Optimyl Benefits

Role Description The Underwriting Director, Mid-Market, is responsible for profitably underwriting stop-loss insurance for new and renewing groups across the 50-300 life space. This is a fully remote, senior individual contributor role with management potential. What you’ll do - Underwrite new business and renewals for experience-rated groups in the 50-300 life space across level-funded and traditional stop loss products. - Build and maintain strong working relationships with sales, actuarial, and clinical teams. - Set clear expectations with sales on turnaround times and consistently deliver on them. - Develop deep familiarity with Optimyl’s products and platform, and contribute feedback that shapes future iterations. - Mentor existing claims-based underwriters. Qualifications - 10+ years underwriting medical stop loss, with a focus on the 50-300 group size. - At least 5 years at an MGU or pure-play stop loss carrier; majority of career at a respected MGU preferred. - Comfort working in a lean, fast-moving environment without heavy oversight. - Familiarity with stop loss manuals and current underwriting tools, including AI-assisted platforms. Benefits - Competitive compensation - Comprehensive health coverage (medical, dental, vision) - Employer-paid life insurance and disability coverage - 401(k) retirement plan with employer match - Generous paid time off and company holidays We support growth through hands-on learning, exposure to new challenges, and opportunities to expand responsibilities as the company evolves.

Role Description The Administrative Assistant will support the sales team in servicing independent brokers marketing the Company’s products, reporting to the Director of Sales Operations. The role will facilitate critical processes throughout the entire new business flow on behalf of the Regional Sales Directors. Note - this is a part-time position, 20-25 hours per week. Responsibilities - Data entry of quoting and underwriting information - Efficiently deliver requested quotes accurately and by agreed-upon deadlines - Perform in-depth reviews of paperwork to ensure documentation for prospective clients and work with sales staff to obtain the necessary information - Support a set of Sales Directors in a team environment - Other duties as assigned Qualifications - Proficient in Word, Excel, and PowerPoint - Self-motivated – ability to work successfully without ongoing supervision - Strong time management and organizational skills - Above-average attention to detail - Strong customer service skills - Strong communication and organizational skills - High School Graduate or GED - Fluent in English - Exposure to health insurance is a plus

About the role We are seeking a highly capable, self-directed Actuary to support and enhance our day-to-day actuarial operations. This role is designed for an individual who thrives on ownership and autonomy and is comfortable independently managing core actuarial processes while partnering closely with leadership on strategy, analysis, and decision support. This position will play a critical role in maintaining and evolving our rating manual, renewal process, and related pricing and analytical workflows, while also supporting ad-hoc analysis and reporting needs across the organization. Key Responsibilities Pricing & Rating - Own and maintain the company’s rating manual, including documentation, assumptions, updates, and ongoing enhancements - Perform pricing analysis for new and renewing business, ensuring consistency with actuarial standards and internal guidelines - Identify opportunities to improve rating accuracy, efficiency, and automation Renewals & Underwriting Support - Lead actuarial components of the renewal process, including experience analysis and rate recommendations - Partner with underwriting, sales, and leadership to support renewal strategy and decision-making Analysis & Reporting - Conduct ad-hoc actuarial and financial analyses to support business questions and strategic initiatives - Develop and maintain recurring actuarial reports, dashboards, and summaries for leadership and internal stakeholders - Translate complex actuarial results into clear, business-focused narratives Process Ownership & Improvement - Independently manage actuarial workflows and timelines for assigned processes - Identify inefficiencies and drive continuous improvement through better methodology, tooling, or automation - Ensure actuarial work complies with applicable standards of practice and internal controls Qualifications Required - ASA or FSA (or strong progress toward credentials with relevant experience) - 3-6 years of actuarial experience - Strong experience with actuarial pricing models and experience studies - High level of comfort working independently and owning end-to-end processes - Excellent analytical, problem-solving, and organizational skills - Strong written and verbal communication skills, with the ability to explain results to non-actuarial audiences Preferred - Experience in health insurance, employee benefits, or related lines of business - Advanced Excel skills; experience with SQL, Python, R, or similar analytical tools is a plus - Experience in improving or redesigning actuarial processes or models - Comfort working in a fast-moving, evolving environment Why Work at Optimyl? At Optimyl Benefits, we’re focused on simplifying healthcare for small employers and building a workplace where people can do meaningful work and continue to grow. Benefits include: - Competitive compensation - Comprehensive health coverage (medical, dental, vision) - Employer-paid life insurance and disability coverage - 401(k) retirement plan with employer match - Generous paid time off and company holidays We support growth through hands-on learning, exposure to new challenges, and opportunities to expand responsibilities as the company evolves.

About the Role The Underwriting Analyst is responsible for managing the RFP workflow, maintaining accurate electronic underwriting files, and supporting the end-to-end processing of new and sold business. The role serves as a key point of contact for Sales, brokers, and external partners, and works closely with Underwriters to prepare eligibility and medical data for risk assessment and pricing. This is a fully remote position. What you'll do: - Manage the RFP workflow by compiling information and reports needed to underwrite quotes. - Load eligibility and medical information into Optimyl's application software in preparation for Underwriter risk assessment and pricing. - Process and maintain orderly electronic underwriting files, ensuring accuracy and completeness. - Serve as a professional and responsive point of contact for Sales, external Optimyl partners, brokers, and suppliers via phone and email. - Prepare sold documentation from proprietary database and route to broker or Producer for client review and signature. - Set up and maintain all sold case files. - Update and maintain the Outstanding Documents Log on a daily basis. - Follow up and collect all sold case documentation from TPAs and brokers, requiring continuous client engagement. - Coordinate communication between clients, TPAs, brokers, and internal Optimyl departments. - Review and save completed sold case files in preparation for policy issuance. - Process all non-renewals and terminations, and notify all required parties accordingly. - Assist with Sold Business Policy support as delegated. - Adhere to company guidelines, policies, and procedures at all times. - Use various systems, tools, and resources to accurately complete and track assigned work. - Perform other duties as assigned as the business continues to develop. Qualifications: Minimum Qualifications - Minimum of 2 years of experience as an Underwriting Analyst or Underwriting Assistant. - Minimum of 2 years of experience working in health insurance policy. Preferred Qualifications - Experience with Small Group Health Insurance participation, group eligibility, and related processes. - Demonstrated ability to work independently while effectively coordinating with cross-functional teams and external partners. - Strong organizational skills with a track record of managing multiple priorities and deadlines in a fast-paced environment. - Proficiency with underwriting systems, document management platforms, and Microsoft Office Suite. Compensation: Base Salary + Bonus Posted range is base salary Why Work at Optimyl? At Optimyl Benefits, we’re focused on simplifying healthcare for small employers and building a workplace where people can do meaningful work and continue to grow. Benefits include: - Competitive compensation - Comprehensive health coverage (medical, dental, vision) - Employer-paid life insurance and disability coverage - 401(k) retirement plan with employer match - Generous paid time off and company holidays We support growth through hands-on learning, exposure to new challenges, and opportunities to expand responsibilities as the company evolves.

• Contributes to the development of underwriting guidelines for clinical underwriting risk management • Guides underwriting strategy in collaboration with VP of Small Group Underwriting and internal stakeholders for targeted profitable risk selection. • Provides expert clinical consulting on underwriting risk initiatives in collaboration with Actuarial Partners, Sales, IT, Underwriters, and Compliance. • Managers direct reports and relationships with key stakeholders as delegated with mentorship and clinical consultations as needed. • Help formulate and execute strategy of how to hit or exceed key target metrics such as loss ratio, underwriting expense, close ratio, and underwriting turnaround times. • Develop and manage relationships with internal business partners, including actuarial, sales, IT, and compliance • Responsible for a book of business of renewing accounts and writing new business at profitable levels to help Optimyl achieve overall business targets or assigned volume of new applications or RFPs. • Uses various systems, tools, and resources to obtain necessary data and accurately complete and track assigned work. • Evaluate the eligibility of groups and the participating employees at the time of a new business quote; evaluate the eligibility of mid-year participating employee additions. • Calculate rates, evaluate different financial arrangements (e.g., networks, plan designs, carveouts), interpret pricing policy, and adapt to unusual situations. • Identifies questionable claim patterns of renewal clients and evaluates competitors’ claims experience for prospective clients, and develops recommendations to account for these situations. • Applies corporate risk management policies and adjusts for unusual situations that may not have been considered in the standard pricing formula. Identifies when clients do not comply with corporate risk management policies, disclosure rules, or conditions/criteria for enrollment. • Enforce Optimyl's business rules (participation, product availability, etc.) Recommends appropriate adaptation of pricing within the appropriate policy or guideline to accommodate each client-specific situation. • Analyzes individual member risk and aggregate to the total group. Supports other internal initiatives which may include but is not limited to underwriting policies and procedures, training, fraud detection, corporate compliance, and product development efforts. Completes renewals, prospective quotes, and review of lower-level analyst (Underwriting Analyst) work in accordance with production and timeliness standards. • Adapts to changing priorities as quotes come in from different markets and adapt to new priorities and requirements. • Communicates recommendations of policy adaptation to accommodate client-specific situations or changes to overall policy supported by a clear rationale or management principles. • Serve as a clinical SME to sales and account management. Influences Sales team and external audiences toward appropriate risk solutions. Influences Sales team toward the appropriate pricing and structure of each quote. When necessary, influences other market partners, e.g. brokers. • Guides, assists, and provides technical assistance to lower-level analysts. As assigned, assume primary support for maintenance of departmental tools and processes. As assigned, represent departmental perspectives and needs on system development and process improvement teams.

The Sr. Medical Underwriting Nurse Manager is responsible for leading clinical risk strategy and underwriting excellence within the Small Group market, reporting to the VP of Small Group Underwriting. This role combines advanced clinical expertise with underwriting leadership to drive profitable risk selection, guide pricing strategy, and support renewal and new business growth. Contributes to the development of underwriting guidelines for clinical underwriting risk management Guides underwriting strategy in collaboration with VP of Small Group Underwriting and internal stakeholders for targeted profitable risk selection Provides expert clinical consulting on underwriting risk initiatives in collaboration with Actuarial Partners, Sales, IT, Underwriters, and Compliance Manages direct reports and relationships with key stakeholders as delegated with mentorship and clinical consultations as needed Helps formulate and execute strategy of how to hit or exceed key target metrics such as loss ratio, underwriting expense, close ratio, and underwriting turnaround times Develops and manages relationships with internal business partners, including actuarial, sales, IT, and compliance Responsible for a book of business of renewing accounts and writing new business at profitable levels Uses various systems, tools, and resources to obtain necessary data and accurately complete and track assigned work Evaluates the eligibility of groups and the participating employees at the time of a new business quote Calculates rates, evaluates different financial arrangements, interprets pricing policy, and adapts to unusual situations Identifies questionable claim patterns of renewal clients and evaluates competitors’ claims experience for prospective clients Applies corporate risk management policies and adjusts for unusual situations Enforces Optimyl's business rules (participation, product availability, etc.) Analyzes individual member risk and aggregates to the total group Supports other internal initiatives including underwriting policies and procedures, training, fraud detection, corporate compliance, and product development efforts Completes renewals, prospective quotes, and review of lower-level analyst work in accordance with production and timeliness standards Adapts to changing priorities as quotes come in from different markets Communicates recommendations of policy adaptation to accommodate client-specific situations Serves as a clinical SME to sales and account management Guides, assists, and provides technical assistance to lower-level analysts

• Own and maintain the company’s rating manual, including documentation, assumptions, updates, and ongoing enhancements • Perform pricing analysis for new and renewing business, ensuring consistency with actuarial standards and internal guidelines • Identify opportunities to improve rating accuracy, efficiency, and automation • Lead actuarial components of the renewal process, including experience analysis and rate recommendations • Partner with underwriting, sales, and leadership to support renewal strategy and decision-making • Conduct ad-hoc actuarial and financial analyses to support business questions and strategic initiatives • Develop and maintain recurring actuarial reports, dashboards, and summaries for leadership and internal stakeholders • Translate complex actuarial results into clear, business-focused narratives • Independently manage actuarial workflows and timelines for assigned processes • Identify inefficiencies and drive continuous improvement through better methodology, tooling, or automation • Ensure actuarial work complies with applicable standards of practice and internal controls

• Develop and maintain features across .NET and Salesforce codebases • Participate in Agile ceremonies including sprint planning, grooming, and standups • Collaborate with business stakeholders to define acceptance criteria • Work with other developers through code reviews and pair programming • Build and maintain REST APIs and data processing workflows • Contribute to integrations with internal systems and external partners • Participate in code reviews and help maintain code quality standards • Contribute to architectural discussions and advocate for clean, maintainable code • Follow security best practices when working with sensitive healthcare data

• Manage ongoing service relationships with brokers and employer clients in the small and mid-sized employer market • Support retention and renewal efforts through proactive, high-quality client service • Serve as a primary point of contact for service-related inquiries and issue resolution • Use internal systems and tools (CRM, reporting, surveys) to track performance and support continuous improvement • Coordinate with third-party vendors to ensure service delivery meets Optimyl standards • Partner cross-functionally with Sales, Underwriting, and Operations teams • Gather and share broker and client feedback to inform product, pricing, technology, and marketing decisions • Maintain working knowledge of agent licensure requirements and commission processes