About Simon
“After three decades of helping advisory firms grow, I’ve seen that strategy alone isn’t enough. Advisors need support that brings clarity to their leadership, alignment to their team, and structure to their systems. That’s what I’m here to provide.”
Strategic Operating Partner to Financial Advisor Business Owners and Agency Leaders
For over 35 years, Simon Reilly has helped financial advisor firm owners and agency leaders grow scalable, sustainable businesses—without sacrificing their energy, peace of mind, or purpose.
As the Founder of Leading Advisor Inc., Simon now serves as a Fractional Chief Operating Officer, offering hands-on support in leadership development, team building, succession planning, systems design, and business execution. His work is grounded in practical strategy and informed by decades of behavioral and values-based insight.
Simon’s approach is particularly suited to growth-minded firms ready to move beyond reactive operations and take deliberate, structured steps toward scaling their enterprise.
From Behavioral Coaching to Fractional COO
Simon’s background includes thousands of hours of coaching, strategy, and facilitation across North America. He brings deep knowledge of:
- Business visioning, team planning, and succession for advisory firms
- Hiring, delegation systems, and accountability frameworks
- Marketing and service systems aligned with consistent growth
- Behavior, values, and mindset alignment for high-performing leaders
He is a member of Advocis and NAIFA, and has spoken at industry conferences including FPA, GAMA LAMP, MDRT, Pro-Seminars, WIFS, and TEDx.
While many coaches focus on surface tactics, Simon’s strength is helping clients uncover and resolve the unseen psychological blocks that limit business growth. His methodology empowers leaders to realign with their values, restructure their organizations, and lead with purpose and clarity.
Publications
Simon is the author of two books:
- Curing the Unmet Needs Disease
- The Inspirational Tipping Point
He is a sought-after speaker and facilitator who has delivered keynotes and trainings at hundreds of industry events, both in-person and virtually.
The people behind our success
Simon Reilly
Financial Advisor Coarch
Mary Alton
Client Services & Operations Coordinator
Belen Silva
Social Media Manager
Dustin Meredith
Web Development Lead
A Message from Simon
“After three decades of helping advisory firms grow,I’ve seen that strategy alone isn’t enough.Advisors need support that brings clarity to their leadership, alignment to their team, andstructure to their systems. That’s what I’m here to provide.”
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Each week, Simon shares practical insights drawn from his work with advisory firm owners—focused on leadership, systems, succession, and team development.