Senior Tax & Payroll Support Specialist

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 a Senior Member Support Specialist at Collective, you will guide new members through a smooth and successful onboarding experience onto our all-in-one accounting platform, serving as a trusted resource for bookkeeping, payroll, and tax inquiries. This is a high-impact, customer-centric role where you will spend the majority of your day conducting video calls, breaking down complex technical topics into clear, easy-to-understand explanations. We’re looking for an expert who pairs deep tax and payroll knowledge with genuine customer service instincts—someone equally comfortable creating P&L reports and supporting solo entrepreneurs with a member-first mindset. The work is fast-paced and dynamic, and you’ll play a key guidance role in helping self-employed people understand their finances and run their businesses with confidence. What you'll do: - Conduct video calls with members each day (approximately 4–5 hours daily), guiding them through onboarding and day-to-day ongoing support needs. - Serve as a go-to resource for members navigating our platform, troubleshooting and escalating issues as needed. - Own complex and escalated member cases end-to-end with minimal oversight. - Guide members through running their first payroll and understanding payroll taxes, including S-Corp payroll considerations. - Break down complex tax and accounting topics into clear, easy-to-understand explanations. - Support Members Pre and Post onboarding with their support questions related to tax, accounting, payroll & overall use of our platforms - Set a high bar for every member interaction—professional, warm, and solutions-oriented. - Handle sensitive or high-stakes member conversations with confidence. - Manage a full portfolio of member conversations and tasks at once without letting quality slip. - Maintain accurate documentation across internal and external systems. - Partner cross-functionally to advocate for members and improve the overall experience. - Identify recurring member issues and share insights that help improve our processes and resources. What you'll bring: - 4+ years in customer experience or support, alongside 3+ years in Tax, or Accounting, or Payroll (combination of experience preferred). With those 3+ years being hands on working directly within accounting, tax, or payroll systems. - Hands-on proficiency with platforms like Xero, QuickBooks Online, Gusto, ADP, or similar accounting and payroll software. - A clear grasp of payroll taxes, with the ability to explain concepts like S-Corp reasonable compensation to a business owner with no financial background. - A genuine drive to support members, paired with strong, professional written and verbal communication skills. - Sharp attention to detail, strong task-management skills, and the self-direction to thrive independently in a fast-paced environment. 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