This is a full-time, remote position based anywhere in the continental United States.

Are you a strategic compliance leader who thrives on building programs that balance regulatory precision with business agility? As MASA’s Compliance Director, you’ll take the lead in shaping, implementing, and managing a robust compliance program that safeguards our integrity and drives our continued success. You’ll partner with senior leaders across the organization to ensure MASA meets contractual, legal, and regulatory standards—while fostering a culture of accountability, trust, and ethical excellence. This is your opportunity to make a lasting impact at a mission-driven company in rapid growth mode.

About MASA

MASA has been a leader in emergency medical transportation insurance since 1974. We’re not just a company – we’re a close-knit team dedicated to “Protecting families with compassion when others don’t.” Our professional yet friendly company culture fosters collaboration, innovation, and a clear mission that resonates through every role as we support our expanding base of 2+ million members across the United States. Learn more at https://www.masaaccess.com.

What You Will Do

Develop, project manage, and oversee the corporate compliance framework, including policies and procedures governing insurance operations, marketing, and general corporate compliance—both domestically and internationally.
Ensure compliance with applicable laws and regulatory requirements, maintaining the organization’s strong commitment to compliance.
Partner with Insurance Operations to ensure all marketing and insurance activities meet state-specific regulatory requirements across all media formats.
Create and maintain policies and standard operating procedures supporting corporate and legal compliance programs.
Design and deliver compliance training covering insurance operations, corporate governance, OFAC, FCPA, conflicts of interest, intellectual property, HIPAA, data protection, cybersecurity, and related areas.
Provide proactive compliance guidance and counsel to company leadership and management teams.
Monitor operational processes through audits, education, and corrective action plans; report findings and recommend improvements.
Manage investigatory processes, documentation, and resolution of compliance matters, ensuring accurate tracking and reporting.
Collaborate with executive management on compliance strategy and planning initiatives.
Partner with cross-functional stakeholders to review and approve marketing materials for regulatory compliance.
Stay current with changes in laws and regulations; communicate required policy or procedural updates.
Promote visibility and accessibility of the Compliance Office to encourage open communication and issue resolution.
Continuously monitor and enhance the effectiveness of the Compliance Program.
Manage outside counsel engagements for specialized legal or compliance matters.
Perform additional legal and compliance duties as assigned.

What You Bring

3–7 years of experience as a compliance professional or legal operations manager within insurance (A&H, P&C, or Travel) or membership organizations.
Experience managing compliance or legal staff.
Licensed to practice law in Florida (preferred) or in another U.S. jurisdiction with authorization to practice in-house in Florida.
Proven success in building and implementing corporate compliance programs from the ground up.
Strong understanding of operationalizing compliance initiatives while supporting business performance.
Practical, common-sense approach to risk management and compliance problem-solving.
Ability to influence leaders and collaborate effectively within a small, fast-paced legal team.

What We Will Provide You

Competitive base salary, bonuses, and comprehensive employee benefits programs, including medical, dental, and vision insurance with highly rated carriers; a 401(k) program with a company match; paid time off; company-paid short-term disability, long-term disability, and basic life insurance; and a free MASA membership.
A professional and friendly company culture that supports a clear mission: “Protecting families with compassion when others don’t.”
An opportunity to unleash your expertise and create a lasting impact on our journey of growth and success!

Why We Think You’ll Love This Opportunity

You’ll have the opportunity to build and refine a compliance function that directly shapes MASA’s continued growth and integrity.
You’ll collaborate closely with experienced executives who value practical, business-aligned compliance leadership.
You’ll work in a supportive environment that values innovation, autonomy, and professional development.
You’ll join a mission-driven organization that makes a meaningful difference for families across the U.S.

If you’re a proactive compliance leader who thrives on building programs and partnering cross-functionally to drive responsible growth, we encourage you to apply today.

PRISM is seeking a highly technical, hands-on Commercial Lines Product Manager to lead the end-to-end development of new insurance programs. You will be responsible for identifying market segments, conducting competitor analysis, and translating business objectives into comprehensive product strategies from initial concept to market delivery.

Core Responsibilities:

Product Development: Lead the creation of initial rates, rules, and form filings. Collaborate with Sales, Underwriting, Actuarial, and Claims to ensure products are profitable and market-competitive.

Regulatory & Filings: Manage the full filing process via SERFF/IRFS, including drafting responses to regulator inquiries and ensuring compliance with multistate laws.

Systems Implementation: Provide detailed programming requirements for policy administration systems and perform pre- and post-launch validation to ensure accurate system behavior.

Data Strategy: Define requirements for KPIs and trend reporting. Use advanced data analysis to monitor program performance and support regulatory data calls.

Strategic Leadership: Maintain expertise in emerging P&C trends and mentor department staff on technical development.

ABOUT PRISM:
PRISM is devoted to modernization and innovation within the world of technology, security, and IT enterprise solutions. We are recognized for meeting performance requirements and exceeding customer expectations since 1994. Our culture is founded on relationships, opportunity, and success. Offering comprehensive benefit plans including medical, dental, vision, and 401K along with our people – first approach sustains our reputation as a premier employer.

PRISM is an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status, or any other protected class.

Come grow with James River Insurance!

James River Insurance is an excess and surplus lines segment of James River Group Holdings, Ltd. and operates on an approved non-admitted basis in 50 states and Washington, DC. Since 2003, James River has provided thousands of commercial property and casualty customers with innovative and creative solutions for particular insurance needs.

At James River Insurance, we are committed to providing a stable and rewarding work environment supported by our Core Values and Guiding Principles: Integrity, Accountability, Innovation, Customer Service, Communication, and Teamwork. We are proud of being recognized the past 5 years as one of The Top Workplaces USA.

James River Group Holdings, Ltd. is a Bermuda-based insurance holding company which owns and operates a group of specialty insurance and reinsurance companies. The Company operates in two specialty property and casualty insurance segments: Excess and Surplus Lines and Specialty Admitted Insurance. The Company tends to focus on accounts associated with small or medium-sized businesses in each of its segments. Each of the Company’s regulated insurance subsidiaries are rated “A-” (Excellent) by A.M. Best Company.

Job Summary

The Manager of Statistical Reporting will lead a team of Analysts to ensure all statistical reporting requirements are completed accurately and in accordance with established deadlines to support the Company’s compliance with regulatory requirements.

Duties and Responsibilities

Strong project and people management experience.
Continuously exhibit and uphold Core Values of Integrity, Accountability, Communication and Teamwork, Innovation and Customer Service
Understand and communicate the impact of statistical reporting to internal stakeholders
Oversee the preparation and submission of monthly, quarterly and annual statistical filings to ISO, NCCI, NISS, insurance departments and Bureaus
Oversee the validity of all data and reporting output from the team
Interpret complex regulatory requirements
Provide subject matter expertise on multiple lines of business
Recommend process improvement to leadership team
Oversee the analysis and design of information, systems, and/or processes for internal and external reporting, data capture and quality specifications and manual processing
Manage multiple intra- and inter-departmental projects
Collaborate with business units to align process to regulations and provide assistance responding to regulatory inquiries
Ensure project and department milestones and goals are met
Guide and help team members with project issues
Responsible for day-to-day tactical team decisions
Track employee performance and provide regular and appropriate feedback
Work with employees to collaboratively establish development plans
Provide constructive feedback through regular check-ins and delivering performance reviews
Lead team through obstacles and time constraints to overcome barriers and successfully deliver results

Knowledge, Skills and Abilities

Extensive knowledge of P&C insurance industry and products
Advanced proficiency with ISO stat reporting and state data calls for property/casualty insurers
Solid knowledge of insurance regulatory and compliance requirements related to statistical reporting requirements
Knowledge of company’s financial and data reporting systems
Intermediate proficiency in SQL programming language
Ability to lead, motivate, influence, and mentor staff
Ability to set clear expectations, effectively monitor progress, provide constructive feedback and guidance, and hold staff accountable
Ability to manage multiple tasks and projects effectively
Excellent written and verbal communication skills
Active listening skills
Ability to exercise sound judgement in making critical decisions
Ability to convey technical process information in a clear and concise manner
Attention to detail
Excellent organizational skills
Proficiency in MS Office (Word, Excel, Outlook)
Ability to provide exceptional customer service
Research, analysis and problem-solving skills
Ability to build effective relationships with business partners and influence decisions
Ability to identify and make process and procedure improvement recommendations
Strategic thinker with creative problem-solving abilities
Ability to lead and support a team
Open to continuous learning

Experience and Education

High School Diploma required
Bachelor’s Degree preferred, or equivalent combination of education, training and experience
Minimum of 7 years of experience in insurance compliance with concentration in statistical reporting required
Minimum of 3 years of people and project management (supervision, mentor, lead) experience required
Certifications (CPCU, AINS, ARC) preferred

As a Regional Product Compliance Specialist, you will prepare and process product changes supporting filing projects and compliance/cleanup schedules. Collaborate and provide feedback supporting product filings with carrier partners, Product Compliance team and Product Implementation activity. Serve as a subject matter resource to include working in conjunction with Product Managers and simple to moderate level problem solving for product filing related to coverage and compliance.
Ready to get in the Driver’s seat? Join us!

What you’ll do

Achieve filing submissions production goals for filing projects, successfully utilizing filing workflow, checklists and teamwork processes. Prioritizing workload with assistance as needed.
Develop, refine, and process simple to moderate level compliance/cleanup product changes to meet regulatory, legal and business needs.
Achieve high quality filing documents minimizing internal review, carrier critique, and state objections.
Coordinate and provide complete information to process approvals for Implementation.
Provide basic assistance researching and interpreting product compliance or competitive issues as needed for participation in meetings with Product Managers.
Exhibit good interpersonal skills in working with teams and others throughout the organization and with carrier partners.
Demonstrates a moderate level of problem-solving ability relating to state issues and questions received from various sources (carrier, Legal, Implementation, UW, PM, etc.) with the assistance of other team members and managers as necessary.
Filings and Forms/Rule/Rate Creation and Updates
Research, interpret, and analyze state requirements for product filings.
Review and refine rate and rule page updates and Underwriting Guidelines, working with Actuarial and Underwriting as needed.
Determine appropriate language and refine forms for filings.
Research and prepare state-specific filing forms and exhibits.
Prepare all filing documents for SERFF.
Respond to BA requests and questions regarding system output changes that may be necessary for a filing update.
Serve as first point of contact and liaison with the carrier partners.
Handle state objections, communicate with the carrier in responding to the state, and recommend, as necessary, alternate strategies to the project-lead or compliance manager.
Peer-review other specialists’ state filings for accuracy and correction.
Maintain Word and Excel documents, emails, and folders in appropriate, historical manner.
Serve as a SME for states or program or project.
Process filing approvals for Support Specialist to hand-off to Implementation Team.
Provide additional communication, as needed, supporting product change and release dates.
This might describe you

Personal Auto Insurance product knowledge and experience.
SERFF experience a plus.
Pro-active, critical thinker.
Other things to note

This position can be worked as a remote position within the United States.
Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.
Say hello to Hagerty

Hagerty is an automotive enthusiast brand and the world’s largest membership organization. Along with being a best-in-class provider of specialty insurance for enthusiasts, Hagerty is also home to the Hagerty Drivers Foundation, Garage + Social, Hagerty Drivers Club, Marketplace and so much more. Committed to saving driving for future generations, each and every thing Hagerty does is dedicated to the love of the automobile.

Hagerty is a rapidly growing company that values a winning culture. We provide meaningful work for and invest in every single team member.

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Vermont, Washington, British Columbia, Canada please email [email protected] for compensation, comprehensive benefits and the perks that set us apart. 

#LI-Remote

EEO/AA

Ensure the organization maintains a robust compliance framework that meets the expectations of group, local, and regulatory stakeholders. Deliver and implement compliance initiatives, risk assessments, and monitoring programs to minimize risk and identify potential exposure areas within the P&C insurance sector. This role requires close collaboration with teams across underwriting, operations and data, finance, claims, and London headquarters Compliance department. The role reports directly to the US Head of Compliance and works closely with the US General Counsel to ensure legal and regulatory alignment.

Regulatory Compliance:
Monitor and implement regulatory changes, including NAIC requirements, and state specific updates applicable to the business.
Review and adjust group and local policies to ensure compliance; collaborate with Group Compliance Officer for amendments.
Respond to regulatory requests from internal and external regulators.
Oversee the process of receiving, investigating, and resolving consumer complaints, ensuring all concerns are addressed promptly and in accordance with regulatory requirements and internal policies.
Work with external vendors to manage insurance license renewals and filings, ensuring all licenses remain current and compliant with regulatory requirements.

Regulatory Filings & Data Reporting:
Coordinate the preparation and submission of required regulatory filings, ensuring accuracy and timely delivery in accordance with applicable laws and regulations.
Oversee the collection, validation, and reporting of data to regulatory bodies, maintaining robust records and supporting the organization’s transparency and accountability.

Underwriting Governance and MGA Oversite:
Oversee the governance of underwriting teams and actively monitor internal thresholds and metrics to assess ongoing compliance, identify potential risks, and drive continuous improvement in underwriting processes.
Provide guidance and training to underwriters on compliance-related matters and regulatory changes impacting underwriting.
Execute audit plan for Managing General Agents (MGAs) by coordinating with external firms to review underwriting activities, documentation, and adherence to agreements. This includes scheduling regular audits, evaluating MGA compliance with established thresholds and metrics, and collaborating with to address any identified deficiencies. Ensure that all audit findings are clearly documented, communicated to relevant stakeholders, and that corrective actions are tracked and verified for completion.
Assist in managing admitted product filings and maintain a comprehensive and up-to-date form library with regular auditing to ensure accuracy.

Advisory & Training:
Provide compliance advice on new and existing products, business initiatives, and processes.
Work with Group to deliver customized compliance training to staff to meet industry standards and regulatory expectations.
Serve as a center of excellence for compliance matters, supporting staff queries.

Risk Management & Monitoring:
Work with Group to conduct risk assessments and compliance monitoring of US Region.
Collaborate with pertinent departments to identify and assess potential areas of compliance risk.
Maintain effective documentation for compliance monitoring and communicate findings to stakeholders.

Operational Oversight:
Create and document internal processes and procedures to ensure standardized compliance practices across the organization.
Ensure entity completion of Own Risk and Solvency Assessment (ORSA).
Provide quarterly reports to the board regarding adherence to compliance KPIs.
Review and approve new Managing General Agents (MGAs); monitor ongoing compliance of MGAs.
Work with underwriting, data, finance, claims, and other functions, including London headquarters, on compliance matters.

The Role

Ensure the organization maintains a robust compliance framework that meets the expectations of group, local, and regulatory stakeholders. Deliver and implement compliance initiatives, risk assessments, and monitoring programs to minimize risk and identify potential exposure areas within the P&C insurance sector. This role requires close collaboration with teams across underwriting, operations and data, finance, claims, and London headquarters Compliance department. The role reports directly to the US Head of Compliance and works closely with the US General Counsel to ensure legal and regulatory alignment.

Responsibilities

Regulatory Compliance:
– Monitor and implement regulatory changes, including NAIC requirements, and state specific updates applicable to the business.
– Review and adjust group and local policies to ensure compliance; collaborate with Group Compliance Officer for amendments.
– Respond to regulatory requests from internal and external regulators.
– Work closely with legal counsel to monitor legal framework updates.
– Oversee the process of receiving, investigating, and resolving consumer complaints, ensuring all concerns are addressed promptly and in accordance with regulatory requirements and internal policies.
– Work with external vendors to manage insurance license renewals and filings, ensuring all licenses remain current and compliant with regulatory requirements.

Regulatory Filings & Data Reporting:
– Coordinate the preparation and submission of required regulatory filings, ensuring accuracy and timely delivery in accordance with applicable laws and regulations.
– Oversee the collection, validation, and reporting of data to regulatory bodies, maintaining robust records and supporting the organization’s transparency and accountability.

Underwriting Governance and MGA Oversite:
– Oversee the governance of underwriting teams and actively monitor internal thresholds and metrics to assess ongoing compliance, identify potential risks, and drive continuous improvement in underwriting processes.
– Provide guidance and training to underwriters on compliance-related matters and regulatory changes impacting underwriting.
– Execute audit plan for Managing General Agents (MGAs) by coordinating with external firms to review underwriting activities, documentation, and adherence to agreements. This includes scheduling regular audits, evaluating MGA compliance with established thresholds and metrics, and collaborating with to address any identified deficiencies. Ensure that all audit findings are clearly documented, communicated to relevant stakeholders, and that corrective actions are tracked and verified for completion.
– Assist in managing admitted product filings and maintain a comprehensive and up-to-date form library with regular auditing to ensure accuracy.

Advisory & Training:
– Provide compliance advice on new and existing products, business initiatives, and processes.
– Work with Group to deliver customized compliance training to staff to meet industry standards and regulatory expectations.
– Serve as a center of excellence for compliance matters, supporting staff queries.

Risk Management & Monitoring:
– Work with Group to conduct risk assessments and compliance monitoring of US Region.
– Collaborate with pertinent departments to identify and assess potential areas of compliance risk.
– Maintain effective documentation for compliance monitoring and communicate findings to stakeholders.

Operational Oversight:
– Create and document internal processes and procedures to ensure standardized compliance practices across the organization.
– Ensure entity completion of Own Risk and Solvency Assessment (ORSA).
– Provide quarterly reports to the board regarding adherence to compliance KPIs.
– Review and approve new Managing General Agents (MGAs); monitor ongoing compliance of MGAs.
– Work with underwriting, data, finance, claims, and other functions, including London headquarters, on compliance matters.

Symetra has an exciting opportunity to join our team as a Sr. Compliance Analyst!

About the Role

In this position, you will provide both product filing and operational compliance support for the Retirement (annuities) Division. You will identify and assess compliance issues, developing recommendations to promote long-term, disciplined growth. Additionally, you will consult on state filings strategy, preparing filing materials accurately and promptly.

You will offer superior analytical and project management support for nationwide initiatives, including conducting research, presenting recommendations to senior analysts or the leadership team, and assisting in implementing solutions. Collaboration with other departments will be frequent to ensure our products remain compliant and competitive.

Additional duties include developing and maintaining training materials and procedures, managing annual filings, implementing regulatory forms, and reviewing forms and marketing materials for state filings as appropriate.

What you will do

Coordinate and prepare accurate and timely filings materials for submission to state Departments of Insurance.
Research, interpret and apply laws, regulations, bulletins and filing requirements relating to Symetra products and research requests.
Assist in drafting policy and application forms that comply with state laws and regulations and prepare materials for filing.
Prepare product filings, statements of variability, forms listings, certifications and other documentation needed for filing forms and/or rates.
Research and respond to state inquiries/objections related to filings.
Prepare and disseminate filing status reports.
Independently research and consult on state-specific filing strategy, represent State Filings team/coordinate responses for nationwide research initiatives and projects.
Monitor tasks and timelines, evaluates risks, provide recommendations and solutions.
Provide subject-matter expertise on key initiatives across multiple product lines.
Support a wide range of projects for lines of business and/or with multi-disciplinary teams.
Independently manage technically demanding compliance projects with minimal supervision.
Identify and assess compliance issues and develop sound recommendations.
Work closely with business teams to provide ongoing support.
Advise business management on compliance issues with limited direction and assists business management in development of practices and procedures.
Act as a mentor to lower-level analysts by independent leadership with a group or team.

Why work at Symetra

“I feel welcome and included at Symetra every day and I really believe you can be you at Symetra.” – Megan H., Deputy Chief Compliance Officer

“I chose Symetra because I heard it was a pro-employee company—and it’s absolutely true. The work environment is supportive, the people are great, and the benefits are generous. Symetra truly cares about its employees. The relaxed atmosphere and opportunities to learn and grow—both within your role and beyond—make it a great place to build your career.” – Alicia L., Claims Examiner

What we offer you

We don’t take a “one-size-fits-all” approach when it comes to our employees. Our programs are designed to make your life better both at work and at home.

Flexible full-time or hybrid telecommuting arrangements
Plan for your future with our 401(k) plan and take advantage of immediate vesting and company matching up to 6%
Paid time away including vacation and sick time, flex days and ten paid holidays
Give back to your community and double your impact through our company matching
Want more details? Check out our Symetra Benefits Overview

The right candidate will serve as the Manager of the Property and Casualty Section within OIRF and be responsible for managing and supervising the operations of the Section. The right candidate will direct and oversee the review of property and casualty insurance rates, rules, and policy forms and contracts in Michigan for compliance with relevant laws, regulations, and Department policies and guidance.

Symetra has an exciting opportunity to join our team as a Sr. Compliance Analyst!

About the Role

As a Sr. Compliance Analyst, you will support the overall product lifecycle in Benefits Division products (Group Life, Disability, Supplemental Health, and/or Stop Loss). You will play a key part in bringing products to market quickly while ensuring regulatory compliance. As an Analyst on the team, you will participate in each phase of our product development and filing efforts – you will consult and provide recommendations on state filings strategy, prepare filings accurately and timely. You will participate in all phases of product development and state filing efforts—providing strategy input, preparing accurate and timely filings, and supporting nationwide compliance initiatives. This analyst collaborates across departments including Product, Legal, Actuarial, Underwriting, Operations, and Marketing.

What you will do

Coordinate and prepare accurate and timely filing materials for submission to state Departments of Insurance
Research, interpret and apply laws, regulations, bulletins and filing requirements relating to Symetra products and research requests
Assist in drafting state exception pages that comply with state laws and regulations
Format all material to the extent necessary for preparation for filing
Prepare filing memos, forms listings, certifications and other documentation needed for filing forms and/or rates
Assist with Marketing material process: research, review/filing
Manage coordination and timely submission of responses to state inquiries related to filings
Prepare data sets that feed our filing status reports (weekly/monthly/annually)
Independently research and consult on state-specific filing strategy, represent State
Filings team/coordinate responses for nationwide research initiatives and projects
Monitor tasks and timelines, evaluate risks, provide recommendations and solutions
Provide subject-matter expertise on key initiatives across multiple product lines
Provide assistance on key compliance projects on as-needed basis