Walking into the Family Ring.
- Denice Sakakeeny
- Apr 29
- 3 min read
As First Professional CFO in a Family-Owned Business
Stepping into a multigenerational family enterprise as its first professional CFO is like joining a championship doubles team mid-tournament: everyone knows each other’s moves, and you need to learn quickly. Over 20 years advising privately held firms, I’ve discovered that thriving in this role requires more than financial expertise—it demands emotional intelligence, cultural sensitivity, and strategic finesse. From day one, I realized that titles carry extra weight in a family setting. My first all-staff email was met with surprise—and a hallway interception from the founder’s sister asking, “Why are you telling us what to do?” That moment taught me to reframe communications around partnership, stressing support and collaboration rather than authority.
Translating Tradition into Structure
Forecasting in a family business often starts on napkins in the break room. In one meeting, the CEO passed me a note pad with last quarter’s sales numbers—“This is how we’ve always done it,” he said. By day’s end, I delivered a rolling forecast in Excel that mapped seasonality and payment terms. The operations team went from reacting weekly to planning months ahead, reducing last-minute crises and reducing dinner-time conversations around cash.
Building Trust through Legacy
At the annual holiday party, after working on understanding the cash was a little more contrained around a certain time of year, a long term sales guy asked me why any of it matters since he has been getting bonunses for decades. Rather than reciting ratios, I shared that I'm interested in freeing up cash sooner so we can pay bonuses sooner in this q particular quarter—directly rewarding him. Focusing on loyalty and legacy unlocked faster buy-in than any balance sheet ever could.
Embedding Controls with Respect
Introducing financial controls can feel like policing family traditions. When I spotted duplicate processes for the same thing, I knew a blanket ban would backfire. Instead, we implemented a quarterly review process co-signed by one of the owners. This approach maintained rigor while honoring the family’s informal culture—and ensured compliance without conflict.
Evolving from "Numbers Guy" to Strategic Partner
Six months in, I joined the founder on a drive to discuss a potential acquisition. Instead of handing over spreadsheets, I sketched a buy-versus-build decision tree on the back of a meeting agenda—and we walked into the meeting with the banker with clear scenarios, ROI projections, and identified risks. That snappy analysis cemented my role as a strategic advisor rather than an afterthought.
Pro Tips for First-Time Family CFOs
Listen Twice as Much as You Speak: In your first 90 days, prioritize one-on-ones with key family members and long-tenured staff to understand unspoken norms and history.
Map the Informal Org Chart: Identify influencers outside formal titles—longtime employees, founding siblings, or veteran vendors who shape decisions behind the scenes.
Translate Jargon into Stories: When presenting financials, tie metrics back to real-world impact—like how improved cash flow funded employee bonuses or capital projects.
Set Clear ‘What-If’ Triggers: Family businesses can be averse to rigid plans. Agree in advance on thresholds (e.g., margin dips below 15%) that automatically trigger review meetings.
Champion Small Wins Publicly: Celebrate quick operational wins—reduced close time, faster invoicing—to build credibility and momentum.
Balance Innovation with Tradition: Propose modern tools (cloud accounting, dashboards) in parallel with cherished legacy processes to ease adoption.
Not for the Faint of Heart
Being the first professional CFO in a family-owned business is a unique test of skill and soft power. As a consulting CFO, I'm used to being the new kid on the block. I pay special care to when I'm joining organizations where the handbook is more like "family values" than a blue print for avoiding litigation. I love to be part of the team, and multi-generational companies are unique in their history and rich in tradition that you just don't see with institutional investors.
