ProtectiveLast verified: 2026-11-14Protective's
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Compliance & Product Specialist - Obsidian

Full-time$120k–170k / yrNot stated

Protective is hiring for a full-time remote role: Compliance & Product Specialist - Obsidian. Pay: $120k–170k / yr.

Who can apply: This listing doesn't say where applicants can be based. Confirm with the employer before applying.

Posted Nov 14, 2026 · still open as of Nov 14, 2026 · apply on Protective's own careers page.

About Protective

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Job Description

The work we do has an impact on millions of lives, and you can be a part of it.

We help protect our customers against life’s uncertainties. Regardless of where you work within the company, you’ll be helping provide protection and peace of mind when our customers need it most.

The Compliance and Product Specialist will support the general insurance and product compliance and legal/regulatory functions performed by the Obsidian Legal team. This role is responsible for assisting in the development and ongoing review of program business and compliance with state and federal laws, regulations, and company policies.

Due to the fast-paced nature of the regulatory and business environments, the position requires the ability to quickly adapt to change and to multi-task various assignments. The individual must be able to provide compliance guidance that balances both regulatory requirements while meeting business objectives. The individual will exercise judgment within defined procedures and practices to determine appropriate action.

Role and Responsibilities:

  • Review coverage forms and endorsements for all Property and Casualty lines of business, including Commercial General Liability, Commercial and Personal Auto, Commercial and Personal Inland Marine, Commercial Property, Professional Liability, Management Liability, Cyber and Homeowners, to ensure they convey underwriting intent and are in compliance with state requirements.
  • Review and interpret new or revised laws, regulations, bulletins and regulatory publications applicable to Obsidian business, as directed.
  • Manage and monitor assigned programs in accordance with Obsidian business standards and regulatory environment. This requires meetings and email communication with general agents.
  • Conduct an initial due diligence review of new program business, including reviewing compliance with OFAC, TRIA, cybersecurity laws, record retention laws, policy issuance and cancellation/non-renewal laws, motor carrier and DMV automobile filings, and other regulatory compliance requirements. Maintain ongoing compliance oversight after program implementation.
  • Work closely with Obsidian’s Underwriting department during the implementation and launch phases for new business and renewal phase for existing business. On all program business, this includes communicating compliance and product findings during the due diligence review to the assigned underwriter; working closely with Underwriting on coverage intent, coverage form and endorsement language, underwriting guidelines, program launch and ongoing program monitoring.
  • Work closely with Obsidian’s Actuarial department during the implementation and launch phases for new business and renewal phase for existing business. On all program business, this includes reviewing rating and associated rules for coverage forms and endorsements.
  • Work with Actuarial and Accounting to identify and gather data necessary to respond to state data calls and regulatory reports.
  • Manage third party vendors’ filing work, including overseeing the filing preparation, signing off on the final filing package, reviewing state objections, escalating objections to Underwriting and Actuarial, and communicating filing approvals to Obsidian stakeholders.
  • Perform due diligence and compliance audits on program business, produce an audit report and communicate findings to Obsidian’s Legal, Underwriting, Actuarial departments and external general agents.
  • Ad hoc compliance related research/projects.

Required Skills, Key Competencies and Experience:

  • Must be able to identify applicable admitted and surplus lines compliance requirements for property and casualty lines of business and articulate those requirements to the internal business departments and external business partners.
  • Effective written and verbal communication.
  • Ability to summarize information clearly and concisely.
  • Ability to effectively organize, prioritize, and meet deadlines for multiple, simultaneous projects.
  • Strong analytical ability to review contracts, underwriting guidelines and policy wording.
  • Strong presentation skills.
  • Demonstrated ability to successfully work independently as well as within a team.
  • Good time management and high attention to detail are critical to this position

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Qualifications and Education Requirements

  • Bachelor’s degree
  • Prior Property and Casualty Program business experience, including admitted and non-admitted regulatory environments
  • Experience drafting coverage forms and endorsements
  • Juris Doctorate from an accredited law school and currently licensed to practice law in at least one U.S. jurisdiction is desired.
  • 7+ years related experience.

#LI-SB1

Employee Benefits:

We aim to protect the wellbeing of our employees and their families with a broad benefits offering. Work/life balance is important and Protective offers a variety of paid time away benefits (e.g., paid time off, paid parental leave, short-term disability, and a cultural observance day). The financial health of our employees is just as important as physical and emotional health. All employees are encouraged to protect their overall wellbeing by engaging in ProHealth Rewards, Protective’s platform to improve wellbeing while earning cash rewards.

Eligibility for certain benefits may vary by position in accordance with the terms of the Company’s benefit plans.

Accommodations for Applicants with a Disability:

If you require an accommodation to complete the application and recruitment process due to a disability, please email eric.hess@protective.com. This information will be held in confidence and used only to determine an appropriate accommodation for the application and recruitment process.

Please note that the above email is solely for individuals with disabilities requesting an accommodation. General employment questions should not be sent through this process.

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