Our Team

As the founder of Obsidian Planning, Patrick has spent the last 35 years helping business owners and families create comprehensive financial plans to protect their assets and legacies. Through his work, he created the Lifestyle Protector Program™, a simple, step-by-step planning process that will fit seamlessly into your already busy schedule and guide you through the process of identifying and realizing your personal and professional goals.

A long-time business owner and family man, Patrick draws on both his professional and personal experience to create customized, comprehensive solutions to provide you with peace of mind for your financial portfolio. He holds a Bachelor of Science from Virginia Tech and a Master of Science from the American College of Financial Services. Patrick is also a CERTIFIED FINANCIAL PLANNER™ professional, and has earned the Certified Exit Planner designation from the Business Enterprise Institute.

If you’ve ever lost sleep because you were worried about protecting your future and growing your business, you are not alone. Todd can’t wait to help you develop a comprehensive strategy and implement effective tactics to help you achieve your ideal future. An innate problem solver, he enjoys working with driven business owners who are ready to plan for the future they deserve.

Todd, leading Obsidian’s business development team, relishes the opportunity to help business owners reach their goals every day. He holds a Bachelor of Science in Finance from the Smeal School of Business at the Pennsylvania State University. Todd is also a CERTIFIED FINANCIAL PLANNER™ professional, and has earned the Certified Exit Planner designation from the Business Enterprise Institute.

When it comes to your most important documents, do you feel scattered? Pam Flick, Obsidian’s Senior Planner, is eager to help. Pam enjoys getting your documents organized, analyzing your data and making strategic recommendations to guide you toward your goals. To Pam, details matter; she diligently scrutinizes every aspect of your plan to ensure your long-term success. With over 20 years at Obsidian, Pam will leverage her extensive experience and unrivaled knowledge base to your advantage.

In addition to being a CERTIFIED FINANCIAL PLANNER™, she holds a bachelor’s degree in Business Administration/Marketing from Indiana University of Pennsylvania and an MBA in Finance and Investments from The George Washington University.

You have questions. Sean will help you find answers. What’s his favorite part of the job? It is providing a comprehensive service to you, our clients. From investment accounts to insurance planning, trusts, estates, and everything in between, a good day for Sean is when you have the information and education to make confident, well-informed decisions.

As a Client Service Specialist, he has been assisting Obsidian clients for over 20 years and holds degrees from the University of New Haven and The George Washington University. He also holds FINRA Series 7, 6, 63, 66 licenses and Life/Health/Property & Casualty insurance licenses in the state of Maryland.

Clients looking for solutions to help them maintain their standard of living through retirement will love working with planning team member Kelsey Easter. Kelsey got her bachelor’s degree in accounting and information technology from Virginia Tech. Her background in both public and private accounting means she is very detail oriented.

Kelsey loves working with clients and getting to know them and understand their unique situations. After being with Obsidian for several years, she feels she knows the clients well and looks forward to meeting new ones in the years to come.

You can count on Becky to bring energy, enthusiasm, and communication skills to Obsidian through her role as Professional Service Partner. She enjoys interacting with clients regularly to keep them in the loop about where they are in the process. Getting to know clients and their stories and goals is her favorite part of the job. She also brings a unique perspective to her role, having been a business owner who successfully sold her own company in 2018. “The impact and guidance our team provides to people can be life-changing, and that is something to be excited about,” she said.

Becky earned her bachelor’s degree in advertising/business administration and her master’s degree in integrated marketing communications from West Virginia University. She looks forward to bringing her expertise and skills to every client at Obsidian.

Jay has been helping people make smart decisions about their financial life and money for over 29 years. He is devoted to making sure his clients receive objective and thorough advice. He has personally completed over 1,800 financial plans. Since every plan is customized, his attention to every detail is a characteristic that sets Obsidian Planning apart from other planning firms.

He earned a Bachelor of Science from the University of North Carolina in Business and Finance.

Jay is an Eagle Scout and remains very active in the local Boy Scouts of America. In his spare time, he enjoys camping, hiking, and reading IFinancial Planning magazine. He lives in Annapolis Maryland with his wife of over 36 years.

Jill is responsible for customer service requests, database management, insurance processing, and client communications. Her prior work experience includes working as an auditor for a public accounting firm and as a financial analyst in the banking industry.

Jill graduated with a BBA from University of Georgia, earned an MBA from University of Baltimore, and her CPA certificate. She is married with one son and three daughters and resides in Ellicott City. Jill enjoys watching her kids play soccer and collegiate sports, reading, and walking her dog.

Anne assists Jay in administering the financial planning and investment parts of the business. She has a unique perspective in that she and her husband were planning and investment clients for years prior to joining the firm.

Anne graduated from McDaniel College and earned a MBA in Finance from Loyola College. She is married and has two grown sons and lives in Ellicott City. Anne enjoys cycling, hiking, watching sports and spending time with friends and family.

Ashley joined Obsidian after nearly 10 years with Northwestern Mutual, where she worked as an associate financial advisor. “As my 10th anniversary approached, I knew I wanted to go deeper into financial planning . . . to understand the models behind the product and plan recommendations,” she explains. “I wanted to work with a group of committed, caring people doing great things for diverse clients. When I met with Pat, Todd, and Sean, I found what I was looking for.”

Ashley holds FINRA Series 6, 7, 63 and Securities Industry Essentials licenses, and insurance licenses in health, life, variable, disability, and long-term care. She has also attainted her Chartered Life Underwriter® (CLU®) designation.

Ashley was born in the San Francisco Bay area and spent years in Arizona before moving to Montana in 2021, where she lives with her three dogs and husband, Shay. She has a bachelor’s degree in public administration from Northern Arizona University, is a science fiction reader, and is a self-motivated, lifelong learner.

Darlene is your first stop for scheduling and general information requests. With multiple degrees in web development, she’s a font of technology- and web-related information. Having worked for ten years as the “connector” between several accountants and 2000+ of their clients, Darlene is also a natural rapport-builder and problem-solver.