Our Team

Derek Cockrell

OWNER, MANAGER OF WEALTH

About Me

I’m passionate about helping people reach their financial goals so they can focus on what matters most: family, friends, and life!

My journey into financial planning began with the values my parents instilled in me. My dad, a naval officer for 21 years, taught me discipline, resilience, and the importance of hard work. Growing up in Melrose, a small town in eastern New Mexico, I learned the significance of community, faith, and helping others. These principles have shaped both my life and career.

After my dad retired from the Navy, he transitioned into finance and passed on his knowledge to me. He taught me the fundamentals of investing, estate planning, and using insurance to help minimize risk and capitalize on tax advantages. My parents taught me that there should be no separation between business and personal ethics; rather, we should apply a consistent, ethical approach to all areas of our lives, focusing on honesty, integrity, and serving others.

My Career Journey

After earning my BBA in 1996, I married my best friend, Jessica, and we began building our life together. I started my career as a loan officer but quickly discovered that financial planning was my true passion. I had the privilege of working alongside my dad in his practice, learning how to serve clients with care, integrity, and attention to their unique goals. His example of serving clients with honesty, respect, and care taught me to prioritize trust and relationships in every client interaction. Whether it’s guiding investment decisions, creating estate plans, or crafting tax-efficient strategies, I’m driven by the opportunity to make a positive difference in people’s lives.

In 2000, I purchased my dad’s firm, Contemporary Benefits, LLC, where I focused on supporting small-business owners and professionals with employee benefit plans and individual wealth management. In 2023, we launched Watershed Wealth Management, a firm dedicated to helping individuals achieve their financial dreams, while Contemporary Benefits continues to serve businesses with employee benefit plan solutions.

Community Involvement

Giving back to my community has always been an essential part of my life, thanks to the example set by my parents. I’ve been fortunate to serve in a variety of roles over the years, including:

• Rotary International: 25 years of membership, 1997-2022
• United Way of Eastern New Mexico: 9 years on the board, serving as campaign chair and board president, 1998-2007
• Boy Scouts Finance Committee Chair: 3 years, 2001-2003
• Chamber of Commerce: 10 years on the board, including 6 years on the executive committee and a term as board president, 2008-2016
• Plains Regional Medical Center: 17 years on the governance board, 2005-2023
• Clovis Music Festival/Draggin’ Main Music Festival: 12 years with the committee, including 3 years as chair of the Draggin’ Main Music Festival, 2009-2021

In addition, I served as an honorary commander at Cannon Air Force Base from 2015 to 2017 and on the board of Clovis Christian School from 2016 to 2024 as a secretary/treasurer.

Life Outside of Work

Family is at the heart of my life. I’ve been blessed with an amazing wife, a wonderful son, daughter-in-law, and precious grandson. I enjoy spending time on the water, playing the drums, and serving in my church.

Living and working in a community I love, surrounded by incredible people, fills me with gratitude. The trust and relationships I have with my clients are one of my greatest joys, and I’m deeply committed to helping them simplify their financial lives and achieve their goals.