For over 40 years, boards, management teams, and private equity firms have turned to me in the moments that mattered most — the audit that couldn't fail, the transaction that had to close, the transition that had to hold. That experience hasn't gone anywhere. I've just put it to a new use.
Bear Hill Advisory Group has moved beyond hands-on consulting. Today, my work is teaching what I once had to learn the hard way — turning overwhelmed CFOs into confident, strategic leaders, one deliberate step at a time. In the age of AI, knowledge is cheap; experience and judgment are priceless.
For CFO's
You didn't take this role to stay in survival mode.
I built the Chaos to Confidence Blueprint ™as the proven, four-phase path I wish someone had handed me — from stabilizing the fundamentals to leading with a clear, authentic strategic voice. Built specifically around what CFOs actually face, not generic executive coaching repackaged for finance.
For Private Equity Firms
I've watched too many portfolio companies struggle to attract and retain strong CFOs — it's one of the hardest, most overlooked challenges in value creation. This program gives your portfolio company CFOs a structured development path — and gives you a concrete, visible way to show them you're investing in their growth, not just their output.
The Program
From Chaos to Confidence: The CFO Transformation Blueprint™
A four-phase journey, each built around a shift in identity as much as a shift in skill:
🛡️ Stabilize the Foundation — Overwhelmed operator → grounded guardian
🌉 Elevate Influence — Silent analyst → strategic influencer
⚙️ Expand Capabilities — Functional executor → operational strategist
🧭 Transform Self & Strategy — Reactive CFO → confident visionary
Each phase stands on its own. Together, they're a complete transformation.
The 12 Disciplines
Beyond the core program, go deeper on the specific skills that separate a functional CFO from a strategic one — from crisis management and governance to negotiation, capital allocation, and authentic leadership. After you have completed "Stabilize the Foundation' each of the remaining disciplines stands alone as its own focused course, so you can build exactly the fluency you need, in the order that matters most to you right now.
Speaking and Thought Leadership
Insights on operational leadership, financial strategy, and what it takes to become a true COFO — the strategic, operationally fluent Chief Operating Financial Officer organizations increasingly need. Delivered through speaking engagements, workshops, and ongoing thought leadership for boards, management teams, and private equity firms building their next generation of financial leaders.
About Jack
Jack Healey's path to this work started in public accounting, where 16 years culminated in a Partner in Charge role at a regional CPA firm. From there, he became a founding executive of a highly acquisitive NYSE/NASDAQ listed distribution company, serving as CFO and COO through years of rapid growth and transformation. Since 2019, he has advised acquisitive and turnaround organizations directly on the finance and operating challenges that make or break a leadership team.
That experience is now channeled into one purpose: helping CFOs build the confidence, skill, and strategic voice that no one ever handed them — and helping the firms who depend on them invest in that growth deliberately.