Chief of Staff to the Head of Sales

Assured•Palo Alto, CA

3d•$180,000 - $200,000•Remote

About The Position

Assured is modernizing the insurance industry, focusing on claims processing, which is currently manual and costly. We provide software solutions to large insurers, including self-service claims filing and fraud detection. Our work involves creating digital experiences for claimants and managing large-scale ML-driven decision-making. The role of Chief of Staff to the Head of Sales is a unique opportunity to be the right hand to sales leadership, acting as a force multiplier across the go-to-market organization. This position bridges sales strategy and execution, working closely with the Head of Sales on decisions, deals, and operational rhythms that drive revenue. The role supports the Head of Sales and accountable sales leaders by improving meeting readiness, internal alignment, resource coordination, visibility into commitments and risks, and follow-through. The Chief of Staff will move between strategic and tactical tasks, such as building deal strategies, unblocking enterprise deals, and establishing new sales operations processes. This role is ideal for someone who thrives in ambiguity, brings structure to chaos, and enhances the effectiveness of those around them, particularly the Head of Sales. It offers direct exposure to how a high-growth company wins in the market and the chance to shape the sales engine.

Requirements

5-7 years of experience, including 2-4 years at a top-tier management consulting firm (Bain, McKinsey, BCG or equivalent) or in a sales strategy, revenue operations, or chief-of-staff role at a high-growth company.
Exceptional communication skills, both written and verbal, with the ability to simplify complexity for any audience, including customers and executives.
Strong analytical horsepower, with comfort in building models, pipeline analyses, and strategic frameworks from scratch.
An execution-oriented mindset: ability to follow through, meet timelines, and get things done without constant supervision.
A high degree of ownership and a low ego: comfortable with both strategic thinking and hands-on execution, with no task being too big or too small.
Experience managing or influencing cross-functional teams without formal authority.
Familiarity with modern sales tooling (CRM, sales engagement, and BI or reporting platforms) is a plus.

Responsibilities

Serve as the right hand to the Head of Sales, acting as a trusted thought partner and proxy, managing the sales leader's strategic agenda, preparing them for high-stakes internal and customer meetings, and ensuring priorities translate into action and accountability.
Own the sales operating cadence, including designing and running pipeline reviews, forecast calls, QBRs, staff meetings, and sales off-sites, ensuring each is well-prepared, decision-oriented, and followed through.
Drive pipeline visibility and forecasting by building and maintaining reporting, dashboards, and analysis for leadership to have a clear, accurate view of pipeline health, forecast accuracy, and team performance.
Own sales enablement by designing and building decks, one-pagers, and narratives for critical customer meetings, and ensuring reps have the necessary resources to win.
Lead cross-functional coordination as the connective tissue between Sales and Marketing, Customer Engineering, Product, and Finance, driving alignment on handoffs, launches, and shared GTM priorities.
Structure complex problems using rigorous analytical frameworks for ambiguous questions such as segmentation, territory strategy, pricing inputs, and win/loss analysis, translating data and qualitative insights into actionable recommendations.
Support key hiring and onboarding by partnering on recruiting, interviewing, and onboarding across the sales organization to attract and ramp top talent quickly.
Prepare executive-level materials, including strategic memos and internal communications, representing the sales function to the executive leadership team.