Chief of Staff to the Head of Sales

About the Company

Assured is on a mission to modernize insurance. We provide large insurers with the software solutions they need to win in a modern, technology-driven world, from self-service claim-filing software to backend fraud detection.

Responsibilities

• Serve as a trusted thought partner and proxy to the Head of Sales, managing strategic agendas and preparing for high-stakes meetings
• Own the sales operating cadence, including pipeline reviews, forecast calls, QBRs, and sales off-sites
• Drive pipeline visibility and forecasting through reporting, dashboards, and analysis
• Lead sales enablement by designing decks, one-pagers, and narratives for critical customer meetings
• Act as the connective tissue between Sales and Marketing, Customer Engineering, Product, and Finance
• Structure complex problems regarding segmentation, territory strategy, and pricing using analytical frameworks
• Support key hiring and onboarding efforts across the sales organization
• Prepare executive-level strategic memos and internal communications

Requirements

• 5-7 years of professional experience
• 2-4 years at a top-tier management consulting firm (Bain, McKinsey, BCG) or in sales strategy, revenue operations, or a chief-of-staff role at a high-growth company
• Exceptional written and verbal communication skills
• Strong analytical horsepower with ability to build models and strategic frameworks from scratch
• Execution-oriented mindset with high ownership and low ego
• Experience managing or influencing cross-functional teams without formal authority
• Familiarity with modern sales tooling (CRM, sales engagement, BI platforms) is a plus

Benefits

• Competitive salary and equity packages
• Platinum medical, dental, and vision healthcare plan
• Free life insurance, including long-term and short-term disability
• Unlimited PTO and paid holidays
• Maternity and paternity leave
• 401(k) with 3% company contribution
• WFH benefits including monthly phone stipend and home office perks
• Health FSAs & HSAs