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Sr. Program and Compliance Manager



Plantation, FL, USA
Posted on Thursday, April 25, 2024

Our Opportunity:

Chewy is looking for a Sr. Program & Compliance Manager to join our business team in location-flexible. This position is an exciting opportunity for a successful candidate to use their expertise to help us build a customer experience that meets Chewy’s high bar in a regulated industry. This is a leadership role that combines three functions namely; 1) core Chewy Program Management; 2) Property and Casualty (P&C, including Pet) Compliance; and 3) Licensing management. The person in role will serve as Chewy’s subject matter expert responsible for partnering with our cross-functional teams to ensure our operations are compliant with applicable regulations, serve as our agency’s Designated Responsible Licensed Producer (DRLP) and manage all agency licensing. This role is responsible for managing programs, Customer Agent training on compliance, interpreting complex compliance requirements, creating and communicating procedures, implementing necessary changes, and evaluation of best practice and compliance regulations as they evolve.

The ideal candidate is detail oriented and enjoys rolling up their sleeves to support the day-to-day operations of a new business. The position will report to Sr. Director of Chewy Insurance and have a dotted line to our legal team.

What you'll do:

Program Management:

  • Have end-to-end ownership of the program from intake, setting & communicating strategy, prioritizing deliverables/milestones, building consensus, and coordinating communications.
  • Lead the program implementation across cross-functional team of internal and external team members.
  • Develop roadmaps for new programs including the implementation plans, resourcing, prioritization and more.
  • Develop and launch programs (processes and tools) to scale the business over the long term.
  • Assess risks, anticipate bottlenecks and provide escalation management while anticipating and addressing Customer's needs.
  • Support multiple parallel workstreams managing projects from kick off through rollout.
  • Develop and manage key business metrics and financials for programs and be accountable for delivering against established business goals/objectives.
  • Communicates overall strategy, status of risks, and changes of program milestones to stakeholders and senior Executives including the C-suite.

Core compliance

  • Responsible for ensuring compliance with all laws and regulations governing across federal, state, and local government agencies.
  • First and primary point of contact for agency audits, both internal and external, as well as market conduct exams.
  • Coordinates with legal counsel to identify, monitor, analyze, and communicate regulatory changes including drafting standard operating procedures for business, marketing, customer service, and technology teams.
  • Review and coordinate approval with internal stakeholders and external business partners for all agency marketing and website copy.
  • Manages Chewy’s licensing needs across all 48 states to include agency, DRLP and licensed agent licensing and appointments. Maintains relationships with regulators to address any compliance issues.


  • Collaborates with key leadership and other employees, to identify, research, investigate and resolve compliance issues.
  • Oversees and documents external regulatory investigations.
  • Audits day-to-day operations for regulatory compliance including tracking data and creating reports to assist in the analysis of compliance issue patterns.
  • Conducts pro-active compliance reviews of data flows and communications with customers, including reviewing training materials, digital and print marketing materials, sales materials, customer calls, website copy and emails.


  • Manage all insurance agency licensing to include entity, DRLP and agent licensing in 48 states
  • Coordinate pre-licensing and continuing education coursework for all agents.
  • Run monthly licensing audits to ensure compliance with all resident, non-resident licenses, as well as appointments.
  • Submit monthly appointment forms to states as required.
  • Develop procedural licensing documentation.
  • In partnership with our external business partners, maintain all entity, DRLP and agent appointments.

Operations support

  • Responsible for identifying, building, and implementing the appropriate review and approval processes and procedures to meet regulatory requirements across all team stakeholders, including customer service, business, marketing, product, and tech teams.
  • Creates and delivers educational content to cross-functional teams on the regulated products.

Business support

  • Proactively monitors and provides analysis of competitive landscape.
  • Creates analysis for leadership on the regulatory implications of product design decisions, including contributing recommendations to the product roadmap to further improve the product for customers.
  • Assists with developing and executing business plans, routinely adjusting strategies and tactics to maximize performance based on market and customer information.

What you'll need:

  • 7+ years of experience, with a track record of delivering large scale projects and leading teams through complex problems in a regulated industry, preferably insurance.
  • 7+ years of experience working cross functionally with tech and non-tech teams.
  • Demonstrated success in building and implementing a compliance function across cross-functional operations.
  • 5+ years of maintaining own an active Property & Casualty General Lines license, currently active.
  • 5+ years or more years of regulatory and compliance experience in the property & casualty insurance industry
  • Five or more years of operations leadership experience, customer service call center or sales is preferred.
  • Three or more years of experience managing large-scale insurance licensing.
  • Experience engaging with regulators.
  • Internal and external audit experience, both leading audits and acting as primary POC for auditors
  • Ability to fit into a fast-paced entrepreneurial environment exercising sound business judgement in ambiguous situations.
  • Ability to articulate complex regulatory concepts and risk to leaders across the company and our external business partners.
  • Ability to negotiate and articulate Chewy’s compliance perspective with external business partners.
  • The candidate should possess sound professional judgment Excellent written and verbal communication skills for both technical and non-technical audiences.
  • Excellent analytical and interpersonal skills, with ability to work successfully across all disciplines.
  • Ability to communicate clearly and effectively with developers, business owners, and senior business leaders.
  • Position may require travel, <10%


  • MBA preferred.

Chewy is committed to equal opportunity. We value and embrace diversity and inclusion of all Team Members. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact

If you have a question regarding your application, please contact

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