Job Description: Director of Sales

About Ledger Investing

Ledger is a Y Combinator-backed Insurtech startup transforming how insurance risk is financed. Ledger is building a marketplace that enables re/insurers to transfer risk to capital markets investors – we have originated over $2 billion of premium volume to institutional investors. Insurance securitization is on the path to becoming a $100 billion market but has been limited by opacity and complexity. Ledger is expanding this market by building a seamless data platform that powers the marketplace, as well as reports and analytics that insurers and investors need to transact. Our $75 million Series B investment funding has successfully set us up for long-term growth.

About the Role

As the Director of Sales, you will be responsible for building, leading, and scaling a high-performing software sales organization. This role blends strategic planning with execution. You’ll lead all efforts associated with net new customer acquisition, expanding relationships with existing accounts, and delivering strong ARR growth in a rapidly evolving environment.

Key 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

Key Background 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
• Capable of 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
• 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
• Bachelor’s degree in Business, Finance, Marketing or other related discipline

For US based positions:

Ledger Investing is an equal opportunity employer and complies with all applicable federal, state, and local fair employment practices laws. We strictly prohibit and do not tolerate discrimination against employees, applicants, or any other covered persons because of race, color, religion, creed, national origin or ancestry, ethnicity, sex, gender (including gender nonconformity and status as a transgender or transsexual individual), sexual orientation, marital status, age, physical or mental disability, citizenship, past, current or prospective service in the uniformed services, predisposing genetic characteristic, domestic violence victim status, arrest records, or any other characteristic protected under applicable federal laws.