Mastering Operations and Finance: A Conversation with Fractional COO Jennifer Hamilton

ryanchenier
May 5
3 min read

Updated: May 9

Welcome to another episode of Mastery Fractional CFO’s Punchy Podcast, the show where we bring you sharp, actionable insights from business leaders across industries. I’m your host, Ryan Chenier, Founder and CEO of Mastery Fractional CFO Services.

In this episode, I sit down with Jennifer Hamilton, Founder of Hamilton COOs. Jennifer is a fractional COO, COO mentor, CPA, and the secret weapon behind many businesses transforming chaos into streamlined success. Together, we unpack the power of operational leadership, strategy, and why fractional executives are reshaping how small and mid-sized businesses grow.

From CPA to COO: Jennifer’s Journey

Jennifer shares how her early years as a CPA at PricewaterhouseCoopers sparked a love for process, metrics, and leadership. Over time, she transitioned into consulting and eventually carved out a niche as a fractional COO — even before the title was common. Today, she’s passionate about helping businesses operate more smoothly, strengthen leadership, and align teams toward shared goals.

What Does a COO Actually Do?

Jennifer explains the COO’s role as the right-hand partner to the CEO — focusing on executing the company’s vision, aligning cross-functional teams, and ensuring strategies turn into results. Whether full-time or fractional, a COO drives:

Strategy execution
Leadership alignment
Cross-functional coordination

In smaller businesses, fractional COOs provide high-level guidance without the cost or need for a full-time executive, fitting both the budget and the stage of growth.

Common Challenges: Why Businesses Call in a Fractional COO

Jennifer and I explored the pain points she often encounters:

Lack of accountability among team members
Over-reliance on the CEO for every decision
Unclear roles and responsibilities
Bottlenecks and missed opportunities

Her diagnostic approach — using tools, interviews, and financial review — helps quickly uncover root causes and prioritize solutions. As she puts it, “It’s about getting people rowing in the right direction, with the right oar, in the right seat.”

When Is a Business Ready for a COO?

Jennifer typically works with professional services firms — boutique law, accounting, and consulting firms — generating $1M to $5M in annual revenue. While businesses often need foundational tools like org charts earlier, they usually only recognize the need after crossing the $2M mark when complexity increases. Without operational improvements, scaling can lead to burnout or even collapse.

How Quality Management, EOS, and Strategy Come Together

We discussed frameworks like EOS (Entrepreneurial Operating System), which Jennifer integrates with her own approach. Beyond mission, vision, and values, she emphasizes three key areas:

Client experience
Cash flow and profitability
Marketing and business development

Her role ensures alignment across departments and turns strategy into practical, measurable action.

The Power of Sales Metrics

During our CFO Question segment, Jennifer asked me about my favorite metrics. My current favorite? Sales conversion rates. Small improvements in conversion at each stage of the sales funnel can deliver massive gains in revenue and profitability. Tracking and intentionally managing these metrics is where financial strategy meets operational execution — and where real impact happens. I get into the interesting details during the discussion.

When to Call in a Fractional COO

If you’re:

Burnt out and making every decision yourself
Complaining about the same issues on repeat
Lacking clarity on roles, priorities, or direction

… it’s time to call someone like Jennifer. She offers educational calls (no selling) via HamiltonCOOs.com and hosts free monthly CEO/COO roundtables — a fantastic resource for business owners craving practical insights.

Why Fractional Executives Work

Jennifer and I agree: fractional leaders bring outside perspective, cross-industry experience, and a cost-effective solution to companies not ready for (or not wanting) full-time C-suite hires. For many, the partnership evolves into a long-term, high-impact relationship that delivers more value than a single in-house hire could.

Call to Action

If you enjoyed this episode, please share it with a business owner or leader you know — especially someone juggling growth, chaos, or leadership gaps. To learn more about Jennifer Hamilton’s services, visit HamiltonCOOs.com.

And if you’re ready to transform your company’s financial strategy, reach out to me at Mastery Fractional CFO Services — let’s discuss how we can move your business forward.