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New collaboration aims to help small businesses find affordable health coverage as insurance costs continue to rise
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TORONTO & SAN FRANCISCO, Oct. 30, 2025 (GLOBE NEWSWIRE) — Amid soaring health-insurance costs and dwindling small-business coverage, FreshBooks—a leading small business management software, built to support service-based small business owners—today announced they are teaming up with Stride, the pioneer in portable benefits technology. The collaboration brings affordable, high-quality health, dental, and vision plans to self-employed professionals and small business owners across the United States, ahead of the Open Enrollment Period (November 1–January 15).
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Average annual premiums for employer-sponsored family coverage now reach $26,993 annually (KFF), while nearly one in three small businesses discontinue health-insurance payments each year as rising costs outpace revenue (J.P. Morgan Chase Institute). Long-term trends reveal the impact: only 30 percent of small businesses now offer health insurance, down from nearly 50 percent in 2000 (NFIB Health Care Coverage Policy Paper).
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“When you work for yourself, every decision is personal,” said Faye Pang, Chief Growth Officer at FreshBooks. “Small business owners should have the same access to affordable benefits as larger companies. Our collaboration with Stride helps make that a reality—giving them practical and personalized options that support their well-being.”
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Through the collaboration, FreshBooks customers can explore Stride’s trusted benefits, making it simple to find, compare, and enroll in affordable health, dental, and vision coverage ahead of Open Enrollment. Stride has served 4.6 million people, saved customers $1.45 billion in premiums, and maintains one of the highest trust ratings among digital benefits platforms.
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“For too long, self-employed professionals have faced a trade-off between independence and security,” said Bryan Giaimo, VP Enterprise at Stride. “Together with FreshBooks, we’re closing that gap—making it easier for small business owners to get the coverage they need without the complexity.”
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About FreshBooks
FreshBooks is a leader in small business management software that is purpose-built to help small business owners simplify the financial complexity of running their business—from invoicing and expenses to payroll and payments—bringing together the tools they need to manage finances, save time, and stay organized. Headquartered in Canada, FreshBooks supports business owners around the world.
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About Stride
Stride is the first portable benefits platform designed for the over 72 million American independent workers without employer-based benefits. Stride works with over 130 companies to deliver portable benefit contribution programs and deliver access to health insurance, financial savings, and tax and expense tracking tools. Stride has helped 4.6million people save over $8 billion on insurance premiums and taxes.
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English (US)