PEO Underwriting & Operations Specialist

PEO Underwriting & Operations Specialist Connectify HR Clive, IA Job Details Full-time 4 days ago Qualifications Workers' compensation law Compliance risk assessment Pricing Sales proposal development Financial model construction Underwriting Financial model development Bachelor's degree in finance Regulatory compliance Bachelor's degree in business Data reporting 3 years Finance Proposal writing Bachelor's degree Continuous improvement Decision making Risk analysis Sales pipeline management Workers' compensation CRM system proficiency Senior level Cross-functional collaboration Business Risk assessment implementation Data-driven decision making Communication skills Technical Proficiency Data manipulation Negotiation Cross-functional communication Excel data analysis

Full Job Description Position Description:

POSITION SUMMARY

The PEO Underwriting & Operations Specialist plays a critical role in evaluating, pricing, and structuring PEO opportunities while ensuring alignment with operational capabilities and service delivery standards. This position partners closely with Sales to assess risk, develop competitive and scalable solutions, and support profitable growth. This role is responsible for analyzing prospective client dataincluding payroll, benefits, workers compensation, and HR-related informationto determine appropriate pricing, terms, and overall deal structure. In addition, the Specialist leverages experience and judgment to incorporate operational considerations into proposals, supporting alignment with internal processes and a smooth transition from sales to operations during implementation.

ESSENTIAL DUTIES AND RESPONSIBILITIES

UNDERWRITING & RISK

ASSESSMENT

Evaluate prospective client submissions, including payroll, employee census, benefits and workers compensation data, to assess overall risk profile. Analyze financial, operational, and compliance risks associated with new business opportunities. Develop pricing, terms, and program structures aligned with company guidelines, risk appetite and profitability targets.

SALES PARTNERSHIP & DEAL STRATEGY

Partner closely with Sales to structure competitive, sustainable proposals that balance prospective client needs with long-term profitability. Provide strategic guidance on deal positioning and solution design. Serve as a subject matter expert in underwriting during prospective client presentations, finalist meetings, and negotiations.

PROPOSAL DEVELOPMENT & DELIVERY

Prepare clear, accurate underwriting summaries and proposal documentation for prospective clients. Collaborate with Benefits, Workers Compensation, Payroll Tax, and HR teams to ensure alignment on pricing, plan design, and service scope. Validate that all proposed solutions are operationally executable and aligned with internal processes and capabilities. Deliver quotes and proposals within established timelines, supporting an efficient and responsive sales cycle.

COMPLIANCE, DOCUMENTATION & REPORTING

Ensure all underwriting decisions comply with company policies, carrier requirements and applicable state and federal regulations. Maintain thorough and accurate documentation of pricing assumptions, risk assessments and approvals. Monitor and report on pipeline activity, pricing outcomes, and underwriting trends to support data-driven decision making. Contribute to continuous improvement of underwriting guidelines, tools, and reporting.

OPERATIONS SUPPORT

Partner with Operations and Implementation teams to ensure a smooth transition from sale to onboarding, minimizing downstream risk and rework. Participate in new client implementations to support successful execution. Provide support for operational initiatives to support scalable growth. Act as a liaison between Sales and Operations to ensure alignment, clear handoffs, and accountability throughout the client lifecycle.

EDUCATION, TRAINING, AND EXPERIENCE

Ownership, accountability, flexibility, and strong critical thinking are essential for success in this role. Bachelors degree in Business, Finance, Risk Management, or related field, or equivalent combination of education and relevant work experience. 3+ years of underwriting and risk analysis experience within a PEO, insurance, employee benefits, or workers compensation environment. Strong working knowledge of PEO services, including payroll, benefits, HR compliance, risk management practices. Demonstrated ability to apply critical thinking skills and sound judgment to analyze financial, claims, and HR data for risk assessment and pricing decisions. Effective communication and presentation skills, with the ability to clearly articulate underwriting rationale to both technical and non-technical stakeholders. Proficiency in Excel and financial modeling skills, with the ability to manipulate and interpret complex datasets; experience with CRM and underwriting platforms preferred. Highly organized and detail-oriented, with the ability to manage multiple priorities, meet deadlines and maintain accuracy in a fast-paced environment. Proven ability to collaborate cross-functionally, balancing sales objectives with operational and risk considerations. Preferred PEO experience preferred

REQUIRED COMPETENCIES

Ownership & Accountability:

Demonstrates reliability and a strong results orientation; takes ownership of outcomes, follows through on commitments, and consistently delivers high-quality work within established deadlines. Analytical Thinking & Attention to

Detail:

Applies strong critical thinking and problem-solving skills to evaluate complex data with a high degree of accuracy, ensuring adherence to processes, timelines, and quality standards.

Business & Financial Acumen:

Understands key financial drivers and PEO economics; uses sound judgment to balance risk, pricing, and profitability considerations.

Collaboration & Relationship Management:

Builds strong, trust-based relationships with Sales and cross-functional partners; operates with a service-oriented mindset while maintaining appropriate risk discipline.

Communication:

Communicates clearly and effectively, both written and verbal; able to translate complex underwriting concepts into practical, actionable insights for diverse audiences.

Organization & Execution:

Effectively manages multiple priorities in a fast-paced environment; maintains structure, prioritization, and attention to deadlines.

Initiative & Continuous Improvement:

Demonstrates a proactive, solutions-oriented approach; identifies opportunities to improve processes, tools, and outcomes.

Professionalism & Positive Mindset:

Brings a positive attitude, flexibility, and adaptability; contributes to a collaborative, respectful, and high-performing team environment.