Influential Women Profiles Lyndsey Olson: Co-Founder And Partner Of Grey Matter Strategic Partners

SAINT PAUL, MN, UNITED STATES, August 21, 2026 /EINPresswire.com/ -- Former St. Paul City Attorney and Retired U.S. Army Colonel Brings More Than Two Decades of Legal, Military, and Executive Leadership to Strategic Advisory

Lyndsey Olson is a strategic legal and leadership advisor, Co-Founder and Partner of Grey Matter Strategic Partners, and former City Attorney for the City of St. Paul. With more than two decades of experience spanning law, military service, municipal government, and executive leadership, she advises mayors, CEOs, boards, executive leadership teams, nonprofits, and government organizations navigating complexity, risk, public accountability, and significant strategic inflection points.

Through Grey Matter Strategic Partners, Olson serves as a strategic legal counsel, crisis advisor, and thought partner to leaders operating in high-stakes environments. Her work focuses on helping organizations assess enterprise risk, clarify strategy, strengthen governance, respond effectively to crises, and make clear, defensible decisions while building institutions capable of enduring periods of uncertainty and change.

Olson’s consulting career builds on an extensive background in public-sector and military leadership. Before co-founding Grey Matter Strategic Partners, she served for eight years as City Attorney for the City of St. Paul, where she led one of Minnesota’s largest public law offices and served as chief legal officer to the mayor and city council. She managed a team of more than 100 professionals and oversaw legal operations for one of Minnesota’s largest municipalities.

During her tenure, Olson guided the City through complex litigation, volatile public crises, major policy reforms, and consequential governance decisions. Her responsibilities extended beyond traditional legal counsel, placing her at the center of executive decision-making during some of the organization’s most challenging periods. She became known for bringing steadiness, legal rigor, and practical judgment to situations involving significant public scrutiny and institutional risk.

Her work also included building and scaling nationally recognized public-safety and restorative-justice initiatives. Olson helped translate policy vision into operational frameworks with measurable results, with an emphasis on strengthening accountability systems, reducing institutional risk, and reinforcing public trust. This experience continues to inform her advisory approach today, particularly when working with organizations that must balance policy, governance, operations, public expectations, and long-term institutional health.

Before her municipal leadership career, Olson held senior legal roles in the Minnesota National Guard, including General Counsel and Staff Judge Advocate for the 34th Infantry Division. She was also the first female General Counsel of the Minnesota National Guard, an achievement reflecting both her legal expertise and her leadership within a complex military institution. A decorated U.S. Army Judge Advocate and veteran of Operation Iraqi Freedom, Olson served for 24 years in the United States Army Judge Advocate General’s Corps before retiring in 2024 at the rank of Colonel.

Her military career provided extensive experience advising senior commanders and navigating situations where decisions had significant consequences. Olson also co-chaired and authored the Sexual Assault Prevention and Response Review Board’s Findings and Recommendations Report, contributing to institutional reforms focused on culture, governance, and accountability within a large and complex organization.

Olson’s academic background reflects the interdisciplinary approach she brings to leadership. She earned a Bachelor of Arts in Philosophy, Law & Rhetoric from Stephens College in Columbia, Missouri, in 1998 and received her Juris Doctor from Hamline University School of Law, now Mitchell Hamline School of Law, in Saint Paul, Minnesota, in 2003. During law school, she served as a Primary Editor of the Hamline Law Review.

In 2010, Olson earned a Master of Laws (LL.M.) in Contract and Fiscal Law from the U.S. Army Judge Advocate General’s Legal Center and School in Charlottesville, Virginia. Her LL.M. thesis was subsequently published in The Army Lawyer. She later graduated from the U.S. Army War College in 2020 with a Master of Strategic Studies.

Her strategic education has been complemented by training in Human Systems Dynamics (HSD), an applied, complexity-based approach that helps leaders identify the underlying patterns influencing organizational behavior rather than treating individual problems in isolation. Olson uses this perspective as a facilitator to help leadership teams navigate uncertainty, conflict, and organizational change while creating greater clarity, alignment, and adaptive action.

The philosophy behind Olson’s current work is straightforward: organizations facing difficult challenges need more than theoretical advice. They need experienced judgment and support through implementation. Grey Matter Strategic Partners describes its approach as emphasizing judgment over methodology, execution rather than strategy alone, independence and discretion, and practical recommendations grounded in operational reality.

That philosophy aligns closely with Olson’s own professional experience. Having spent much of her career operating inside complex organizations, she understands that even strong strategies can fail if they do not account for organizational culture, competing priorities, stakeholder dynamics, operational realities, and the people responsible for implementing change.

Olson attributes her success to education, military service, and a lifelong commitment to helping others. Her decision to pursue military service was first sparked by a volunteer experience following a tornado in southern Minnesota. That experience clarified her desire to serve and ultimately led her toward the National Guard.

Her commitment to service was also influenced by her family. Her father retired as a Lieutenant Colonel, while her grandparents served during World War II. Growing up surrounded by examples of military service gave Olson a strong appreciation for responsibility and commitment, but it was her own experiences serving military families and communities that ultimately defined her professional purpose.

Over more than 24 years in uniform, including 15 years on active duty and a deployment to Iraq during Operation Iraqi Freedom in 2008–2009, Olson developed leadership, resilience, and crisis-management capabilities. As a JAG officer, she provided legal support to military families, including around the time of 9/11. Later, as a city attorney, she continued using her legal and leadership skills to serve the broader community.

Today, she carries that same purpose into consulting, coaching, mentoring, and board service.

For young women entering law, Olson encourages them to remain committed to areas that genuinely interest them. She believes women should not be discouraged simply because others question whether law is the right path for them. While law school and legal practice can be difficult and very different experiences, she emphasizes that perseverance matters when the profession is genuinely aligned with a person’s interests.

She also cautions against pursuing professional opportunities based solely on money or prestige. Olson believes that choosing roles simply because they look impressive on paper can eventually lead to burnout or dissatisfaction. Instead, she encourages young women to identify areas of law that align with their values and interests and build careers that provide a sense of meaning and fulfillment.

As Olson transitions from leading a large government organization to building a consulting business, she is experiencing entrepreneurship from an entirely different perspective. Rather than overseeing more than 100 employees across multiple divisions, she now manages everything from operations and technology to client development with a small team.

That transition requires her to wear many hats and adapt to constant day-to-day challenges. At the same time, she sees substantial opportunities in government contracting and in leveraging certifications as a disabled veteran-owned and woman-owned business.

Olson’s current work also reflects her ability to operate across sectors. Through Grey Matter Strategic Partners, she advises governments, nonprofits, and businesses facing scrutiny, transition, organizational complexity, or significant strategic decisions. Her goal is not simply to provide recommendations but to work alongside leaders as they translate those recommendations into action.

Her leadership has earned significant recognition, including the In-House Counsel Award, two Attorney of the Year honors, and a 40 Under 40 distinction. These recognitions reflect a career that has combined legal excellence with practical leadership and a demonstrated commitment to institutional improvement.

Despite those accomplishments, service remains the value at the center of Olson’s work and personal life. Whether she is advising a government leader, supporting an executive team, mentoring another professional, or helping an organization navigate a crisis, she remains motivated by the opportunity to use her skills to make a meaningful difference.

Her career has demonstrated that service can take many forms. It can mean providing legal support to military families, guiding a city through crisis, strengthening public institutions, developing public-safety initiatives, advising boards, or helping an executive make a difficult decision.

As she continues building Grey Matter Strategic Partners, Olson is bringing together the lessons of military leadership, legal practice, municipal government, and strategic education to help organizations move from uncertainty to action.

Her approach is grounded in discretion, integrity, practical judgment, and results. She believes leaders facing complex challenges need the confidence to confront uncertainty directly, the discipline to make defensible decisions, and the strategic perspective to understand how those decisions will affect an organization over the long term.

Ultimately, Lyndsey Olson’s career reflects a consistent commitment to service and leadership. From the U.S. Army Judge Advocate General’s Corps and Operation Iraqi Freedom to the Minnesota National Guard and the City of St. Paul, she has repeatedly stepped into environments where the stakes are high and the path forward is not always clear. Now, through Grey Matter Strategic Partners, she continues that mission by helping leaders navigate the grey, strengthen organizations, and turn difficult challenges into strategic action.

Learn More about Lyndsey Olson:

Through her Influential Women profile, https://influentialwomen.com/connect/Lyndsey-Olson or through her profile on Grey Matter Strategic Partners, https://thegreymsp.com/about/lyndsey-olson

Influential Women

Influential Women provides a platform where women from all backgrounds can connect, share their perspectives, and create content that empowers themselves and others. Through storytelling, thought leadership, and creative expression, Influential Women amplifies voices that inspire change.

Editorial Team
Influential Women
email us here