Lead change management initiatives, ensuring readiness for process changes and driving adoption across the organization.
• Develop and maintain workflows, metrics, and dashboards to drive operational efficiency and consistency across teams.
• Oversee centralized intake and prioritization of product requests for BenOps, providing clear recommendations on product asks.
• Use data-driven insights to improve customer experience and drive continuous improvements across BenOps and CX.
• Step in to manage teams as needed, ensuring business continuity during transitions or high-demand periods.
• Manage organizational communications, including newsletters, All Hands updates, and team-related announcements.
• Enable senior managers and foster a culture of accountability, engagement, and continuous learning across the organization.

Here’s what we're looking for:

• 10+ years of total experience in analytical, operating roles at high-growth startups 
• 5+ years in a CX Strategy or Senior-Level CX Operating Experience
• Experience as CoS or CX Strategy lead in a large tech company, working with CX or Product leaders
• Exposure to scale of 1000+ employee organizations with a mix of exempt and non-exempt workforce
• Industry: meaningful work in tech (can’t be the first time). 
• Business builder mindset
• Empowered a team of 2+
• Demonstrated ability to mentor / advise execs on people topics
• Stellar program management: you will be called on to develop, and manage programs for BenOps-wide initiatives.
• Deep empathy and obsession for small business customers.
• Grit, hustle, and the ability to flex into problems at all altitudes.
• The ability to keep all the trains on the tracks and the clear communication flowing.
• A deep passion for helping others.
• Prior chapter outside of Tech is a nice to have

Our cash compensation amount for this role is targeted at $152,000 - $179,000/yearly in Denver & most major metro locations, and $178,000 - $210,000/yearly for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.