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Specialty Tax Advisory Services for Middle Market Businesses

As your business grows, so does the complexity of your tax landscape. We provide practical, high-impact tax strategies tailored to the unique challenges faced by middle market companies.

Tax Strategy That Grows With Your Business

Middle Market companies often find themselves in a challenging spot: they’re big enough to face thorny tax challenges, but not large enough to have sufficient in-house resources to manage them effectively. From multistate expansion and international operations to M&A and equity compensation, the stakes are high, and the right guidance can make a real financial difference.

With experience advising companies with an average revenue range of $5 million to over $250 million, we’ve worked closely alongside CFOs, controllers, and business owners on all manner of tax issues. Whether you’re scaling, restructuring, or planning a transaction, we can help you navigate complexity with clarity and confidence.

Industries Served

We serve clients in every industry, but have particular expertise across the following areas:

Technology & SaaS
eCommerce & Consumer Products
Investment Funds & PortCos
Startups
Manufacturing & Distribution
Life Sciences
Cannabis
Cryptocurrency & Digital Assets

Comprehensive Tax Support for Middle Market Needs

Companies face evolving tax challenges as they grow—whether it’s navigating multistate expansion, managing global operations, or preparing for a transaction. Our specialty tax solutions bring the technical expertise and responsive service you need to move forward with confidence.

Entity and Transaction Planning

As middle market businesses grow, structural changes can present significant challenges. We help you make smart, tax-efficient decisions as you reorganize, take on new investors, or prepare for an acquisition.

  • Acquisitions, Reorganizations, and Exits for Mid-Market Businesses: We help middle market buyers and sellers navigate the tax complexities of asset, stock, and reorganization transactions, balancing tax efficiency, basis step-up opportunities, and multistate and cross-border exposure to support long-term value creation.

  • Partnership Agreements & Restructurings: We help review and structure operating agreement tax provisions, restructure existing arrangements to optimize allocations, preserve intended economics, and ensure compliance with partnership tax rules such as Section 704(b) and 704(c).

  • Entity Structuring & Operational Alignment: We evaluate and help optimize entity structures in light of growth plans, ownership goals, and tax exposure—advising on conversions, reorganizations, and other changes that support scalability and reduce long-term tax burdens.

  • QSBS and Other Tax Opportunities: Evaluate eligibility and structure to capture key tax benefits.

We bring deep technical experience to entity and transaction structuring decisions, helping you move forward with confidence.

Multistate and Local Tax Compliance

Operating across states presents a web of tax obligations. We help businesses navigate nexus rules, manage audits, and stay compliant with state and local requirements.

  • Income & Franchise Tax Nexus Studies: Identify where your business is required to file based on physical presence, economic nexus thresholds, affiliate activities, and apportionment factors.

  • Sales & Use Tax Nexus & Taxability Reviews: Determine where you have sales tax obligations and clarify the taxability of your products or services across jurisdictions, including digital goods and bundled offerings.

  • Voluntary Disclosure Agreement (VDA) Support: Proactively resolve historical issues and reduce penalties.

  • Sales Tax System Setup & Support: Establish processes to handle tax collection, remittance, and exemption management across platforms.

  • State & Local Credits & Incentives: Identify and pursue tax-saving opportunities tied to hiring, investment, R&D, and geographic expansion—while staying compliant with program requirements.

Our clients rely on us to reduce risk and proactively manage their state and local tax posture.

International Tax Planning and Reporting

Global markets promise huge opportunities but also present serious tax complexity. We offer practical guidance on cross-border structuring, reporting, and risk management.

  • Outbound & Inbound Structuring: Optimize the structuring of international expansions to achieve tax efficiency.

  • Permanent Establishment (PE) and Other Taxable Presence Analyses: Assess cross-border activities to determine whether a taxable presence exists under U.S. and foreign laws, factoring in applicable treaties to help mitigate unexpected exposures and avoid triggering filing obligations prematurely.

  • Global Tax Minimization Strategies: Structure operations and intercompany flows to reduce effective tax rates, leveraging treaty benefits, foreign tax credits, and entity structure to improve global tax efficiency.

  • Customs & Tariff Strategy: Support planning for customs classification, first sale strategies, and supply chain optimization.

We help you manage global tax issues with the same sophistication as larger firms.

Equity Compensation Tax Strategy

As companies grow, equity and compensation strategies evolve. We help you align tax strategy with employee retention and long-term value creation.

  • Restricted Stock Awards (RSAs) & Restricted Stock Units (RSUs): We advise on restricted stock and RSU grants, considering vesting schedules, liquidity events, and 83(b) election strategies to align business priorities with timing and tax implications for the grantees.

  • Nonqualified Stock Options (NSOs) & 409A Compliance: We advise on the structure and timing of NSO grants to align with hiring goals and minimize ordinary income exposure. We also ensure compliance with Section 409A valuation and deferral rules to avoid costly penalties.

  • Incentive Stock Options (ISOs): We help structure ISO grants to support retention and exit strategy goals, while meeting the requirements of Section 422.

  • Partnership Profits Interests, Capital Interests, and Options: For partnership and LLC structures, we help you optimize the granting of equity interests through profits interests, capital interests, and options to align incentives while addressing allocation and valuation issues.

Our guidance helps you retain top talent and avoid common equity compensation-related tax pitfalls.

Tax Advocacy and Dispute Resolution

Middle market businesses are increasingly facing tax examinations and other issues with tax authorities, often with limited internal resources. We provide the support you need to respond strategically and protect your position.

  • Audit & Appeals Representation: Take charge of tax audits and lead communication and documentation with the IRS or state authorities to work toward favorable results.

  • Pre-Audit Readiness Assessments: Diagnose areas of exposure and take proactive steps to mitigate them, reducing audit risk.

  • Penalty Abatements and Other Waiver Requests: Identify opportunities to reduce or eliminate tax penalties.

We help clients work through tax disputes with confidence, protecting outcomes and minimizing disruption.

How to Restructure Your Supply Chain to Mitigate Tariffs and International Tax Exposure

In recent months, the global trade landscape has shifted dramatically with the introduction of tariffs from the U.S. and reciprocal tariffs from other nations such as China. These tariffs directly impact profitability, cash flow, and competitive positioning for businesses with cross-border supply chains.

Schedule a Consultation

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