Stephanie Laitala-Rupp

Managing Director


Stephanie thrives at the busy intersection of people, processes, and finance. With nearly three decades of experience in the field, including CEO and CFO roles as well as numerous board seats, Stephanie leverages depth and breadth of expertise to drive performance and growth when the stakes are high and the margin for error is low. Stephanie is known for inordinate calm amid chaos, making her a valuable asset in high-pressure environments.

Areas of Expertise

Finance & Accounting Operations

While I hold an MBA, I credit my true finance and accounting operations acumen to hands-on experience, having spent decades working with complex, layered budgets, payroll, P&Ls, and more.

Process Improvement

Complacency isn’t in my vocabulary. I am constantly evaluating processes to identify areas for improvement, taking a methodical approach that considers the human, logistical, and financial impact of each step. I am known for creating and executing process improvements that are both bold and thoughtfully considered, leading to reliable, measurable results.

Executive Leadership

Multiple long-term CEO roles have allowed me to balance my penchant for “bean counting” with a wholehearted love for working with people. I am a true collaborator and measure my own success by the success of people around me.

Strategic & Financial Planning

I blend big-picture vision with meticulous attention to the tiniest minutiae, resulting in watertight strategic plans that drive results. I have a (repeatedly field-tested) ability to quickly assess complex situations, develop a strategy, and execute.

Industry Experience

  • Professional Services
  • Hospitality
  • Manufacturing
  • Non-Profits
  • Commercial Leasing
  • Technology


  • Creating calm order in chaos
  • Quickly assessing complex situations
  • Building high functioning teams
  • Presenting financial information to non-financial people
  • Grit
  • Tenacity



Commonwealth Companies

CEO / Founder

Owl Bookkeeping & CFO Services

Vice President & CFO

Strategic Advantage, Inc.



Metropolitan State University

BA, Accounting

Metropolitan State University





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