Compliance Director

Group 1001   is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.

Why This Role Matters

Gainbridge is a subsidiary of Group 1001, recently rebranded, and in the middle of a serious investment in growth. Gainbridge has a new brand identity, a new product lineup, and significant media spend across digital, social, print and other customer facing channels – all coupled with strong engineering, product, and design teams.

To support this growth, the Compliance Department within Group 1001’s Life and Annuity Business Unit seeks an outstanding compliance professional who can be a trusted partner and help Gainbridge innovate with confidence by balancing business objectives, customer experience, and regulatory requirements.

You will sit at the intersection of a fast-moving consumer brand and a highly regulated industry, translating complex insurance, annuity, and advertising regulations into practical, risk-based guidance that enables the business to move quickly and confidently.

How You'll Contribute

Lead the design, implementation, and oversight of the compliance framework for the direct-to-consumer annuity platform, ensuring adherence to applicable state insurance laws, NAIC model regulations, FINRA/SEC requirements, advertising standards, privacy requirements, electronic delivery rules, and consumer protection obligations.

Partner with Product, Operations, Marketing, Engineering, Design, and Technology teams to review and approve digital customer journey, marketing and advertising, disclosures, online applications, and sales processes, ensuring regulatory compliance while supporting an efficient customer-friendly experience.

Serve as the compliance lead for new product development initiatives, advising cross-functional stakeholders on product design, features, disclosures, distribution strategy, and implementation to ensure regulatory compliance and successful market launch.

Build scalable review workflows, checklists, and self-service tools so business partners can move fast without compromising compliance.

Lead regulatory change management by identifying emerging laws, regulations, and industry guidance affecting annuity products and digital distribution channels, assessing business impact, and driving timely implementation of required enhancements.

Develop and deliver training that raises compliance fluency across the Gainbridge organization.

Contribute to the broader Group 1001 Life and Annuity compliance program, sharing best practices and helping to raise the bar enterprise-wide.

What We’re Looking For

• 7+ years of progressive compliance experience within the life and annuity industry, ideally including direct-to-consumer or digital distribution.
• Bachelor’s degree required; advanced degree preferred.
• Deep working knowledge of fixed and fixed index annuities, including state insurance laws, NAIC model laws, advertising standards, consumer protection requirements, and electronic delivery.
• Demonstrated experience providing strategic compliance guidance for product development, digital distribution, and direct-to consumer sales models within the life and annuity industry.
• Extensive experience reviewing marketing and advertising for annuity products across digital, print, social media, and other distribution channels, ensuring compliance with applicable state insurance laws, advertising regulations, and company standards.
• Strong partnership and influencing skills, with experience collaborating effectively across product, operations, technology, marketing and leadership to balance regulatory compliance with business objectives, low-ego, and thrives in a fast-paced, startup environment where innovation, agility, and collaboration are valued.
• Exceptional analytical, communication, and problem-solving skills, with the ability to translate complex regulatory requirements into practical risk-based guidance and actionable business solutions - knows when to escalate, when to push back, and when to say “yes, and here’s how.”
• A builder’s mindset – comfortable creating processes and tooling where none exist, and iterating as the business scales.
• Comfortable operating in ambiguity and moving at startup speed inside an established insurance enterprise.
• Nice to Have
• Prior experience supporting a direct-to-consumer fintech or insurtech platform.
• Experience with digital marketing compliance tooling, review workflow platforms, or content management systems; familiarity with SEC/FINRA advertising principles a plus.
• Series 6, 7, 24, or 26 registrations, or willing to obtain.
• Juris doctor or other advanced degree.
• Experience leading regulatory examinations, market conduct examinations, audits, or responding to regulatory inquiries.