Director of Sales – Property & Casualty Insurance

This is a fully remote position, open to applicants in Illinois, +2 more states.

📋 Description

• Develop and implement a comprehensive sales strategy in collaboration with the Vice President of Sales, as well as the Product, Market Planning, and Strategy teams.

• Convert strategic objectives into actionable plans that drive both short- and long-term revenue growth.

• Personally spearhead sales initiatives for high-value strategic accounts, focusing on opportunity development, proposal strategy, and client engagement.

• Exhibit sales excellence in managing client relationships and executing deals.

• Attract, nurture, and retain top-tier sales talent.

• Offer structured coaching, feedback, and career development through regular one-on-one meetings, team sessions, and customized growth plans.

• Lead the team in identifying and developing new business opportunities that align with client needs and market trends.

• Maintain a robust and well-qualified pipeline to support revenue objectives.

• Collaborate with Legal, Product Development, and Marketing to synchronize go-to-market strategies and client solutions.

• Provide market insights and client feedback to guide product innovation and strategic planning.

• Report directly to the Vice President of Sales.

⛳️ Requirements

• Over 10 years of proven sales experience.

• A minimum of 5 years in a sales leadership or management capacity.

• Bachelor's degree in Business, Marketing, Finance, Insurance, or a related discipline; an advanced degree is preferred.

• Demonstrated success in selling data, analytics, SaaS, fraud, risk, claims, underwriting, or customer acquisition solutions to Property & Casualty insurance carriers.

• Extensive knowledge of the Property & Casualty insurance sector, including underwriting, claims, risk management, carrier operations, distribution channels, and regulatory environments.

• Proven ability to lead high-performing sales teams, surpass revenue goals, and foster growth through strategic account planning and complex enterprise sales.

• Strong consultative selling skills.

• A track record of establishing executive-level relationships and influencing C-suite, business, and operational stakeholders.

• Familiarity with pipeline forecasting, territory management, and CRM-driven sales execution.

• Experience in coaching talent and collaborating across functions.

• An existing network of senior relationships within the Property & Casualty Insurance industry is preferred.

🏝️ Benefits

• Day-one eligibility for medical, dental, and vision coverage.

• Options for supplemental plans.

• Coverage for spouses, domestic partners, and eligible dependents on select plans.

• Health Savings Account (HSA) and Flexible Spending Account (FSA) options.

• Company-paid basic life and AD&D insurance.

• Optional voluntary life and AD&D insurance.

• Short- and long-term disability coverage.

• Legal plan access.

• Pet insurance options.

• Travel accident coverage.

• Adoption assistance provided.

• Fertility planning coverage available.

• Caregiver support services.

• Dependent Care FSA with the possibility of employer matching.

• Complimentary Care@Work membership.

• Up to 12 weeks of paid parental leave with eligibility for a gradual return.

• 401(k) plan with employer matching.

• Employee Stock Purchase Plan (ESPP) available.

• Financial wellness resources offered.

• Career coaching services.

• Optional long-term care insurance.

• Tuition reimbursement program.

• Flexible time off for exempt employees or paid time off for non-exempt employees.

• Up to 12 paid holidays annually.

• Commuter benefits provided.

• Employee discounts available.

• Charitable gift matching program.

• Paid volunteer time off.

• Opportunities for corporate volunteer events.

• 24/7 support including professional therapy, coaching, emotional well-being programs, guided meditation, and wellness resources.