General Counsel/Chief Legal Officer

Total Warranty Services is seeking an experienced, strategic Chief Legal Officer to serve as both a trusted business collaborator and a vision-oriented legal operating leader. The CLO will transform and lead a modern legal, compliance, and regulatory-affairs function capable of supporting three regulated, fast-scaling lines of business and the corporate transactions, capital activity, and organizational changes that come with doubling the enterprise. The successful candidate will partner directly with the co-founders, a small board, and fellow C-suite leaders to shape strategy, anticipate risk, and convert legal and regulatory complexity into durable competitive advantage. The CLO is expected to lead transformation across the legal function itself and as a contributor to enterprise-wide initiatives while keeping the business moving with speed and commercial judgment.

Essential Duties & Responsibilities

Strategic and Business Leadership

• Serve as principal legal advisor to the co-founders and board, and as an active member of the senior leadership team shaping enterprise strategy, growth initiatives, and capital activity.

• Translate TWS’ growth ambitions into a forward-looking legal, regulatory, and governance roadmap.

• Act as a true business collaborator: bring commercial, solutions-oriented judgment to product design, pricing, distribution, partnerships, and new-market entry across all three divisions.

• Lead or co-lead organizational transformation efforts, integrating legal strategy with operational and financial objectives.

Legal, Compliance, and Regulatory Affairs

• Scale and lead an integrated legal and compliance function spanning the warranty/service contract, dealer lending, and regulated insurance divisions.

• Own regulatory affairs and, collaborating with an experienced financial and treasury leader, manage TWS’ relationships with insurance, consumer finance, and other applicable regulators. Oversee licensing, examinations, filings, and ongoing regulatory engagement.

• Oversee the full range of corporate, commercial, and transactional legal matters: contracts, M&A and corporate development, financing, vendor and dealer agreements, consumer-facing terms, intellectual property, employment, and litigation/dispute management.

• Design and maintain an enterprise compliance program appropriate to a regulated multi-division financial services and insurance enterprise, including policies, training, monitoring, and controls.

• Anticipate legislative and regulatory developments affecting the retail-automotive, consumer finance, warranty, and insurance markets, and position TWS to respond ahead of change.

• JD from an accredited law school and active membership in good standing with the Florida State Bar Association.
• Minimum of 15 years of relevant professional legal experience, including substantial time in senior in-house or legal operating leadership roles.
• Experience divising regulated financial services and/or insurance businesses providing consumer-facing services contracts, regulated insurance products, or business lending/private credit functions, with direct exposure to the applicable regulatory regimes, strongly preferred.
• Experience building, scaling or transforming a legal department and leading successful organizational growth and change.
• Experience supporting M&A and corporate finance in a fast-growing closely-held company.