Skyward Specialty Insurance

Senior Underwriter, Transactional Surety

United States full-time Senior $100,000 - $125,000
full-time Senior level Technology & IT Salary listed Curated
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About the role

Position Summary
The Transactional Commercial Surety Underwriter is responsible for underwriting, pricing, and managing a portfolio of transactional surety business across a broad range of bond types nationwide. This role partners closely with agents and brokers to drive new business growth, maintain profitability, and deliver exceptional service standards in a fast-paced, high-volume environment.

Key Responsibilities
Underwriting & Risk Assessment

Evaluate and underwrite transactional commercial surety submissions, including but not limited to motor vehicle dealer (MVD), license & permit, subdivision, court, contract-related transactional, mortgage broker, and specialty bonds.

Analyze financial statements, credit reports, and supporting documentation to assess risk and determine appropriate terms, conditions, and pricing.

Apply underwriting authority to approve, decline, or modify submissions in alignment with company guidelines and risk appetite.

Ensure compliance with internal underwriting standards, regulatory requirements, and state-specific bond obligations.

Production & Portfolio Management

Manage a high volume of transactional submissions while maintaining strong turnaround times and service levels.

Monitor and manage a book of business to ensure profitability, retention, and appropriate risk diversification.

Identify opportunities for cross-selling and account expansion within existing agency relationships.

Agent/Broker Relationship Management

Build and maintain strong relationships with agency partners to drive submission flow and grow market share.

Communicate underwriting decisions effectively, including providing clear rationale and alternative solutions when appropriate.

Negotiate terms, pricing, and commission structures to remain competitive while maintaining underwriting discipline.

Act as a market-facing representative to support agency growth and retention initiatives.

Business Development

Support new business development efforts by identifying target agencies and producers within the transactional surety space.

Participate in agency visits, industry events, and networking opportunities to strengthen relationships and increase brand presence.

Collaborate with leadership to execute strategic growth initiatives within the transactional surety segment.

Operational Excellence

Maintain accurate documentation and records within underwriting systems.

Ensure timely issuance of bonds, endorsements, renewals, and cancellations.

Partner with internal teams (claims, legal, compliance, operations) as needed to support business objectives.

Qualifications & Experience

2+ years of experience in commercial surety underwriting, with a focus on transactional business required

Established relationships within the surety agency/broker community required

Proven experience underwriting a broad range of bond types (e.g., MVD, subdivision, license & permit, court, contractor-related transactional, specialty bonds)

Strong understanding of credit analysis, risk assessment, and financial statement review

Demonstrated ability to manage high submission volume while maintaining underwriting discipline

Experience negotiating terms, pricing, and commissions in a competitive marketplace

Knowledge of state-specific bonding requirements and regulatory environment preferred

Skills & Competencies

Strong analytical and decision-making skills

Excellent communication and negotiation abilities

Relationship-driven, with a strong customer-service orientation

Ability to work independently in a fast-paced environment

High attention to detail and organizational skills

Results-oriented mindset with a focus on growth and profitability

Compensation & Benefits
The applicable base salary for this opportunity is $100,000 - $125,000. The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. In addition to the base salary, this opportunity may be eligible for performance-based incentives.​ We are excited to offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401k savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance.
Originally posted on Himalayas

Interview prep

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Senior
Technology & IT Business Development Operations Writing Senior Underwriter Senior level

Likely questions

  1. Tell us about work you have done that is close to the Senior Underwriter, Transactional Surety role.
  2. How would you approach your first 30 days at Skyward Specialty Insurance?
  3. Which of Business Development, Operations and Writing have you used recently, and what did it help you achieve?
  4. How have you led people, improved a process, or made a hard decision in a previous role?
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Business Development, Operations and Writing.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Senior Underwriter, Transactional Surety role because I can bring practical experience in Business Development, Operations and Writing, learn the team quickly, and contribute to the outcomes Skyward Specialty Insurance needs from this hire.

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