CX Chief of Staff - Benefit Operations

About the Role:

The Chief of Staff to the Head of Benefit Operations is a senior operator responsible for turning strategy into durable execution by designing and owning the operating systems that allow the organization to scale. This role exists to increase clarity, accountability, and momentum by reducing reliance on ad hoc coordination and individual heroics in a complex, fast-moving environment. Operating with a systems-first, AI-aware mindset, the Chief of Staff uses automation and well-designed workflows to improve decision quality, execution speed, and organizational resilience. Working closely with cross-functional partners, this role ensures high-priority initiatives are aligned, tradeoffs are clear, and the organization can sustain progress through change. Success in this role is measured by better decisions, fewer escalations, and operating systems that continue to run effectively without constant intervention. This is a leadership role that works closely with cross-functional teams to support high-priority initiatives, align teams around shared goals, and ensure continuity through change. As part of a fast-paced, high-growth environment, the Chief of Staff will have the opportunity to help shape and scale a high-performing Benefits organization while directly influencing outcomes and driving transformation.

Here’s what you’ll do day-to-day:

• Partner with the department head to shape strategy and translate it into clear priorities, operating rules, and execution plans.


• Act as a strategic advisor to leadership, providing guidance on decisions, trends, and growth opportunities.


• Design, run, and continuously improve the BenOps operating cadence (OKRs, performance reviews, leadership rhythms), with a focus on automation and explicit ownership for clarity, decision hygiene, and follow-through.


• Lead change management initiatives by setting clear expectations, sequencing work, and holding leaders accountable for adoption.


• Design, evolve, and maintain workflows, metrics, and dashboards that leaders actively use to make decisions, not just to report status.


• 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.


• Provide interim leadership coverage when needed, with real ownership for priorities, delivery, and team health, not just continuity.


• Own executive-ready narratives and communications (memos, updates, All Hands content) that surface tradeoffs, risks, action, and decisions—not just updates.


• 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 + non-exempt workforce


• Business builder mindset: experience designing and scaling operating models, not just running existing processes


• Demonstrated ability to advise and influence senior leaders on strategy, organizational design, and people topics with sound judgment


• Strong program leadership: ability to lead complex, cross-functional initiatives from ambiguity to measurable outcomes without escalation


• Systems-first orientation: experience building durable workflows, operating mechanisms, dashboards, or automation that replaces recurring meetings, follow-ups, or manual coordination.


• Comfort operating at multiple altitudes — from executive narrative and strategic framing to hands-on problem solving


• Judgment over heroics: knows when to execute directly and when to invest in systems so the organization does not depend on personal intervention.


• Clear, concise communicator who keeps stakeholders aligned and decisions moving


• Deep empathy for small business customers and a strong sense of service


• High integrity, curiosity, and resilience; brings energy without burning out the system


• AI fluency: hands-on experience using AI or automation to reduce planning, reporting, or synthesis load—paired with strong judgment around trust and guardrails.


• Prior chapter outside of Tech is a plus, especially in regulated or service-oriented environments

The target level for this role is Level 5, and our cash compensation range for this role is $152,000 to $179,000 in Las Vegas, Denver, and Orlando, and $178,000 to $210,000 in San Francisco and New York. Final offer amounts are determined by multiple factors, including candidate location, experience, and expertise, and may vary from the level and amounts listed above.