General Counsel (GC) at Trustwill, Remote

General Counsel (GC) at Trustwill, remote. Contract. $280,000 to $315,000 a year. Apply with swipeandhired.

Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by over one million users. We provide modern, accessible solutions to help families protect their legacies with attorney-approved, legally valid documents tailored to individual state requirements. Our seamless online platform simplifies the estate planning and settlement process, empowering individuals to create wills and trusts while also partnering with financial advisors, attorneys, and large institutions to make legacy planning more inclusive and affordable.

If you'd like to join us, we are looking for a General Counsel who will serve as a key member of our leadership team, owning the legal function and translating business strategy into practical legal guidance. Reporting directly to the CFO, this role will manage a focused in-house legal team and work cross-functionally with key stakeholders: product, engineering, finance, sales, marketing, and beyond, as well as external partners.

About You:

You’re a business-minded legal leader who thrives in a fast-paced, mission-driven startup. You have a deep understanding of regulatory frameworks (especially in fintech, estate planning, AI, and privacy), and you’re excited about the opportunity to lead a legal function that supports innovation, manages risk, and protects our customers. You’re collaborative, practical, and enjoy finding solutions that balance risk with business opportunity.

About the Role:

• Serve as General Counsel and key legal advisor to the CFO, CEO, President, and executive team.

• Lead our in-house legal team, including attorneys focused on privacy, AI, our estate planning product, and corporate matters.

• Oversee all legal matters across the company, including regulatory compliance, employment law, privacy, AI use and application, intellectual property, litigation, and contracts. You’ll also assist in corporate governance matters.

• Own and optimize relationships with outside counsel, ensuring alignment with company goals and budget.

• Provide strategic guidance on consumer protection, fintech regulations, data privacy, and emerging AI legal frameworks.

• Drive development of legal process automation and scalable workflows.

• Collaborate with the People (HR) team as a legal resource on employment law, risk assessment, regulatory compliance, and employee relations matters; serving in an advisory capacity to support and strengthen HR initiatives.

• Support cross-functional partners on strategic initiatives, especially in product development and sales.

• Anticipate and proactively assess legal risk as the company scales into new markets and product categories.

Qualifications:

• 15+ years of legal experience, including senior in-house leadership at a growth-stage company.

• JD from an accredited U.S. law school and active bar membership (California or New York preferred).

• Experience managing and growing legal teams.

• Expertise in corporate law, product counseling, contract negotiation, and regulatory compliance.

• Strong working knowledge of privacy, AI, and data use frameworks in tech companies.

• Exceptional communication skills and proven ability to advise executive teams and Boards.

• Able to navigate ambiguity, drive alignment, and lead with a solution-oriented mindset.

• This position is available only to candidates in the southern California region (including Los Angeles, Orange, Riverside, San Bernardino, San Diego, Ventura, Santa Barbara, San Luis Obispo, Kern, and Imperial counties) .

Bonus Points for:

• Experience in estate planning, insurtech, or consumer-facing SaaS.

• Prior support of AI/ML product development from a legal lens.

• Experience with venture-backed growth companies through late-stage scaling or M&A.

Employee Benefits & Perks:

• Compensation: Salary + Equity

• Our salary range for this position is $280,000 - $315,000, in addition to compensation, we also include an employee equity package as a component of our offer, along with other benefits and perks outlined below.

• PTO

• Flexible time off that you are encouraged to use

• Generous paid company holidays and breaks throughout the year

• Monthly friends & family day

• Paid time off to volunteer in your community

• Health and Wellness Benefits

• Exceptional health benefits including medical, dental, vision, life, and disability insurance - we cover 100% of premiums for employees and dependents on medical coverage

• Mental health support through Spring Health, plus access to One Medical for primary care and Cleo for family planning and caregiving

• Financial wellness benefits (unlimited 1:1 sessions with a UBS financial coach and employer-sponsored 401k with up to 4% company match)

• Extra

• Flexible work schedule + hours

• Family-friendly work environment. We support the complexity of a remote world with the needs of families

• Up to $1,000 annually in learning & development reimbursement

• Optional company-sponsored events and travel throughout the year

• $500 Work from home stipend + Apple accessories

About Trust & Will:

• We are a remote-first company, giving our employees the flexibility they need to work in an environment that best suits their needs. Our hiring process is also conducted virtually unless otherwise noted. We are a company that was founded in San Diego, CA, and offer a collaborative co-working space that is available for you to use if you'd like but not required. #LI-Remote

• We are proud to be a certified B Corporation, using business as a force for good. We are committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. We publish an annual impact report to outline our positive contributions to our world and set an example for all employers.

• Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning. That starts with the people we hire and the ways in which we support the development of their unique talents and capabilities. We are committed to prioritizing ways to make our company and industry more inclusive. This means we must be revolutionary in the way we value diversity to revolutionize our business sector. At Trust & Will, everyone has a seat at the table and space to be their authentic selves because only in a company that is inclusive and diverse can we truly stand in our members' shoes.

California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information to evaluate qualifications and communicate about your application. California residents have the right to know what information we collect, request a copy, correct inaccuracies, or request deletion (subject to exceptions). To exercise these rights, contact [email protected]. For more information, visit our privacy policy .

Trust & Will may use AI tools to assist with administrative recruiting tasks. All final hiring decisions are made by people. For accommodations, contact [email protected] .

Applications will be accepted through November 20, 2026. If the deadline is extended, this posting will be updated.