Build a Scalable, Purpose-Driven Financial Advisory Firm
Leadership, Systems, and Strategy to Grow with Confidence and Peace of Mind.
See how Leading Advisor can support your financial services firm:
Meet Simon Reilly
Chief Fractional Operating Officer
Weekly Strategic & Purposeful Advisor Insights
Get Simon’s Weekly Strategic & Purposeful Advisor Insights
Each week, I share practical guidance and deeper reflections from working with financial advisor firm owners and agency leaders. Insights span leadership, hiring, succession, marketing systems, mindset alignment, and purpose-driven business strategy—delivered straight to your inbox.
Free Gift for Strategic Advisory Leaders
Build a 5–10 Person Advisory Team Without Losing Your Mind
Get instant access to this foundational guide—complete with a downloadable PDF and video walkthrough. You’ll discover the exact steps to grow your team with clarity, purpose, and structure—without burning out or compromising your standards.
Whether you’re transitioning into an agency leadership role or feeling overwhelmed by growth, this free resource will help you start building the business behind your advisory work.
Featured Articles
The Inner Compass
⏱ 5 – min read
Why leadership begins with alignment of purpose, values, and inner clarity.
The Purpose Behind The Plan
⏱ 4 – min read
Business plans work when they’re anchored in deeper meaning – not just numbers.
Hiring Beyond the Resume
⏱ 4 – min read
The right hire isn’t just about skills – values-based hiring builds a team that lasts.
Legacy Isn’t a Transaction
⏱ 5 – min read
Succession is more than timelines – it’s about mentoring, meaning, and letting go.
From Operator to Orchestrator
⏱ 4 min read – The right hire isn’t just about skills – values-based hiring builds a team that lasts.
Scaling with Soul
⏱ 4 – min read
Systems matter, but they must reflect your purpose and culture.
From Firefighting to Flow
⏱ 4 – min read
Accountability is about clarity and rhythm – not micromanaging.
Who We Serve
At Leading Advisor, we work with financial advisor firm owners and agency leaders ready to scale their businesses with clarity, confidence, and purpose. Our clients are committed to building something sustainable, transferrable, and deeply aligned with their vision and values.
You might be a fit if:
You’re Transitioning from Advisor to Agency Leader
You’re evolving from being the lead producer to becoming the strategic leader of your firm. You’re ready to shift your energy from day – to – day client work to vision, systems, and team development
You Lead a 5 – 10+ Person Advisory Team - But You’re Still in the Weeds
You’ve built a strong business, but you’re still carrying too much of it yourself. You want to lead with clarity—not exhaustion—and empower your team without sacrificing quality or values.
You’re Ready to Build a Team That Actually Lasts
You’ve learned that resumes don’t tell the whole story—and you want to hire based on values, fit, and long-term growth, not just quick fixes.
You’re an Agency Owner Seeking Structure That Reflects Your Values
Your advisors and clients rely on your vision—but personality alone won’t scale. You’re ready for frameworks and systems that not only support growth, but uphold the culture and care you’ve worked hard to create.
You're Preparing for Succession - But It’s Not Just About the Exit
You’re thinking beyond retirement. You want your transition – whether gradual or immediate—to honor what you’ve built, elevate the next generation, and ensure your legacy endures in both process and spirit.
What I Do
Clarity, Capacity, and Continuity for Your Business and Legacy
Running a financial advisory business while leading a team and serving clients isn’t just a full-time job—it’s three full-time jobs. I partner with advisory firm owners and agency leaders to build the business behind the advice—one that sustains your growth, your team, and your purpose.
Services Overview
Fractional Chief Operating Officer
Lead with clarity and scale your firm sustainably and purposefully.
Learn More
Elevate from advisor to business leader. I partner with founders to design and implement the operational foundation of a scalable advisory firm aligned with your values.
- Behavior & Mindset Coaching
- Vision & Business Planning
- Strategic Hiring & Team Building
- Succession & Continuity Planning
- Leadership Coaching & Delegation
- Marketing, Sales & Service Systems
- Accountability & Performance Management
Content Strategy & Development
Say what you mean. Communicate with clarity, consistency, and authenticity.
Learn More
I help you build a consistent voice and brand message that reflects who you are and where your business is going.
- Brand Messaging & Story Development
- Website Copywriting
- Email & Brochure Content
- Blog & Thought Leadership Ghostwriting
- Book Ghostwriting & Editorial Strategy
Implementation & Operational Coaching
I support your team with coaching call follow-ups, custom assignments, tools, meeting rhythms, and accountability systems that turn plans into practice.
Learn More
I support your team with coaching call follow-ups, custom assignments, tools, meeting rhythms, and accountability systems that turn plans into practice.
- Coaching Call Recaps with Actionable Follow-Ups
- Custom Assignment Design
- Integrated Communication Systems
- Proprietary Tools, Templates & Docs
- Meeting Rhythm & Leadership Cadence
Why This Work Matters
Building More Than a Business
For me, this work isn’t just about operations or revenue. It’s about helping leaders build businesses that sustain their families, empower their teams, serve their clients with excellence, and leave a meaningful legacy. When your business reflects your deepest values and intentions, growth becomes more purposeful—and life becomes more peaceful.
Simon Reilly
Chief Fractional Operating Officer
What Our Clients Have to Say
Josée Brisson
Josée Brisson Insurances Inc. | Co- operators
Orléans, Ontario
"Working with Simon is transformational for me and my agency. His guidance goes far beyond traditional coaching - he acts as a true Fractional Chief Operating Officer, helping me make successful hires, onboard key team members, and strengthen my leadership skills. With Simon’s support, I am able to align my vision with actionable systems that drive both growth and integrity. His insights, frameworks, and unwavering support give me the clarity and confidence to take bold steps forward. Thank you, Simon, for your help and support in my growth plan!"
Greg Johnson
President & Investment Advisor Representative
Bell Plaine, IA
“Working with Simon as our Fractional COO is transformative for Vantagus. He brings clarity and structure to our team by implementing the Advisor Diamond Structure, aligning roles and responsibilities, and creating processes that elevate both client service and team performance. Simon’s ability to integrate assessments, coaching, and strategy provides us with the insight we need to address leadership challenges and unlock our team’s potential. His guidance d elivers the systems and scripts to run the business more effectively while strengthening our overall leadership approach. The result is a stronger, more cohesive team and a clear path forward for growth. Simon continues to be an invaluable partner in helpi ng us build a business that is both scalable and sustainable.”
Memberships
Speaking Engagements
Let’s Build a Business That Reflects Your Purpose
Whether you’re scaling, hiring, or planning for succession, you don’t have to figure it all out alone. Let’s create a clear plan and implement it together so your business reflects your values and fulfils your vision.
Before we talk, grab your free guide, How to Build a 5-10 Person Advisory Team Without Losing Your Mind below: