Medical Controller

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 institutions to make legacy planning more inclusive and affordable.

Reporting to the CFO at Trust & Will, we are looking for a Controller who will be instrumental in steering our financial operations during a period of exciting growth. Your role involves overseeing financial reporting, leading the accounting team, designing and implementing internal controls, and owning the evolution of accounting at Trust & Will. You'll play a crucial role in maintaining financial health and compliance, all while navigating the challenges of a dynamic and fast-paced business environment.

About You:

At Trust & Will, we are looking for a Controller who is not only adept in accounting management but also thrives in a fast-paced environment, bringing qualities such as:

• Dynamic and Experienced: With significant experience in accounting, including leadership roles, you're ready to jump into a fast-paced setting. Experience at a big 4 firm and in a startup company would be a big plus.
• AI-Native Operator: You’re fluent in modern accounting systems like Rillet, and you default to AI and automation first, building repeatable workflows that make a lean finance team more effective.
• Communicative Leader: You're as good at crunching numbers as you are at explaining them to others.
• Analytically Inclined: You've got a sharp mind for analysis and strategy, helping steer the business side of things with your insights and foresight.
• Adaptable: Change doesn't faze you. In fact, you thrive in environments that evolve and grow.

About the Role:

• Accounting Operations: Own accounting at Trust & Will and its subsidiaries. Manage the month-end closing cycle, tax compliance, and accounts payable/receivable. Ensure accurate and timely financial data.
• Control and Compliance: Develop and maintain internal controls that keep us on track, safeguard assets, and position us to scale our operations.
• Audits and Reconciliations: Lead audits and keep our accounts in check, ensuring accuracy down to the last detail.
• Technology and Systems: Manage and optimize our accounting tech stack. Work closely with FP&A to keep our financial systems running, fully integrated, and efficient.
• Cost Analysis and Optimization: Partner with the CFO on financial strategy and planning, and work closely with FP&A to analyze costs and expenditures to identify opportunities.
• Vendor Management: Oversee vendor relationships and manage compliance with company policies.

Qualifications:

• Minimum of 10 years of accounting experience, with at least 4-5 years in a Controller or similar leadership role within a high-growth environment. CPA certification is preferred.
• Proven track record in financial reporting, compliance, and implementing financial controls.
• Hands-on experience applying AI or automation (e.g., LLM tools, reconciliation or close-management software, scripting) to accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.
• Proficiency in accounting software (e.g., Ramp, Rillet) as well as Google Sheets & Excel.
• Familiarity with financial regulations and reporting requirements, particularly those relevant to startups and IPO preparation.
• Proven experience managing and developing direct reports.
• Excellent communication and interpersonal skills, capable of explaining complex financial information to non-finance stakeholders.
• Strong analytical skills with a strategic mindset, able to contribute to business strategy and support decision-making processes.
• This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), Pennsylvania (PA), Texas (TX), Vermont (VT), Nevada (NV), Utah (UT)

Bonus Points for:

• Prior experience at a big 4 accounting firm
• Prior experience in a VC-backed startup or D2C company

Full-time Employee Benefits & Perks:

• Compensation: Salary + Equity
  • Our salary range for this position is $165,000 - $185,000, 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.
  • Financial wellness benefits (unlimited 1:1 sessions with a UBS financial coach and employer-sponsored 401 (k) 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 the 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 View email address on click.appcast.io. 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 View email address on click.appcast.io.

Applications will be accepted through 10/30/26. If the deadline is extended, this posting will be updated.