Senior Tax Advisor

Two Roads co; Knoxville (TN); Remote; USD 140,000 - 190,000; Full time

Job summary

Two Roads co is expanding its tax practice and seeking a senior tax professional to own complex client relationships from planning through return preparation. You will provide advisory-level guidance, entity-structure decisions, and proactive communication within a fully remote, distributed team.

The role emphasizes year-round client service, mentorship to junior staff, and leadership in adopting AI-driven workflows to improve quality and speed. Compensation reflects depth and judgment.

Qualifications

• CPA or EA license, active and in good standing.
• 5+ years preparing and 3+ years reviewing complex individual and business returns (Forms 1120S, 1065, 1120, 1040).
• Experience advising on entity structure, reasonable compensation, tax planning, and business expansion.
• Experience reviewing and mentoring less experienced preparers, comfortable being the final technical checkpoint before a return goes out.
• Track record of proactive client communication: following up before a client asks, and communicating candidly and early.
• Comfort working fully remote as part of a distributed team.

Responsibilities

• 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.
• Advise clients directly on entity classification, reasonable compensation, and tax-minimization strategy.
• Review and troubleshoot the most complex returns before they go out, including work 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.
• Partner with 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.

Skills

CPA or EA license

5+ years tax preparation

3+ years reviewing tax returns

Mentoring preparers

Proactive client communication

Remote work experience

AI workflow adoption

Tools

Karbon

TaxDome

AI-assisted research tools

Claude tools

Job description

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.

About Two Roads

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, TaxDome, 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.

About the Role

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.

What You’ll Do

• 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, TaxDome, and AI-assisted research, so each season gets better, not just busier

What We’re Looking For

Required:

• 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 part of a distributed team

Preferred:

• CPA license
• A history of being an individual a team and its clients rely on, even without a formal management title
• Experience in a fractional CFO, outsourced accounting, or multi-client advisory environment, rather than a single-company in-house tax role
• Familiarity with TaxDome or comparable practice-management and workflow tools
• Comfort using AI tools as part of a research and review workflow
• Experience using AI tools such as Claude or Claude Code in research and review, and to build workflows, automations, or tools for a team

This is a senior-level position and compensation will reflect the technical depth and judgment you bring. We’ll talk specifics once we understand your background and experience.

An overview of our interview process:

• Online Application
  • This application could take 1+ plus hours to complete and you can’t save as you go, so plan to complete this in 1 sitting.
  • You’ll need your resume handy in an electronic format.
  • You will be asked to record a video of yourself.
• We will review your application and when we see a potentially great fit, we’ll follow up with an initial video interview.
• Once we’ve discovered your values, goals, and vision align with ours, a second video interview will take place with your potential Team Lead and a team member, where you will have an opportunity to discover if we’d be the right fit for you.
• At this point we’ll check references and if all of that checks out, a final video interview will take place with the upper management of Two Roads to answer any final questions either party may have to ensure a win‑win.
• We’ll then perform a background check, draft the offer letter, finalize details on start date, etc., and get started!