Senior Tax Advisor

We’re growing our tax practice at Two Roads and looking for a senior tax professional ready to strengthen the team: an individual other preparers and clients turn to for complex returns and thoughtful guidance. This is a senior individual-contributor role with real room to grow as the practice does.

Two Roads is a tech-forward, remote financial firm offering bookkeeping, tax, and CFO advisory services to small businesses and nonprofits. We’re building our reputation on relationship-first, high-touch client service: the belief that great tax work means more than filing a return correctly and on time. Our team uses modern tools, including Karbon, Tax Dome, and AI-assisted research tools, to work efficiently, but the differentiator is always the advice: entity structure, tax planning, and proactive guidance clients can’t get from a once-a-year preparer.

This role reports to our Tax Service Lead and exists because our tax clients increasingly expect year-round, advisory-level partnership, not just compliance, and because our growing practice needs someone senior enough to own that standard for our most complex client relationships and to be a steady technical reference point for the rest of the team. In your first year, you’ll take on a book of complex clients and become an individual clients and teammates turn to for technical guidance: multi-entity structures, election decisions, and situations that call for real judgment and a clear, proactive conversation.

We’re looking for someone with the depth and composure to take on that role fully, including guiding less experienced preparers as they grow, with compensation and scope that grow to match what you bring.

• Own a book of complex tax clients end-to-end: return prep and review, entity structure and tax planning conversations, and proactive year-round communication, not just at deadlines
• Advise clients directly on entity classification, reasonable compensation, and tax-minimization strategy, meeting with them regularly and translating technical positions into plain-English guidance
• Review and troubleshoot the most complex returns before they go out the door, including work prepared by others on the team
• Serve as a mentor to other preparers, becoming a go-to resource for technical questions
• Own the judgment calls on your client book, providing candid, proactive communication and raising the biggest decisions to the Tax Service Lead
• Dig in when needed to reconcile and adjust client books so figures for tax planning and preparation are accurate
• Partner with our bookkeeping and CFO advisory teams so tax fits into the bigger picture of each client’s finances
• Help lead the adoption of AI and workflow tools across the tax team, including Karbon, Tax Dome, and AI-assisted research, so each season gets better, not just busier

• CPA or EA license, active and in good standing
• 5+ years preparing and 3+ years reviewing individual and business tax returns, including Forms 1120S, 1065, 1120, and 1040
• Experience advising clients directly on entity structure, reasonable compensation, tax planning, and business expansion, not only preparing returns to spec
• Experience reviewing and mentoring less experienced preparers, comfortable being the final technical checkpoint before a return goes out
• A track record of proactive client communication: following up before a client has to ask, and communicating candidly and early, even when the news isn’t what a client hoped to hear
• A detail-oriented professional with a servant’s heart
• A track record of improving how a team works, whether by adopting new tools, building better processes, or using AI to raise quality and speed
• Comfortable working fully remote as…