Carolyn Woodruff

Founder and CEO, Woodruff Family Law Group


​Carolyn Woodruff

Carolyn J. Woodruff, JD, CPA, CVA, is a visionary and leader in accounting, law, and banking. She is a preeminent lawyer, a Family Law Specialist, a North Carolina Certified Public Accountant, and a Certified Valuation Analyst with the National Association of Certified Valuators and Analysts®.

Carolyn serves as a director on the public board of Blue Ridge Bankshares, Inc. (BRBS)(NYSE). She is chair of the Audit Committee and serves on the FinTech and Wealth Management Committees.

She is an instrument-rated multi-engine airplane pilot and regularly flies private aircraft. As an active member of First Presbyterian Church in downtown Greensboro, where she is on the finance committee, Carolyn also serves on a study committee to research and envision a multi-use facility to benefit adults with disabilities.


Her philanthropy focuses on organizations that have an impact on families and children. She is a long-time supporter of Family Service of the Piedmont and has held various leadership positions. She currently serves as vice chair of the Greensboro Foundation Board. She has been an integral part of the annual Big Hair Ball since its inception as a major sponsor. With over a million dollars raised, the proceeds from the Big Hair Ball benefit Family Service of the Piedmont’s Greensboro programs.

Giving back to her community is a core value for Carolyn. Her law firm is a sponsor of the annual “PTI Run on the Runway” event, which raises funds to alleviate food insecurity in the Piedmont Triad region of North Carolina. The Woodruff team is enthusiastic about both running and helping with this endeavor that benefits the Second Harvest Food Bank, the Greensboro Urban Ministry, and High Point Open Door Ministries.

Carolyn supports the work of the Women’s Resource Center of Greensboro, which helps women achieve self-reliance and access community resources. Each year, the Woodruff Family Law Group sponsors “Men Can Cook,” an event which helps fund the work of the center.

Captain Green Eyes Dance Troupe

Through the Salvation Army Boys & Girls Club, Carolyn created the Captain Green Eyes Dance Troupe and coached the children to achieve two national television showings on “So You Think You Can Dance” on National Dance Day. She and her late husband, Dwight Ensley, developed programming for disadvantaged children in the Piedmont Triad and led a summer dance camp for five years. They brought in nationally known dance artists, such as Fik-Shun and Comfort, to help inspire children in the arts.

Additional Philanthropy

For over a decade, Carolyn was a sponsor of the Greensboro Symphony Guild, recognizing the importance of the Guild’s mission to advocate for music education and appreciation in the Greensboro community. She served as mistress of ceremonies on several occasions for fundraisers.

Carolyn helped raise tens of thousands of dollars for Operation Smile through “Dancing with the North Carolina Stars” over a ten-year period. Operation Smile provides surgery and ongoing care for children affected by cleft lip and cleft palate in developing countries.

Other philanthropic endeavors through the years include sponsorship of the Juvenile Diabetes Research Foundation through the Hope Gala, and Triad Goodwill’s “Rock the Runway.”

Carolyn is a published author. Her books include The Seven Nights of Santa, written for children who have more than one home due to divorce. Her other books, Ask Carolyn and Ask Carolyn Two are written for adults who are going through a divorce. She has written many continuing education manuscripts, including Financial Guide to Divorce in North Carolina and Business Valuation Principles in North Carolina.

As a Family Law Specialist, Carolyn sees firsthand the impact of family structure on women and children. She is a passionate advocate for domestic violence reform. She drafted the Armstrong Domestic Violence Reform Bill aimed at giving Judge’s more latitude on granting domestic violence protection orders and granting potential victims a “right to know” when an estranged partner applies for a gun permit [the Bill stalled in a Study Committee].

In addition, she served as pro bono legal advisor to the Sherri Denese Jackson Foundation for the Prevention of Domestic Violence from its inception, until that foundation closed in 2021.

Academic and Professional Credentials

Carolyn was graduated from Duke Law School with High Honors and served as Research and Managing Editor of the Duke Law Review. She has a Bachelor of Science degree from Purdue University in Business Administration.

Through the North Carolina Association of Certified Public Accountants (NCACPA), Carolyn has been a speaker and trailblazer in continuing education for CPAs who need knowledge of taxation related to divorce and business valuation in divorce in North Carolina. She has written many continuing education manuscripts, including Financial Guide to Divorce in North Carolina and Business Valuation Principles in North Carolina.

Carolyn holds a 2021 FinTech certification from Harvard Business School where she did her Capstone paper on Central Bank Digital Currency. She holds AICPA badges in Blockchain and Cybersecurity. She is a frequent speaker on FinTech. Presentations include:

  • “Demystifying FinTech” – North Carolina Association of Certified Public Accountants (NCACPA) at the 82nd Annual Symposium (November 2021).
  • “FinTech and Regulatory Sandboxes” – North Carolina Banking Commission (January 2022).
  • “FinTech and Innovation” – Wake Forest University School of Law given to students in the course on State and Local Government taught by the Hon. Don Vaughan (October 2022).
  • “FinTech and Innovation” – NCACPA at the 83rd Annual Symposium (November 2022).

She is the first North Carolina female fellow in the distinguished American College of Tax Counsel.

Carolyn began her legal career with Tuggle Duggins and Meschan, P.A., where she became a principal and shareholder in only four short years. Following her tenure at Tuggle Duggins, she branched off and formed a law firm concentrating in family law, where she remains today, serving as CEO and lead counsel in high profile, high net worth divorces.

Awards and Recognitions

In 2022, Carolyn was awarded The Order of the Long Leaf Pine by North Carolina Governor Roy Cooper in recognition of her significant contributions to the state and to her community through exemplary service and exceptional accomplishments.

She was recognized as one of the Class of 2022 Leaders in the Law by North Carolina Lawyers Weekly. This award honors legal professionals who have gone above and beyond in their profession and in their community. She was previously recognized in 2014.

Since 2007, she has been selected to North Carolina Super Lawyers.

She has been recognized since 2009 in Best Lawyers in America

She is an AV Preeminent Peer Rated Attorney by Martindale-Hubbell for 2023 and received a Platinum Client Champion designation.

She was named to the 2022 Power List for Family Law by North Carolina Lawyers Weekly. The Power List recognizes the top 20 most influential attorneys in family law in North Carolina.

In 2021, she was a C-Suite Award Winner honored by The Triad Business Journal, in recognition of exemplary leadership, performance, and innovation.

In 2017, she was named by North Carolina Super Lawyers to the Top 50 Women.

She was named as one of the top 50 women attorneys in North Carolina by Charlotte Magazine in 2016.

Carolyn was recognized as one of the Best Lawyers in North Carolina in 2015 by Our State Magazine.

She received the R. Donald Farmer award in 2015 from the NCACPA.

Amateur Ballroom Dance Career

Carolyn is a now-retired Gold Star Amateur Ballroom Dancer, which is the highest level for an Amateur in the Fred Astaire system. She started a dance partnership with Alosha Anatoliy in April 2006. Ms. Woodruff and Mr. Anatoliy were featured in the following world shows:

  • Dance Legends live appearances 2012- 2016 at the Hammerstein Ballroom in New York City. Performances include You Lost Me, Ameno, Tribute to Isadora Duncan, Masquerade, and
  • The Kremlin Palace, Moscow in Star Duo for a live audience and 100 million television viewers with Mystery of Masquerade in 2017
  • Star Duo at the Kremlin Place for a live audience and 100 million television viewers in June 2018 with Maria
  • Star Duo live appearance in 2015 in Moscow, Russia at the Kremlin Palace with Tribute to Isadora Duncan

In September 2019, Woodruff and Anatoliy were invited to dance at King’s Landing, Croatia, where Game of Thrones was partially filmed. In an unfortunate dance accident, while executing a flip, Woodruff broke her arm. That, along with the pandemic, sent Carolyn into retirement from showdance.

Other appearances include:

  • 2014 – Television Show Ballroom Blitz shown in 10 countries and the United States on TLC
  • 2015 – Made two appearances in Dance League American Sports network, including Tribute to Isadora Duncan
  • 2016 – United States Dancesport title gold medalist in Pro-Am Classic Showdance with Gypsy
  • 2016 – Las Vegas at Bellagio—World Amateur show dance title with her late husband, Dwight
  • Three-time Fred Astaire National Champion in Pro-Am American Smooth
  • Fred Astaire National Pro-Am Cabaret Champion
  • Three-time Fred Astaire National Amateur Show Dance Champions with her late husband, Dwight