Gambit is building the tax firm of 2030.
AI is already changing the industry with over 6 million tax returns prepared and filed in the 2025 tax season relying on AI tools. The White House Council of Economic Advisors identified tax preparation as one of the professions most exposed to AI disruption. But the work will shift, not disappear. The invention of Excel replaced 1M bookkeeping jobs with 1.5M financial analyst jobs. AI will do the same for tax. Compliance gives way to tax advisory and strategy.
Most taxpayers play defense. We play to win. Our clients come to us because they want a partner who finds every strategy they qualify for, calculates the precise benefit, and helps them execute. Not just a firm that files accurately and on time.
We have raised $4.3m in capital and have offices in San Diego and Palo Alto. Gambit’s culture is built around 5-Star Service, comfort with change, and humility. Join us.
About the Tax Manager Role
The shift from tax compliance to tax advisory is already underway. This role is built around that shift. You\'ll prepare and review returns (that\'s the foundation and it matters) but what we\'re building toward is a firm where the return is the starting point for strategy, not the end product. You\'ll work directly with founders who have rethought what a tax firm can be, develop real fluency in AI tools that are already changing how this work gets done, and have a genuine say in how we operate. If your idea of a great day is clearing a return queue, this isn\'t the right fit. If it\'s finding something most preparers miss and making sure the client knows about it then keep reading.
- Report directly to the CEO, who built and scaled his previous company to $100M in revenue.
- Work alongside our COO/cofounder who has been a pioneer in using AI to boost the productivity of human experts in organizations including the NBA and Salesforce.
- Future-proof your skill set and become fluent in AI tools
- Hybrid Role. San Diego or Bay Area based. Minimum 2 days/week in the office. This is not a remote role.
About You
- CPA or EA
- Minimum 5+ years of tax preparation experience. Management experience is a plus but not a requirement.
- Tax expert. You know the tax code well enough to go on offense. Comfortable with complex individual returns, S-corps, partnerships, multi-state situations, and real estate. You\'ve seen enough variations to spot an opportunity most preparers miss.
- You can explain a complex tax strategy to a client who doesn\'t know what a K-1 is, and to one who does. Client-facing from day one you will own onboarding, strategy calls, and tax season check-ins. You won\'t be responsible for sales or business development. Your job is to make clients feel like they have an unfair advantage.
- Tech-fluent. Comfortable with technology and excited to go deeper. You\'ll develop fluency in AI tools on the job. You need to already be at ease with practice management software, cloud storage, and Zoom.
- You take it personally when a client overpays. When someone gets a great outcome, that\'s the best part of the job.
- You\'re comfortable not having all the answers. We\'re building something that doesn\'t fully exist yet.
Key Responsibilities
- Own client relationships for a portfolio of high-net-worth individuals, S-corp owners, and real estate investors. Be responsive and proactive all year (not just during tax season).
- Partner with the founders on service offerings, pricing, and the technology roadmap
- Prepare and review complex individual, S-corp, partnership, trust, and multi-state returns. This is the core of the role and where the client relationship is built.
- Identify tax strategies most preparers miss and bring them to clients with a clear calculation of the benefit
- Build and enforce quality control processes as the team grows
- Be a voice on how we operate. If you see a better way, say so.
- See full details in on our website: