Overview
This role sits within the Service Operations tax and accounting team and serves as a bridge between tax and accounting functions. You will provide strategic direction on complex financial scenarios to help optimize books for successful tax delivery, act as a subject matter expert and advisor to internal teams, and lead a team as the function scales.
Responsibilities
- Understand complex-tier members’ financial background, business structure, goals, and tax situation; identify optimization opportunities so books-to-tax feels like a single, connected deliverable.
- Support a team of bookkeepers and tax staff by ensuring continuous growth, mentoring, and providing feedback on complex scenarios.
- Manage ongoing tax and bookkeeping delivery for complex-tier members, including reviewing year-round financial activity to bridge books-to-tax implications of business decisions.
- Handle escalations from less-complex members when circumstances move into complex-tier territory (e.g., unexpected rental property income, multi-state/nexus exposure). Determine whether it is a one-off issue or a broader need and resolve root causes.
- Review bookkeeping and federal/state tax returns, including Form 1040, 1120-S, 1065, and schedules such as C/E/SE, delivering high-quality work aligned with compliance requirements and member goals.
- Serve as the in-house technical expert for complex situations encountered by accounting and tax teams, including multi-state apportionment, nexus considerations, rental property basis, K-1 flow-through, payroll sourcing, and more.
- Partner with enablement to build playbooks and training modules so the team can learn and handle increased complexity over time.
- Upskill into additional service types or more complex work areas (e.g., payroll, additional business tax realms).
- Balance immediate member needs with the broader goal of raising what the organization can handle. Document complex scenarios, identify patterns, and translate them into training and process improvements.
Requirements
- Credentials: Active CPA, EA, or JD in state of residency.
- Experience: 5+ years scaling and bridging bookkeeping and tax operations.
- Technical proficiency in complex books and tax preparation, including multi-jurisdictional compliance and preparation of 1040, 1120-S, and related materials.
- Hands-on experience managing high-volume workflows and large client portfolios.
- Strong analytical and data-driven problem-solving skills.
- Ability to translate deep tax complexity into scalable workflows, bridging technical tax practice, bookkeeping, and high-volume service delivery.
- Tooling: Comfortable using Google Workspace, Slack, tax research/preparation tools (e.g., CCH, GoSystems, etc.), and issue/documentation tools (e.g., Jira, Confluence, etc.).
Preferred Qualifications
- Experience in documenting complex scenarios and turning findings into training and process improvements.
Compensation & Benefits
- Health & Wellness: $200 quarterly reimbursement to support well-being.
- Time Off: Flexible PTO plus 14 company holidays.
- Comprehensive Coverage: 100% medical, dental, and vision for employees; 75% coverage for dependents.
- Parental Leave: 16 weeks fully paid.
- Retirement & Ownership: 401k plan plus an equity package.
- Retirement & Ownership: 401k plan plus an equity package.
- Commuter Support (hybrid schedule): $150 monthly reimbursement for transit expenses.
- Team Connection: Quarterly virtual events and an annual in-person summit.
Location
- Remote-friendly environment with flexibility to work from home while staying connected to the team.
- Open to remote candidates within the U.S. for this role.
- Bay Area-based employees follow a hybrid schedule.
- Fresh lunch is provided on in-office days for those in a hybrid schedule.