Our panel of experts breaks down the financial and technology hurdles facing small businesses in 2026 and how to overcome them.
Tom Sullivan
Senior Vice President of Small Business Policy, U.S. Chamber of Commerce
What are the top financial barriers small businesses face in 2026, and what solutions should be prioritized?
The biggest barrier small businesses face in 2026 is uncertainty. While entrepreneurs are risk-takers, they are cautious about taking on too much debt in an uncertain economic environment. Right now, many small business owners are reluctant to embrace aggressive growth strategies without some assurance that prices and inflation will stabilize.
Whether it’s around tax, trade, energy, artificial intelligence (AI), or workforce policy, agreement from leaders in Washington on long-term solutions helps small business owners prioritize aggressive growth strategies.
For example, every new regulatory mandate raises the cost of a small business loan. Small business lenders need a reprieve to continue to help small businesses grow and thrive.
Last year, pro-growth tax provisions for small businesses became permanent through the One Big Beautiful Bill Act. We need more stable, bipartisan agreements like this to bolster small business owners’ long-term confidence.
What technology gaps are preventing small businesses from staying competitive in 2026, and how can we address them?
Small businesses’ adoption of AI is skyrocketing. Our research found that 58% of small businesses report using generative AI. However, there continues to be a need for training and trusted information when it comes to harnessing the full potential of AI.
Programs like Small Business B(AI)sics, recently launched by the U.S. Chamber of Commerce and U.S. Chamber of Commerce Foundation, with support from Google.org’s AI Opportunity Fund, are filling this need. The program offers free online and in-person AI training courses to equip entrepreneurs with skills to save time, grow revenue, reach new customers, and strengthen local economies.
Continued AI adoption also hinges on regulatory certainty at the federal level. According to our survey, 65% of small business owners say they are anxious that varying state laws on AI and data privacy will expose them to crushing compliance and litigation costs.
When a family-owned retailer or a local tech startup has to untangle complex, overlapping compliance mandates just to reach out-of-state customers online, the cost of doing business quickly becomes prohibitive. That is why the U.S. Chamber is working with Congress to establish clear, consistent national standards for both data privacy and AI.
What educational or operational support do small businesses need most in 2026 to successfully scale and grow?
One thing every small business I meet has in common is a fierce dedication to their community: their families, employees, teachers, coaches, business peers, friends, and neighbors. Oftentimes, operational support — whether it’s workforce training, access to capital, or access to markets — is close to home. Local and state chambers of commerce supply localized, peer-led support systems for entrepreneurs and founders.
At the national level, predictability, stability, and trust are the critical ingredients for a healthy free enterprise system where small businesses and the communities they operate in can thrive.
Danielle Kane
Senior Vice President and Head of Small Business Banking, Grasshopper Bank
What are the top financial barriers small businesses face in 2026, and what solutions should be prioritized?
In 2026, the most prominent financial barriers are persistent inflation, the management of unpredictable cash flow, and the quiet drain of stagnant capital. The U.S. Chamber of Commerce’s Q1 2026 Small Business Index highlights that inflation remains the leading challenge. At Grasshopper Bank, we consistently see that poor cash flow visibility and the “set it and forget it” mentality regarding cash reserves leave small businesses vulnerable when market demands shift.
Prioritized solutions include:
- Making Every Dollar Work Harder: In a high-inflation environment, idle cash loses value. Businesses must prioritize optimizing their capital by moving operating balances into high-yield checking and savings accounts that earn meaningful interest without sacrificing liquidity.
- Proactive Cash Flow Visibility: Small businesses must shift from reactive tracking to proactive forecasting. Utilizing banking partners that provide a unified, 360-degree view of cash positions allows owners to navigate supply chain costs and eliminate financial blind spots.
- Establishing Lending Relationships Early: Opportunities don’t wait, and delayed funding can cost a business. Small business owners should prioritize securing predictable access to capital, such as SBA 7(a) or term loans, long before the need arises. Building this foundation early allows the bank to accelerate decision-making when the business is ready to move.
What technology gaps are preventing small businesses from staying competitive in 2026, and how can we address them?
The primary technology gap preventing competitiveness today is a heavy reliance on disconnected, fragmented systems. Many small businesses hit an efficiency wall where manually “tab-switching” between isolated platforms and spending hours on data reconciliation drains valuable time. Furthermore, while the market is evolving rapidly, many businesses have not yet structurally embedded real-time payments or AI into their day-to-day operations.
Here’s how to address them:
- Consolidate Financial Data & Leverage AI-Powered Tools: Start with visibility by consolidating financial data into a single digital ecosystem, and use AI to move beyond static spreadsheets and manual reporting. While only a limited number of banks currently offer direct AI-connected banking experiences, early adopters like Grasshopper are helping businesses leverage AI-driven workflows to automate routine tasks like categorization and reporting. This gives owners the ability to query their data in real time, uncover spending patterns, and confidently predict their 30-to-60 day cash flow. Small businesses should also take advantage of resources like the U.S. Chamber’s AI training initiatives to shift from simply “trying AI” to meaningfully automating routine administrative tasks and improving operational efficiency. By combining Chamber education with a digital-first banking partner like Grasshopper, small business owners can drastically cut operational bloat and transform their raw data into a forward-looking growth strategy.
- Adopt Real-Time Transfers & Payments: Waiting on payments or dealing with standard clearing delays creates unnecessary operational friction. Utilizing real-time transfers and payment options allows business owners to send and receive funds instantly, helping them cover payroll, pay vendors, and jump on inventory opportunities without waiting on a bank’s schedule.
- Embrace Embedded Finance: The days of application switching are over. To close the gap, businesses must seek banks that integrate financial services like payments and lending directly into the operational workflows and accounting tools they already use, such as QuickBooks or Xero. When data flows automatically across systems, it eliminates weekend reconciliation.
What educational or operational support do small businesses need most in 2026 to successfully scale and grow?
To successfully scale in 2026, small businesses urgently require operational support that shifts them out of reactive “survival mode” and into a position of strategic growth. The expectation is no longer just a place to store money; businesses need a banking partner that acts as a proactive growth engine.
Essential support structures include:
- Advisory Banking Partnerships: Small business owners shouldn’t have to become experts in commercial lending just to access capital. Operational support means having a financial partner that takes on the burden of navigating technical requirements and deal structures, ensuring the logistics of lending never slow down the business’s momentum.
- Actionable Data and Insights: Small businesses need continuous support to make sense of their numbers. Rather than just handing over an end-of-month statement, modern financial partners must provide educational support through personalized dashboards and predictive analytics, helping owners understand how their cash data impacts financing and credit decisions.
- Preparation for Speed-Driven Lending: Lenders are increasingly placing greater weight on real-time financial data over traditional credit scores. Small businesses need operational guidance on how to maintain pristine data hygiene and properly connect their books to their bank, ensuring they remain “capital-ready” to secure rapid, right-sized financing the moment scaling opportunities arise.
