Tax Manager

Are you a seasoned tax professional who’s ready to lead, not just do?

Do you find joy in solving complex problems, mentoring team members, and making a real difference in the lives of small business owners?

If you\’re looking for a tax manager role that values strategy over stress, and impact over hours, you’ve just found it.

Imagine working with clients who appreciate your proactive approach to their finances, rather than bringing everything to you at the last minute (or even after that).

If the following appeals to you, you\’ll love this job:

• You\’ll work directly with entrepreneurs who value your insights.
• You’ll help grow and lead a high-performance, mission-driven team. This is non-negotiable, as we are building a world-class team.
• You’ll do meaningful, year-round work that makes a visible difference.
• You won’t suffer through another overloaded, burnout-inducing busy season.
• You’ll join a team where innovation is welcomed, not stifled.
• You\’ll be in the audience for an abundance of puns and dad jokes. Maybe you\’ll be a contributor to them…

Responsibilities

• Leading strategic tax planning for a portfolio of small business clients.
• Reviewing returns and planning work to ensure accuracy, compliance, and value.
• Managing team workflow and project deadlines across multiple clients.
• Coaching and developing staff accountants and junior strategists.
• Collaborating with firm leadership to improve systems, tools, and processes.
• Serving as the point of contact for high-value client relationships.

Qualifications

• CPA or EA designation (active and in good standing).
• 6+ years of progressive tax experience, with at least 2 years in a managerial role .
• Strong experience with S-Corps, LLCs, and high-income entrepreneurs.
• Track record of mentoring team members and leading successful client engagements.
• Strong organizational and workflow management skills.
• Excellent communication — both with clients and your internal team.
• Experience with modern, cloud-based accounting software (we love tech-forward thinkers).
• A strategic mindset paired with a roll-up-your-sleeves attitude.

Compensation: $120,000 – $165,000 yearly

About Pennywise Tax Strategies:

At Pennywise Tax Strategies, we’re not just a tax preparation firm. We help small business owners take control of their income taxes and align their financial goals with their missions. Our team redefines the term “tax accountant” into “trusted advisor.” We are a fast-growing business following in the footsteps of our other company.

We are an equal-opportunity employer committed to diversity and inclusion. We ensure that all qualified applicants are considered for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status. Your unique perspective and background are valued here.

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