Chief Legal Officer

Total Warranty Services•Boca Raton, FL

99d•Onsite

About The Position

Total Warranty Services (TWS) is seeking a strategic Chief Legal Officer to lead and transform its legal, compliance, and regulatory-affairs function. TWS is a closely held, founder-led enterprise serving the automotive finance and insurance product ecosystem through warranty and service contracts, dealer lending, and a regulated insurance company. The company is pursuing a goal of doubling revenue over the next three to five years. The CLO will serve as a trusted business collaborator and legal operating leader, partnering directly with the co-founders, a small board, and C-suite leaders. The role will shape enterprise strategy, anticipate risk, and help the company address legal and regulatory complexity while supporting growth, capital activity, transactions, and organizational change. The legal department has six members, and the company has already invested in legal operations transformation. The position is based on-site in the Boca Raton, Florida area, with the option for weekly flex days. Residency in the Boca Raton region is required, and a relocation package is available. The role offers competitive executive compensation, including base salary, performance incentive, and equity or equity-like participation.

Requirements

Juris Doctor degree.
Active membership in good standing in at least one U.S. state bar; Florida admission or eligibility to register as in-house or authorized house counsel.
At least 15 years of relevant professional legal experience, including substantial senior in-house or legal operating leadership experience.
Demonstrated strategic and legal operating leadership, including partnering as a peer with senior business leaders, ideally in a high-growth or rapidly evolving organization.
Experience building, scaling, or transforming a legal department and leading organizational growth and change.
Breadth across corporate, commercial, transactional, regulatory, and governance matters, with the judgment to lead specialists and outside counsel.
Executive presence and communication skills sufficient to advise founders and a board and influence at all levels of an organization.
Strategic and vision-oriented, while also hands-on and execution-minded.
Commercially pragmatic, with the ability to find paths to solutions while protecting the enterprise.
Comfort with ambiguity, speed, and the demands of a rapidly growing business.
High integrity, sound judgment, a collaborative instinct, and a growth mindset.
Residency in the Boca Raton region.

Nice To Haves

Experience advising regulated financial services and/or insurance businesses, including consumer-facing service contracts, regulated insurance products, or business lending/private credit functions, with direct exposure to 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.

Responsibilities

Serve as principal legal advisor to the co-founders and board and participate in the senior leadership team.
Shape enterprise strategy, growth initiatives, and capital activity, and translate growth ambitions into a legal, regulatory, and governance roadmap.
Provide commercial, solutions-oriented legal judgment on product design, pricing, distribution, partnerships, and new-market entry across the company’s divisions.
Lead or co-lead organizational transformation, integrating legal strategy with operational and financial objectives.
Scale and lead an integrated legal and compliance function for the warranty/service contract, dealer lending, and regulated insurance divisions.
Own regulatory affairs and manage relationships with insurance, consumer finance, and other applicable regulators in collaboration with an experienced financial and treasury leader.
Oversee licensing, examinations, filings, and ongoing regulatory engagement.
Oversee corporate, commercial, and transactional legal matters, including contracts, M&A and corporate development, financing, vendor and dealer agreements, consumer-facing terms, intellectual property, employment, and litigation or dispute management.
Design and maintain an enterprise compliance program, 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.
Manage board and committee processes, materials, minutes, and entity governance.
Advise the co-founders and board on governance, fiduciary, and risk matters, and maintain clean corporate records across the corporate family.
Evolve the legal operating model, structure, staffing, technology, and outside counsel strategy to support a large national enterprise scaling over the next three to five years.
Develop and lead a high-performing legal team and foster accountability, business partnership, and pragmatic risk-taking.
Set and manage the legal budget and improve efficiency through process, technology, and disciplined use of external resources.