Deputy Chief National Commercial Underwriting Counsel

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Deputy Chief National Commercial Underwriting Counsel in Massachusetts.

In this role, you will lead and oversee commercial underwriting operations while providing expert guidance on complex real estate and title insurance matters across multiple legal jurisdictions. You will manage a geographically dispersed team, ensuring that agents and internal stakeholders receive timely, accurate, and strategic support for their underwriting and closing activities. This role combines leadership, risk assessment, and business development, including customer engagement, educational initiatives, and talent management.

You will collaborate closely with senior executives, assist in shaping policies, and help drive consistent and high-quality underwriting practices. Ideal candidates thrive in remote, flexible environments and have a strong legal and industry background in real estate and title insurance. This is an opportunity to influence commercial underwriting strategy at a national level and develop high‑performing teams that support long‑term business growth.

• Provide expert underwriting guidance and risk assessment on real estate closings and title insurance matters across multiple jurisdictions
• Build, manage, and mentor a geographically dispersed commercial underwriting team
• Establish and maintain strong relationships with new and existing customers, supporting business development efforts
• Deliver educational presentations via live seminars, webinars, and recorded sessions for customers and internal teams
• Support executive leadership, including responding to urgent requests from Chief Underwriting Counsel and other senior executives
• Assist underwriters in evaluating complex commercial transactions and providing risk‑based recommendations
• Oversee human resource coordination for the commercial department, including training, performance reviews, goal setting, and disciplinary actions

• Juris Doctorate (JD) degree from an ABA‑accredited law school
• Licensed attorney in good standing with a state bar association
• Minimum 10 years of experience in title insurance or real estate, including at least 3 years managing teams
• Strong written and verbal communication skills, with the ability to craft coverage language that balances risk management and business needs
• Experience delivering live, web‑based, or recorded educational content
• Proven ability to assess complex transactions and provide clear, actionable guidance
• Comfortable working remotely with occasional travel

• Remote work flexibility with a supportive home‑office environment
• Comprehensive benefits package including medical, dental, and vision coverage
• 401(k) retirement plan and tuition reimbursement
• Paid time off, sick leave, life and disability insurance
• Inclusive and collaborative work culture focused on career development and employee growth
• Opportunities to lead and develop high‑performing teams across multiple regions

We use an AI‑powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top‑fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre‑contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.