WHY LOOKAHEAD
Building a meaningful partnership to transform your financial future.
Meet the Team
Who we are
We’re entrepreneurs and forward-thinkers who know what it takes to build something meaningful.
Our diverse backgrounds—ranging from nuclear submarine officers to corporate business strategists—shape our work. We share one purpose: making financial guidance accessible and actionable for real people and businesses.
Whether you’re planning for retirement, growing your business, or building generational wealth, we craft straightforward strategies that meet your needs and dreams—without the Wall Street jargon.
Head of Business Planning
Kathy Gregory
Head of Accounting & Tax
Lorilyn Wilson, CPA, PFS
Head of Wealth Management
Maximillian Morgan
Head of Strategy
Peter Gregory
HISTORY
How we got here
For years, our founders worked independently, often referring clients to one another due to the interconnected nature of tax planning, business strategy, and wealth management.
As we witnessed our clients juggling multiple advisors and fragmented financial guidance, we realized we could better serve them by bringing our expertise under one roof.
So, in 2024, we brought Investment Design Management, Lookahead Live, and Lake Oswego Tax together to provide our clients with seamless and comprehensive financial guidance.
When you thrive, we thrive.
How we're different
Customized Solutions
We deliver proven systems tailored to you.
