Tax Strategist

9 hours ago

remote us Pennywise Tax Strategies Full time

Tax Strategist - Small Business AdvocateDo you feel like there’s something missing in your current accounting role? Could you add more value to your clients' lives than just filling out tax forms? Do you hate the pressure and intensity of the busy season?What if you could work with clients interested in proactively approaching their taxes? Imagine a world where your clients work with you throughout the year, and you can show them how much money you help put into their pockets. They’re actually grateful for the work you did.Well, imagine no longer. Such a place exists.About Us:At Pennywise Tax Strategies, we are not just a tax preparation firm; we help small business owners take control of their income taxes and find hope for businesses supporting their professional mission and personal goals. Our team is driven by passion, expertise, and the desire to redefine “tax accountant” into “trusted advisor.” We are building a team of trusted advisors to guide our small business clients through the planning, implementation, and filing of their income taxes with tax planning that supports both their business and life in accordance with the law.The Role:We are looking for someone who takes pride in solving tricky problems for struggling venture creators.Generally, we meet with our clients once per month to review their business's progress for the year. We build tax plans and help implement and document strategies that put more money in our clients' pockets. This is not a traditional tax prep role. This is more in line with tax advisory, and we serve primarily small businesses and venture creators.Compensation:$75,000 - $90,000 yearlyResponsibilities:Identify and implement cutting-edge tax strategies for a diverse portfolio of clients.Stay ahead of the curve with continuous research on tax laws, regulations, and best practices.Provide expert tax planning and advisory services tailored to each client's unique needs.Collaborate with our financial advisors and wealth management team to deliver holistic solutions.Represent clients in tax audits and liaise with tax authorities as needed.Mentor fellow team members and foster a culture of continuous learning and innovation.Qualifications:We would prefer an EA, CPA or Tax AttorneyPrefer 3-5 years of experience in tax strategy, planning, and compliance.Exceptional analytical skills and attention to detail.Strong communication skills with the ability to explain complex tax concepts clearly.Proficiency in tax software and technology-driven solutions.A proactive, problem-solving mindset with a passion for innovation.About CompanyPennywise Tax Strategies is built on a simple belief: small business owners deserve better tax advice—and better tax experiences.We are a growing firm focused on raising the standard in small business tax accounting. That means thoughtful preparation, real planning, and professionals who care deeply about the work and the people behind it.We live by four core values:Find the TruthFigure It OutBe Curious, Not JudgmentalTake Our Job Seriously, But Not Ourselves Too SeriouslyWe’re scaling intentionally—our team, our systems, and our impact. We value people who take ownership, ask good questions, and want to be part of building something that actually matters.If you want to do work you’re proud to sign, serve clients you respect, and grow into deeper responsibility over time—we’d love to hear from you.

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