SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 165,000 - 185,000 / annual
Trust & Will is the leading digital estate planning platform, trusted by over one million users. Founded in 2017, the company provides modern, accessible solutions to help families protect their legacies with attorney-approved, legally valid documents tailored to individual state requirements.
Reporting to the CFO, the Controller will be instrumental in steering financial operations during a period of exciting growth. This is a hands-on leadership role overseeing all accounting operations for Trust & Will and its subsidiaries.
Key Responsibilities:
- Own accounting operations including month-end closing cycles, tax compliance, accounts payable/receivable, and ensure accurate, timely financial data
- Develop and maintain internal controls that safeguard assets and position the company to scale operations
- Lead audits and reconciliations, ensuring accuracy across all accounts
- Manage and optimize the accounting technology stack, working closely with FP&A to keep financial systems integrated and efficient
- Partner with the CFO on financial strategy and planning; analyze costs and expenditures to identify optimization opportunities
- Oversee vendor relationships and manage compliance with company policies
- Lead and develop the accounting team
The ideal candidate is dynamic, thrives in fast-paced environments, and brings an AI-native mindset to accounting operations. You will be fluent in modern accounting systems, default to AI and automation first, and build repeatable workflows that make a lean finance team more effective. Strong communication skills are essential—you must be as comfortable crunching numbers as explaining them to non-finance stakeholders. You are analytically inclined with a strategic mindset, adaptable to change, and ready to contribute to business strategy and decision-making.
Requirements:
- Minimum 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 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 and 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
- Strong analytical skills with a strategic mindset
- Must reside in one of the following states: CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, PA, TX, VT, NV, or UT
Bonus Points:
- Prior experience at a Big 4 accounting firm
- Prior experience in a VC-backed startup or D2C company
