Pharmacists Mutual Insurance Group has an opening for a Middle Market Underwriting Leader. This role will provide leadership and oversight for the Middle Market underwriting team. Leads and oversees Middle Market underwriting, guiding a team to effectively evaluate, price, and manage complex risks while modeling strong underwriting judgment. Drives development to remain competitive and monitors performance and claims trends to inform actionable strategies that support sustainable growth and portfolio stability. Accountable for P&L results, manages key metrics, and implements corrective actions as needed. Fosters a culture of accountability and excellence through coaching, audits, and governance of underwriting authority. Collaborates cross-functionally with Distribution, Claims, Pricing, and Risk Management, while building strategic partnerships to drive profitable growth. Contributes to identifying emerging risks and opportunities, balancing strategic vision with operational leadership. May lead other underwriting segments, such as Programs and/or Excess and Surplus Lines.
Middle Market Underwriting Director
- Leads the Middle Market underwriting portfolio, driving disciplined growth, execution, and sustained performance through strategic portfolio management.
- Directs the Middle Market strategy, translating company objectives into actionable plans for the portfolio.
- Oversees and optimizes the operational performance of the Middle Market portfolio, driving alignment with profitability, risk appetite, and regulatory requirements while identifying and implementing improvements to enhance portfolio outcomes.
- Designs and drives training programs to enhance team capabilities, aligning development efforts with performance goals and business needs.
Assistant Vice President, Middle Market Underwriting
- Leads the strategic direction of portfolio Middle Market operations, driving sustained profitability, strengthening risk discipline, and advancing enterprise-wide improvements aligned to regulatory and business objectives.
- In partnership with the VP, Underwriting, shapes and executes the Middle Market strategy, translating company objectives into actionable plans for the portfolio.
- Oversees the strategic governance and operational performance of the Middle Market portfolio, ensuring alignment with underwriting profitability, risk appetite, and regulatory standards.
- Sets the strategic vision for training and development, elevating organizational capabilities and shaping performance outcomes across the portfolio.
Essential Functions
Essential functions may include, but are not limited to the following:
- Understands the Middle Market marketplace and agent and customer expectations.
- Participates in Guidelines Leadership Team to develop underwriting guidelines.
- Models effective leadership, motivating the team to achieve shared goals while reinforcing professionalism and accountability.
- Recruits, trains, coaches, and develops underwriting staff.
- Conducts goal-setting activities and individual performance reviews.
- Manages department workflow to ensure proper controls and procedures are documented, maintained, and followed.
- Establishes workload and territory assignments and monitors productivity.
- Coordinates regular and systematic quality control audits for each assigned staff member.
- Supports VP, Underwriting with participation in Underwriting and/or cross-functional projects and strategic initiatives.
- Ensures compliance with underwriting guidelines, authority levels, company policies, and regulatory requirements.
- Maintains expenses at or below budget for assigned team.
- Drives innovation and capability enhancements in portfolio management, AI utilization, underwriting processes, and performance metrics by identifying opportunities, developing recommendations, and leading implementation.
- Uses data and analytics to inform decisions, identify trends, and improve underwriting practices.
- Stays informed on industry trends, emerging risks, and competitor offerings to enhance underwriting effectiveness.
- May underwrite complex Middle Market business.
Knowledge, Skills and Abilities
- Thorough knowledge of principles and practices of commercial insurance underwriting.
- Expert knowledge of commercial policy language.
- Expertise in building and maintaining relationships with distribution partners and individual account negotiations.
- Ability to develop, build, and lead highly-effective teams.
- Demonstrates the skills needed to drive financial performance of the Middle Market portfolio.
- Demonstrated experience in influencing and leading teams of underwriters.
- Knowledge of employee management principles including hiring, supervision, training, retention, and performance evaluation.
- Ability to develop a plan and execute it.
- Ability to make timely decisions independently, using personal knowledge and discretion.
- Ability to organize and prioritize work.
- Strong interpersonal skills.
- Deep problem-solving skills.
- Work independently and use initiative.
- Possess critical thinking skills and sound judgment in underwriting decisions.
- Determine when and how to escalate concerns.
- Ability to understand and apply laws, rules and regulations.
- Ability to deal with confidential information.
- Establish and maintain effective working relationships with those contacted in the course of work.
- Interact externally and internally with professionalism and confidence.
- Possess a high level of executive functioning skills to organize and prioritize work.
- Meet finite deadlines and deal with pressure situations.
- Maintain records; prepare reports/correspondence related to the work.
- Read, interpret and input data efficiently and accurately.
- Communicate and work effectively with others (oral and written).
- Follow oral and written directions.
- Correct English usage, spelling, grammar, vocabulary and punctuation.
- Knowledge of management information and business systems such as Word, Excel, PowerPoint etc.
- Utilize computer and related software effectively.
Experience and Education Qualifications
Middle Market Underwriting Director
- High School Diploma or equivalent and 20 year of related experience with at least 5 in leadership; or
- Associate’s Degree or equivalent and 15 years of related experience with at least 3 in leadership; and
- One of the following industry related certifications: Chartered Property Casualty Underwriter (CPCU), or Certified Insurance Counselor (CIC)
OR
- Bachelor’s Degree and 8 years of related experience with at least 2 in leadership; or
- Master’s Degree and 6 years of related experience with at least 1 in leadership
Assistant Vice President, Middle Market Underwriting
- Bachelor’s Degree and 10 years of related experience with at least 5 years in leadership; or
- Master’s Degree and 8 years of related experience with at least 3 years in leadership
Preferred Qualifications
- Successful completion of CPCU or AU designation
Work Environment
- Hybrid or fully remote work environment designed to provide flexibility, autonomy, and productivity while working from another location
- Primary work environment is in a climate-controlled office setting
- Work may involve travel to attend meetings at other locations
Benefits
In addition to a competitive salary, eligible employees may receive an annual discretionary bonus and access to our benefits package, including:
- Health, Dental, Vision & Life coverage
- 401(k) with Company Match
- Paid Time Off
- 8 Paid Holidays
- Volunteer Time Off
- Paid Parental Leave
- Hybrid/Remote Work Options
- Employee Assistance Program
- Tuition Reimbursement
Pharmacists Mutual Insurance Group is an Equal Opportunity Employer.
Skills Required
- Thorough knowledge of principles and practices of commercial insurance underwriting.
- Expert knowledge of commercial policy language.
- Experience building and maintaining relationships with distribution partners and account negotiation.
- Demonstrated experience developing, building, and leading underwriting teams.
- Proven ability to drive financial performance and manage P&L for a Middle Market portfolio.
- Experience influencing and leading teams of underwriters; coaching and performance management.
- Knowledge of employee management principles including hiring, supervision, training, retention, and performance evaluation.
- Ability to make timely independent decisions using judgment, organize and prioritize work, and meet deadlines.
- Strong interpersonal, communication (oral and written), critical thinking, and problem-solving skills.
- Ability to understand and apply laws, rules, regulations, and handle confidential information.
- Experience using data and analytics to inform underwriting decisions and identify trends.
- Familiarity with management information and business systems such as Word, Excel, PowerPoint.
- May underwrite complex Middle Market business.
- High School Diploma or equivalent and 20 years related experience with at least 5 years in leadership (alternate education/experience tracks listed in job).
- Bachelor's Degree and 8 years related experience with at least 2 years in leadership (other degree/experience permutations allowed).
- For Director track: one of the following industry certifications: CPCU or CIC.
- Preferred: Successful completion of CPCU or AU designation.
What We Do
Pharmacists Mutual Insurance Group (PMIG) is a family of insurance businesses dedicated to delivering expert service and comprehensive risk management solutions. By combining deep industry knowledge with sound financial strategies, the company aims to help its clients thrive. Their mission is to provide protection and peace of mind through sustainable, economically responsible practices, creating value for policyholders and the communities they serve throughout the United States.
