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.

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.

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 recognized as Member of the Year in 2012 and 2013. 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

• 28+ years in leadership roles

• 18 years building and leading Simply Strategy

• $2.1M peak annual revenue

• 10 full-time employees at peak; 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

• Program Chair + Board Member, St. Louis Forum

Recognition + Leadership Development: Top Young Entrepreneur, Small Business Monthly, 2015 · Most Influential Business Women, St. Louis Business Journal, 2023 · Best in Consulting, Small Business Monthly, 2026 · NAWBO–St. Louis Member of the Year, 2012 & 2013 · Focus St. Louis Women In Leadership, 2013 · WBENC WeTHRIVE

Let's start with the problem

The most meaningful conversations rarely begin with a predefined solution. If you're working through a complex challenge, exploring an opportunity, or simply looking for an objective perspective, I'd welcome the conversation.

Whether that conversation leads to executive leadership, board service, advice, or an introduction to someone ideally suited to the need, my goal is the same: helping organizations move forward thoughtfully.