Director / Principal, Tax Controversy & Strategic Tax Advisory

Apply Job Type Full-time Description Director / Principal, Tax Controversy & Strategic Tax Advisory Location: Remote (U.S.) Preferred Work Schedule: Pacific Time Zone or ability to support Pacific Time Zone business hours Job Type: Full-Time Salary: $150,000-$300,000 annually, depending on experience Bonus Opportunity: Performance-based bonus tied to leadership, quality, profitability, and practice growth Build and Lead a Specialized Tax Practice at the Intersection of Controversy, Research, and M&A Keystone CPAs is seeking a senior tax leader to direct and grow our Tax Services Group (TSG), a specialized national practice that helps small and midsize business owners, CPA firms, and advisors resolve complex tax matters and make better strategic decisions. This is not a traditional engagement-manager role. The successful candidate will own the growth and direction of the practice, serve as a primary bridge between Keystone’s principals and managers, lead our most complex controversy and research matters, and support tax planning for mergers and acquisitions involving Keystone Business Brokers clients. Depending on experience, credentials, leadership history, and demonstrated practice-building ability, the successful candidate may be considered at the Director or Principal level. About Keystone Keystone is an integrated advisory firm focused on helping small and midsize business owners build stronger companies and better financial lives. We help clients improve performance, increase enterprise value, create scalable businesses that are not overly dependent on the owner, prepare for and potentially execute a business sale, and convert business success into long-term personal wealth. Our platform brings together Keystone CPAs, Keystone Business Brokers, and Keystone Wealth Advisors. This allows us to support owners throughout the business lifecycle - from accounting, tax compliance, CFO advisory, and strategic planning, through transaction preparation and execution, and ultimately into personal wealth planning, investment management, and legacy planning. The Tax Services Group is a key part of this integrated model. TSG handles sophisticated tax issues that extend beyond traditional return preparation, including federal and state controversy, advanced tax research, technical memorandums, strategic planning, and transaction tax consulting. Position Summary The Director / Principal will be the senior practice leader for TSG. This individual will combine technical tax depth, executive-level client service, business development, team leadership, and sound commercial judgment. The role is accountable not only for the quality and delivery of engagements, but also for growing the practice, strengthening Keystone’s market position, and ensuring TSG expertise is effectively deployed across the firm. A central responsibility is serving as the primary technical and leadership interface between Keystone’s principals and managers. The Director / Principal will help identify client needs, frame the right scope, assemble the right team, guide complex analysis, communicate recommendations, and ensure that controversy, research, planning, brokerage, and wealth-advisory opportunities are coordinated in the client’s best interest. What You Will Do Practice Leadership and Growth Set the strategic direction and annual operating plan for the Tax Services Group. Grow practice revenue, qualified pipeline, referral relationships, and market visibility while maintaining strong quality and profitability. Identify and develop new service offerings that respond to recurring client and referral-source needs. Lead business development efforts with business owners, attorneys, CPA firms, investment bankers, lenders, and other professional advisors. Develop pricing, scoping, staffing, and delivery models that allow the practice to scale without sacrificing technical quality or client service. Represent TSG in firmwide planning and help Keystone principals evaluate opportunities, priorities, risks, and resource needs. Principal and Manager Interface Serve as the primary technical point of connection between Keystone’s principals and managers on complex controversy, research, and strategic planning matters. Help principals and managers recognize when a client issue requires specialized tax controversy, research, transaction, or planning support. Translate client objectives into clear engagement scope, technical workstreams, staffing plans, budgets, and deliverables. Provide practical, timely guidance that enables managers to lead client relationships with confidence while appropriately escalating high-risk or judgmental matters. Create repeatable processes, tools, training, and communication protocols that make TSG expertise accessible across the firm. Tax Controversy and Technical Leadership Lead significant federal and state tax controversy matters, including examinations, administrative appeals, collection matters, penalty disputes, and other complex IRS or state agency proceedings. Research and interpret the Internal Revenue Code, Treasury Regulations, IRS guidance, Revenue Rulings, court decisions, and other authoritative tax sources. Develop defensible technical positions, legal and factual arguments, risk assessments, and practical resolution strategies. Prepare and review high-quality technical memorandums, opinion-level analyses, protest letters, responses to information document requests, and other written advocacy. Coordinate effectively with clients, CPAs, attorneys, valuation professionals, and other outside advisors. Act as a trusted technical resource for Keystone professionals and partner CPA firms nationwide. M&A and Transaction Tax Planning Partner with Keystone Business Brokers and Keystone principals to identify and address tax issues early in the transaction process. Advise business owners on transaction structure, pre-closing tax planning, entity restructuring, tax modeling, purchase price allocation, rollover equity, and other seller-focused planning considerations. Assist with tax due diligence, quality-of-earnings follow-up, transaction document review, and coordination with buyer and seller advisors as appropriate. Explain tax tradeoffs in practical business terms so owners can evaluate after-tax proceeds, risk, timing, and deal certainty. Coordinate with Keystone Wealth Advisors when transaction planning affects liquidity, investment strategy, charitable planning, estate planning, or long-term wealth objectives. Develop transaction-planning tools and standardized processes that allow Keystone to deliver a consistent, differentiated experience to business owners. Client and Market Leadership Own senior-level relationships with key clients and referral sources. Lead high-stakes client meetings and present complex conclusions clearly, directly, and credibly. Build Keystone’s reputation through articles, presentations, webinars, professional education, and other thought leadership. Develop durable relationships with CPA firms that need specialized controversy, research, or transaction tax support without displacing their core client relationships. Identify broader Keystone opportunities while maintaining a client-first, needs-based approach. Team Leadership and Talent Development Lead and develop a fully remote, project-based team of approximately four tax professionals located throughout the United States. Clarify roles, set priorities, assign work based on expertise and capacity, and maintain accountability for deadlines and quality. Coach managers and professionals through complex technical issues rather than simply reviewing work at the end. Conduct thoughtful quality reviews and ensure work product is technically sound, persuasive, practical, and consistent with firm standards. Recruit, onboard, retain, and develop high-performing professionals and future practice leaders. Create a culture of urgency, ownership, collaboration, candor, and continuous improvement. Engagement Economics, Quality, and Risk Oversee engagement acceptance, scope, budgets, staffing, timelines, realization, profitability, billing, and collections in coordination with firm leadership. Proactively identify technical, legal, reputational, independence, staffing, and delivery risks. Establish quality-control and documentation standards appropriate for controversy, technical research, and transaction planning engagements. Communicate status, risks, and decisions clearly to firm leadership and clients before deadlines or budgets are compromised. Balance technical rigor with commercial practicality and efficient delivery. What Success Looks Like Within the first 12 months, the Director / Principal will: Establish credibility as the firm’s senior leader for tax controversy, advanced research, and strategic transaction tax planning. Build strong working relationships with Keystone principals and managers and create a reliable process for identifying, scoping, and delivering TSG engagements. Develop and begin executing a multi-year growth plan for TSG, including priority services, target referral sources, pipeline development, staffing, and profitability. Strengthen the integration of TSG with Keystone Business Brokers and Keystone Wealth Advisors, particularly for owner transition and liquidity events. Deliver high-quality work on time, within agreed scope, and with strong client satisfaction and engagement economics. Develop managers and team members so the practice can scale without becoming dependent on one individual. Expand Keystone’s reputation as a practical, technically sophisticated resource for business owners, attorneys, and CPA firms nationwide. Why Keystone This role offers more than technical complexity. It is an opportunity to build a differentiated advisory practice inside an entrepreneurial firm that serves business owners across the full lifecycle of enterprise value creation, transaction readiness, sale execution, and wealth planning. Lead and grow a specialized national practice with direct access to firm leadership. Work on sophisticated tax controversy, research, planning, and transaction matters. Shape firm strategy, service development, talent, and market position. Collaborate across accounting, CFO advisory, business brokerage, and wealth management. Build long-term relationships with business owners, CPA firms, attorneys, and other advisors. Work in a flexible, fully remote environment while making a visible impact. Benefits and Perks Competitive salary and performance-based bonus opportunity. Medical, dental, and vision insurance. Company-paid life insurance. 401(k) with company match. Paid Time Off (PTO) and paid holidays. Fully remote work environment and flexible scheduling. Company-issued laptop and technology. Continuing education support and professional membership reimbursement. Leadership development opportunities. Collaborative and entrepreneurial culture. Equal Employment Opportunity Keystone CPAs is proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive workplace for all employees and applicants. Employment decisions are made based on qualifications, merit, and business needs, without regard to race, color, religion, sex, pregnancy, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, veteran status, or any other characteristic protected by applicable federal, state, or local law. Requirements Qualifications Required Juris Doctor (J.D.) from an accredited law school and an active attorney license in good standing. 10+ years of progressive experience in federal tax law, tax controversy, technical tax consulting, or a closely related specialty practice. Deep knowledge of the Internal Revenue Code, Treasury Regulations, IRS administrative procedures, tax research, and controversy principles. Demonstrated experience leading complex technical matters and producing exceptional written work product. Proven ability to lead senior client relationships, influence executives, and explain complex tax issues in practical business terms. Demonstrated success developing business, expanding client relationships, building referral networks, or growing a specialty practice. Experience leading managers and professionals in a remote or project-based environment. Strong commercial judgment, project discipline, communication skills, and personal accountability. Strongly Preferred LL.M. in Taxation and/or CPA license. Experience representing clients before the IRS and state taxing authorities. Experience in public accounting, a national tax practice, a tax law firm, or a specialized consulting environment. Experience with closely held business M&A tax planning, transaction structuring, seller tax modeling, or tax due diligence. Experience supporting CPA firms and other professional advisors as a specialized technical resource. A meaningful network of business owners, attorneys, CPAs, bankers, brokers, or other referral sources. Experience managing practice economics, including pricing, realization, margin, pipeline, and staffing. Familiarity with CCH Axcess, Microsoft Teams, and remote collaboration tools. Salary Description $150,000–$300,000