The posting
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:
When something goes wrong for a member, the outcome should not depend on who they happen to reach or how loudly they complain. Today it too often does. Escalations are handled by whoever picks them up, context is spread across Jira, Zendesk, Slack and email, some cases stay open for months, and the hardest ones pull executives and line managers away from running the business. As Collective grows from about 9,000 to 22,000 members by mid-2027, escalation volume will grow with it.
As the founding Member Resolution Lead, you own every escalated member issue at Collective and the system that resolves them. For our most complex cases you are the single-threaded owner: you take over the member relationship, calm the situation, set a resolution plan, drive the fix with our accounting and tax teams, represent the member before the IRS or a state when needed, and close the loop. At the same time, you design and implement the system that makes this scale: the taxonomy, the decision rights, the resolution economics model that decides what can be auto-approved, the rules that fast-track small claims, and the root-cause loop that removes the reasons members escalate in the first place.
If you are a CPA or EA who has practiced tax and accounting, has run operations, thinks in systems and models, and stays calm and clear with an upset member or a CEO, this is the role.
What you'll do:
- Own every escalation end to end, from routine fee-waiver and refund requests to complex service failures and cases with legal, regulatory or reputational exposure.
- Act as the single point of contact for escalated members: listen, explain what happened in plain language, commit to a resolution plan with dates, and deliver it.
- Diagnose tax and accounting failures yourself, set the resolution plan, and direct the back-office fix with Accounting, Tax and Entity Ops.
- Hold Power of Attorney and represent members before the IRS and state agencies when a case requires it.
- Resolve vendor-caused harm for members, document it, and recover costs from the vendor.
- Build the resolution economics model that weighs payouts against handling cost, retention and legal or reputational exposure, and use it to set auto-approval thresholds.
- Write the resolution policy and decision-rights matrix: what you decide alone, what needs a second reviewer, and what goes to Legal or executive leadership.
- Specify the rules, routing and case record that Strategic Operations and Engineering build, and own their performance once live.
- Stand up a single case record and an escalated-member flag, retire Slack channels and direct messages as places where escalations are managed, and set SLAs by lane.
What you'll bring:
- An active CPA license or IRS Enrolled Agent credential, with authority to represent taxpayers before the IRS.
- 8+ years across tax and accounting practice and operations, including hands-on preparation or review of returns and books for small businesses or self-employed clients.
- A track record owning high-stakes client or customer escalations end to end, including cases with financial, legal or reputational exposure.
- Evidence that you have built a system, not only worked a queue: written policies, decision frameworks, rules or automation, workflows and dashboards. You can show what you built and what changed because of it.
- Comfort with quantitative modeling such as expected value, thresholds and cohort analysis. You build your own models in spreadsheets or SQL and explain them to non-specialists.
- Working knowledge of the legal and regulatory side of tax practice: Circular 230, Section 7216, penalty abatement and reasonable cause, notice response, and where a tax question becomes a legal one.
- A calm, warm and direct manner with upset people. Members mostly want the problem fixed and to feel heard, and you can do both in the same conversation.
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.
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