Remote Technical Underwriter Jobs (NOW HIRING)

Position Summary

The Lead Account Executive serves as a Senior-level Transportation Underwriter responsible for underwriting, managing, and growing a profitable portfolio of transportation business. This role partners closely with brokers to identify new business opportunities, retain high-quality accounts, and deliver profitable underwriting results.
As a key member of Freberg Environmental\'s Transportation practice, the Lead Account Executive evaluates complex transportation risks, develops strong distribution relationships, and provides technical underwriting expertise across new and renewal business. Success in this role requires strong transportation insurance knowledge, sound underwriting judgment, and a consultative approach to broker engagement. This individual will play an important role in supporting the continued growth, profitability, and market presence of the transportation portfolio.
Location: Denver, CO or Chicago, IL preferred; Open to remote for the right candidate if located outside of these areas.

What will your job entail?

Key Responsibilities

Underwriting & Portfolio Management

• Underwrite and manage a large transportation insurance portfolio, balancing growth, profitability, and retention objectives.

• Evaluate and price new and renewal transportation risks in accordance with underwriting guidelines and carrier appetite.

• Analyze submissions, loss experience, financials, operational exposures, and risk characteristics to make sound underwriting decisions.

• Monitor portfolio performance and proactively identify opportunities to improve profitability and premium growth.

• Maintain underwriting discipline while delivering exceptional service to distribution partners.

• Negotiate terms, conditions, pricing, and coverage structures on new and renewal accounts.

Broker & Client Relationship Management

• Develop and maintain strong relationships with wholesale and retail broker partners.

• Serve as a trusted underwriting resource for brokers and key clients.

• Collaborate with brokers to identify new business opportunities and implement growth strategies.

• Respond to underwriting inquiries and resolve escalated account issues in a timely and professional manner.

• Participate in broker meetings, marketing initiatives, and industry events to strengthen market presence.

New Business Development

• Identify, evaluate, and pursue profitable new business opportunities within the transportation marketplace.

• Collaborate with leadership on production goals and business development initiatives.

• Support strategic growth efforts through proactive agency management and pipeline development.

• Review and assess new business submissions for profitability, risk quality, and fit within program appetite.

Team Collaboration & Leadership

• Serve as a senior underwriting resource for team members.

• Mentor and support junior underwriters through technical guidance and knowledge sharing.

• Collaborate with underwriting, operations, claims, and leadership teams to deliver consistent client and broker experiences.

• Contribute to process improvement initiatives that enhance operational efficiency and underwriting effectiveness.

Compliance & Operational Excellence

• Ensure compliance with underwriting guidelines, carrier requirements, regulatory standards, and internal policies.

• Maintain accurate account documentation and underwriting records.

• Monitor production, renewal retention, and portfolio trends to support business planning efforts.

• Utilize underwriting technology platforms and data analytics to support portfolio management decisions.

Required Qualifications

• Bachelor\'s degree in Risk Management, Business, Finance, Insurance, or a related field, or equivalent industry experience.

• 5-7+ years of transportation underwriting experience.

• Experience underwriting commercial transportation risks.

• Proven ability to manage a book of business and achieve profitability objectives.

• Strong broker relationship management and business development skills.

• Experience evaluating complex transportation risk exposures.

• Strong negotiation, analytical, and decision-making abilities.

• Excellent written and verbal communication skills.

• Ability to work independently while collaborating effectively within a team environment.

Preferred Qualifications

• Experience with environmental transportation risks and specialty transportation accounts.

• Commercial Auto underwriting expertise.

• Wholesale broker distribution experience.

• Experience mentoring or providing technical guidance to junior underwriting staff.

• Existing transportation broker relationships.

• Experience managing larger transportation portfolios.

Licenses & Certifications

• Property & Casualty License required or ability to obtain.

• Surplus Lines License preferred.

• Certified Insurance Professional (CIP), CPCU, ARM, AU, or similar industry designations are highly desirable.

Training & Development

Freberg Environmental is committed to investing in the success of new team members. This role includes an initial onboarding and training program in Denver, where the successful candidate will spend dedicated time working alongside senior transportation underwriters to gain product knowledge, underwriting expertise, and organizational insight.

Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization. Our vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression, sexual orientation, and many other characteristics bring together varied perspectives and add value to the service we provide our clients, trading partners, and communities. This policy extends to all aspects of our employment practices, including but not limited to, recruiting, hiring, discipline, firing, promoting, transferring, compensation, benefits, training, leaves of absence, and other terms, conditions, and benefits of employment.

How We Support Our Teammates 

Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them — and their family members — achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more.

The target salary range for this position is $100,000.00 - $125,000.00 annually.

The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards, visit our website https://benefits.ryansg.com/. 

We provide individuals with disabilities reasonable accommodations to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation at HR@Ryansg.com 

The above is intended to describe this job\'s general requirements. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management\'s right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.