WINSOMEPAC
The Honorable
Winsome Earle-Sears
From arriving in the United States as a young child to becoming the first woman elected Lieutenant Governor of Virginia, Winsome Earle-Sears has built a life defined by service, perseverance, faith, and the courage to break barriers.
Born in Kingston, Jamaica, Winsome’s story began with her father, who immigrated to the United States in the early 1960s with just $1.75 in his pocket and a belief that America was a place where anything was possible.
Years later, he brought his young daughter to the United States at the age of six, determined to create opportunities for his family through hard work, sacrifice, and faith.
Winsome often says she is living proof of the American Dream her father pursued.
Her story is more than history — it is leadership in action and a continuing commitment to expanding opportunity and strengthening communities across Virginia.
The Making of a Leader
Winsome’s understanding of leadership was shaped early by the conversations and experiences that surrounded her growing up.
In her family, discussions about government, responsibility, and civic life were common. Her grandmother in particular encouraged thoughtful conversations about politics and the role citizens must play in shaping the future of their communities.
Those conversations left a lasting impression. Watching how government decisions could affect everyday life reinforced a belief that people cannot remain on the sidelines. Citizens must be willing to step forward and become part of the solution.
At eighteen years old, following the loss of her grandmother, Winsome found herself searching for direction and purpose. While preparing to begin college, she came across a magazine advertisement that read:
“The Few. The Proud. The Marines.” The challenge spoke to her immediately.
In 1983, Winsome joined the United States Marine Corps, serving as an electrician and becoming the only woman in her engineering class. The Marine Corps instilled discipline, resilience, and a leadership philosophy that continues to guide her life today.
During her time in the Marines, she witnessed something that would shape her understanding of leadership. A warrant officer chose to work alongside the Marines rather than simply give orders — demonstrating that leadership is not about position or authority, but about example.
That moment left a lasting impression and reinforced a principle she has carried throughout her life and public service:
“Leadership is not what you say
it’s what you do.”
Family, Faith, & Resilience
Winsome Earle-Sears with her husband, Terence Sears,
and their daughters.
Winsome’s life has always been grounded in faith, family, and partnership.
In 1986, she married Marine Corps Lieutenant Terence Sears.
Together, they built a life centered on service, perseverance, and commitment to their community, raising their three daughters — DeJon, Tiffany, and Tricia — while balancing the responsibilities of family life, military service, and public leadership.
Like many families, their journey has included both seasons of joy and deep challenge. Winsome experienced the heartbreaking loss of her daughter DeJon and two young granddaughters, Victoria and Faith.
Through that difficult time, her Christian faith became an enduring source of strength, guiding her forward with resilience and hope.
Today, family and faith remain at the center of Winsome’s life, shaping her belief that leadership begins with compassion, courage, and a commitment to serve others.
Author & StoryTeller
In 2023, Winsome Earle-Sears released her memoir, How Sweet It Is: Defending the American Dream. In it, she reflects on her path from immigrating to the United States as a child to breaking historic barriers in public service.
The memoir traces her life from Jamaica to America, her service in the United States Marine Corps, and her conservative, faith-based approach to overcoming personal and professional challenges.
Through personal stories of faith, perseverance, and leadership, it offers a deeper look at the values that have shaped her life and continue to guide her commitment to serving others.
Prior to her memoir, she authored Stop Being a Christian Wimp!, a faith-centered work that emphasizes spiritual discipline, resilience, and living with conviction—principles that continue to influence her leadership and public service today.
Breaking Barriers in Leadership
The lessons Winsome learned in the Marine Corps shaped the way she approached leadership long after her service ended.
Before entering statewide office, she dedicated herself to strengthening communities and helping individuals rebuild their lives. She directed a Salvation Army women’s homeless shelter in Hampton Roads, working closely with women seeking stability and a fresh start.
She also led a men’s prison ministry, encouraging accountability, faith, and personal responsibility among incarcerated men. These experiences reinforced her belief that leadership is rooted in service and investment in people.
Alongside her community work, Winsome pursued education and leadership development, earning:
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an Associate Degree from Tidewater Community College
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a Bachelor of Arts in English with a minor in Economics from Old Dominion University
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a Master of Arts in Organizational Leadership from Regent University
These experiences — both in service and in education — helped shape the leadership perspective she would later bring to public service.
Her commitment to service ultimately led her into public service, where she would go on to break historic barriers and open doors for others across Virginia.
The milestones that followed would reshape the landscape of leadership in the Commonwealth.
1983–1986
Virginia House of Delegates
She became the first female veteran
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First naturalized citizen delegate elected to the body
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First female Black Republican
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First Republican to represent a majority-Black House district in Virginia since 1865
2011
Historic Election
Elected Lieutenant Governor of Virginia, becoming the
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First woman
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First woman of color
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First female veteran elected to statewide office in the Commonwealth
2022–2026
2002-2004
United States Marine Corps
Served as an electrician in the
United States Marine Corps where
she developed the discipline and
leadership philosophy that guide
her public service.
Virginia State Board of Education Appointed to the Virginia State Board of Education and later elected Vice President in 2014.
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Received a presidential appointment to the United States Census Bureau's African American Committee
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Received separate appointment from the secretary of veterans affairs to the Advisory Committee on Women Veterans.
2021
42nd Lieutenant Governor of Virginia
Served as the 42nd Lieutenant
Governor of Virginia and presided
over the Virginia Senate.
The milestones that shaped Winsome Earle-Sears’s journey continue to guide her leadership today — not only in office, but in the communities she serves.
Leadership in Action
Leadership is not only about positions held — it is about showing up, serving others, and building stronger communities.
A life of service.
A future of leadership.
Winsome Earle-Sears has spent her life breaking barriers and opening doors for others.
Today, that mission continues through WinsomePAC — a leadership and training political action committee dedicated to preparing citizens across Virginia to step forward and serve.
Whether running for office, working on campaigns, or supporting their communities, WinsomePAC equips individuals with the tools, knowledge, and confidence to make an impact.
“We didn’t come this far to only come this far.”
A Voice That Continues to Lead
From making history in Virginia to speaking on education and community leadership, Winsome has consistently used her voice to engage the issues shaping the Commonwealth’s future.
Richmond Free Press
Sears Makes History as Virginia’s Lieutenant Governor
Winsome Earle-Sears made history when she was elected Lieutenant Governor of Virginia, becoming the first woman of color elected to statewide office in the Commonwealth.
The Northern Virginia Daily
A Dream Come True: Nonprofit Celebrates Growth
This feature highlights community leadership and service efforts connected to Winsome’s longstanding commitment to strengthening families and communities.
Why Do We Trust Parents With Food but Not Education?
In this opinion piece, Winsome shares her perspective on empowering parents and strengthening their role in shaping their children’s education.
A Commitment That Endures
Winsome’s journey has always been guided by a commitment to service, faith, and the belief that strong communities are built by people willing to step forward and lead.
As Virginia continues to grow and face new challenges, that commitment remains unchanged — to strengthen families, expand opportunity, and equip people across Virginia to step forward and serve.
