Jessica Osterloh

Jessica Osterloh is an estate planning, trusts, mediation, and business law attorney whose practice is rooted in a deep commitment to guiding individuals and families through some of the most complex and emotionally challenging moments of their lives. She approaches her work with clarity, patience, and compassion, taking care to transform intimidating legal processes into experiences that feel manageable and understandable. Jessica believes that the most meaningful role an attorney can play is to replace uncertainty with insight and to help clients move forward with confidence and peace of mind.

Jessica’s interest in estate planning grew from her family’s long-standing involvement in the insurance industry, where she saw firsthand the importance of thoughtful preparation and sound financial and legal structure. After earning her business degree from Virginia Tech’s Pamplin College of Business, she began her career at the National Life Insurance Company’s home office in Vermont. She later attended the University of Baltimore School of Law, continuing to support National Life remotely—an experience that strengthened her understanding of the intersection between business, risk management, and long-term planning.

Before joining BKBH, Jessica served as In-House Counsel for the Montana Department of Commerce, where she advised on complex regulatory issues and played a key role in implementing statewide initiatives, including the rollout of the American Rescue Plan Act. She then joined U.S. Bank’s Wealth Management department as a Corporate Fiduciary, managing trusts, special needs trusts, and significant fiduciary matters for clients across Montana. During this time, she founded Exodus Mediation, a nonprofit dedicated to providing accessible mediation services and creating a space where individuals feel heard, respected, and empowered to resolve conflict outside of court.

Jessica joined BKBH in 2025, bringing with her a deep well of legal experience, strong financial and fiduciary insight, and a passion for helping clients find clarity, closure, and direction in moments that matter most.

Estate Planning, Trusts & Special Needs Trusts

Jessica’s estate planning practice places a strong emphasis on the creation, management, and administration of trusts. She assists clients with revocable and irrevocable trusts, special needs trusts, and complex fiduciary structures designed to protect assets and provide long-term security for loved ones. Drawing from her experience as a Corporate Trust Officer, Jessica brings a deep understanding of fiduciary duties, trust mechanics, and the day-to-day realities of administering trusts of all sizes.

In addition to her trust-focused work, Jessica helps clients with wills, incapacity planning, guardianships, conservatorships, and comprehensive long-term planning strategies. Her background enables her to guide clients through the legal and practical aspects of estate administration with clarity and confidence. Clients rely on her for thoughtful and informed advice that provides stability, peace of mind, and a clear path forward.

Business Law & Financial Services

Drawing on her background in wealth management, insurance, and business operations, Jessica advises clients on business formation, transactions, contracts, and operational matters. She understands how legal decisions intersect with financial planning and risk management, and she brings a practical, forward-thinking perspective to business owners, families, and entrepreneurs.

Administrative Law & Public Housing Matters

Jessica has substantial experience in administrative law from her work at the Montana Department of Commerce, where she helped implement and interpret regulations affecting communities across the state. She also represents clients in landlord-tenant matters and public housing issues, offering guidance that balances regulatory compliance with compassion for the individuals involved.