About Collective:

Collective is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork.

Featured in Forbes, Business Insider, Yahoo, Bloomberg, Financial Times, TechCrunch, and more. We are backed by General Catalyst, Sound Ventures, QED Investors, Google’s Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft.

About the role:

As part of the Service Operations tax and accounting team, you will play a vital role bridging our tax and accounting teams, providing strategic direction on our most complex financial scenarios to ensure our books are optimized for successful tax delivery. You will operate as a subject matter expert and advisor to internal teams, leading a team as the function scales.

What you'll do:

• Understand Complex-tier members' financial background, business structure, goals, and tax situation, helping identify optimization opportunities making books-to-tax feel like a single, fluid deliverable.

• Support your team of bookkeepers and tax staff, ensuring their continuous growth and capability. Mentor and provide feedback on complex scenarios they encounter.

• Manage our complex-tier members for ongoing tax and bookkeeping delivery. This includes reviewing year-round financial activity to bridge books-to-tax implications of business decisions.

• Handle escalations from less-complex members whose situations have crossed into complex-tier member territory (e.g., unexpected rental property income, multi-state/nexus exposure, etc.). You will make the call on whether it's a one-off issue or a larger need, and solve it at the root.

• Review bookkeeping and federal/state tax returns (Form 1040, 1120-S, 1065, and schedules such as C/E/SE), consistently delivering high-quality results that align with compliance requirements and member goals.

• Serve as the in-house technical expert when our accounting or tax teams encounter complex situations: multi-state apportionment, nexus considerations, rental property basis, K-1 flow-through, payroll sourcing, etc. Partner with enablement to build playbooks and training modules so the team continuously learns and handles more complexity over time.

• Willing to upskill into additional service types or more complex work areas (e.g., payroll, additional business tax realms, etc.)

• Balance immediate member needs with the broader goal of raising the bar on what the organization can handle. Document complex scenarios as they come up, identify patterns, and turn them into training and process improvements for the wider team.

What you'll bring:

• Credentials: Active CPA, EA, or JD in state of residency.

• Experience: 5+ years of experience scaling and bridging bookkeeping and tax operations. Technical proficiency in complex books and tax preparation (multi-jurisdictional compliance, 1040, 1120-S, etc.) combined with hands-on experience managing high-volume workflows and large client portfolios.

• Skills: Strong analytical and data-driven problem-solving skills; ability to translate deep tax complexity into scalable workflows, acting as the bridge between technical tax practice, bookkeeping, and high-volume service delivery.

• Tools: Comfortable working within Google Workspace, Slack, tax research/preparation tools (e.g., CCH, GoSystems, etc.), and issue-documentation tools (e.g Jira, Confluence, etc.).

What we offer:

• Remote-Friendly Environment: Flexibility to work from home while staying connected to the team. Please note that we're open to remote candidates within the U.S. for this role, but Bay Area-based employees follow a hybrid schedule.

• Health & Wellness: $200 quarterly reimbursement to support your well-being.

• Fresh Lunch: Provided on in-office days for those in a hybrid schedule.

• Commuter Support: $150 monthly reimbursement for transit expenses for those in a hybrid schedule.

• Health & Wellness: $200 quarterly reimbursement to support your 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.

• Team Connection: Quarterly virtual events and an annual in-person summit.

#LI-Remote