Chief Legal Officer, Total Warranty Services

CHIEF LEGAL OFFICER

Total Warranty Services

Boca Raton, Florida (On-Site/Flex)

THE COMPANY

A rare opportunity for a strategically-minded attorney and legal operating leader to be a key lever in enterprise transformation for Total Warranty Services, a closely held, founder-led enterprise operating at the center of the automotive finance and insurance product ecosystem. Through three distinct but complementary divisions, TWS serves consumers, franchised and independent dealers, and the broader retail-automotive market:

• Warranty and Service Contracts: Designs and administers vehicle service contracts and related warranty products for automobile purchasers.
• Dealer Lending: A commercial finance business providing lending and capital solutions to automobile dealers.
• Regulated Insurance: A fully regulated insurance company that designs and issues insurance products supporting the consumer warranty and protection offerings.

TWS is already one of the largest in this space and is looking to double revenue over the next three to five years.

THE OPPORTUNITY

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. This is not a caretaker role. TWS has a talented legal department of six in place and has already invested in legal operations transformation over the last two quarters. 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.

KEY 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.

Governance

• Manage board and committee processes, materials, minutes, and entity governance for a closely held enterprise.
• Advise the co-founders and board on governance, fiduciary, and risk matters, and ensure clean corporate records across the corporate family.

Function Building and Team Leadership

• Evolve the legal operating model, structure, staffing, technology, and outside counsel strategy for a legal function built to support a large national enterprise increasing in scale over the next three to five years.
• Develop and lead a high-performing team; enhance the culture of accountability, business partnership, and pragmatic risk-taking.
• Set and manage the legal budget; drive efficiency through process, technology, and disciplined use of external resources.

CANDIDATE PROFILE

The ideal candidate is a seasoned legal executive who has operated at the intersection of business strategy and regulated industry, and who is energized by the prospect of leading the legal function of a company evolving quickly to double in scale.

Required Qualifications

• JD and active membership in good standing in at least one US state bar (Florida admission or eligibility to register as in-house/authorized house counsel).
• Minimum of 15 years of relevant professional legal experience, including substantial time in senior in-house or legal operating leadership roles.
• Demonstrated record of strategic and legal operating leadership and of partnering with senior business leaders as a peer, ideally in a high-growth or rapidly evolving organization.
• Experience building, scaling, or transforming a legal department and leading successful organizational growth and change.
• Breadth across corporate, commercial, transactional, regulatory, and governance matters, with the judgment to lead specialists and outside counsel across all of them.
• Executive presence and communication skills sufficient to advise founders and a board and to influence at every level of the organization.

Strongly Preferred

• Experience advising 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.
• Familiarity with the automobile sales, dealer, and retail-automotive ecosystem.
• Experience supporting M&A and corporate finance in a fast-growing closely-held company.

Attributes

• Strategic and vision-oriented, yet hands-on and execution-minded.
• Commercially pragmatic: a partner who finds the path to “yes” while protecting the enterprise.
• Comfortable with ambiguity, speed, and the demands of a rapidly growing business.
• High integrity, sound judgment, a collaborative instinct, and a growth mindset.

REPORTING, LOCATION, AND COMPENSATION

• Reporting: Reports directly to TWS’ co-founders and small board of directors.
• Location: On-site in the Boca Raton, Florida region with option for weekly flex days. This position requires residency in the Boca Raton area. A relocation package will be provided to help the right candidate make the move.
• Compensation: Competitive executive compensation, including base salary, performance incentive, and equity or equity-like participation appropriate to a senior leader of a closely held, high-growth enterprise.

APPLICATION PROCESS

A cover letter is welcome but not required. If you choose to include one, we’re most interested in why this role appeals to you and a brief example of legal function growth or transformation you’ve led.

Please use this link to apply: https://totalwarrantyservices.breezy.hr/p/f8eb263b76bd-chief-legal-officer??source=goinhouse

Total Warranty Services is an equal opportunity employer and is committed to a diverse and inclusive workplace.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, age, national origin, disability, protected veteran status, gender identity or any other factor protected by applicable federal, state, or local laws.