Dorothy Carlin

The best strategies don't begin with answers. They begin with understanding.

Leadership has been a throughline throughout my career. I moved into operations management within my first two years in advertising and went on to lead major client relationships before founding Simply Strategy. For 18 years, I built and led the firm while advising organizations navigating complex strategic, operational, and organizational challenges.

Simply Strategy grew from an idea into a $2.1 million professional services firm serving Fortune 500 companies, nonprofits, foundations, public-sector organizations, and growing businesses. Building it gave me the opportunity—and responsibility—to lead across virtually every dimension of an organization: strategy, operations, talent, client relationships, financial performance, business development, and culture.

As Simply Strategy evolves, I am continuing to take on select consulting and advisory work while exploring what comes next. I am particularly interested in how organizations are adapting as technology changes the way we research, evaluate, develop strategy, and put it into practice—and where experience, context, and human judgment remain essential.

Leadership

Good judgment has been central to my work as a leader. I learned to bring together data, qualitative evidence, operational realities, financial considerations, and the perspectives of the people closest to an issue. Data matters—but never in isolation. The strongest decisions come from understanding what the evidence says, what it doesn't say, and what an organization is capable of doing with it.

I've also learned that leadership requires knowing when to stand firmly behind a conviction and when to change course. Conviction and humility are not opposites. Some of the most consequential decisions I've made required challenging my own assumptions, responding to new evidence, or standing alone when thoughtful judgment led me there.

Building a company taught me about resilience and adaptation, too. I launched Simply Strategy in 2008 as the country entered a major recession and later led the firm and its employees through the disruption of the pandemic and the years of change that followed. Those experiences reinforced an important distinction: perseverance matters, but leadership isn't simply about holding on. Sometimes it requires recognizing that circumstances have changed and having the judgment to change course.

Building organizations

Organizations grow when people do. One of the greatest privileges of my career has been identifying talented people, investing in their potential, and watching them become trusted leaders.

I worked hard to hire well, then invested continuously in people's growth through time, training, resources, increasing responsibility, and opportunities to lead. At its largest, Simply Strategy employed 10 full-time professionals, and the team averaged more than 6.5 years of tenure.

Strong organizations require more than strong people. They require clear direction, sound financial stewardship, accountability, disciplined operations, strong client relationships, and the ability to adapt. Over 18 years, Simply Strategy developed enduring institutional relationships, including major corporate relationships spanning more than a decade and a seven-year foundation engagement renewed multiple times.

Entrepreneurship gave me a particular perspective on executive leadership. Every decision carries consequences—for employees, clients, partners, financial performance, and the organization itself. That responsibility shaped how I think, how I lead, and how I support other leaders facing difficult choices.

Perspective

My career has put me in the room with leaders confronting questions that don't have obvious answers. Growth, complexity, organizational change, competing priorities, and changing environments often require more than experience or intuition alone.

As technology and AI reshape how work gets done, I am particularly interested in the leadership questions that come with that change—how organizations use new capabilities while applying the judgment, experience, and perspective needed to make better decisions.

My contribution is often helping people see the situation more clearly: synthesizing multiple forms of evidence, challenging assumptions, distinguishing what matters from what merely demands attention, and connecting strategic choices to operational realities and organizational capacity.

That perspective extends beyond my own organization. I have more than 14 years of board and civic leadership, including six years on the YWCA Metro St. Louis Board, four as Vice Chair of Governance, helping govern a human-services organization with nearly $34 million in annual revenue. I also served four years on the board of the National Association of Women Business Owners–St. Louis and was twice recognized as Member of the Year. Today, I serve on the board of the St. Louis Forum and as Program Chair, with responsibility for leadership programming for an organization of senior women leaders.

Whether leading an organization, serving on a board, or advising other leaders, my focus remains consistent: strengthen decisions, strengthen leadership, and build the organizational capacity to move forward.

Experience + Recognition

• MBA, Washington University in St. Louis, Olin Business School

• 28+ years in leadership roles

• 18 years building and leading Simply Strategy

• $2.1M annual revenue

• 10 full-time employees; 6.5+ year average tenure

• 13+ years developing and leading major corporate relationships

• 7-year foundation engagement, renewed multiple times

• Research and strategy engagements conducted nationwide

• 14+ years of board and civic leadership

• 6 years on the YWCA Metro St. Louis Board, including 4 years as Vice Chair of Governance

• 4 years on the NAWBO–St. Louis Board

• Current Board Member, Programs + Events Chair, St. Louis Forum

Recognition + Leadership Development: Best in Consulting, St. Louis Small Business Monthly, 2026 · Most Influential Business Women, St. Louis Business Journal, 2022 · NAWBO–St. Louis Member of the Year, 2013 & 2014 · Coro Women in Leadership, Class 55 · Olin Board Fellow, Washington University in St. Louis

Let's start with a conversation

I'm continuing to take on select consulting and advisory work, particularly where research, strategy, organizational change, and implementation intersect. I'm also interested in meaningful board service and conversations about what may come next.

If my experience could be useful in something you're building, navigating, or changing, I'd welcome the conversation.