Five things I've learned from moonlighting as a synagogue CFO
When a unique opportunity presented itself, I used it as an opportunity to learn and get better at my full-time marketing work. Here are my top takeaways from year one.
If you told me five years ago that one day I would one day have an opinion about double-entry bookkeeping, I probably wouldn’t have believed you. That’s because I never imagined myself working closely on finance in a professional capacity, except for maybe writing articles about it.
But that all changed for me when I had the opportunity to serve a nonprofit I love—my synagogue!—as board treasurer.
I took on the role at the same time I was getting started in marketing at Bessemer Venture Partners. At first, I wasn’t sure how I’d square my day-to-day work—venture capital thought leadership content—with being a synagogue treasurer. But when I started producing content geared toward CFOs, everything clicked.
I’m of the mind that the best way to cover a topic well is to deeply understand it, and there’s no better way to accomplish this than with first-hand experience.
In this post, I’ll share how this opportunity came about, where we’re at now, and my five biggest takeaways from year one.
How this came about
My spiritual home in San Francisco was in the midst of a period of significant transition: our long-time rabbi was departing; we didn’t have a music, education, or even an executive director; and we were temporarily leasing space, something we’d done for years without a long-term solution. Somehow, for 30+ years, this place kept going. As COVID-19 eased, it was finally time to help usher the organization from surviving to thriving.
From my perspective in the world of tech and venture-backed startups, this seemed like a fascinating set of problems to solve.
I first got involved just by raising my voice and sharing an idea. My pitch was, our community is a hidden gem, but we could do better in reaching out to young adults and offering programming for people in their 20s and 30s.
That pitch turned into a board seat, and a few months later, the board nominating committee reached out with a pretty incredible proposition: “if we coach you and help set you up for success, would you like to be our treasurer?” The deal was that I’d get a lot of mentoring from other board executives and past treasurers, most notably from a C-level finance leader at UCSF Health who oversees budgets many times larger than the one at our small but mighty congregation.
From a professional development standpoint, how could I say no to that? So I buckled down, studied financial statements, scheduled a ton of 1:1s, and began flexing a muscle I didn’t even know I had. I also made it through a trial by fire in time management, prioritization, leadership, and learning how to get stuff done (GSD!).
One year in: writing about CFO topics and applying it in real life
Today, a little over a year later, we’ve bought and moved into a building, transitioned from an interim rabbi to a new settled rabbi, hired an executive director and communications assistant, and begun building a dynamic new program for youth education (my Hebrew school was nowhere as cool as this). Being on the leadership team that made this all happen—and playing the critical role of finance leader during these major growth spurts—has been one of the greatest privileges of the early innings of my career.
The combination of my marketing work at Bessemer and my volunteer work as synagogue treasurer couldn’t have been more harmonious: each opportunity made me better at the other. My immersion into financial leadership helped me ask the right questions to real-world CFOs as part of the articles I wrote, edited, and curated to create the SaaS Finance Course at Bessemer. And the best practices I learned at Bessemer helped me become a better operator and leader on my synagogue’s board of directors.
Now as I step into the second fiscal year of my two-year term at Or Shalom, and continue to build out operator-focused thought leadership content at Bessemer, I’ve been reflecting on all that I’ve learned, what I wish I knew at the start, and how I’ll lead an even better strategic planning process for the organization in 2024.
Here are my five biggest takeaways from year one as board treasurer, influenced by all that I’d learned from creating finance thought leadership content from the best in the business:
1. A huge part of being an effective finance leader is having the courage and confidence to initiate hard conversations—ones that are honest, direct, and actionable.
Money is incredibly hard to talk about, and I found it’s just as true in organizational settings as it is in personal finance conversations.
When patterns emerge in financial reports, finance leaders have the opportunity to dig in, name them, and interrupt them before they turn into longer-term problems.
In addition, it always helped to come prepared with possible solutions. One advantage of being in-house is that you understand how the organization works—knowledge of existing workflows, resources, and constraints makes it easier to propose suggestions that could actually work.
To effectively influence leadership, I had to brush up on emotional intelligence (EQ) and professional relationship skills, like giving feedback and determining when to raise something as an issue. Just like the folk tale “Chicken Little,” constantly raising imminent doom can dilute the message when leadership needs to hear it most. But it’s of course central to the role to warn about possible challenges down the road.
Finally, I found it critically important to approach these conversations as the team vs. the problem, not finance leader vs. other leaders. It’s a lot easier to tackle challenges from a place of collaboration instead of offense and defense.
Lesson learned: Proactively identify possible speed bumps, and share them with messaging that conveys credibility and trust.
2. The numbers are meaningless without a qualitative interpretation—always ask yourself, “what’s the story behind the data?”
To explain how the business is doing, finance leaders have to provide qualitative context behind financial results. Here’s an art comparison: data points alone are like a line sketch, whereas financial results presented with an interpretation, storyline, and recommendations are like a full landscape painting with color and texture.
Context points are drivers—the possible reasons behind business changes and results. Why was X figure down or up more than Y prior period? What were the conversations the board was having around that time? Was timing an issue? Answering questions like these help paint a detailed picture of an organization’s situation.
I’ve found it helpful to frame my presentations to the executive committee and board with a high-level headline, and then explain the biggest underlying drivers from there (several bullet points), focusing on the few that moved the needle the most.
Lesson learned: Once you understand all the drivers, then you’re best equipped to sum up the overall picture and create an elevator pitch.
3. Do what it takes to understand your financial statements inside and out.
At first it was daunting to make sense of the P&L and balance sheet, particularly because I was still pretty new to the organization.
What helped me most here was studying past reports and taking note of questions—e.g. Is XYZ program always breakeven? What are the biggest drivers behind a good vs. bad year for membership renewals? What does X committee do? How does that committee chair think about ROI? What are their biggest priorities this year and next? Etc.
I also found it helpful to remind myself of the people and programs behind each line item. Not only was this useful for making sense of new spreadsheets, but it also gave me items to follow up on, and new people to connect with throughout the organization. Some of my most helpful learning moments came from the occasional fifteen-minute call, weekend lunch, or walk in the park with someone I hadn’t previously spent time with.
Lesson learned: Ask questions, gather information, and learn how the organization works early on. Then, continue to do your homework, and treat it like a marathon, not a sprint.
4. Good strategy = data + behavior.
It’s difficult, costly, and risky to operate without data. To do that is to throw darts with a blindfold on.
Once you review the data and determine why results came in the way they did, then it’s time to make actionable recommendations—what the organization can do differently at a tactical level to better achieve its goals.
I think good strategy isn’t worlds apart from habit-building and goal-setting outside of work. Before making day-to-day changes, it helps to understand:
Where you are today;
What got you there;
What continuing down that path could look like in the future;
What continuing down other, better paths could look like in the future;
and what new day-to-day habits will compound over time to help you reach one of those better future options.
Most importantly, it’s important to leave emotion out of data and strategic recommendations (as much as possible). Emotions can certainly fuel a motivation for change or a new vision for the future, but you don’t want them to color your decision-making.
Lesson learned: Figure out the so-what? from your results. Determine what the organization needs to do differently in its day-to-day operations to get from its latest results to a more desirable scenario.
5. When times are tough, monitor the situation more closely than usual—and act accordingly.
When we figured out the right reporting cadence for the organization, the work didn’t stop there. I found it helpful to monitor the books and balances more frequently than usual during a few important moments.
For critical revenue periods, I kept closer tabs on the situation during big, seasonal campaigns tied to membership dues and fundraising.
For the balance sheet, I kept closer tabs on the situation during the banking crisis this past spring. More on that below.
My favorite anecdote on this topic: Shortly after Silicon Valley Bank collapsed this spring, my synagogue’s primary banking partner was on the brink, too. And we had a lot of uninsured deposits there.
I briefed our leadership team, set daily times to check on the situation, and crafted a game plan at night and on weekends.
I will never forget a 9:30pm phone call with our banker—he made time after putting his kids to bed to help us secure additional FDIC insurance, fully protecting our funds. (Legendary.) We were fully insured before things got really bad, and before the FDIC had placed the bank into receivership, we had already opened new bank accounts and diversified our cash management.
Lesson learned: During challenging periods, conduct financial reporting and monitor the situation at a more frequent than usual cadence.
Cheers to year two!
My immersion into finance leadership has left me with a huge amount of respect for the profession. It’s not just about money—it’s about truth-telling and leadership.
From a marketing standpoint, I found that testing the waters and developing a real-world understanding of new subject matter made the unfamiliar, familiar, and helped me create effective, resonant content.
I didn’t know it was possible to grow so much in a year, but I owe it to two organizations who believed and invested in me. This surprising harmony of thought leadership content and nonprofit finance work have helped me become a better professional and leader. It’s also been great for life outside work—since I now think in terms of cash flow forecasts and ROI, I’ve experienced a new level of control and comfort with personal finance, too.
I’m looking forward to more learning- and marketing-by-doing in 2024.