Connor Whittemore

I built Penni because bookkeeping shouldn't cost a fortune.

I'm Connor Whittemore, founder of Penni. I've spent my career in strategic finance and FP&A — building cash flow models, leading financial operations, and managing financial systems at high-growth, venture- and PE-backed SaaS companies. After watching small business owners drown in QuickBooks while paying $500-1,500/month for bookkeepers who quit, raise prices, or simply make mistakes, I built Penni to give them the same level of financial precision and insight that enterprise teams take for granted — at a fraction of the price.


The problem I saw.

Every small business owner I know has the same story. They started a business because they're great at something — building, creating, selling, serving. Not bookkeeping. But suddenly they're spending 14 hours a week chasing invoices, categorizing expenses, and dreading tax season.

The options are bad. Do it yourself — spend hours in QuickBooks doing work you hate. Hire a human bookkeeper — pay $500-1,500/month and hope they don't quit, make mistakes, or raise prices. Use accounting software — congratulations, now you have a prettier way to do the same work.

None of those options actually solve the problem. The problem isn't the software. The problem is that someone still has to do the work.

So I built the thing that does the work.


What I bring to this.

Strategic finance is pattern recognition — the same cash flow problems, the same expense categorization mistakes, the same overdue invoice spirals show up over and over again. AI is finally good enough to fix those patterns automatically. Penni is what happens when someone who's spent years building financial systems for fast-growing companies turns that toolkit on small businesses.


What I believe.

Your books are yours.

Everything stays in QuickBooks. Cancel anytime. No lock-in, no data hostage. I believe you should be able to walk away at any moment — and that confidence is what makes you stay.

Price should be honest.

No bait-and-switch. No 75% increase after year one. The price you sign up at is the price you keep. I'm not here to extract maximum revenue — I'm here to earn trust.

AI should save you money.

If AI makes the work faster and more accurate, the savings should go to you — not inflate someone's margins. That's why Penni costs a fraction of a human bookkeeper.

Proactive beats reactive.

A bookkeeper who waits for you to send receipts isn't working hard enough. Penni scans your email, categorizes your bank feed, and alerts you about cash flow — before you ask.


Let's talk.

I'm personally onboarding every customer right now. If you want to see what enterprise-grade bookkeeping looks like for your business, let's talk.

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