Resources, Curated with Intention
Explore My Trusted Favorites
A refined collection of the tools, software, and exclusive perks we rely on to keep businesses organized, efficient, and growing with clarity.
This page contains affiliate links. Every recommendation is thoughtfully selected based on what we use and stand behind.
Hi I’m Jessie,
I’m the founder of Oak and Ledger.
Before starting my own bookkeeping practice, I spent nearly a decade doing the books for my family’s company after leaving public accounting to build a life that worked better for me. Because I worked from home for so long, I had very little local network when I decided to start my firm, and no clear roadmap for how to grow it.
I’m also a mom of two, and both of my kids were under the age of three when I felt the pull to build something of my own. My time was limited, my capacity was real, and my original goal for 2025 was simply to have five clients by the end of the year. I ended up with nine, without spending a single dollar on advertising or paid marketing.
What surprised me most was how much I genuinely loved the process. The systems. The learning curve. The small wins. Even the challenges. And through that experience, I realized I wanted a place to document what this journey actually looks like, not the polished version, but the real one.
I also wanted to step back from constant short form content and create something more intentional. A space to write, reflect, and share what I have learned without the pressure of algorithms or trends.
That is why I created this space.
This blog is where I share the behind the scenes of building a bookkeeping business. What worked, what did not, the systems I rely on, and the parts of this work that often go unspoken. My background spans from micro businesses to mid sized companies, and that experience shapes how I approach both bookkeeping and business ownership.
If you are a bookkeeper who cares about structure, sustainability, and building something that fits your real life, you are in the right place.
If you want to start at the beginning, the first post shares the story behind this space and how it all started. Otherwise, check out some of my favorite tools below that save me hours (and money) every single month!
The tools that support the workflows
These are the systems I use inside Oak and Ledger to stay organized, protect client data, and create repeatable processes.
The Essentials
Because as a bookkeeper, you’re managing logins across multiple clients, banks, and POS systems. You need more than sticky notes and reused passwords and most bank accounts require a different username for each company access! Securely store credentials, share access safely, and keep everything organized without the mental load.
The backbone of your bookkeeping business. From unlimited meeting minutes to Docs, Sheets, file storage, e-signatures, and calendar scheduling, everything you need lives in one place. It keeps your client communication, documents, and workflows organized without the chaos. Easily one of the best values for what you get.
Your business bank account should do more than hold your money. It should help it grow. Earn interest on your balance while keeping your finances clean, separated, and easy to manage. As a bonus, join the accountant referral program and earn when your clients sign up.
Build a Website That Reflects Your Business
Squarespace
Your website should do more than exist. It should communicate your value, build trust, and support your growth from day one. That’s why we build on Squarespace, a platform designed for clean, professional, and scalable websites.
At Oak and Ledger, we offer Squarespace website design for business owners who want a refined, strategic online presence without the guesswork. If you prefer a more hands-on approach, you can still create something beautiful with the right foundation.o life.
The Bookkeeper’s Edit
A must-have for large cleanups and data-heavy clients. Saasant makes it easy to import bulk transactions into QuickBooks Online, whether you’re handling a big catch-up or bringing in point of sale data. Save hours of manual entry and keep your books accurate and organized.
Your client communication hub. Keep all requests, follow-ups, and outstanding items organized in one place. It streamlines monthly workflows, keeps clients accountable, and gives you a clear system for managing everything without the back-and-forth.
Content, done for you. Perfect for bookkeepers who want to stay visible without spending hours creating posts. Get industry-specific captions, graphics, and ideas so you can show up consistently and professionally and 50% off your first month.
Latest Articles
more coming soon!
Follow Along
Learn alongside me
If you enjoy systems, structure, and thoughtful conversations about bookkeeping as a profession, you are in the right place.