Sales Director

Summary

Join Ledger Investing, a Y Combinator-backed Insurtech startup, as the Director of Sales. You will build, lead, and scale a high-performing software sales organization, blending strategic planning with execution. Lead efforts in net new customer acquisition, expanding existing accounts, and driving strong ARR growth. This role requires exceeding product revenue targets, partnering cross-functionally, and leading demand generation. You will guide complex deal cycles, represent Ledger at industry events, and maintain sales performance KPIs. The ideal candidate possesses extensive B2B Insurtech sales leadership experience and a proven track record of exceeding sales quotas.

Requirements

• 10+ years of B2B insuretech sales leadership experience in SaaS products targeting the traditional reinsurance market
• Proven track record of exceeding sales quotas and scaling revenue-generating teams in high-growth start-up environments
• Strong background in enterprise software sales, including strategic deal management and executive-level selling
• Deep understanding of pipeline generation strategies, sales operations, and scalable sales methodologies
• Ability to lead through influence in a matrixed organization, with excellent cross-functional collaboration skills
• Strong business acumen, with an ability to develop and implement territory plans, financial models, and performance dashboards
• Reviewing and providing guidance on complex proposals, RFPs, and strategic sales engagements
• Capable of thriving in a remote environment and traveling as needed for client or internal meetings
• Bachelor’s degree in Business, Finance, Marketing or other related discipline

Responsibilities

• Build and execute a scalable sales strategy tailored to emerging markets, enterprise clients, and industry-specific segments
• Own and exceed product revenue targets for our software and AI-powered solutions
• Partner cross-functionally with Product GMs, Finance, Marketing, Operations, and others to align GTM strategy with customer needs and market trends
• Lead demand generation efforts and pipeline development initiatives, leveraging marketing campaigns and strategic partnerships
• Maintain and improve forecasting accuracy, pipeline health, and sales performance KPIs and advanced sales analytics
• Guide complex deal cycles from discovery to close, offering commercial guidance and thought leadership to align with client objectives
• Represent the company at industry conferences and customer meetings, serving as a key spokesperson and evangelist for our products

Preferred Qualifications

• Domain knowledge in financial services, insurance, risk, compliance, or emerging technologies (e.g., AI) is highly desirable
• Experience building high-performing teams, with a focus on coaching, career progression, and talent development is preferred