Director, Insurance Licensing & Compliance

PEAK6; Town of Texas (WI); Hybrid; USD 140,000 - 210,000; Full time

Job summary

We Insure Group is seeking a Director, Insurance Licensing & Compliance to build and lead the licensing program across corporate entities, franchises, and acquired agencies. This role will establish a reliable view of authorized operations, translate state requirements into auditable workflows, and own licensing standards, filings, and the system of record.

The director will collaborate with Franchise Operations, Carrier Relations, HR, Finance, Tech & Data, M&A, and outside counsel to ensure

Qualifications

• Bachelor's degree or equivalent; active property & casualty license preferred or willingness to obtain.

Responsibilities

• Own the enterprise insurance licensing policy, procedures, and exception process.

Skills

Licensing program ownership

Regulatory licensing knowledge

Communication skills

Cross-functional collaboration

Project management

Education

Bachelor's degree

SILA Associate or SILA Fellow designation

Tools

NIPR

Sircon

AgentSync

RegEd

CRM systems

Job description

Who We Are.

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision. As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results. What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.

Your Impact.

We Insure is seeking a Director, Insurance Licensing & Compliance to build and lead the insurance licensing program across our corporate entities and producers, franchise entities and producers, and acquired agencies. This role will establish a reliable view of who and what is authorized to operate and will translate state requirements into practical, auditable workflows. The director will own licensing standards, verification, exceptions, regulatory filings, and the system of record. Licensing status must be reflected in onboarding, system access, carrier appointment readiness, commissions, franchise expansion, and acquisition integration. The role will work closely with Franchise Operations, Carrier Relations, Human Resources, Finance, Technology and Data, M&A, and outside regulatory counsel. This is a hands‑on director and player-coach role. The successful candidate will personally resolve difficult filings and data issues while building repeatable processes, clear service levels, and a scalable operating model. Franchisees remain responsible for their own licenses, filings, fees, continuing education, personnel, and submitted information; this role sets the standards, verifies compliance, and manages exceptions and escalation.

Key Responsibilities.

• Own the enterprise insurance licensing policy, operating procedures, responsibility matrix, control calendar, evidence standards, and exception process.
• Maintain a state-by-state requirements framework covering individual and business-entity licenses, lines of authority, designated responsible licensed producers, affiliations, continuing education, assumed names, branch or location rules, renewals, and required filings.
• Manage corporate applications, renewals, amendments, reinstatements, affiliations, responsible-producer changes, address and officer updates, assumed names, and related filings. Verify required authority before production access, licensed activity, or licensing-dependent compensation, and coordinate prompt offboarding when authority ends.
• Define and monitor licensing requirements for franchise onboarding, renewals, ownership changes, transfers, producer additions, relocations, terminations, and expansion. Manage deficiencies, cure periods, approved exceptions, and contractual escalation while preserving each franchisee's independent obligations.
• Establish the licensing prerequisites and evidence required before Carrier Relations submits appointments or grants market access, and reconcile licensing, appointment, carrier portal, and internal producer records.
• Own licensing-related annual and periodic filings, regulatory inquiries, examination support, document production, remediation plans, and management responses; escape novel or material legal questions to outside counsel.
• Establish and maintain a controlled licensing system of record using NIPR, state portals, and other authoritative sources. Automate renewal alerts, exception queues, reconciliations, and dashboards while preserving review of state-specific requirements and material exceptions.
• Partner with Human Resources, Franchise Operations, Finance, Technology and Data, and Carrier Relations to connect licensing status to onboarding, access, appointment, commission, and offboarding workflows.
• Monitor regulatory developments and convert changes into clear owners, due dates, system updates, communications, and training for corporate and franchise stakeholders.
• Lead licensing diligence and integration for acquisitions, including inventories of entities, producers, responsible producers, assumed names, locations, appointments, continuing education, and disciplinary history.
• Provide quarterly risk and performance reporting to executive leadership, including coverage, upcoming renewals, exceptions, remediation status, service levels, and material regulatory matters. Train support staff, document recurring processes, and recommend future staffing based on workload and risk.

Qualifications.

• Bachelor's degree or an equivalent combination of education and directly relevant experience. An active property and casualty producer license and a SILA Associate or SILA Fellow designation are preferred, or a willingness to obtain relevant credentials.
• Seven or more years of progressive insurance producer, agency, or regulatory licensing experience, including substantial multi-state property and casualty work.
• At least three years owning a licensing program, leading complex licensing workflows, or supervising licensing professionals.
• Hands‑on experience with individual and business‑entity licenses, designated responsible licensed producers, lines of authority, affiliations, renewals, continuing education, appointments, and state‑specific exceptions.
• Demonstrated ability to build controls, reconcile data, manage exceptions, document procedures, prepare for regulatory examinations, and work across distribution or franchise operations, carrier relations, Human Resources, Finance, Technology, and Legal.
• Experience with NIPR and one or more licensing platforms such as Sircon, AgentSync, RegEd, or Creative Compliance, together with CRM and workflow systems.
• Strong judgment and communication skills, including the ability to explain requirements, document uncertainty, and deliver direct recommendations to executives, employees, and franchise owners.

Preferred.

• Experience in a national independent agency, insurance franchise, aggregator, or acquisition‑led brokerage is strongly preferred.
• Licensing diligence and integration experience in mergers and acquisitions is strongly preferred.

Our Values.

The We Way.

At We Insure, Group our values shape how we work, how we lead, and how we grow together. They’re more than just words, they guide every interaction, every decision, and every customer experience. We Way Reflects Our Commitment to. We personalize protection at a price you can trust We hustle to find opportunity We care authentically We thrive in ambiguity We own our results We have fun along the way And—we’re just getting started We’re a leader in the space. We foster ongoing innovation. You get all the benefits of a growing and fast‑paced company, while enjoying a very entrepreneurial culture. The team is really motivating. You’ll work with people who are as energetic, smart, and determined as you are. You’ll be managed by the best, too. Your work will be immediately impactful. You’ll be able to see your direct impact on our growth. You won’t be just another cog in the wheel.

We embrace change.

We embrace change. This is not where you'll find ‘predictable’. Our team wears many hats and has to go with the flow to deliver on our goals and get the job done. We are a team of collaborators. We work together to ensure the best possible solutions for our internal teams. It is common for us to get outside our swim lanes. Our environment provides continuous learning. Team members often have to branch out of their comfort zone. Taking ownership is an opportunity and we believe failures might lead to a better solution.

We Insure, LLC. is an independent insurance franchise that takes immense pride in providing like‑minded entrepreneurs with successful agency ownership. With more than 200 agency locations in 35 states, We Insure continues to grow rapidly and supports our agency owners, customers, and carriers by facilitating faster service, greater efficiencies, better choices, and improved bottom lines.

What makes We Insure stand out: we are data‑driven for better value and people‑led for better service. And our leadership is seeking more highly motivated, career‑driven people to help lead our efforts!

We Insure has received countless awards including Jacksonville Business Journal’s Best Places to Work and Fastest‑Growing Private Companies, and Inc.’s 5000 Fastest Growing Companies.

If you are looking for a long‑term career in a supportive, goal‑driven, growth environment with a company that believes in developing its people, We Insure is the right fit for you.