How I run finance solo at a hypergrowth startup

Anyone who’s worked in accounting can relate: You take time off, grateful for some R&R, but a sense of dread creeps in as your first day back nears. Instead of soaking up the final hours of relaxation, you’re already stressing about the hours of transaction coding and syncing that await.

Imagine my delight when I returned from a two-week break and cleared my entire backlog in just 30 minutes.

How? Of the 2,000-plus transactions over that period, I only had to review 67. Our platform automatically coded and synced the other 97% while I was out — without me so much as logging in. A few months ago, the process would’ve taken three-plus hours.

This experience shows what’s possible for finance teams today. Purpose-built tools and intelligent automation can eliminate the kind of manual work that defined the profession when I was coming up.

Of the 2,000-plus transactions, I only had to review 67. Our platform automatically coded and synced the other 97% while I was out — without me so much as logging in.

I operate as a one-person finance team at Skool, a fast-growing community platform for creators. I handle work that’s typically split up across a team of three or four: AP, AR, payroll, treasury, cash management, FP&A — with almost no help from outsourced firms.

When people hear that, they’re often stunned. But to me, it’s simply a reflection of what modern finance systems are capable of: allowing me to work smarter, not harder. And it inspired me to share my playbook.

The a-ha moment that made me rethink accounting

I’ve worked in finance for 12 years, but a veteran CPA changed the trajectory of my career years ago when he said this: "If you think about it, accounting is more of a liability to a company than anything else. Your job is to become an asset.” Translation: I needed to find a way to make contributions that would directly improve decision-making or boost margins.

So I shifted my focus from journal entries and tax filings to FP&A work. I learned SQL to self-serve most data analytics and financial modeling work. I eventually started my own consulting firm to help other finance teams scale up automation and rethink how they operate with the help of ever-improving systems.

How I automated Skool’s finance admin

It’s not like I just turned AI loose and hoped for the best. I invested time upfront to save much more time long term by building a connected network of systems that can do a lot of work for me. Here’s what makes this work:

• Card-level controls. I create virtual cards restricted to specific vendors and amounts. The system then accurately codes and categorizes each transaction (including the memo and department) almost every time.
• AI learns from my decisions. In cases where I do need to change a category or code, the system asks why I made the change and learns from it. The system is constantly getting better at mirroring my decisions.
• Auto-sync keeps the books current. Transactions that the system has high confidence in automatically sync to QuickBooks at the end of each day. That's why I only had those 67 transactions to go through when I returned from vacation.
• Account creation at onboarding. Our HR software is integrated with financial systems so when we add a new employee, it automatically creates accounts for them in our equity and spend management tools with funds that every employee receives.
• Self-managed travel. All employees can book travel themselves using trip-specific funds. This eliminates work in two ways: Preset rules ensure they stay within policy, and I avoid the headache of reimbursements.

The result: Most days, I only spend 30 minutes on this type of admin work.

Where that newfound time goes

With the time I’ve gained from cutting busywork, I can focus on more meaningful work. The type of work that drew me to this profession in the first place. Here’s how I usually spend my time:

• Cash management and financial planning. At a hypergrowth startup like Skool, monitoring cash burn is critical. That requires working closely with teams like marketing to ensure we’re hitting ROI benchmarks and tightening up scenario planning so that we’re ready for anything.
• Strategic projects. Cutting busywork has freed up more time to focus on strategic initiatives. For example, I studied video usage metrics on Skool’s platform and tied them back to financial KPIs so we can measure the bottom-line impact of optimization efforts. I also worked hand-in-hand with Skool’s CEO to negotiate payment processing pricing with Stripe.
• Cross-functional partnerships. When our data team needs help understanding how retention and churn rates impact the P&L, I can be a resource. When engineering asks about adding more compute, I can explore how that investment would affect the budget, and what our expected return would be.

Thanks to deep automation, most days I only spend 30 minutes on admin work.

This is the kind of work that gets me out of bed in the morning, because I know I’m directly contributing to Skool’s growth.

The future is already here

I’m often asked when I plan to hire another finance person. The honest truth: it's not on my radar. I’ve designed our systems so that more transactions don’t = more work.

The finance function is forever changed. And if you ask me, it’s for the better. I started my career as a bookkeeper, painstakingly reviewing transactions one by one. A true grind. Now, junior hires can take on more of the thought-provoking strategic work.

You need to adopt the mindset of "how do I build systems that do this work for me?,” rather than "how do I do this work?”

This new playing field requires a different skillset. A strong understanding of accounting fundamentals is still necessary, but you also need to be comfortable with data analytics, model building, and hands-on experimentation with innovative tools. Most importantly, you need to adopt the mindset of "how do I build systems that do this work for me?,” rather than "how do I do this work?”

I'm more energized about finance now than I've ever been. Innovation is finally letting me do the job I always wanted to do.

If you want to learn more, I’d love to connect. Find me on LinkedIn or Skool.