Compliance Specialist

What We Do

We provide savings on insurance premiums for commercial businesses that are leveraging modern technology on their worksites.

While we began with commercial construction, we're expanding into adjacent sectors, including Energy, Agriculture, and Real Estate.

Our Investors

To date, Shepherd has raised over $20M from leading investors, including:

• Y Combinator – W21 cohort
• Susa Ventures – lead our Pre-Seed round
• Spark Capital - lead our Seed round
• Costanoa Ventures + Intact Ventures – lead our Series A round
• And several more.

Our Team

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our team page to meet some of us

The Role

About The Role
We are seeking a detail-oriented Compliance Specialist to manage day-to-day insurance compliance operations. Reporting to the Compliance Lead, you'll be the first point of contact for compliance inquiries, triaging requests from internal stakeholders and external vendors as well as supporting audit-readiness by maintaining critical systems and tracking key compliance and licensing matters.

Key Responsibilities
Regulatory Guidance

• Responds to basic (Tier-1) compliance inquiries from Underwriters, Customer Experience, and Engineering by applying established guidance found within the Compliance Repository.
• Escalates more complex or unique inquiries (Tier 2 and 3) with context and a proposed response.
• Maintains Shepherd's Compliance Repository, including logging resolved inquiries to ensure uniform guidance across the organization.
• Assists with the creation and supports the development of micro-trainings, guidelines, and reference sheets tied to the Regulatory Repository.

Forms & Filings Management

• Manages the Policy Forms filing process, including tracking all approved, filed, and manuscript forms with approval/effective dates and usage notes as well as coordinating with external filing services.
• Maintains the filing calendar, prepares filing packets, manages vendor portal submissions, and maintains version control library for all filed forms.
• Supports responding to state objections and assists the Compliance Lead in response preparation as Shepherd continues to expand its insurance offerings.

Licensing & Producer Onboarding

• Facilitates the producer onboarding process and renewals including maintaining our internal producer management database, ensuring data hygiene, document collection, and gathering all necessary items.
• Maintains Shepherd's producer licenses and coordinates Shepherd's surplus lines filings in coordination with the Customer Experience team and escalates filings issues when needed.
• Manages renewal calendars for licenses and surplus lines filings, coordinating with Customer Experience to resolve any issues.

Audit & File Review

• Maintains organized audit files and regulatory correspondence in the event of a regulatory audit.
• Conducts periodic underwriting file spot-checks against the Compliance Repository.
• Tracks remediation tasks and maintains compliance audit checklist.

Qualifications
Required Qualifications

• 2–5 years of experience in insurance compliance, regulatory affairs, or related roles.
• Knowledge of insurance regulations, state filing requirements, and/or licensing processes.
• Experience maintaining compliance trackers, audit files, and regulatory documentation systems.
• Excellent organizational skills with meticulous attention to detail.
• Ability to work with AI-assisted or automated workflows.
• Strong written and verbal communication skills.
• Sound judgment on when to escalate complex or novel issues.

Preferred Qualifications

• Experience with filing insurance forms and filing platforms such as SERFF.
• Understanding of surplus lines regulations, filing requirements, and taxes.
• Experience with commercial insurance products (GL, property, workers comp).
• Familiarity with producer licensing requirements.

This is an onsite position in our New York City, San Francisco, or Dallas Fort Worth offices.

Benefits
Premium Healthcare
100% contribution to top-tier health, dental, and vision

Unlimited PTO
Flexibility to take the time off, recharge, and perform

Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

SF, NYC, or Dallas-Fort Worth Offices
Premium office spaces on both coasts with daily lunches provided

Professional Development
Access to premium coaching, including leadership development

401(k) Plan
Competitive 401(k) plan offered

Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office

Compensation Range: $100K - $140K