Kaitlyn O’Shaughnessy

Kaitlyn O’Shaughnessy is a trusted immigration partner for investors, entrepreneurs, and start-up founders navigating the complex U.S. immigration system. With over a decade of experience practicing exclusively in immigration law, Kaitlyn has built a focused practice helping visionary business builders secure and maintain their legal status in the United States — so they can stay focused on growing their companies and supporting their families.

Kaitlyn counsels foreign national founders, executives, and international investors on the full spectrum of business immigration pathways, including E-2 treaty investor visas, EB-5 investor visa matters, O-1A extraordinary ability visas, EB-1 A and C petitions for those with extraordinary ability in business and multinational managers, and L-1a new office petitions for business owners seeking to expand an existing business into the USA. She works closely with start-up leadership teams, small-business owners, and investors to align immigration strategy with business milestones, funding timelines, and workforce planning objectives.

Additionally, Kaitlyn has a wealth of experience working with religious organizations of many faiths seeking to sponsor foreign religious workers or religious leaders for temporary R-1 visas, or for lawful permanent residence. She is committed to working closely with faith leaders to ensure they can employ the people they need.

Beyond individual visa matters, Kaitlyn is a skilled corporate immigration compliance advisor. She advises companies on I-9 employment eligibility verification processes and internal audits. She is a fierce advocate for her clients when they receive an I-9 Notice of Inspection or Notice of Suspect Documents. Kaitlyn understands that immigration compliance is not just a legal obligation — it is a cornerstone of investor confidence and due diligence readiness. Her proactive, systems-oriented approach helps companies build compliance frameworks that scale as their teams grow.

Multilingual in English, French, and Spanish, Kaitlyn brings a genuinely global perspective to her practice — a natural fit for the international founders and investors she serves. She is a member of the New York Bar, an active participant in the American Immigration Lawyers Association (AILA), and a graduate of McGill University Faculty of Law.

Bar Admissions

• New York State Bar
• Fourth Circuit, U.S. Court of Appeals

Memberships

• American Immigration Lawyers Association (AILA)
• ParadiGM Global Mobility

Representative Matters

• Developed and implemented a company-wide I-9 compliance training program for multiple restaurant groups, identifying and remediating exposure to guard against worksite enforcement actions
• Defended corporate client faced with the possibility of significant I-9 compliance-related fines
• Advised an international investor on E-2 treaty investor visa options for a tech start-up
• Secured continuous work authorization for multiple start-up business owners through E-2 status extensions

Interesting Fact

• Kaitlyn is an avid international traveler who has visited over 40 countries — an experience that gives her genuine insight into the journeys her clients undertake to build their futures in the United States.